Years ago, we published articles on personal finance goals to strive for in your 20s and in your 30s.

Now that I’m in my 40s, I decided to revisit this series to see if I needed to update my financial goals in my first decade of midlife.

Your 40s are an interesting time, money-wise. Many men enter their peak earning years during this decade. Yet their expenses often increase significantly at the same time. High-school-aged kids may need cars, and those same teenagers may subsequently need help paying for college. Your parents are retiring and aging into their 70s, and you’re starting to think about what financial support they may require in the last decades of their lives. Meanwhile, your own retirement shifts from a distant abstraction into an approaching reality.  

During this decade where you’re both starting to enjoy the fruits of your labors, but feeling the pressure of additional demands, you want to make moves to ensure you’re on stable ground now and in the future.

Below are 10 goals, backed by research and the advice of personal finance experts, that will help you not just survive your 40s, but thrive in that decade and in the decades to come:

1. Consider Consulting a Financial Advisor

With higher income and more responsibilities, your financial life is more complex in your 40s.

So consider hiring a fee-only financial advisor to help you navigate these complexities. Fee-only financial advisors don’t make money from selling financial products like insurance or mutual funds, reducing conflicts of interest.

You can pay a fee-only financial advisor by the hour to get advice on planning for retirement, paying for college and potential weddings, updating your estate plan, and reviewing insurance.

If you’re looking for more comprehensive guidance, you can set up an arrangement where the financial advisor gets a percentage of the assets they manage for you.

You can find fee-only financial advisors in your area by searching https://www.napfa.org/.

2. Maintain a Robust Emergency Fund (6–12 Months of Expenses)

By now, you should have a solid emergency fund. In your 40s, the goal is to increase its balance to match the expenses you likely have as a middle-aged man.

Aim for at least six months of essential expenses, or up to a year if you’re in a volatile industry or single-income household. Job hunts for people in their 40s often take longer than for those who are younger. If you were to lose your income, a six-month cash reserve ensures you can keep paying the mortgage and feeding the family while you find your next role. It also prevents you from raiding retirement accounts or going into debt.

Keep this fund in a liquid, low-risk account. Don’t touch it unless it’s a true emergency; replenish it as soon as possible if used.

3. Maximize Your Income

For many men, their 40s are the highest-earning decade of life. The median annual salary for men usually peaks between 45 and 54. Make it a goal to leverage these years as much as possible to set yourself up for true financial security.

To make the most of this decade, you’ll want to maximize your income.

Raises won’t usually fall into your lap. You’ll need to ask for them proactively.

If your boss won’t budge on giving you a raise, consider switching roles or even companies. Changing jobs mid-career can often substantially increase your salary, but so can moving up the ranks at your current job; be sure to check out our podcast on getting a promotion for some solid advice on how to continue to work your way toward the literal or metaphorical corner office.

Additionally, look into creating extra income streams through side businesses or freelancing. At this stage in your career, you probably have valuable expertise others will pay for. Consider moonlighting as a consultant. The extra income you earn now could even evolve into part-time work after you retire.

It’s worth noting that your 40s are not only peak earning years, but may be the last years you have your kids at home. You don’t want to be so focused on maximizing your income that you miss out on maximizing the time you spend with them before becoming an empty nester. It’s a tough line to walk, but strive to strike a balance between filling up your financial treasury, and your memory bank.

4. Avoid Lifestyle Creep

It’s natural to want to reward yourself as your income rises — to finally get that dream car, upgrade to a bigger house, or take more vacations. And you should allow yourself to start splurging a little more in your 40s; you’ve earned it by grinding through your 30s.

But don’t go overboard; every dollar spent on upgrading your lifestyle is one less dollar available for debt reduction or savings. Remember, too, that the cost of another car or a bigger house isn’t just the initial purchase price, but what it will cost you in maintenance, insurance, etc.

Start enjoying yourself more in your 40s, while saving enough to ensure that the next four to five decades are enjoyable as well.

5. Double-Down on Retirement Savings (Aim for 3X Your Salary)

In your 40s, retirement is no longer the abstract-seeming thing it was in your 20s. It will potentially be a concrete reality for you in twenty or so years.

Experts suggest having about three times your annual salary saved by age 40. Don’t worry if you’re not there yet — many aren’t — but use that benchmark to motivate you.

In your 40s, strive to save at least 15% of your income (ideally 20% or more) for retirement. As you save for retirement, take full advantage of tax-advantaged accounts like 401(k)s and IRAs.

How should you allocate your retirement savings in your 40s? When I put this question to personal finance expert Nick Maggiulli, he suggested that for many, it might mean reducing risk due to the increased liabilities they likely have in midlife: “In your 40s and 50s, you should consider reducing this risk to fit your liability profile better. For example, you could consider going from an 80/20 stock/bond portfolio to a 70/30 (or something similar). The key here is not maximizing your net worth, but maximizing your chance of long-term survival.”

6. Eliminate Non-Mortgage Debt and Work Toward Being Mortgage-Free

Ideally, you’ll have paid off all non-mortgage debt in your 30s. If you haven’t, make that a priority in your 40s. Aggressively tackle any lingering debts, like car loans and student loans.

Once you’ve eliminated all non-mortgage debt, start focusing on your mortgage. While you don’t necessarily need to pay it off during your 40s, you should have a clear plan for eliminating it as soon as financially feasible.

If you can swing it, start making extra principal payments. Even one extra payment a year (or adding, say, $200 extra each month) can knock years off a 30-year loan. Check with your lender that extra payments go toward the principal.

7. Bolster Kids’ College Funds (But Not at the Expense of Retirement)

In your 40s, your children may be in high school, and college costs are looming. Ideally, you started a 529 account for your kids in your 30s; if not, start one now. With 529 accounts, gains and distributions/withdrawals for education aren’t taxed.

As you save for your kids’ education, don’t do so at the expense of your retirement. Your retirement should always be the priority when saving. Your kids have options for education financing, but you don’t have one for retirement.

8. Plan for Aging Parents and Family Care Responsibilities

More than half of 40-somethings are either raising children under 18 or financially supporting adult children, and have at least one parent aged 65 or older. About a quarter of adults in their 40s and 50s actively provide financial assistance or regular care to their aging parents — a percentage that only increases as members of this “sandwich generation” and their parents grow older.

Prepare for a future with aging parents by talking to Mom and Dad about their financial health. Do they have sufficient retirement savings, a will, power of attorney, or healthcare directives? Knowing this upfront can prevent surprises during a crisis.

Second, discuss future care preferences. When their health declines, would your parents prefer living with family or moving into an assisted living facility? Clarifying this sets expectations and shapes future plans. If you have siblings, hold a meeting to define roles and discuss shared costs.

Finally, consider preparing financially by creating a “parent fund” for predictable expenses like medical bills or housing.

Check out the book Mom and Dad, We Need to Talk: How to Have Essential Conversations With Your Parents About Their Finances. I thought it had a lot of good advice.

9. Do an Insurance Check-up

If you bought term life insurance in your 30s (as we recommended), revisit your coverage. Major changes — like more kids, a bigger mortgage, or a higher income — might require additional coverage. A common guideline is 10–15X your annual salary, ensuring your family could replace your income if needed. Term policies are still affordable in your 40s (though premiums rise), so lock in coverage until kids graduate college and your mortgage is paid off.

Also consider umbrella insurance to protect accumulated wealth from liability lawsuits, and disability insurance to replace your income if you can’t work.

10. Do an Estate Plan Check-Up

You should have started your estate planning in your 30s; in your 40s, it’s time to do a check-up.

• Revisit and update your will to reflect current realities, like new assets or guardians for your kids.
• Double-check beneficiary designations on retirement accounts, insurance, and investments; these override your will, so accuracy is crucial.
• Ensure you have durable powers of attorney (for financial decisions) and healthcare proxies, naming people you trust.
• Explore advanced strategies like trusts or charitable giving if your estate is sizable.
• Communicate with your spouse and estate executor about your plans and where key documents are stored.

11. Plan Your Next Chapter of Life

Having a clear retirement vision guides your financial choices today. Outline your ideal retirement. When will you retire? Where will you live? How will you spend your time? Cruising? Volunteering? Working part-time? Answers to these big-picture questions will shape how you save in your 40s.

Next, calculate your retirement “number.” Most aim for savings that generate 70–80% of pre-retirement income annually. Use retirement calculators or a financial planner to check your progress, adjusting your savings or expectations if needed.

Finally, prepare for potential healthcare costs. You might live into your 90s, so your savings could need to last over 30 years after you retire.

Your 40s are a busy and sometimes stressful decade, but with thoughtful planning and strategic actions, you can balance today’s demands with tomorrow’s dreams. Use these goals as your financial roadmap, and you’ll enter your 50s with confidence and clarity, knowing you’ve laid a strong foundation for the years ahead. I’ll see you in 10 years with an article on financial goals for that decade of life!

This article was originally published on The Art of Manliness.

The era of artificially intelligent large language models is upon us and isn’t going away. Rather, AI tools like ChatGPT are only going to get better and better and affect more and more areas of human life.

If you haven’t yet felt both amazed and unsettled by these technologies, you probably haven’t explored their true capabilities.

My guest today will explain why everyone should spend at least 10 hours experimenting with these chatbots, what it means to live in an age where AI can pass the bar exam, beat humans at complex tests, and even make us question our own creative abilities, what AI might mean for the future of work and education, and how to use these new tools to enhance rather than detract from your humanity.

Ethan Mollick is a professor at the Wharton business school and the author of Co-Intelligence: Living and Working with AI. Today on the show, Ethan explains the impact of the rise of AI and why we should learn to utilize tools like ChatGPT as a collaborator — a co-worker, co-teacher, co-researcher, and coach. He offers practical insights into harnessing AI to complement your own thinking, remove tedious tasks from your workday, and amplify your productivity. We’ll also explore how to craft effective prompts for large language models, maximize their potential, and thoughtfully navigate what may be the most profound technological shift of our lifetimes.

Connect With Ethan Mollick

This article was originally published on The Art of Manliness.

Think of all the texts, emails, and social media posts you’re inundated with each day. Sometimes you read them, and sometimes you swipe them away, telling yourself, perhaps not so honestly, that you’ll revisit them later.

If you’re the sender of such missives and memos or the creator of content, you hope the recipient has the first response, that, instead of deep-sixing your message, they take the time to engage and take action on it.

How do you increase the odds of that happening? Rather than just guessing at the answer, Todd Rogers has done empirical experiments to discover it. Todd is a behavioral scientist, a professor of public policy at the Harvard Kennedy School, and the author of Writing for Busy Readers: Communicate More Effectively in the Real World. Today on the show, Todd explains the four-stage process people use in deciding whether to engage with your writing, whether in a personal or business context, and how influencing these factors not only comes down to the style of your writing, but its overall design. Todd offers tips to improve both areas, so that you can effectively capture people’s attention.

Resources Related to the Podcast

• AoM Podcast #971: The 5 Factors for Crafting Simple (Read: Effective!) Messages
• AoM Podcast #666: The Power of Brevity in a Noisy World
• AoM Podcast #580: Why People Do (Or Don’t) Listen to You

Connect With Todd Rogers

• Todd on X
• Todd’s faculty page
• Writing for Busy Readers website

Listen to the Podcast! (And don’t forget to leave us a review!)

Listen to the episode on a separate page.

Download this episode.

Subscribe to the podcast in the media player of your choice.

Read the Transcript

Brett McKay: Brett McKay here, and welcome to another edition of The Art of Manliness podcast. Think of all the texts, emails, and social media posts you’re inundated with each day. Sometimes you read them and sometimes you swipe them away, telling yourself, perhaps not so honestly, that you’ll revisit them later. If you’re the sender of such missives and memos or the creator of content, you hope the recipient has the first response. That instead of deep six-ing your message, they take the time to engage and take action on it. How do you increase the odds of that happening? Rather than just guessing at the answer? Todd Rogers has done empirical experiments to discover it. Todd is a behavioral scientist, professor of public policy at the Harvard Kennedy School, and the author of Writing for Busy Readers, Communicate More Effectively in the Real World. Today on the show, Todd explains the four stage process people use in deciding whether to engage with your writing, whether in a personal or business context, and how influencing these factors not only comes down to the style of your writing, but its overall design. Todd offers tips to improve both areas so that you can effectively capture people’s attention. At the show’s over, check at our show notes at aom.is/busyreaders.

All right. Todd Rogers, welcome to the show.

Todd Rogers: Thanks for having me.

Brett McKay: So you are a professor of public policy and you recently co-authored a book about how to write for busy readers. What’s the connection between researching and writing about public policy and writing for harried people living in the TikTok age?

Todd Rogers: I’ve never been asked to actually defend why this is public policy. I guess it starts with I spent a decade working on how do we communicate to busy voters trying to mobilize voters to participate in elections, and then a decade working on how do we communicate with busy families from schools to get kids to go to school and kids to do better. And then five or six years before Jessica and I wrote this book, working with leaders across industries on how do we communicate to our employees, stakeholders, customers, constituents, and yeah, so I guess the common thread is across all these categories, across every domain of life, we are communicating to busy people. And if we wanna be effective at doing it, we have to understand that our readers are busy and we should write in a way that makes it easy for them.

Brett McKay: Yeah. With public policy, you’re trying to get people to do things, but in order for them to do the thing that you want them to do, you have to communicate that to them?

Todd Rogers: Yeah. I describe it as stage zero of every intervention we deliver. Is do we capture people’s attention long enough to deliver whatever we’re trying to communicate? So yeah. So if we are trying to have people sign up for a program or, you know, comply with the law or show up to court on a specific court date, we need to make sure we are communicating to them effectively.

Brett McKay: So you start off the book defining what effective communication is, what effective writing is, and you’ve developed this definition based on research as well as your own experience as a reader and writer. So what makes writing effective?

Todd Rogers: I think we probably start with the reader. So it’s funny, we talk about writing as if we are teaching writers, but the entire question of effectiveness is, do we succeed in communicating some thought from our head into the head of a reader? And so when we talk about this work, we’re like, okay, imagine you own a radical different take on writing. It’s not enough to have everything in there and then shift the responsibility to the reader. Imagine if it was always your fault if the reader did not read what you gave them. If it was always your fault, and so it’s your responsibility to make sure they read it and you don’t control their lives. All you control is what you put in front of them. Then just, it takes a whole new orientation. Effective writing is writing that we succeed in delivering the key content into someone else’s head at their leisure.

Brett McKay: And then at the beginning, I loved how you applied the things you write about in this book, in your book, and you lay out these sort of bullet points of what you found to be effective writing. Things like effective writing has a well-defined purpose. There’s a reason why you’re doing it, like, you know, and the reader can pick that up right away. It says, effective writing helps the writer as well as the reader. How does effective writing help the writer as well as the reader?

Todd Rogers: Writing often helps us clarify our own thinking, and I think we conflate that with the other use of writing, which is getting an idea from me to you. And they are two totally different functions. And often we write our first draft and then at the end it was clear what we think that the highest order goal is. But that’s actually stage one. Stage two is then we need to actually make it as easy for the reader as possible to get it. The way it makes it easier for the writer. Writing effectively helps writers because one, it helps us achieve our goals, which is Jessica and my objective with this book, helping writers be more effective in achieving their goals. But it also, and we’ve all experienced this, the haranguing and harassment of people who haven’t read or responded to what we sent them, ineffective writing becomes a huge burden on the writer because people aren’t showing up, people aren’t responding, people are asking you questions. So writing effectively helps writers because it saves us all the follow up and all the hassle that we are experiencing as a part of hassling other people to respond to us. It saves you from that irritation.

Brett McKay: Yeah. Another point you make, effective writing is not the same as beautiful writing. Flesh that out for us.

Todd Rogers: We are all taught how to write well. K through 12, K through college, we are taught these ideals of what good writing looks like, what beautiful sentences are, and using advanced vocabulary to be more precise. And I think that’s a critical stage on the road to becoming an effective person. But there’s a totally different project, which is not meeting some ideal, but actually communicating in the world to people who are not paid to read your writing and people who are most of the time trying to move on as quickly as possible. Like their goal is to hit delete or hit next as quickly as possible, often without even knowing what your point was. And so it’s like effective writing is writing for those people, not for people who are paid to give you feedback on your writing.

Brett McKay: Or it’s not for a novel for example. Like you might use some flowery language in a novel ’cause that’s what you’re trying to… You’re trying to do something. It’s basically beautiful writing and effective writing have two different goals.

Todd Rogers: Totally, yeah. A novel’s just a different function. We think of effective writing as being about professional practical writing where you’re texting a friend or you’re writing a web content or you’re writing an email to a coworker. All of it is like, it is not, you know, we’re not trying to layer in a third level of meaning with close reading about what adjective we used. We’re actually just trying to practically communicate something.

Brett McKay: Right. So effective writing is about getting stuff done, and you guys aren’t arguing in this book that we need to, you know, do sort of like an Orwellian news speak where all of our writing becomes effective writing. There’s still a place for New Yorker articles, there’s still a place for Tolstoy in writing like that. It’s just that you’re focused on how can we write so people get stuff done. That’s the focus.

Todd Rogers: Yeah, I like that. I mean, we probably could have incorporated that into the title. Yeah. There is a place for all that stuff, although that is a totally different function. It is leisure. You read the New Yorker Tolstoy because you are reading it recreationally to entertain yourself. And that is different than working your way through your text messages or your inbox.

Brett McKay: As a guy who’s on public policy, what have the consequences been of ineffective writing? Like real world consequences?

Todd Rogers: You could go across any domain for… It could be ineffective. Let’s say you’re a government and you’re communicating to the people who are delinquent in taxes, you’re mailing them and they’re not reading it. There’s all these studies on people are released from arrest and they’re given court summons. And if it is written in a way that is easy to read, they’re way more likely to actually show up to court and not have bench warrants issued for their arrest or signage in your public park asking you to pick up your dog’s poop written in pretty incomprehensible ways. Personally, like I have started two organizations. One is the Hub in Washington DC of using behavioral science and behavior change on public political communications and effective political communications, whether it’s Get Out the Vote or Fundraising or Volunteer Recruitment or Persuasion.

Another is a company that works with K12 school districts in communicating to families effectively, gets kids to go to school or not. And so writing in a way that makes it hard to understand, or just writing the way we sometimes do can undermine these important goals that organizations, campaigns, schools, companies have, which is trying to achieve some goal that is good for both the person who’s reading and the goal of the writer.

Brett McKay: Yeah. And I’m sure everyone’s seen examples of the bad consequences of ineffective writing at their own work. You know, the company sends out a memo trying to get you to do something, but it’s written in this convoluted way or there’s just too much going on in the memo that there’s hardly any compliance at all.

Todd Rogers: Yeah. There’s, I mean, there’s some great examples. So there’s like a sign, there is a center for plain language. It is an organization that gives an award every year called the WTF Award for just the worst signage that has been created that year. WTF means words that failed, obviously, and the sign, a real sign, getting people to pick up their dog’s poop was persons shall remove all excrement from pets. I am certain that that was an ineffective sign and that 90% of people didn’t read it and understand that the goal was to scoop your pet’s poop. So yeah, it’s comically bad, but it’s clear. I mean, I’m sure the lawyers understood it.

Brett McKay: Yeah. So before you start writing, the thing you say we need to do first is get inside your reader’s head. What do people need to understand about readers today so they understand like how a reader decides whether or not they’re gonna read something, whether they’re gonna read it all the way through, et cetera.

Todd Rogers: I think the TLDR of the whole thing, the too long didn’t read of the whole book or of this entire project that we’re doing is everyone is skimming everything, right? No one is spending as much time reading as we are writing and thinking about it. And so we need to write in a way that accommodates the reality that everyone’s skimming. So you get inside their head and know that they’re super busy and they have a long list of things to do and a lot of things they’d rather do than read whatever you’re sending them. And that includes text messages. We’ve run these experiments where even text messages, writing them so they’re easier to read makes people more likely to understand and respond to them. So if you’re gonna get in the reader’s head, it all starts with everyone’s busy and everyone’s skimming. And rarely do people care as much about what we’re writing as we do.

Brett McKay: And I love this too. You lay out a four stage process that readers go through when they’re deciding whether they’re going to engage with a piece of text, and this is whether it’s an email, a text, a Slack message, a social media post. The first part is you have to decide whether you’re gonna engage with it at all. So you just look at the thing and you kind of skim it and you’re like, well, am I even going to dig deeper into this? Second is, if you decide to engage, you must decide when to engage. Like what does that mean? Like sometimes you don’t read it right away?

Todd Rogers: Yeah, it’s a combination of the first and second. The second and third, which is the first most is the… I think the most important and kind of the most subtle, but everyone will relate to, which is if you have a long thing in front of you and a short thing in front of you, which are you gonna do first? Almost everyone is gonna do the short easy thing first. And so you look at it, it’s a wall of words and we call that deterrence. You are just deterred from reading it at all. And that’s like, I think that everyone should relate to. You open something, even a text message like, I can’t deal with that right now. Or you go to a webpage and it’s a long wall of words. The second and third are basically like, okay, so do I engage with it now or later?

And whenever I engage with it, how deeply do I read it? And I assume we actually have lots of evidence. What happens is the more difficult it is to read, the more you just sort of dart around, bounce around, see if you get the gist and eventually give up and move on. So those are the one through three. And the fourth one is deciding whether to respond or not, if you’re asking for some kind of response. And the easier the response, the more likely people are to do it. Just like the shorter the message, someone’s more likely to read that than a long one. If it looks like it’s gonna require a lot of research or it’s unclear what the question is, all these things make it just less likely people will deal with it at all, but definitely less likely they’ll deal with it now.

Brett McKay: Okay. So let’s talk about what we can do as writers to increase the odds that someone will want to engage with whatever we’re throwing at them. They’ll want to maybe act on it faster, sooner rather than later. And, you know, engage with all of it and as well as, you know, respond, get more of response so we can get stuff done. And you and your co-author lay out six principles that writers can use to make sure that their writing is effective. The first principle, and you just kind of referred to it just a minute ago, less is more. So how does more often get in the way of your readers engaging with your text?

Todd Rogers: This is my favorite. I don’t wanna speak for Jessica on this. I love this. Less is more. You could probably go back to there’s a quote that every clever person who’s ever been alive has been credited with this quote, which is, I would’ve written you a shorter letter if I’d had more time. And what I love about that is it is worthy of apology. I have wronged you by giving you this longer than it needed to be text. And second, it takes more time to write less. Both of those are sort of central to this less is more idea. And the idea is, and we’ve run randomized experiments, lots of them, where the more sentences you add, the more ideas you add, just the longer it is, the less likely people are to read and understand and respond. Whether it’s soliciting a response, getting people to fill out a survey, getting people to… We worked with the, I don’t know if we named the party, but one of the big political parties, Democrat or Republican on a big fundraising email with 700,000 donors and arbitrarily deleted every other sentence.

So it didn’t even make sense anymore. So we cut it in half by making it incoherent and still increased donations. We’ve done lots of versions of this, but the idea is just you need to know there’s a trade off. The more you add, the less likely someone is to read, understand, and respond. And the optimal length in content is not nothing or one sentence. It’s just a trade off. You just need to know, the more you add, the less effective it’ll be. But you gotta make those trade-offs.

Brett McKay: Yeah. So you lay out some rules to apply this less is more. First one, use fewer words. And I mean, if you went to college or even high school, they taught, you know, this whole elements of style, just eliminate, and that was one of the rules. Eliminate needless words. You know, have everyone seen these wordy phrases for the reason that instead of saying that, just say, because you know.

Todd Rogers: Right. In order to.

Brett McKay: Yeah.

Todd Rogers: Just say to.

Brett McKay: Just to. Whether or not, well, just weather.

Todd Rogers: Yeah, exactly.

Brett McKay: Personal opinion. Well, there’s only one type of opinion. I mean, so just things like that can go a long way. But I love this idea. Rule number two, to include fewer ideas. So we’re talking about, maybe it’s a memo or an email you’re trying to write. Oftentimes you wanna try to cram as many things as you can in that piece of text. But what your research shows is like the fewer, the better. The fewer ideas you have in your email or memo, the more likely people are going to read what you wrote.

Todd Rogers: Yeah. And that’s hard. I mean, it’s hard for people because it requires judgment and prioritizing. Like what’s the most important thing I’m saying here? And it would be good for you to know this, but it’s not necessary. And so there’s trade offs all the way, like there are workarounds, like if it’s a webpage, you could have a link to the more content, or if it’s an email, you could have it below the sign off or as an attachment. Or if it’s a report, it could be an appendix. You can keep the detail, but you just need the core thing to be the core thing. And what we have is all this experimental evidence showing that when you dilute it with more content, you just are less likely to achieve your goal. And it just requires judgements and trade-offs the whole way.

Brett McKay: Yeah. You gave this great example. This was like a text. Could be a text to get together with some friends for dinner. The original one is, I’m looking forward to our 6:30 dinner tonight. Let’s eat at Tina’s Italian restaurant at 651 Ocean Drive. Their breadsticks are awesome. I haven’t had their lasagna, but I’m ready. It’s supposed to be tasty. Let’s meet at my place 15 minutes early and we’ll walk from there. Sam and Joy, are gonna join us for dinner too. Man, if I got that text, I’d be like, oh, geez, I’m gonna just have to look at this later. But you know, you could have just said, Hey, we’re having dinner, it’s at 6:15, meet at my place. That’s all you needed.

Todd Rogers: Right. And there is information in the rest of it. It’s just you got… And if you’re aware that there’s a trade off, then you have to treat it differently. Since writing the book, I’ve worked with a guy who’s in the CIA on who writes intelligence assessments in this group, in this intelligence group, and there’s 70 pages and that’s the norm. And he was like, well, how do I write less? Because if I write 35 pages, they’re gonna think I didn’t do my job. ‘Cause the norm is the norm. The norm is 70 pages. And so I actually love that because the answer is you can’t. Like, you have to write for your audience and what your audience expects, it has to look like what your audience expects. I mean, Jessica and I wrote a 207 page book where one of the principles is write less. The book, expect the book to look like a book. And so you have an audience that has norms and expectations, it has to look like what they expect, but then within those constraints, the easier you make it for them, the better. And so with a text message, I don’t think anyone cares whether you are interested in the breadsticks or not. They’re just like, when do I show up and who’s gonna be there?

Brett McKay: Right. Okay. Let’s move on to the second principle. Make reading easy. How do we typically make reading more difficult for our audience?

Todd Rogers: We write in grammatically correct, complicated ways. And so whether it is a long sentence or using unfamiliar, uncommon words, or writing in a like grammatically complicated way, it just makes it more cognitively taxing. So like a different way of thinking about all this in length and also writing style is just how do you make it less cognitively effortful? The easier it is, the more likely people will be to do it. So even if they’re gonna work their way through it, it’s just unkind to write in a way that taxes them and burdens them. We ran one experiment with Vice President Harris when she was the Attorney General of California, where, and I mean, I don’t know, the listeners are not, I hope no one is writing like this, but the California State Legislature required that schools send families letters when their kids are late or absent. And it starts with California Education Code, section 48260 provides that a pupil, child, subject to compulsory, I mean, it’s not even written for humans, and it’s like being sent to hundreds of thousands of families so the idea is we just add a round of editing where we just ask how do I make it just easier to pull the key info out? Even if we are correct, complete, and grammatically accurate, we just make it easier.

Brett McKay: Yeah, so you apply some rules. Use shorten common words, so there’s that whole quote. I think it was Mark Twain. Don’t use a $5 word when a 50-cent word will do. So instead of saying acquiesce, you can just say agree. You know, you don’t have to get fancy. You can save the $50 words for your New Yorker article you’re writing for yourself.

Todd Rogers: Yeah, for yourself, exactly.

Brett McKay: Yeah, rule two, just use straightforward sentences. So this is, you’re not gonna do clauses and using semicolons and et cetera. Like, just really straightforward. Like, you can just glance at it, you know exactly what it says. Yeah, and then rule three, write shorter sentences. So, you know, just gotta edit, edit, edit, edit until you can get it down. You start writing like Hemingway, basically.

Todd Rogers: Yeah, that’s the idea, but no simpler than it needs to be. Right, like as simple as it can be, but no simpler.

Brett McKay: Yeah, so you give an example of a hard to read complex sentence and then editing it so it’s easier to read. Here’s the hard to read version. Often crafted from insidiously complicated language designed to abstract contentious details, ballot measures are propagated as a tool of direct democracy in 24 states in Washington, DC. So yeah, grammatically correct, but that was hard to read. Here’s the edited version. Ballot measures are used as a tool of direct democracy in 24 states and Washington, DC. They’re often written with deceptively complex language designed to hide controversial details. So yeah, that was a lot easier to read. We’re gonna take a quick break for a word from our sponsors. And now back to the show. Okay, second principle again, make reading easy. So we’re just gonna use fewer words, write shorter sentences and make sure your sentences aren’t hard to read with those parentheticals and semicolons and references back to things you said in a previous clause. Third principle is design for easy navigation.

Now, I’m sure a lot of people are listening to this. They probably learned in high school or in college, you know, some ideas or some rules about being concise with your writing. We’ve all probably read elements of style and that’s one of the rules. But I don’t remember being taught this. Well, actually I was taught this in law school, but I wasn’t taught this in undergrad or high school is thinking about the design of your writing so that it’s easy to read. So what does that look like? How can we lay out our writing so that it’s easier to navigate?

Todd Rogers: Yeah, I like this one. This is, I like all of them equally, but I like this and less is more the most. But the idea is it’s not even about writing, but realizing that people are gonna look at it and decide, do I read or not? Remember that stage of deterrence. Or once they’re reading, they’re just gonna dart around and see if they can get something out of it before they give up. And one metaphor or at least framework we use for thinking about it is that people may allocate like a fixed budget of time to reading your thing. And so then the question is just how do you make it easier for them to get what you want them to get out of it in that budget? And so that could be like adding headings. So it’s easy to know the structure. And when we actually do eye tracking, you see people jump around and read the headings first when they’re moving fast. Sometimes they just go first line, second line, but that’s when they’re anticipating reading the whole thing. But often they’ll just dart around and figure out what’s in here.

And we’ve actually run experiments where when you add headings in newsletters, you double the likelihood that people will read past the second paragraph and use anything in it past the second paragraph. The other one that people really like, and I really like, and I don’t know if you’re a veteran or how many of your listeners are veterans, but I work with a lot of active duty people in different branches of the military. One thing that they have in the US, started in the US Army and it spread across the militaries around the world is a thing called BLUF, bottom line up front, B-L-U-F, BLUF, bottom line up front. And it is a rule in the US Army, a rule that anything written to anybody, the first line has to be the bottom line. So there’s no long introduction, an enlisted person writing to a general, bottom line is the first line. And it makes it so much easier for readers and writers to know where’s the key info, where do I put the key info, where do I find the key info? But it especially helps people who are lower status, like an enlisted person writing to a general might have to say in the absence of that rule, like we ran into each other in Kandahar, you may not remember me, we chatted in the mess, I went to rival high school, we laughed about how the Philadelphia Eagles are gonna win the SuperBowl this year.

But I wanna ask you for a meeting. And so instead of the whole throat clearing, which would decrease the likelihood we get read at all, now they have this rule that doesn’t work everywhere, but having this rule in that environment and with that organization makes it just easier for everybody. And so another way to design for navigation is to have this kind of structure. So it’s easy to pull the key info out and jump around, but also when possible, make the bottom line super easy to pull out.

Brett McKay: Okay, so yeah, when you write an email, for example, just right at the very top, don’t you have to do the throat clearing stuff, just like here’s what this email is about.

Todd Rogers: Maybe, but it doesn’t work every, like it just depends on the expectations and norms, ’cause that can come off as too aggressive. I don’t do that. I still have a hope you’re well or good talking to you the other day. And I usually add that back. Like I’ll write my like all business part and then I’ll add some humanity to it because I don’t wanna come off as too aggressive. And so, but like within organizations, when we talk like the next step that Jessica and I are thinking and working on is like, so okay, so you’ve become more effective as a communicator. How do we get your team to be more effective? And it starts with just being intentional and explicit. Let’s just have a conversation. How do we write so we can all be on the same page instead of just letting these norms evolve without intention or guidance? Let’s be intentional about it. How do we write? Like the US Army decided BLUF so we can all be on the same page.

Brett McKay: Okay, I really like using headings. Like that’s something I learned in law school. When you write a memo, you break things up in headings so that the partner that you wrote the memo for can just glance at it and get to the information they might be particularly interested in. Another thing for easy navigation, add bullet points. Like using bullet points can help out a lot, especially if you’ve got more than two ideas or two requests in your communication.

Todd Rogers: Yeah, there’s a subtle one on the bullet points too where, which I think you were pointing to, is that if the bullet is kind of long, a skimmer still has to read the bullet to figure out what it’s about. And so one of the things that we have found is putting a title to the bullet, which may seem counter to fewer words. We’re just saying add a three-word title, which is extra words, makes it easier for a skimmer to know whether they should bother engaging with this bullet or whether they are free to move on. And so it’s a subtle thing, but the goal is just making it as easy for your reader to move on and get the key info that you want them to get. And then when we start talking about design, you can see that you want it to be aesthetically good-looking and consistent. And so you want the headings and titles to always look the same and things like that.

Brett McKay: Yeah, another rule you can apply for easy navigation, order your ideas by priority. That’s kind of that BLUF thing, maybe. But if you have more than one idea, like put the stuff that you care about the most right at the top, because the person’s gonna read that far and then they’re gonna start jumping around a lot after that point.

Todd Rogers: Yeah, yeah, exactly. And if they are gonna jump around, you wanna make it easy for them to jump around, which is why, like you said, you like to space it out with bullets or things, just making it visually easier.

Brett McKay: And then another rule, consider using visuals. Like don’t be afraid to put pictures in your communication. If that picture or visual can convey the message, what you’re trying to convey more efficiently.

Todd Rogers: Yeah, a colleague of mine and friend and mentor, Nancy Gibbs used to be the editor of Time Magazine. And I was really surprised to hear her say that a common feedback she would give to her reporters was does this have to be words? And I like, ’cause she’s a word person. And she said that that was a common challenge for writers, is like, is there an easier way to show this? Like, can it be a diagram instead of a full paragraph or two?

Brett McKay: And so the thing about designing for easy navigation, that takes time on your part as the writer. So it’s easy just to just crank out just a big block of text, maybe put a few paragraphs here and there. But thinking about headings, thinking about what could be bolded, thinking about the BLUF, that’s gonna take a bit more time than just cranking that thing out in just one fell swoop. You have to really be thoughtful about this. But the payoff is in the end. You invest that time upfront, so you save yourself some time and frustration on the back end.

Todd Rogers: Right, and if it’s really important for you, you wanna make it easy for the reader because you will be more effective. It’s also this kindness that I also think it’s kind of a subtle implication of all of it, is that it’s just nicer to your reader to make it easy in that way.

Brett McKay: All right, so the fourth principle is use enough formatting but no more. So I think one thing people do to help ensure that certain ideas stand out, they’ll use things like bold or underlines or all caps in a text message. How do people mess up formatting though when they’re trying to get their points across to the reader?

Todd Rogers: This has been the bigger surprise of writing this book for me. The biggest surprise has been people being really excited because they say, this has been a fight my entire career. And I have been saying, we need to write in a way that makes it easier. And people are like, this is just your taste and just your preference and has been dismissed. And now we bring to it all these randomized experiments and a lot of evidence from different ways of research. And it’s now actually a question of like scientific effectiveness. The other surprise has been when people email me, one, there’s a lot of anxiety I think that I’m gonna be judgmental and anyone who’s gonna email me, you do not have to worry. It turns out writing, reading and communicating are all hard. But the second thing is when I started saying use enough highlighting, but no more, it leads to people using different font colors, underline, bold, highlight, italics, all in the same thing. It was only eight sentences and there are six different kinds of stylistic formatting variants in the message. And the irony is that that actually is worse than nothing because it makes it harder for the reader to figure out what you think as the writer is the most important thing. Because if you only format, let’s say you bold one sentence, it is unambiguous to the reader. The writer thinks this is really important.

But if you do lots of different things, the six of the eight sentences, I have no idea as a reader what you think is most important and what any of the formatting even means. So use enough formatting. In surveys and experiments, we’ve seen that people jump to bold, underline and highlighted text. They jump to that and they think the writer is saying to them this is the most important content, get this. So it’s incredibly effective. It also licenses readers to not read anything else because they’ve gotten the key info and everyone’s goal is to move on. So you’ve got to use it carefully because it gets people to read that and also crowds out reading anything else. But then we use lots of kinds of formatting. It just confuses readers about what any of it means.

Brett McKay: Okay, so bolding, underlining, highlighting, it’s effective in getting the reader to think here’s what the writer thinks is important and to put their focus on that if that’s what you wanna do. And you see that a lot in online writing. Any formatting things that you see in online writing that aren’t effective?

Todd Rogers: I don’t like how links all get font color change and underlined because you actually, there is eye tracking research showing that people jump to that. And often the link is not the key info. The link is just the link. And so there’s this tension, there’s this norm. Everyone knows that’s what a link is, but it also kind of undermines the speed of consuming whatever we’re writing for people. And so actually the trade-off for me on that is like we wanna minimize the number of words that are linked if you can while still accurately describing whatever the link is. That’s sort of a small point, but one that aesthetically I don’t think we have a good solution to yet.

Brett McKay: All right, so use formatting, but don’t go crazy with it. You don’t have to use all the formatting options. Just pick one or two and then stick with that. And again, it’s gonna, the formatting use is gonna vary by context. Maybe in your organization you have a rule or a norm that you use in regards to formatting in order to show that this is important. So just follow that. The fifth principle is tell readers why they should care. But this is all about making sure that the reader actually engages with your content. So what can we do to show the reader like you should care about this and engage with this more than just a cursory glance?

Todd Rogers: Yeah, the way we thought about this is the obvious way to get a reader to read something is to write about something they care about. But we take it as given. The writer has the thing they wanna write about and the thing they’re trying to communicate. And it doesn’t really matter from the writer’s objectives whether this is the most interesting thing in the world for the reader, right? So we take as a given, you have your goal, your goal as a writer. Within that set of ideas or content, all we’re saying is you may as well emphasize the part of the things you’re going to say that they may value the most. So we report this experiment with Rock the Vote, which is like a voter registration organization that tries to target young people. And they were sending an email out to potential volunteers saying, will you volunteer to work at concerts to register concert goers to vote? And in one condition, the subject line was volunteer with Rock the Vote. And in the other condition, it was attend concerts for free. Maybe it was like volunteer and attend concerts for free. And so the subject line there is like drawing attention. The content is the same, exactly the same. You’re gonna volunteer at a concert and you’re gonna register voters. But we may as well emphasize the thing that people will value out of that set.

And so they ended up four X more effective, four times more effective, by just making the subject line focus within the set of ideas they’re gonna say in the message on the thing they think the recipient might care the most about. So that principle is just emphasize what the reader might care about within the bounds of what you’re already gonna say. We’re not saying you need to say something different. We’re just saying you may as well focus on the thing they may care about.

Brett McKay: Yeah, and then put that up front. Like don’t bury the lead on that. Don’t wait till the very end. Say, hey, this is why, you know, start off this like in the subject line. Here’s why you should care about this. And then put all the other information after that. And then another rule that you have for that for tell the readers why they should care is emphasize which readers should care. This is important ’cause sometimes you send out a message and it’s only going to a certain segment of the population. And if you make it too broad, you might end up causing the group of people you’re trying to communicate to just to ignore it completely.

Todd Rogers: Yeah, at minimum, it’s kind to your reader to let them loose. This is not for you, you’re free to go. But also in the intermediate term, as you communicate more, if you let people go when it’s not relevant to them, they’re gonna be more likely to attend when it is relevant to them.

Brett McKay: Yeah, you gave the example, like let’s say you have a grocery store and there’s been a recall on a product for safety. You know, the grocery store might put up a sign, notice important product safety recall information. Well, you know, if someone sees that and it’s like, well, I don’t know, maybe is it the product that I bought? I don’t, who knows, maybe I’ll just ignore this. And then you said, if you wanna have a reader’s perspective, the top line of that notice should say, if you bought soup XYZ in June, it has been recalled. And so like, oh, immediately the person seeing that, it’s like, well, did I buy that soup in June or not? And then they can make that decision whether they need to engage with it or not.

Todd Rogers: Right, well, Brett, also, I applaud you for getting, these are deep tracks in the book. You read it closely.

Brett McKay: I read the book.

Todd Rogers: Nice, yeah.

Brett McKay: And you make it easy to read. So it made me wanna keep reading it.

Todd Rogers: Yeah, we wrote it so it was skimmable. For anyone listening, it is easy to skim. But if you want the details on any topic, you can dive deep in it.

Brett McKay: You can dive deep. So the sixth principle is make responding easy. Not all communications require response, but a lot of the communications that we put out there to get stuff done, they require responses. So what can we do to make responding easier?

Todd Rogers: I know that there are other, that your listeners and you follow other behavioral scientists, like behavioral economists or social psychologists who work on behavior change, which is basically what my research has been on for the last 25 years. And all of that is this, which is the takeaway is, if you want someone to do something, we should make it easy for them. And so whether that means reducing the number of steps required to take the action or providing checklists or pre-populating forms, or even like, here’s something completely basic that we’ve all had, which is let’s schedule a meeting. There are four of us on an email thread. These six times work for me, which worked for you? And then if you reply in a paragraph, well, I can do the first time, but I’d have to move a couple meetings. The second time’s better for me, but the third doesn’t work. And the fourth could work if nothing else works. Like the amount of effort required to decipher which of the times you’re proposing actually work is, you know, you’re adding 35, 40 seconds to the next person to figure it out. If we actually wanted everyone to respond, you say, of those times…

These two work for me.

Brett McKay: Period.

Todd Rogers: Nobody cares whether it means you have to move a meeting. So the idea is if it’s important to you that someone get back to you you wanna make it as easy as possible. If it’s important for us we wanna make it easy for them. I’ll often ask students imagine you have a task that will take five minutes and a task that will take 30 seconds. Both of them are on your to-do list and you plan to do both eventually. Which are you gonna do first. Almost everybody’s gonna do the 30-second task first. And so the idea is you just wanna make it easy. As easy as possible.

Brett McKay: Right. And so that means maybe you have to do some decision structuring for the person. Like here I need you to make this decision. Just this one decision. And then after that you can maybe follow up if you need to make other decisions but just pick one thing you want them to respond to.

Todd Rogers: Yeah. In the less is more there’s fewer requests. If you ask someone to do two things you are less likely to get them to do any one of them than if you ask them to do just one. The idea is we’ve got to prioritize. We have our goals and we need to write in a way that makes it easy for the reader to help us achieve our goals. And that means simplifying the request. Like you’re saying if I asked you what do you think versus I’m going to submit this. Agree or disagree? Yes or no? Do you sign off? They end up being… It’s much easier to say yes agree submit than an open-ended what do I think? And so it’s just my prediction and some of the evidence is… All the evidence is consistent with. People are more likely to respond and more likely to respond sooner when it’s a yes no question than open-ended.

Brett McKay: Yeah. Another rule you have in this make responding easy is organizing key information that’s needed to take action. So let’s say you make a request for something at your work or something but then in order for the reader to answer that they have to start trolling through all this information or kind of doing this scavenger hunt to even start putting together a response. Well, if that’s the case they’re gonna drag their feet on that or they’re gonna take a long time. Instead if there’s an answer you need right away provide the reader with as much information as possible that they need in that communication so they can give you the response you need. Okay. So those are the six principles and I think if people had those in mind as they wrote they’d get a lot more done with their writing. At the end of the book beyond these six principles you talk about some other ideas that you’ve seen in your research and your own personal experience when it comes to communicating and getting people to respond to your writing and getting stuff done with writing. And one topic you talk about is frequency of communicating.

This is something I struggle with when it comes to communication in my business or in organizations that I belong to ’cause I worry about communicating too much. ‘Cause I don’t wanna bug people. But something I’ve noticed is that when I do communicate more I get more responses. I get more people showing up for things or doing things. So what’s the research say? How often should I hit people with the same information so that it’s effective?

Todd Rogers: There is not a single answer for this just like there’s not a single stable answer for when should you communicate because the equilibrium changes. If the answer is Thursday at 3:00 PM everyone is gonna communicate on Thursday at 3:00 PM making yours less effective and then the equilibrium moves around it’s an unstable equilibrium. Similarly for frequency of communication I think there isn’t a good answer but my first pass at it is if you think that your reader wants your communication and values it like your newsletter? If you think that they really want it then you wanna be consistent so they know when to expect it and have it look the same so they can recognize quickly what it is. In the intermediate term if we communicate all the time we will decrease people’s likelihood that they associate us with something they should read and they will start to view us as a pest and they will unsubscribe. And so I know there are a lot of organizations that have big lists. The balance that we’re always talking about is you can increase donation for example by sending more messages you also increase unsubscribes and so what’s the two, three-year horizon consequence is you may end up being worse off for having gotten more donations in this week by sending more messages.

But in the intermediate horizon you’re worse off. There isn’t a great answer. I don’t know. Do you have thoughts on this? It sounds like you wrestle with it.

Brett McKay: I wrestle with it. No. So it sounds like it’s the killing the goose that lays the golden egg problem.

Todd Rogers: Right. Yeah exactly.

Brett McKay: Right. You can extract a lot of value by doing a lot of frequency in the short term but in the long term you end up killing the thing that provides you value. So when it comes to let’s say you belong to I don’t know a sports league or I don’t know a church congregation there’s an event coming up. That’s the thing where I’ve found that more frequent communication helps up to a point. You can’t just do one and expect to get a response ’cause people might just miss that first email or they read it and then they forgot about it and then the event comes up two weeks later and they’re like I didn’t know about it. It’s like well I sent you that email. So I think something like that I need one email maybe two weeks out and then maybe a week out you send a reminder and then two days before you send a final reminder that could work. I mean, if you did a reminder every single day people are just gonna tune you out.

Todd Rogers: I think there’s consistency in that too Brett where it’s like I’m on a board where they send materials out a week in advance and then they send them the night before again. And so I know two weeks in advance I don’t need to deal with this ’cause I know it’s coming back right before. And so if they stopped doing that and they just did it occasionally I think I and the other members would all be less prepared because we’ve come to expect that oh this is just the forewarning before the real one. I think consistency is probably key there. People start to associate you with that pattern.

Brett McKay: Yeah. But I also think yeah frequency can be a tool to help a harried reader because people are just getting inundated with stuff and they’re gonna miss things. This can even happen with your friends with text messages, right? You send a friend a text and you don’t hear back from them and you think oh man they hate me. They don’t like me anymore. So now they… If their text inbox is anything like yours it’s just getting inundated with two-factor authentications, reminders about their kid’s doctor’s appointment. So maybe the friendly thing to do would be, Hey, follow up two days later if they haven’t gotten back to you because they needed that. So I think with frequency yeah there’s a balance but I think maybe don’t be afraid of nudging more than you think ’cause you’re probably not actually nudging ’cause the people probably didn’t see your initial message anyways.

Todd Rogers: Yeah, I like that. I also think when you talk about a friend or a coworker with whom you communicate a lot I do think the answer, and this is probably the answer for most questions is to communicate better and to actually have a discussion about it. And this is something that we stumbled into. Well, there isn’t a universal rule for this. Some people will view you pinging them again as like yeah man I read it. I got you. Stop harassing me. Others will be like Thank you. And so a different way if this is someone you communicate with a lot is to just ask. Would it be useful if I send follow-ups or not? I actually have all sorts of people that they have incredibly varied preferences and for people I communicate with a lot. I actually have started to learn what they are because I ask.

Brett McKay: I’m curious are there any AI tools that you’re seeing out there that are helping writers write more effectively?

Todd Rogers: Are you setting me up for… Did I show you mine?

Brett McKay: No.

Todd Rogers: Or is that…

Brett McKay: No.

Todd Rogers: So early on we trained GPT-4 or GPT-3.5 and then now GPT-4o the OpenAI’s latest LLM on the… With your listeners in the show notes I hope we’ll share the checklist. There’s a one-page checklist for how to write for busy readers and we trained the large language model on these principles and then we fed it what’s called Few-Shot Learning just three pre-post examples of emails an original and an edited. Original edited original edited. It’s incredible at editing emails so that they are skimmable and it now has hundreds of thousands of uses and I get emails all the time from people saying that they put any important message through it to just get suggestions. So it’s on our website. I’ll share it with you. It’s writingforbusyreaders.com but it’s very cool. The large language models you could think of as they learn inductively they consume all the way we’ve ever written and then they infer rules and predictions.

This is much more deductive top down. We’re like look there are these six principles. We should edit through the lens of these principles because this is actually what the science suggests people are more likely to read and respond to and it learns those and then it can revise in accordance with and we shouldn’t use words like in accordance. We shouldn’t use… It writes in ways that are consistent with that. So writingforbusyreaders.com but I love it. We’re trying to get it internalized by the other big large language model especially the ones who work in email clients.

Brett McKay: Well, Todd this has been a great conversation. Where can people go to learn more about the book? So I guess that one website?

Todd Rogers: Writingforbusyreaders.com writingforbusyreaders.com and the Too long didn’t read of this whole thing. If you made it to the end and you don’t know the big takeaway. The big takeaway is we should add a round of editing to everything we write where we ask ourselves how do I make it easier for the reader? How do I make it easier for the reader? Because the easier it is for the reader the more effective we are at achieving our goals and it’s just kinder.

Brett McKay: I love it. Well Todd Rogers thanks for your time. It’s been a pleasure.

Todd Rogers: Thanks Brett.

Brett McKay: My guest today’s Todd Rogers. He’s the author of the book Writing for Busy Readers. It’s available on amazon.com and bookstores everywhere. You can find more information about the book at the website writingforbusyreaders.com. Also check out our show notes at aom.is/busyreaders where you can find links to resources and we delve deeper into this topic.

Well, that wraps up another edition of the AOM Podcast. Make sure to check out our website at artofmanliness.com where you can find our podcast archives as well as thousands of articles that we’ve written over the years about pretty much anything you’d think of. And if you haven’t done so already I’d appreciate it if you’d take one minute to give us a review on Apple Podcast or Spotify, it helps out a lot. And if you’ve done that already. Thank you. Please consider sharing the show with a friend or family member who you think would get something out of it. As always. Thank you for the continued support. Until next time this is Brett McKay reminding you to not only to listen to AOM Podcast but put what you’ve heard into action.

This article was originally published on The Art of Manliness.

Many people think becoming wealthy is all about having the right job, inheritance, or just lucky breaks. And those things can certainly give you a leg up. But according to my guest, the biggest key to building wealth is your mindset, as research shows that even high earners can stay broke forever if they’re trapped in poor thinking patterns, while others can build lasting wealth on modest incomes by developing the right mental approach.

Dr. Brad Klontz is a financial psychologist, wealth manager, and professor, and the co-author of Start Thinking Rich: 21 Harsh Truths to Take You from Broke to Financial Freedom. Today on the show, Brad explains the critical difference between being broke and being poor, how learned helplessness keeps people financially stuck, and practical ways to develop an agentic, wealth-building mindset. We also tackle thorny issues like the role of homeownership in building wealth and how to handle relationships that might be holding back your financial future.

Resources Related to the Podcast

• Brad‘s previous appearance on the AoM podcast: Episode #529 — The Money Scripts That Are Holding Back Your Financial Future
• AoM Podcast #321: How to Think About Money
• AoM Podcast #536: How to Achieve a “Rich Life” With Your Finances
• AoM Article: Taking Control of Your Life
• AoM Article: Avoiding Learned Helplessness
• AoM Article: A Young Man’s Guide to Understanding Retirement Accounts — IRAs
• Compound Interest Calculator 

Connect With Brad Klontz

• Start Thinking Rich website 
• Brad‘s website

Listen to the Podcast! (And don’t forget to leave us a review!)

Listen to the episode on a separate page.

Download this episode.

Subscribe to the podcast in the media player of your choice.

Read the Transcript

Brett McKay: Brett McKay here, and welcome to another edition of the Art of Manliness podcast. Many people think becoming wealthy is all about having the right job, inheritance, or just lucky breaks. And those things can certainly give you a leg up. But according to my guest, the biggest key to building wealth is your mindset, as research shows that even high earners can stay broke forever if they’re trapped in poor thinking patterns. While others can build lasting wealth on modest incomes by developing the right mental approach. Brad Klontz is a financial psychologist, wealth manager, and professor, and the co-author of Start Thinking Rich: 21 Harsh Truths to Take You From Broke to Financial Freedom. Today on the show, Brad explains the critical difference between being broke and being poor, how learned helplessness keeps people financially stuck, and practical ways to develop an eugenic, wealth-building mindset. We also tackle thorny issues like the role of home ownership in building wealth. And how to handle relationships that might be holding back your financial future. After the show’s over, check out our show notes at awim.is/thinkrich.

All right. Brad Klontz, welcome back to the show.

Brad Klontz: Excited to be here.

Brett McKay: So you are a psychologist who specializes in helping people with their money issues. And we had you on the podcast way back in 2019 to talk about this idea of money scripts. And that’s episode number 529 for those who wanna check that out. You got a new book out called Start Thinking Rich: 21 Harsh Truths to Take You From Broke to Financial Freedom. This is a book you co-authored. And you start off the book in the introduction talking about the difference between being poor and being broke. What’s the difference between the two and why is it important?

Brad Klontz: So our chapter titles are very insulting to poor people. And we felt like it was important to make a distinction here, ’cause I see it as two very different things. So broke is when you don’t have any money. I’ve been broke. A lot of us have been broke. Poor is a mindset. And the problem with a poor mindset, it’ll keep you broke forever. And there’s a lot of people who are broke. For example, are very high earners, but they’re living paycheck to paycheck, it doesn’t really matter how much money you’re bringing in. You’re never really gonna get ahead in terms of your net worth and lowering your financial stress if you have that poor mindset. And so a lot of my work has been trying to identify what is the mindset of wealth? What do the mindset that ultra wealthy people, what do they have? And then what is the mindset of middle class and lower? And what can I glean from the research on the ultra wealthy? And how they got there to teach as many people as possible. And really, it started as a personal mission coming from a low-income family myself, trying to figure out why do all these hardworking, intelligent, God-fearing people that I’m around, why are they… Why have we been broke for generations?

Brett McKay: Okay, so being broke is just not having money. But being poor, it’s about a mindset. And it sounds like you can be poor even though you have a lot of cash flow. You can still be poor.

Brad Klontz: Absolutely. I think that many, many Americans are in that position right now.

Brett McKay: And something I think we need to say from the start is that you and your co-author aren’t saying that there aren’t systemic problems that work to keep people poor and that there aren’t injustices that may need to be addressed. What this book is about is, okay, even if there’s changes you’d like to see, and even if those changes may come in the future, you’ve gotta operate and figure out how to get ahead in the current system. So like, what do you need to understand to do that?

Brad Klontz: Right. And so looking at it like the system is, well, first of all, it’s obviously unfair. I mean, I hope that’s obvious to everybody. Like if you grow up lower income, it’s very unfair. You are not getting access to things that people who have higher income, live in better neighborhoods, better school districts are getting. It’s just absolutely unfair. And certainly I applaud efforts to, improve the system, make it better, whatever. And that’s really, really important. See, I’m a clinical psychologist, though. And so when people come into my office, I am trying to help them succeed in a very unfair world. We even talk about capitalism in the book. It’s like, we’re not, economists in that sense. We’re not out to change a system or whatever. Is capitalism good? Is it bad? I mean, you can go ahead and decide that. The bottom line is, it’s a game, and that’s the game we’re in.

And if we lived actually in a communist country, this book would be a survival guide for how to thrive in a communist country. That’s essentially what we’d be writing. So we’re pragmatic about it. We’re not taking a side here. It’s really, really powerful to look at it like it’s a game. And so how are you feeling about the game you’re playing? So first of all, recognize that it’s a game. We talk about multiple ways to approach, making money. You know, there’s the entrepreneur game. There’s the, corporate game. It’s like, just recognize that it’s a game. So if you’re not happy with the results you’re getting, you have to ask yourself, am I playing the right game? Maybe you need to shift up the games. And then also, do I know the rules? So if you want to grow your net worth, since that’s what we’re talking about here, find out how people are doing it and then go ahead and do what they’re doing.

Brett McKay: And as you mentioned earlier, you’re coming at this from the perspective of personal experience. Like you yourself grew up poor.

Brad Klontz: Yeah. Grew up low income. My parents divorced when I was two years old. And if you weren’t sort of low income before that happens, you’ll be afterwards. And so my mom was a part-time teacher and I grew up not having much money. And this was something that I faced all along my development and it really does suck.

Brett McKay: And your coauthor, he weaves his story in as well. His parents were immigrants and they were millionaires by the time they retired and they weren’t working like a Silicon Valley entrepreneur type thing. They were just doing workaday stuff that most people do. Like his dad started washing cars at a car dealership and then worked his way up to being the parts manager.

Brad Klontz: Yeah. Adrian’s is a fabulous story. His father immigrated from Mexico, had nothing, had to steal food in Mexico to even eat, experienced a level of poverty that I’ll never experience and Adrian certainly never experienced. And what I find fascinating about his family’s story and he really traces it to his grandma’s entrepreneurial nature and hustling and doing everything she could do to get her family in America. I sort of compare his family who his dad first generation and he became a millionaire and he was a radical saver. Right. So Adrian talks about the story, his dad and all the family pictures, his dad had a Toyota shirt on that was his work shirt. And in retrospect, he’s asking his dad, Hey, what’s going on? Why are you always wearing that shirt? And he’s like, well, I didn’t buy clothes for five years. That was his mindset. I’m gonna save every penny I possibly can. And I sort of compare his family to my family and no disrespect. I love my family. Some branches of my family, we’ve been in the United States since the Mayflower and both sets of my grandparents were living in trailer parks. And so they actually never were able to accumulate any money. And it’s just such a curious thing to examine. And we’ve really nailed it down to the mindset they had around money.

Brett McKay: So let’s talk about that mindset. What are the big differences between a poor mindset and a rich mindset?

Brad Klontz: Fairly simple and logical, but I’ll talk about the psychology behind it. So essentially, how do you become rich? Well, first of all, it’s really important to understand that most wealthy people in the United States are self-made. And this is a very empowering understanding. Like when I was growing up lower income, I thought the only way to get rich was to be born rich or you had to go to private school. I had all these myths about millionaires in the United States. And it’s really, really empowering to know that no, no, no, most of them are self-made, like upwards of 90%, in between 80 to 90%. So just understanding that they got it on their own, they didn’t inherit it. And then you have to ask yourself, well, what are they doing differently than people who aren’t able to climb the socioeconomic ladder? And there’s a few psychological elements. The financial elements are living below your means, saving a percentage of every dollar you make and investing it. Like this is probably the mindset that’s the most important. And if you have this mindset at an early age, you’ll be a millionaire, plain and simple.

You can work in fast food your entire life. I’ve actually done the numbers with a lot of young people over the years. The job actually doesn’t matter nearly as much as having this mindset. And so they’re looking to buy assets. They’re looking to invest. They’re not racking up credit card debt. They’re not buying stuff to try to impress other people, which is a real constant draw in our culture, especially if you’re on Instagram and social media, you’re always feeling less than. And they’re looking to invest for the long term. That’s the rich mindset. The poor mindset, conversely, people, they get money, they spend it. They’re buying labels instead of stocks. They’re trying to impress other people. They’re not investing at all. And so those are the like the behavioral patterns. But we’ve also found some really deep psychological beliefs that have a profound impact. And the one I that I think is the most important. And this is based on all the research in psychology related to success in education, success in relationships, financial success. And I have an 11-year-old and a seven-year-old, and this is the number one mindset that I’m trying to instill in them. And that is something called an internal locus of control. And so this is really the location in which you attribute control of the outcomes you’re getting in life. This is a rich mindset that if you have it, you will become unstoppable. And I would imagine you’d succeed in every area of your life.

Brett McKay: Okay, so if you don’t have an internal locus of control, you basically blame your external circumstances for your situation.

Brad Klontz: That’s exactly right. And so when something’s going bad in your life, you know, easy examples like when I walk in the door and my wife’s grouchy and she takes it out on me, it’s so tempting to just blame her for the fact that I’m not feeling understood. And does she really realize how hard I’m working? And an internal locus of control would say, so I wonder if there’s anything I can do to improve my relationship with my wife. It’s a powerful mindset shift because it’s so tempting to blame everybody else for your problems. And the problem with it is there’s a lot of people out there you can pin blame on. And a lot of these people are not very nice. And so you could get stuck in this never-ending cycle of every time something bad is happening in your life financially, you blame the stock market. You blame somebody at the bank loaned you money for a house you couldn’t afford. Why did they do that to me? And you can find people who are blameworthy, but that is gonna keep you stuck in a cycle of failure.

Brett McKay: And so having an internal or a strong sense of an internal locus of control, it’s all about developing your sense of agency that you’re able to act on the world and you’re not just acted upon.

Brad Klontz: Right. And that’s ultimately where this strength comes from. It’s not about belittling you or shaming you. It’s about actually getting quite excited that what’s happening in your life, you have an impact, you helped create it consciously or unconsciously. And if you can recognize that, that’s when you can make these shifts that are really, really important in terms of becoming wealthy.

Brett McKay: So related to this concept of an internal locus of control, it’s like the opposite of it. It’s something called learned helplessness. How does learned helplessness play into all this?

Brad Klontz: Yeah. So learned helplessness really does help explain why so many people are stuck in a poor mindset and can be there for generations and pass this poor mindset down to their kids. And really dates back to some horrific studies that psychologists did on dogs. And so what they would do is they would stick a dog in a cage and they would electrify the bottom of the cage and see what would happen. Well, you could probably imagine what would you do in that situation? The dogs try to escape. They’re yelping, they’re barking, they’re jumping up and down. And eventually they realize escape is impossible. And so they sort of shut down. And this is also an adaptive response. And they just lay down and they whimper. Okay. So they have learned that I cannot escape from this, and it’s entirely accurate. Now, the scary part about this, and I’ll say this too, if you grow up in poverty, if you grow up in an abusive home, this is a mindset you will learn.

It’s like, I can’t fight back. I can’t escape. I’m going to try to survive, and so I’m gonna get real small. I’m gonna stay in the corner. Escape is impossible. I have learned that I’m helpless. Now, this is the challenge. What they did with those dogs in the next experiment, they put them in a cage that had a barrier in the middle. Half the cage would get electrocuted, the other half, no electrocution. And then what they would notice is that they’d stick a dog in there who hadn’t been in the previous trial where they got traumatized and the dog would jump around and then find that, I jumped to the other side, there I’m safe, no more shock. But the dogs that were in that first condition who learned that escape is impossible, they wouldn’t even try. So literally all they had to do is hop over this barrier, no more pain, there’s escape. And you think about it metaphorically for us, there’s abundance, there’s the financial goals you want, there’s the happiness, it’s right there.

And as a psychologist working with people who are stuck in this learned helplessness, it’s so obvious to me that all they have to do is this, it’s right there. They don’t believe it. They don’t believe that it’s possible because they’ve been so beaten down earlier on in life where escape was indeed impossible. They developed this learned helplessness attitude. And so it’s so crippling. It’s so sad to see, but it makes sense how people end up there. And you’ll find that they will tell you all the reasons why they can’t get it, why it’s impossible for them. And it’s based in a real experience. Like these experiences they had were very, very real. What’s so fascinating and so should be inspiring is that there’s escape right there. They could do it. And if you have that learned helplessness mindset, you’ll hear things like, oh, nine out of 10 millionaires are self-made in the United States. And you’ll start to discount that. You’ll look for evidence to suggest that’s not true. And I get this on social media all the time. Self-made, you know. Somebody changed your diaper. So they’ll essentially redefine what the word self-made means to try to prove themselves right. And so that’s one of those instances of a poor mindset that just keeps people down.

Brett McKay: Well so how do you increase the size of your locus of control and overcome learned helplessness? I think this is like the base issue as a clinical psychologist that you’re dealing with. It’s like, what are the research-backed and then also experience-backed tactics that people can do to start increasing their sense of agency and decreasing the amount of learned helplessness.

Brad Klontz: Well, first of all, you have to be somewhat open-minded. So you have to want something better and you have to believe it’s possible to a degree, even if it’s like 1%. Do you have 1% agency over your life? I can work with that. We just need to get you to the 1%. I think you probably have like 99% ’cause there are certain things that are gonna happen that are outside of your control. But I’d love to talk to you about that ’cause maybe we can find some areas in which you do have control. But it’s just like opening the crack a little bit. And I think one of the things that helps the most. And it’s one of the reasons why in this book, I’m telling a lot about my personal story and Adrian’s telling a lot about his and he has such a incredible story. He’s most famous on social media for making $1.7 million in one year while living in a van, becoming a multimillionaire in his early 30s. What we’re trying to do there is tell stories because what we want you to do is find an example of somebody who came from a similar situation that you are in right now or that you came from and was able to find that success. Because I think that all you need to do is see somebody who is like you comes from an area you came from that you can relate to. And then all of a sudden the light bulb can switch on for you and be like, oh, you mean maybe I can do it.

Brett McKay: Okay. So it sounds like you got to have a little bit of hope, a little bit of faith in order to overcome these things.

Brad Klontz: I think so. And it’s one of the reasons why, I’m passionate about trying to spread that hope and healing around.

Brett McKay: Yeah. And then also just start off small with small things. Like Stephen Covey talks about in his book, The Seven Habits of Highly Effective People. He talks about the locus of control and he talks about just doing small things to increase your locus of control. So maybe you can’t become a millionaire in a year, but like, what can you do now within the range of possibilities that are in front of you? What are you able to do? And then do those things. And as you do those things, your sense of agency increases. So you can start doing bigger and bigger things.

Brad Klontz: I love it, Brad. And so one of the things we really encourage people to do is save and invest a dollar today. And, ideally I try, I shot for like 30% of my income that I saved and invested. And by the way, I did it immediately when I started making money. So I felt like I was rich, I was making like 25,000 a year. I was like, oh my gosh, I’m making so much money. Well, Luckily, I had had this mindset by then. I was in school forever, so I was in my late 20s. And I had read books about it. I’m like, okay, so I got to do this if I wanna become wealthy. And so that’s immediately what I did. And to tell people like, oh, you gotta save 30% of your income. And Adrian saved 95% of his income that year living in a van.

That’s like an impossible dream for most people. Find, catch it just before you get your first job, it’s very, very easy. But many of us have a life. And we have kids, and we have a mortgage, and we have car payments, whatever. So do 1%, like commit to investing 1%. And we have chapters in the book too, that sort of challenged this notion that you can’t afford to invest. I hope you had a chuckle with some of those. They’re very real examples with good math behind them, but you can’t afford to invest. Like I just wanna sort of push back a little bit on this, but just do 1% ’cause what it takes for you to invest 1% of your income, you gotta go open an account. You gotta look into, oh, should it be a Roth IRA? You got to figure out what I’m gonna invest in it. By the time you do that groundwork, that’s essentially most of the work it takes to become wealthy. So start with 1%.

Brett McKay: We’re gonna take a quick break for a word from our sponsors. And now back to the show. I wanna get into more specific tactics, personal finance tactics. So you have a chapter about investing early and investing, even if it’s just a dollar or just a percent of your income. And there’s some personal finance advice out there. I’m sure you see a lot of it ’cause you’re like in that. Personal finance TikTok Instagram world where there’s a whole bunch of talking heads giving out different bits of advice. And there’s this idea that, well, you shouldn’t invest until you have paid off your debt. But you say, no, you don’t need to wait until you pay off your debt to start investing.

Brad Klontz: Yeah, like as a psychologist, I think it’s a terrible idea for several reasons. First of all, I get it on the math side. You know, if you’ve got like a credit card that’s got 35% interest, here I am saying, well, you need to start investing. And you’re like, whoa, I’m gonna be shooting for an 8 or 10% return and this, yeah, I understand. I get it, I get it. I just want you to start investing right now. Now let’s say that you can put 10% of your income towards paying off debt investing, whatever, make it 1% and do the 9% over there. But the problem is for a lot of Americans is you’re never gonna be out of debt ever. You know, what’s gonna happen is you’re gonna pay off your credit card debt, then you’re gonna pay off your student loan.

Now you got a mortgage for 30 years, then there’s another car payment, but then your kids go to school. I mean, the idea that once I pay off my debt, then I’ll start investing. You are gonna lose the most important thing in the wealth formula. And that is time. Time is the most important thing. You want to have money invested for as long as possible because that’s where that magic of compound interest really starts to snowball. And that’s where these small amounts you’re putting in each month become worth millions. It’s that time factor. So invest as early as you can, and if you’re not doing it now, start as soon as you can.

Brett McKay: Okay. So for someone who’s listening to this and they’re feeling overwhelmed because they got student loans, I mean, they got a mortgage, they got a car loan, and they’re like, I just don’t, I don’t have room for investing. So what would that look like? I know it’s gonna vary from person to person, but broad strokes, how do you balance paying off debt and doing investing at the same time?

Brad Klontz: Yeah, I say don’t make it too complicated. I love the idea of identifying like three financial goals, getting really excited about them, we did a study on this where we had people visualize those goals and we saw a 73% increase in savings after just doing it that for an hour. So people went from about 10% to over 17% because they were so excited about it. So whatever that is, whatever that goal is for you, maybe it’s financial freedom at a certain age, maybe it’s a house someday. Like get a real exciting, clear vision of it and then just decide how much you can right now. Like maybe you have a goal, you want to save 10% of your income towards this goal or whatever. You can only do 1%. You just commit to doing it and, learning what it takes to do because it’s really not all that complicated.

Brett McKay: And then you, also recommend when people do start investing, don’t complicate your investments. You don’t have to do the whole penny stock, Robinhood, AMC stuff. Like just get an index fund and pile your money in that so you don’t have to think about it.

Brad Klontz: That’s exactly right. And I, as I mentioned, grew up low income and that was a huge mistake I made when I had $100,000 in student loan debt and I saw a buddy of mine make $100,000 in one year trading stock and he was trading stocks on margin. This guy knew nothing about what he was doing. ’cause I even asked him, I said, why are you buying that stock? He’s like, I have no idea. Click. And I was like, it’s really that easy. And, I got appalled. The reason I make TikTok videos is because I got appalled because a few years ago I’m like, oh my gosh, day trading’s back. I saw it on TikTok. And so now I’m a psychologist, but I also own an asset management company. So I actually manage money like close to a billion dollars for ultra wealthy people.

So I actually know what wealthy people do because I do it for them. And what they don’t do is any of the stuff that you’re seeing people sell you on get rich quick ideas. Whether it’s I’m gonna be a trading crypto, I’m gonna be trading stocks, this new NFT. To me, I put it in the same bucket as lottery and it’s a get rich quick scheme. I fell for it Coming from a lower income environment. You’ll hear stories about people who made it so big on this coin or that coin. It’s so seductive. It’s a poor mindset. It’s a poor mindset. Even on like day trading, like 97% of day traders lose money, 3% make money, but only one of those people make more than minimum wage. Their studies show that the longer you do it, the worse you do.

Even the pros on Wall Street can’t consistently beat the market. And so what makes you think you can do it? Some of that’s random error, it’s just not how people get rich, but it is how people stay poor because they have this idea, I’m gonna make it quick and I get why, I get why you have it, man, I had it. You know, it’s like being poor sucks. And so you don’t know how people become wealthy. So that’s what you’re very tempted to do. And so to your point, and I can’t give financial advice because I don’t know what, everyone’s circumstance is, but I’ll tell you that a lot of personal financial experts suggest as, starting out look at a Roth IRA. So just investigate that. And then when it comes to investing research, something called a target date fund. And what you’ll notice is it has a few key factors in there that are really important.

It’s diversified. So instead of like buying one stock, you own thousands of stocks. Instead of buying one size of stock like a small company, a large company, you got all of them across the world. It’s very diversified. It adjusts as you get older. So it’ll become more conservative as you get older. The point is you open that up and then you forget about it. And then you focus on what wealthy people focus on. Self-made. Wealthy people don’t focus on trading stocks. They don’t do that. They outsource it to these fund companies or in a financial advisor as we’re describing right now. And what they do is they focus on making more money so that they can invest more money. And that’s how they get there faster.

Brett McKay: Okay, so it sounds like becoming wealthy is pretty boring.

Brad Klontz: It’s pretty boring. And I know it sounds terrible and I know that many people aren’t believing me right now. And I just, a big part of our book too here is we don’t want you to make the same mistake. Save yourself some time. The poor mindset towards investing too is like, I’m gonna take this thousand bucks and I’m gonna turn it into 20,000 bucks this year. There are so many sharks out there waiting for you to do that. And they’re just gonna make money off you. Nobody does that. Who’s wealthy, nobody. And people who do that don’t become wealthy.

Brett McKay: So you got a chapter with another provocative title, get rid of your poor friends if you want to get rich. When I read that, I was like, man, this is harsh. What do you mean by that?

Brad Klontz: It is harsh. And I wish I could blame Adrian. I wish he was here. I like to blame the most offensive chapters on him. But if you’ve read any self-development books, you have probably heard something like you’re the average of your five closest friends. Like this is very common knowledge and in psychology it makes sense. So we have spent 99% of our time on earth in hunter gatherer tribes of about 100 to 150 people. And we’re very closely connected. You know, we ate what they ate, we wore what they wore. We were, we did what they did. Okay. And so that’s the way we’re wired. And so if you are hanging around a bunch of people who have a poor mindset, now remember we’re talking about a poor mindset. We’re not talking about being broke because I know a lot of broke people and I spend five minutes with them and I’m like, oh, oh, this kid’s gonna be a multimillionaire, like slam dunk.

Like I could just tell they have a rich mindset. I also know people who make six figure incomes, multiple six figure incomes. And I’m like, oh, they’re gonna be broke forever. Because they have a poor mindset. They just spend the money as soon as they get it. And so what we’re talking about here is if you want to climb the socioeconomic ladder, you are gonna have to distance yourself from people who have a poor mindset. ’cause they’re gonna suck you right into it. They’re gonna suck you into the spending. They’re gonna suck you into the competition around who can have the fanciest watch, who can have the most expensive car? And that mindset does keep you broke. It’ll keep you broke forever. And so what you wanna do is find people, first of all, if you don’t want to lose all your friends, immediately, try to convince them to come with you on this journey.

Let’s start there. And you’ll find a lot of them sort of refusing. What you want to do is be looking for people who have this rich mindset who are bragging about. It’s so cool too. I’ve met some communities. There’s this whole thing called the FIRE community, which is stands for Financial Independence, retire early. And I just went to one of the meetups over here in Colorado. These, people and, they’re crazy. They’re having conversations that are very different. They’re like bragging about what percentage of their income they’re investing. They’re having competitions on who’s paying the least amount for the best coverage for their auto insurance. If you rolled up with a Tesla or an expensive car at one of these things, they would look at you like you’re an idiot. I mean, they would just like look down on you.

Because that is a tribe that is focused on getting financial independence. And so they’re using all the tools even to the degree, which I don’t connect with, right? But because it’s so extreme, but they want it so bad, they’re willing to do that. So the general idea here is if there’s a goal you want to achieve, you should surround yourself with people who are moving in that direction or who are even a step or two ahead of you because you are going to, subconsciously you’re gonna drift towards what your closest friends are doing.

Brett McKay: Yeah. And you talk about your friends of the poor mindset. You can often be like crabs in a bucket, right? You’re trying to get, trying to improve yourself, but then like, ah, I don’t like that. And they’re gonna try to bring you back down. Did you experience that when you’re trying to work your way up in the world?

Brad Klontz: I did. I did. And it’s easy to look at those crabs as being nefarious. You know, they’re not, they love you. This is really what it comes down to. It’s that tribal mindset. It’s like all of a sudden they see you and you’re packing up your stuff and you’re about to leave the tribe and they love you and they don’t wanna lose you. And so they will try to sabotage you. They’ll try to keep you back in the tribe because they’re afraid you’re gonna drift away and you’re not gonna be a part of their life. And so that’s the way I look at it. It’s not like they’re trying to tear you down because they’re trying to be mean. They don’t wanna lose you. And so I would hear things like, oh, it must be nice and that could be like, must be nice that you have this car must be nice that you have some retirement savings, must be nice that you’re able to take a vacation or you’re able to work less.

And I’ve spent a lot of time too trying to teach the people closest to me how to make more money. And one of the things I love about collaborating with Adrian is that’s his deal. Like he teaches people how to make money online. And, just, just as an example too, I got an 11-year-old who’s making five grand this month by doing one of these side hustles that Adrian talks about in his book, that’s true too. I’ll show you the receipts. So I tried and I will continue to try to support and model, but the bottom line is there’s pressure and you feel guilty. And what I’ve noticed over time, not just in my life but many other people’s lives, there tends to be a bit of a drift because people start to feel bad around each other. And if you think about it as an example, let’s say that all of a sudden you’ve got 50 times the net worth of your best friend.

It’s like, when is it gonna start to be awkward? You know, is it like you pay for their dinner every time? You’ll say, of course I do. Well what about your trips? You’re gonna pay for the first class ticket or like in that movie bridesmaids, you’re gonna make them go and coach while you’re up in first class. It creates all these awkward situations and people don’t really want to talk about it. They don’t know how to deal with it and then they sort of drift apart. And so I think people know that on a visceral level. And so I see people come into money and then blow it all because they actually don’t wanna leave their tribe because of all that deep emotional connection and stress that ensues as you start to leave your tribe. And so that’s why I think it’s really important to make connections in, this tribe that you want to join someday, whatever tribe that is, whatever your, goal is in life.

Brett McKay: And you, also talk about you don’t have to cut off your friends completely or even family members. Like you just have to learn like it’s an issue. As you try to make yourself better and try to make a better life for your immediate family and for yourself, there’s gonna be that awkwardness. You’re just gonna, you’re have to learn how to deal with it and you might have to just learn how to live with that tension and be okay with it without having to resolve it.

Brad Klontz: Yeah. And maybe you don’t talk to them about some of the things you’re doing, you know? Maybe you’re just not as open about your income. You know, I talk about Adrian a lot because we’re buddies, but like when I call Adrian and I tell him about my net worth went up this or I got this business. He’s like, yeah, that’s awesome. And, there are people I wouldn’t call because I’d feel guilty and they’d be like, yeah, that’s great. You know, you’re talking about this business deal that you just signed. You know, that’s three years of my income, you know? And so you just have to be careful because that’s a terrible feeling and subconsciously you’re actually gonna probably try to sabotage yourself subconsciously because you feel terrible about it.

Brett McKay: Another observation you make and you write about this in the book is that poor people, people with a poor mindset, they don’t ask for help. How have you seen this manifest itself in your work as a clinical psychologist?

Brad Klontz: Yeah, so this is something that, came out in one of the studies I did on the ultra wealthy comparing them to, it was actually upper middle class, the ultra wealthy, We were much more likely to have professional help like financial advisors and CPAs and attorneys. And I’ve noticed this as a self-inflicted glass ceiling that a lot of lower income middle class people have. I call it do it yourself itis. ’cause I come from a family of do it yourself itis. And by the way, this is a survival technique when you don’t have much money. So I had an, one of my aunts did everybody’s taxes in the entire family ’cause she had a semester of taxes and getting an associate’s degree and she did it all for us. My dad grew up on a farm. You know, something breaks, you fix it yourself. You can’t afford to pay for it.

And so the challenge here, ’cause I get that, the challenge is that it can keep you stuck because, for example, with your taxes you could pay CPA hundreds of dollars. And the first time I did this, by the way, I outsourced my taxes immediately I had a 10x return. Like these people found some stuff I could write off and found some ways to do this or that. And all of a sudden I’m like up $1000 So I paid them a couple hundred and I’m, and then I just, I’ve seen this pattern repeatedly. So don’t be afraid to ask for help because the do-it-yourself itis that lower income middle class mindset’s gonna sort of shame you for doing it. And so the intervention there is only poor people are afraid to ask for help. That’s a poor mindset.

Rich people are actually, they’re actually, it’s easier for them to humble themselves and saying, look, I don’t know. I don’t know how to do this investing stuff. That’s sort of a tribe thing too. Like when you’re, as you become wealthier, you’re much more comfortable outsourcing some of that. And part of it is your social circles because you know, an accountant you know attorneys like when I was growing up, I didn’t know any of those people. So for me there were foreign outsiders and we didn’t trust them at all. So it was really hard to make that leap to asking for help. And so just to understand, most rich people in the US are self made and most of them have no problem asking for help. And so when I discover that in my own research, I’m like, oh, I started to look around. Are there areas of my life I could ask for more help? I mean, if that’s the rich mindset, I want it.

Brett McKay: So you have a chapter on building wealth about home ownership. And this is like in the personal finance world, it’s a very contentious topic and you and your co-author have divergent views on home ownership when it comes to becoming wealthy. So what’s your take on the role home ownership can play in developing wealth?

Brad Klontz: Yeah, so Adrian has a bunch of spreadsheets in the appendix if you want to nerd out on if you paid rent and then you invested the difference, how you would be better off 20, 25 years from now. And it’s, his math is really compelling. It’s like, okay, fine. The thing that tripped me up though is that nine out of 10 millionaires own their own homes and there’s a large percentage of people’s net worth is accounted for by home ownership. And so when you look into it a little bit deeper, you realize, first of all, nobody’s gonna go invest the difference in terms of how most people do it. And it so it becomes a forced savings for you. And so you’re gonna pay your mortgage, right? You’re gonna pay your mortgage before you go blow it at fancy dinners or on a car you can’t afford, you’re gonna pay your mortgage. And so I think that’s the association and there are other benefits to owning a home. But I think that’s the reason why you see that close correlation between wealth and home ownership. It’s because it’s a four savings that you’re gonna pay every day. It’s sort of forces you to pay yourself first, which is one of the main concepts in becoming wealthy.

Brett McKay: I’m curious, like what would you say to someone who you know, is listening to this podcast? I know a lot of our audience might be in their 40s, 50s and they feel like they’re behind on their financial goal timeline. Any advice for them? Like they feel like, ah, it’s just too late for me. And maybe that’s a like a learned helplessness or a lack of locus of control. What would you say to these guys who are in their 40s, 50s, 60s, who are just like, ah, it’s too late for me.

Brad Klontz: Yeah, I get it. And first of all, it’s not too late. I see this a lot too. Like, people are like, oh I’m in my 70s, I don’t wanna invest money because I’m afraid of losing it. I’m like, dude, you’re gonna live 30 more years. Like we need to have some money invested that’s gonna grow. We’ll put some in a more conservative area. But this isn’t an all or nothing thing. Like if you’re 40, 50 or even 60 you got 10, 15 more years to make more money, you can dramatically increase the quality of life you’re gonna have in retirement. Now you, might have some social security coming in. You could have an extra 1000 or 2000 a month even starting in your 60s. And just think about what that would be like for you. And so people underestimate the power of compound interest even under shorter time periods, 10, 20, 30 years.

We use 25 years as an example in our book on where people, if they cut down expenditures, how they can have millions more 25 years from now. But when, I’ve actually run the numbers with people who are in those age categories, they’re sort of blown away by looking at how much they could have. And I would just encourage listeners, if you don’t believe me, just find online something called a compound interest calculator. Just Google it, there’s a bunch of them and start putting in the numbers. So what if I invested 10,000 a year? What if I invested 1000 a year? And you play around and you say like, well I’ll just give you this number because this is the average return the US stock market for a hundred plus years. Just throw in there like what if it was an eight or 10% return a year? How much money would I have? And that type of calculator. I think if you do it, you are going to instantly realize that you could do a lot even starting out later.

Brett McKay: Do you have any advice for dads who want to help instill a rich mindset in their kids?

Brad Klontz: Yes. So first of all, talk about money with them. The biggest mistake parents make is they just don’t talk about it. And they don’t talk about it because they’re stressed or they feel like they’re not, they hadn’t done exactly what they wanted to do. Who am I to teach my kids? Your kids are learning, they’re learning all the time. That’s the first thing. Second is, I would encourage them if you’re doing allowance or if you’re helping them make money, model it for them, but then also make them invest it. You know, one of the things I hear parents complain about, oh, I give my kid the money and they just blow it. It’s like, well of course they just blow it. That’s what everybody does. You gotta train them. So my kids know they get a dollar, they’re investing right off the top. So half of it isn’t even theirs.

Half of it is their financial freedom, their future. And my kids are so into it. They asked me to show them their balances every day, their investing, their every dollar they get, they wanna invest it. I mean they’re fired up about it. And so funny, my 11-year-old, my wife is like, well, why don’t you spend some of that, Ethan? And he is like, why you guys, I don’t need anything. You guys give me food. You give me clothes. He goes, I’m gonna retire when I’m 40. That’s my 11-year-old. He’s fired up about it. So you, have to model it for them and put strings on it. So whatever values you want to teach, if you want to teach them that, oh, it’s important to be charitable, a third year allowance goes to spending a third goes to investing, a third goes to charity. And help them sharing your values, help them decide what charity to contribute to, and maybe even go down and hand the check over in person. So think about money is a huge reinforcer. It’s a huge part of their lives. And it always will be. What values are you wanting to pass down to them? And then figure out how can I structure that to show it?

Brett McKay: Yeah. Starting a Roth IRA account, I did that for my kids and it’s amazing like how fired up they get about it because you try to explain to them compound interest in the abstract and it’s, they might not get it ’cause they don’t like, wow. Doesn’t make any sense. But then when they get that vanguard statement every month, they’re like, oh wow, this is crazy. Like how much money I’ve made in the stock market for the past three years.

Brad Klontz: Absolutely. And it’s the pictures, it’s the emotion talking about why this matters. You can have a profound impact on your kids, and they’re hungry. They want to be taught by you. So make sure you do it around money.

Brett McKay: Well, Brad, this has been a great conversation. Where can people go to learn more about the book in your work?

Brad Klontz: Yeah, so the book is called Start Thinking Rich. And so go to startthinkingrich.com/artofmanliness. And so for any listeners of yours who go there, we’ll have some special bonuses for them, but, you’ll see the book and some other tools we have to help people really start thinking Rich.

Brett McKay: Fantastic. Well, Brad Klontz, thanks for your time. It’s Been a pleasure.

Brad Klontz: Thanks For having me.

Brett McKay: My guest today was Brad Klontz. He’s the co-author of the book Start Thinking Rich. It’s available on Amazon.com and bookstores everywhere. You can find more information about his work at his website, bradklontz.com. Also check out our show notes at aom.is/thinkrich. Where you find links to resources where we delve deeper into this topic.

Well, that wraps up another edition of the AOM podcast. Make sure to check out our website at artofmanliness.com where you find our podcast archives as well as thousands of articles that we’ve written over the years about pretty much anything you think of. And if you haven’t done so already, I’d appreciate it if you’d take one minute to give us a review on Apple podcast or Spotify. It helps out a lot. And if you’ve done that already, thank you. Please consider sharing the show with a friend or a family member who you think would get something out of it. As always, thank you for the continued support, Until next time, this is Brett McKay reminding you to not only listen to AOM podcast but put what you’ve heard into action.

This article was originally published on The Art of Manliness.

Money can’t buy happiness. It sounds good as a bumper sticker platitude.

But the truth is, money can buy happiness. At least sometimes. In certain circumstances. If we view it and use it in the right ways.

Here to unpack the conditions under which money can buy happiness and facilitate our flourishing is Dr. Daniel Crosby, a psychologist and behavioral finance expert and the author of The Soul of Wealth: 50 Reflections on Money and Meaning. Today on the show, Daniel shares the minimum income level at which money buys happiness, at least in the sense of avoiding pain. We talk about how to purchase material things in a way that increases happiness, while avoiding materialism, and the value of using your money to buy health and freedom. And we discuss the importance of finding an overarching why that guides the way you allocate your money and doing a values audit to see if your purpose and spending habits are aligned.

Resources Related to the Podcast

• Daniel’s previous appearances on the AoM podcast:
  • Episode #222: The Laws of Wealth
  • Episode #511: Mastering the Psychology of Investing
• AoM Podcast #659: Do You Want to Be Rich or Wealthy? (And Why the Difference Matters)
• AoM Podcast #321: How to Think About Money
• “Experiences Won’t Make You Happier Than Possessions”
• Die with Zero by Bill Perkins

Connect With Daniel Crosby

• Daniel on X
• Daniel’s podcast, Standard Deviations
• Daniel on LinkedIn

Listen to the Podcast! (And don’t forget to leave us a review!)

Listen to the episode on a separate page.

Download this episode.

Subscribe to the podcast in the media player of your choice.

Read the Transcript

Brett McKay: Brett McKay here and welcome to another edition of the Art of Manliness podcast. Money can’t buy happiness. It sounds good as a bumper sticker platitude, but the truth is money can buy happiness, at least sometimes, in certain circumstances, if we view it and use it in the right ways. Here to unpack the conditions under which money can buy happiness and facilitate our flourishing is Dr. Daniel Crosby, a psychologist and behavioral finance expert and the author of The Soul of Wealth, 50 Reflections on Money and Meaning. Today in the show, Daniel shares the minimum income level at which money buys happiness, at least in the sense of avoiding pain. We talk about how to purchase material things in a way that increases happiness while avoiding materialism and the value of using your money to buy health and freedom. And we discuss the importance of finding an overarching why that guides the way you allocate your money and doing a values audit to see if your purpose and spending habits are aligned. After the show’s over, check out our show notes at aom.is/soulofwealth. All right, Daniel Crosby, welcome back to the show.

Dr. Daniel Crosby: Man, thanks for having me back.

Brett McKay: So you are a behavioral financial expert who’s written books about how to leverage our psychology so we can invest better. We’ve had you on the podcast to discuss those books. But your latest book, you get a bit more philosophical with your approach to money. You’re trying to figure out how our relationship with money fits into the larger picture of the meaning of life. I’m curious, what caused this shift in focus?

Dr. Daniel Crosby: Yeah, it’s a great question. There’s really a micro and a macro response to this. At the micro personal level, I’m just getting old. I’m middle-aged now. I’m thinking about mortality. I’m thinking about legacy. And I think my first couple of books, I’m proud of them. I stand by everything I wrote there, but they were written in a very calculated, specific way. They were to get me where I needed to go in my career and to make me a subject matter expert in places where I wanted to be viewed as an expert. And mission accomplished, it did that. But now as I age, I’m sort of surrounded by people who have achieved some level of professional success, and I see that their personal lives aren’t always as successful as their professional lives.

And so yeah, a big piece of it is just getting older, considering my own legacy, my own contributions to the world, and seeing myself and my peers achieve some financial and professional success, but not always have the wellness to go along with it, the soul to go along with it. And then at the macro level, I’m just, this is the thing I think about more than anything. I’m a big Viktor Frankl devotee, and he has this great quote about ever more people have the means to live, but no meaning to live for. And I think you’d be hard-pressed to find a better descriptor of the world we find ourselves in. When the US was founded, 85% of the world was living in poverty, what would today be $2 a day adjusted for inflation. And today that number is about 8.5%, which I don’t wanna be insensitive, is still millions and millions of people too high. But the progress that we have made, there has never been a time of greater worldwide abundance than the time we find ourselves in today. Forever, war and disease and famine and all these things have made human life very hard. And while all those things still exist at some level, and we should remain vigilant in fighting against them, we have never been healthier, more peaceful, more prosperous.

And yet when you look in the US, I’m Gen X, Gen X and younger, every single one of those age cohorts describes themselves as very lonely and isolated and living sort of a meaningless life. And so we’ve got this weird problem where we have the means to live, but no meaning to live for. And I wanted to take that on directly.

Brett McKay: Yeah, that is interesting. It seems like it’s a paradox ’cause that prosperity comes with its own set of curses if you’re not careful.

Dr. Daniel Crosby: Certainly.

Brett McKay: Yeah. So what do you do in this book, The Soul of Wealth? You basically, it’s like a compilation of 50 different thoughts, reflections, essays about money and meaning. And in one of them, you talk about how money is a great tool that can fix a lot of problems in life, except for a few. First, let’s talk about the problems that money’s really good at solving. What are those problems that money that, hey, you can throw money at this and it can help you improve your life?

Dr. Daniel Crosby: Yeah. One of the greatest things about modern life that I don’t know is fully appreciated is just how much free time we have. And I know that we conceptualize of our lives as being full to the brim. And I would say the same thing, work and kids and all this stuff. But we have dramatically more leisure time than any previous generation. Now, what we do with that is a different conversation. All the research shows that all that excess free time has basically been directed at TV. But we have more leisure and more free time than we ever have in human history. And that’s a wonderful thing. Money’s also great at buying you wellness, right. It can buy you nutritious food. It can buy you good health care. It can get you a gym membership or a personal trainer. And all of that stuff has a material positive impact on your life. It can buy you self-improvement in education. College grads make over a million bucks more than people who graduate from high school. And they also enjoy lower rates of divorce and heart disease and sadness. So there’s a lot that money can do to help human flourishing that way.

The final thing that I’ll talk about, and one of the things that sort of buys us a great deal of joy, is novelty. Another thing that we’re uniquely positioned to do is just have new experiences. One of the things that’s true of humankind is that we quickly become habituated to our circumstances. Whatever our day-to-day is, that quickly becomes the norm. But going on a vacation, going to a new place, trying a new dish, all of these things introduce us to novel experiences that bring us a great deal of joy.

Brett McKay: Okay. So money can buy us time. It can help us get novelty. We can get healthcare with it. What are some of the problems that money can’t solve?

Dr. Daniel Crosby:Well, the part where it can’t solve problems, I think, is perhaps the more interesting conversation because it’s riddled with half-truths. Even among the things that I talked about money can buy you access to college, but it can’t take the test for you. Money can buy you a gym membership, but it can’t do the bench press for you. And so the things that it can’t help, there’s a lot of half-truths there as well. I think a lot of people treat money as an indent to itself, but money can’t buy you purpose. What it can do is give you the free time to think about your purpose. Gandhi, I’m misquoting him here, but he effectively said, to a poor man, bread is God. Because if you’re so mired in the struggle for those bottom two rungs of Maslow’s hierarchy, you don’t have a lot of time to think about God or self-actualization or love or friendship. And so money can’t buy us purpose, but it can buy us the bandwidth to think about and pursue purpose. Money can’t buy us love. The Beatles were right about that, but we do know that it can buy you chocolate and roses for a date, and it can make you more attractive to your potential mates, as the research shows.

So I think one of the reasons why people conflate money with just the good life itself is because it certainly facilitates the pursuit of many of these things, but ultimately it leaves off and we’re required to sort of take that first step in the dark.

Brett McKay: Okay. So money doesn’t directly buy us the good life, but it does give us access to the things that can make a good life if we avail ourselves to them. And this gets to the larger question the common question people debate, which is can money buy happiness? And the answer is yes, but as you’ve kind of been saying, it’s nuanced. So what does the research say about money’s ability to buy us happiness?

Dr. Daniel Crosby: The first conversation we have to have is, how are you measuring happiness? Because one measure of happiness is basically about needs reduction and sort of the absence of pain. And so I think animal behaviorists would say that even animals can experience happiness. They may not be able to experience purpose, but they can experience happiness, which is sort of the lack of a negative state. So one of the most famous studies is of course, this Kahneman study that people like me and others sort of shouted from the rooftops because it confirmed all of our prior assumptions, which is that happiness with money plateaus around $75,000 a year at the time of the study, which is almost perfectly $100,000 a year today adjusted for inflation.

And that is true of needs reduction because at about $100,000 per year you have enough food to eat. You have a warm place to lay your head. Your kids can go to a safe school. Sort of the basics of life are met and there’s not a whole lot of negative sort of physical moment to moment pain in terms of your needs. So the need reduction measure of happiness is met at a relatively low level of about $100,000 per year. But there’s a more philosophical, sort of more existential way to measure happiness as well, which is just self-appraisal of life. If I say as we did before we pressed record, just like, hey, Brett, how are you doing? Tell me how your life is. Like, how are you doing? And we find with this more qualitative, this more subjective life appraisal, happiness and money are basically up and to the right as far as the eye can see. I mean, they’ve measured it up to about half a million dollars a year in earning. There’s not a ton of people who make more than half a million dollars a year. And so that’s where they stop. But they find that at every income level, people’s life appraisal improves monotonically.

So in a stepwise fashion from zero to half a million dollars a year. So it really matters. Like, are we talking about moment to moment physical pain or are we talking about happiness with respect to how we sort of account for our lives? Another piece of nuance that I would add to this conversation is depending on the study, about 10 to 15% of folks, money doesn’t move the happiness needle at all. And these people it’s widely assumed are suffering from sort of a clinical depression or sort of an emotional state that keeps money from having any sort of impact. So if you’re making more money and it’s not moving the needle in any respect, I think there’s this idea of wherever you go, there you are. You may need to take a different approach to trying to achieve that happiness. And then the last thing that I would say that that I think is maybe the most interesting point of the whole thing is there’s newer research that shows how you spend money materially impacts your happiness.

My favorite piece of research around this has to do with cars. If I go out tomorrow and buy a Lambo to stunt on my neighbors and show everyone how rich I am, that doesn’t buy much happiness. There’s a very sort of high peak for the first couple of weeks, and then that habituation sets in. Quickly, that Lamborghini that was so nice and new, the door gets dinged you get bird poop on the window, you throw your gym clothes there, and suddenly it’s just not so hot anymore. You just kind of get used to it, and the happiness falls off rather precipitously. But there’s research that shows that people who buy a car to join a car club get massive happiness dividends, because really it’s a relational exercise. What they’ve done is, yeah, you spend a lot of money to get an antique Porsche or whatever you did, but now you’re part of the Atlanta Cars and Coffee Club, and you get to meet with your buddies and look at your engines on Saturdays, and you have a social cohort. So there are definitely examples where if you spend money, even splurge on something that gives you relational access or something that’s consistent with how you wanna be viewed as a human being and your personality, there’s a big happiness dividend there.

Brett McKay: Okay, so if you’re spending the money for those bigger things, it’s gonna bring you happiness.

Dr. Daniel Crosby: That’s right.

Brett McKay: Yeah. I’m sure people have seen that research a lot. It’s like, well, if you wanna be happy, you got to spend your money on experiences to maximize happiness. I think that’s true, but I’ve also, like you said, there’s things that I’ve bought in my life, I’ve splurged on that they brought me happiness and they still bring me happiness. I’ve got a few things in mind. Do you have anything, like some items that you bought that continue to bring joy to your life?

Dr. Daniel Crosby: Yeah, there’s a few. For me, I got a nice award from my alma mater last year. And to mark that event, I bought myself a watch. And so when I look at that watch, it’s not crazy, but certainly you could get the time for a lot less. And when I look at that watch though, I’m reminded of my hard work, my accomplishment, the recognition of a university that turned me away when I initially applied there, which was a pretty sweet thing. And I’m very proud of that. My guitars, I have some expensive guitars and I’m a decidedly mediocre guitarist, but having these nice guitars on the wall right here in my office where I’m talking to you encourages me to practice and try and grow and become better and test myself and struggle in new ways.

And then the last thing is something I’m in the midst of right now. You and I were talking before, I’ve lost a lot of weight this year and my clothes were falling off me. I had to get all new clothes. And I’ve really taken the time to try and put together a kind of classic American menswear vibe, really nice fitted stuff, high quality, fewer clothes, higher quality. And every time I see one of those shirts or jackets that wouldn’t have fit me six months ago, I go, Hey, you did it. And it’s a really nice feeling. So I think we have to move towards a more nuanced view of this and spending can really buy you happiness. I’d be curious, what are some of yours?

Brett McKay: First one I can think of, I bought a sauna a couple of years ago, a barrel sauna, and I’d been wanting, I love the sauna at the gym, but then I shifted to a home gym and I would still go, I still paid for like a 10 gym membership, $10. So I could just use their sauna, but it was always crowded. And they’re just gross people in there. They like pick their toenails and the teenagers blasting music while you’re in there trying to like just zone out. So after a couple of years, I finally decided to pull the trigger. I bought a barrel sauna and I love it. My wife loves it. I go in there, right now it’s perfect sauna season. It’s getting cold, starting to get cool at night and just sitting there in the heat for 30 minutes and you go out in the cold and it’s just, it feels good. I’ve had friends over and we’ve had some great conversations in the barrel sauna. So it’s a thing that facilitated relationships.

The other thing, a recent purchase that I made that’s brought a lot of happiness in my life, I bought a wood pellet smoker earlier this summer. And it’s been great ’cause I can grill on it. So do burgers, chicken, things like that. But then I can like smoke brisket, I’ve smoked tenderloins and I’m using that thing all the time. And I think one of the things that does, it facilitates relationships. Like I’ll smoke a brisket or something when I’ve got friends or family coming over. That’s one thing that’s brought me a lot of happiness. And with the cars, we bought a 96 Buick Roadmaster, the wagon a couple of years ago, where it’s got the backward facing seat.

Dr. Daniel Crosby: Oh nice.

Brett McKay: And we did that so we could carpool with our kids’ friends. And it’s been, yeah, I love that thing. Every time I get into it, it’s so fun to drive. We’ve made some good memories in there.

Dr. Daniel Crosby: See, I think all the things you just named are perfectly demonstrative of some of the stuff I’m talking about, right. It’s facilitating relationships.

Another thing we know about money and happiness is one reliable path to that is by getting out of stuff we hate. And I was cringing hard over here when you were talking about people picking their toes in the sauna. So if it frees us from people picking at their feet, that’s something you hate. That’s a good use of money. I joke that I will never mow my lawn again. I mean, I live in Georgia. It’s way too hot. I got a big yard. It brings me a great deal of joy to see that high school kid out there sweating it out instead of me. So getting out of stuff you hate is another big one.

Brett McKay: Yeah. And going to that idea that experiences, if you spend on experiences, that will bring you the most happiness. My experience, not necessarily so. There’s some experiences that I’ve gone on like that was actually, I did not enjoy that. And when I think about like, why did I go on this thing? It usually was ’cause like, oh, some person said you should do this thing. It wasn’t because I actually wanted to go there or do the thing. So yeah, I think if you buy the experience or spend money on experiences just because you wanna impress somebody or you saw somebody on the internet said, hey, this is the greatest thing in the world, you should do it too. And it’s not actually something you’re interested in. You’re not gonna get any joy out of that.

Dr. Daniel Crosby: Well, I think that’s worth commenting on because we live in a weird time, where it’s kind of become socially okay to brag about experiences in a way that it wouldn’t be okay to brag about more obvious material things. People will post pictures of a $25,000 vacation and it’s just, sort of gets filed under, oh, look how beautiful the world is or something.

Brett McKay: Right.

Dr. Daniel Crosby: And I think there’s a lot of mimetic desire around experiences now. And my family and I were talking about going on a trip in November, and I’m like, I don’t really wanna do this. I’m like, I travel all fall. I’m like, I don’t really wanna do this trip. I think I just wanted to show off. And so I think even experiences have been corrupted somewhat in our social media age.

Brett McKay: Okay. So, buying things can bring you happiness. It’s nuanced, this is not an excuse to go spend your money willy-nilly, but it can if you do it right. But one of the dangers of spending money on stuff to find happiness is that you could become materialistic. And there’s actually, the psychologists have studied this and they’ve actually figured out there’s three characteristics of a materialistic person. So, what are those three characteristics?

Dr. Daniel Crosby: Yeah. This was news to me. I was really excited to come across this research and happy to share it here, that the three characteristics, the first is possessiveness. So, this is just around an inclination to control both things and people. So, that possessiveness is sort of the first and perhaps the most dangerous of this trifecta. The second, understandably, is non-generosity. Sort of an unwillingness to share back to the happiness conversation. One of the most reliable paths to happiness with money is by giving it away.

And yet people misapprehend that dramatically, like better than 90% of people think they’ll be happier when they buy something for themselves versus give it away. And that’s flipped in terms of actuality. So possessiveness, non-generosity, and then finally, envy, and especially ugly piece of this envy, in addition to sort of the way we use it in everyday language, is anger at others’ success. Being unhappy when others people are successful. So possessiveness, a lack of generosity and envy at other success are the three. And I cited 259 studies in the book that show that it’s associated with lower wellbeing, lower life satisfaction. And this is true, and you can’t say this about many psychological phenomena, but this is true across demographic and cultural lines. So men, women, all over the world, people possessed of this materialistic triad, just don’t have great lives.

Brett McKay: Yeah. So, if you find yourself acting like a scrooge, that’s probably a warning sign. You need to do something…

Dr. Daniel Crosby: Yeah.

Brett McKay: To fix it. So, how do you stave off the materialism?

Dr. Daniel Crosby: You are visited by three ghosts in the night, no. There’s a couple of things you can do. The first is you gotta prioritize community. Community is sort of an antidote for this. Being other-centered is one of the most reliable paths to meaning when it comes to setting goals and measuring your own success. You’ve gotta run your own race and measure your own success. Again, it becomes very, very easy in our time to benchmark to the wrong stuff and to have a bad reference class. A zillion years ago, you would’ve known about 150 people and you would’ve benchmarked your life and your wealth to someone who lived probably within a mile of you. Now we have instant access through Instagram and everything else to the lifestyles of the rich and famous. And it becomes very easy for us to pick a poor reference class. And that is a recipe for misery.

Another tip is to ground yourself in the moment and really work on that presentness. Materialists are often focused on the future and do a lot to let the beauty of a moment slip by always sort of anticipating that next big dopamine hit. And then the final thing, which is just one of these simple but overlooked things, is to practice gratitude. My wife has a bullet journal, literally, two lines where she tries to write down something good that happened that day. And this simple practice has been shown to give about a 10% bump in wellbeing experimentally, which is equivalent to the bump that folks get from taking SSRIs, which is an insane thing, to say that hey, psych meds and writing what you’re thankful for in a journal have about the same sort of impact on happiness, but gratitude cannot be overlooked. It’s big piece.

Brett McKay: That idea of generosity and just spending your money on others. Going back to the Christmas Carol example, like, don’t be a Scrooge. The antithesis of that, I think is Fezziwig. Remember Fezziwig?

Dr. Daniel Crosby: I do, I read that book every year.

Brett McKay: Yeah. So, it’s like one of my favorite parts in the book where it’s the, it’s he’s doing the Ghost of Christmas Past and Scrooge goes back and he sees his old boss Fezziwig, and Fezziwig put on this big party. And it is just a great time. Everyone’s having a great time. It’s something that Kate and I, we do every year. We like, we just, it brings us so much joy is having a big holiday party we invite our friends too. And it’s just, it’s awesome. ’cause we always think we wanna be Fezziwig. Like Fezziwig was a baller. [laughter] We want to be Fezziwig. We want to provide like, those memories that people have when they’re, ’cause we have a lot of kids there. We want them to be like, Hey, we, this is a great thing that I had a lot of good memories.

Dr. Daniel Crosby: So, that’s one way you can counteract the materialism. Be Fezziwig.

I Love that.

Brett McKay: Don’t be Scrooge. Be generous with your hosting and hospitality. We’re gonna take a quick break for a word from our sponsors.

And now back to the show. So, one aspect of our lives that you recommend that we don’t skip on is our health. And you mentioned this earlier, but in this essay, you started off talking about your experience with a toothache, that really brought this principle home of spending money on your health. What happened there with your toothache?

Dr. Daniel Crosby: Yeah. So I began to have like bad migraines, sensitivity to light, just enormous pain in my head. And I assumed that it was a toothache. I had never had a cavity in my life. I had never had a single dental problem in my life, but I’m like, this feels for the life of me, like a toothache. So I went to my dentist, my dentist looked me over, and he is like, it’s not your teeth. And so the pain persisted. I mean, I could barely get up off the couch. I was like incapacitated by the pain. The headaches were so horrible, sensitivity to light and sound. And so I go on this multi-month, nearly a four month journey of trying to figure out what the heck was wrong with me. And I went to the hospital. I mean, I went to the emergency room once when the pain got so intense.

I went to psychiatrist and sinus doctors and got a CAT scan and got MRIs. I mean, just on and on and on, trying to figure out what this thing was. And it just wouldn’t go away. And the pain got so intense. One day I was just driving with my family and the pain was so bad and I just started crying. I mean, I just started crying in the car. ’cause I’m like, I’m gonna die. I’m gonna die. Like I have some mystery illness. And at this time, at that moment when I’m crying in the car, I would have given you every dollar I had for the reassurance that I was gonna be okay. And for relief from that pain. Well, about two weeks later, I was at a client event down in Atlanta, and we were breaking for lunch, and I bit into a sandwich and the whole side of my face swole up.

And sure enough, it had been my tooth the whole time. My dentist had missed it. I had a crack in my tooth. It was, I won’t go into gory details, but it was enormously abscessed once it broke. And the minute… So, I [laughter] my face starts swelling. I’m looking crazy. I excuse myself from my client engagement. I drive straight to an emergency dental place, get that tooth pulled. And immediately I felt incredible. I mean, I felt a relief that I had not felt in months, but it drove home this platitude. We all know that health is wealth, but a sick person only wants one thing. A healthy person has a million desires, but a sick person only wants one thing. And when you dig into the research around health and wellness and money, you see that there’s this incredibly powerful reciprocal relationship.

Brett McKay: Oh yeah. So, the takeaway there; it doesn’t matter how much money you have, if you don’t have your health, it’s all for naught, pretty much. So, how can people use their money to invest in their health?

Dr. Daniel Crosby: I think one of the most powerful things you can do is control the controllable. You find these statistics where people who are taking care of themselves just do a lot better financially than people who don’t. So, frequent exercisers make 10% more than their no exercise peers with similar educational and professional backgrounds. People who had a mentor make way more than people who don’t. Men who go to therapy make some astounding [laughter] some astounding double digit increase in their pay versus their same education peers who don’t go to therapy. So, there’s all these ways that we see that controlling the controllable, taking care of yourself just leads to not only better health, but better financial health as well. And then, just because of the soapbox I’m on right now with sort of this fitness journey that I’ve been on this year, one of the biggest things for me was to get current information.

The thing that really transformed my relationship to my body was just having daily input on what I weighed, how I was doing, what volume of exercise I was doing. We lie to ourselves in some really big ways. People under-report their calorie intake by between 25 and 50% a day. People overestimate their level of exertion and exercise by 47%. So, a lot of times I think just having information, just monitoring these things and keeping an eye on them, that that knowledge is real power that helps us to not sacrifice a replaceable thing like money with an irreplaceable thing like our health.

Brett McKay: So, it sounds like we should be thinking of investing in our health as more than just investing money. You can invest time in tracking things, and when you do invest money, you can motivate yourself to do so by remembering that it’s actually a good financial investment. It’s gonna pay off actual dividends eventually. And it’ll also improve your health. Going back to the material things that we’ve spent money on or splurged on that’s had a lot of ROI, I’d say my home gym, like over the past decade we’ve built up, there’s been a significant ROI on putting money there. Like, first off, I just enjoy exercise and training, but like the health benefits have, I’m sure been phenomenal.

Dr. Daniel Crosby: Yeah.

Brett McKay: Yeah. Okay. You have an essay that I really enjoyed, it’s entitled, You don’t really want to Be Rich, you want to Be Free. What do you mean by that?

Dr. Daniel Crosby: So in the book, [laughter] in the book, I don’t name this person by name, but I guess I will, on the podcast I’ll be impolitic and name the person on your podcast. I was reading a story about Elon Musk. And so Elon Musk was talking about this standing 9:00 PM Saturday meeting that he has. And he is like, yeah, I was in my standing 9:00 PM Saturday meeting, and I don’t know why [laughter] that piece of information hit me like a ton of bricks, because in that moment I was like, I am richer than this guy. I know that he has hundreds of billions of dollars, but at 9 o’clock on a Saturday, I’m having fun and he’s not. And that is true wealth. And so I think that’s sort of the point of this chapter. One of the things that I talked about in a previous book of mine, The Behavioral Investor, you can demonstrate this with brain scans and other things, is that people value money for its own sake, independent of what it buys, which is a very goofy, backward stance to take towards money.

Because you don’t want money for its own sake. You want what it can do for you. And one of the things that it can do for you is free you up from having to do things you hate or be around people you don’t wanna be around or do things that you don’t wanna do. So, this chapter is all about making money your servant and not your master, and not getting wrapped up in this idea of just more and more, and more. But what is it that I really want this money to do for me? And I think if we’re honest with ourselves, very often, for most people, the highest and best use of wealth is to buy back your life, to buy back your independence.

Brett McKay: Yeah. I mean, I’ve seen, I’m sure you’ve seen this too with your work, people who’ve gotten richer and richer and they’ve just become less and less free because they build those what gilded bird cages for themselves that they can’t get out of. They say, well, I can’t quit this job, or I can’t stop this business that’s I don’t enjoy. Because if I do, then I’m gonna lose everything that I have.

Dr. Daniel Crosby: Yeah. I have seen that again and again. That was a big impetus for writing the book. Just by virtue of my day job, I am proximal to lots of people with really, really, really big bank accounts like sent to millionaires, billionaires. And more often than not, I would say that these folks lack a sense of freedom. They are so wrapped up in the pursuit of more, even in cases where they have more money than they could ever serviceably spend in a lifetime, even in those cases, there is an inertia and a lack of freedom that makes them less free with people with a lot less money who’ve been more thoughtful about its deployment.

Brett McKay: All right. So, if you have an opportunity to buy freedom, do it. You’ll be happier. That might mean you take more vacation. You talk about that. A lot of Americans, I think Americans are really bad at vacation.

Dr. Daniel Crosby: Oh yeah.

Brett McKay: I think most of us don’t use all of our vacation time, but take it, like, take that. The other things too, if you have the means, buy a lawn care guy, buy an hour of babysitting so that you can go on a date with your wife, there’s all different little ways you can buy back some time.

Dr. Daniel Crosby: Yeah.

Brett McKay: Yeah. You also talk about finding a why for your money. This is kinda like the meta meta theme of your book. What does that look like? ’cause I don’t think most people, when they think about their money, they’re not thinking about the purpose of money or like their why. So, how do you go about figuring out your why for money?

Dr. Daniel Crosby: Yeah. I think you’re right. Most people aren’t thinking about this. And one of the things that I wanna do is encourage them to, because the power of tying your dollars to your purpose is so incredible. It almost sounds like science fiction when you read some of the research, but people who had named their dollars. So, not just, account A, B, C, 1, 2, 3, but Brett’s retired to The Bahamas Fund. Something that simple, just labeling it for purpose. One study found that in tough markets, they were 10 times less likely to bail on their investments and go to cash. Another study out of Canada found that when people looked at a picture of their kids before they logged into their bank account, they were twice as likely to save. Morningstar, big financial firm found that, that accounts that were labeled with a specific purpose had 15% more in them than their peers.

So, one reason to do this is just because it elicits a host of good financial behaviors. I mean, it really takes investing, saving, spending, out of the ether, and it ceases to become a video game, and it becomes this real thing that’s tied to life. But in some research that I’ve done since this book, I really have found that there’s sort of three facets to meaning. If we look back over the research, a life purpose has three legs to that stool. And I think if you apply it here, that the three are believing, belonging, and becoming. So, people with purposeful lives, first of all, believing they have a philosophy, a religion, or a moral framework that guides their life. You see this again and again and again and again. Religious people are reliably happier on average. And this is one of those reasons.

They have a moral framework to help them make sense of the good times and the bad times in life. Doesn’t have to be religion, but you need to have thought through your sort of personal philosophy of why things are the way that they are, and let that guide how you spend money. The second piece, the most powerful piece is belonging. Again, back to relationships. If you say you value relationships, are you spending money like, that’s the case?

And then the third piece that people with meaningful lives have is becoming, which is they are growing, they are learning, they’re progressing. So, you need a moral framework. You need a group of people to love and who love you back, and you need a vision of the kind of person you want to become. And if you’ve got those three things, you are on your way. And each one of those three things has a financial component to it. And if you value those things, it should show up in your budget.

Brett McKay: Yeah. You recommend if to people, I like this idea of doing like a values audit of your bank account. If you don’t know what you value or what’s the why of your money, just take a look at your statement from the last month and see where you’re spending your money. And then you can start kind of putting things in the categories like, oh, I spent a lot of money eating out with friends. Okay, well friends seems like friends are important, and saving time is important. But then you might see, well, I’m spending a lot of money on subscriptions that I don’t use. Maybe I can do something better with that money.

Dr. Daniel Crosby: Yeah. That’s exactly right. I love this idea. There’s sort of two things at work here. The first is that your money is your vote. And I mean, I had this conversation with my youngest kid the other day. We always go to the local farmer’s market on Saturdays, and we were buying some spaghetti sauce, and she was like, that’s a lot. That’s really expensive. Like, that’s a lot more than it is at the store. And I was like, yeah, that’s right. But I wanna live in a world where local entrepreneurs who are growing tomatoes in their backyard and working hard can make a living. So yes, it is twice as much as the Prego or whatever, but it brings about an outcome that I care about. And it’s just, it’s a powerful way to think about money is am I spending it in a way that brings about the kind of world that I wanna live in? And am I casting my vote wisely? And the flip side of that is, is the ultimate BS detector. We’ll say, oh, I value growth and spirituality and purpose and relationships. And then, I look at my budget and it’s all Netflix and Doritos, then maybe it’s time for a reckoning. And it just, it’s very easy to lie to yourself about what’s important to you. And money shines a very bright light on what you truly value.

Brett McKay: Yeah. What’s that saying on, I tangently very loosely follow like financial Twitter. And then you’ll see every now and then this big blow up when some financial guy gives a bit of advice and then someone will respond like, show us your books. Show us… What are you doing? ’cause they wanna make sure that like they got skin in the game, they’re actually putting into action what they’re encouraging people to do.

Dr. Daniel Crosby: Yeah. Yeah. And Nassim Taleb wrote about that, Never ask a person their opinion, just ask to see their portfolio. Like, I don’t care about your hypothesis. Like, what are you doing with your money?

Brett McKay: Yeah. Yeah. So, that’s something I do, once a month I go through the bank statement and see what I’m spending my money on. It has a couple purposes. One, it just helps me figure out, okay, my spending my money on anything dumb and can we cut back on that? Or am I spending too much on a certain area? So just you got your eye on the till basically.

Dr. Daniel Crosby: Yeah.

Brett McKay: Then also the same time I’m saying, well, is my spending matching up with our family’s values?

Dr. Daniel Crosby: Yeah.

Brett McKay: And if it’s not, then you can do some correction. I think once a month like that, I think that’s plenty of, you don’t have to do it every day or every week, but like, just do it once a month. It doesn’t take a lot of time. So, something else to talk about, and we’ve had conversations about this, there’s a temptation in some people, not everybody. There’s a certain segment of the population where they just want to keep squirreling away money for retirement. Like they’re aggressive, aggressive savers. And there can be some upsides to that. But the downside is like, you just don’t enjoy your life now and you can’t spend money on other people now. Are there any biases that might lead some people to excessive money hoarding?

Dr. Daniel Crosby: Yeah. There’s a host of them. So, I [laughter] I actually did some research at Orion, my employer, where we interviewed 425 couples. And we asked them, effectively, we did it more delicately than this, but effectively we asked them, what do you fight about when you fight about money? And the number one point of friction among couples was whether money was best used to enjoy today or to secure against an uncertain tomorrow. And it was almost 50/50. And if you think about it, the appropriate response is somewhere in the middle. I mean, both things are important. Like it is both important to use money to seize a moment, because tomorrow tomorrow’s not promised, and we need to be setting aside for that future self and that rainy day. But we found that people tended to be far more decamped into sort of extreme sides of this position.

And so there were a lot of moral judgments around this too. Like if, for folks who find themselves in the ‘save for tomorrow’ camp, they see the other folks as sort of frivolous and unserious. And for people who were in the, “enjoy the moment” camp, they see the savers as sort of fun haters and sticks in the mud. And so the behavioral biases that load onto this are, there’s a few of them. One of them would be loss aversion. We perceive spending as a present loss, and we are two and a half times as upset about a loss as we are happy about a comparably sized gain. So that a hundred dollars hurts worse coming out in retirement than it felt good to save it when we were in the accumulation phase. The other thing is uncertainty aversion. Uncertainty is perhaps the thing which humankind finds most distasteful.

Like we hate not knowing even more than we hate bad news. And then we also engage in anchoring, which is sort of benchmarking to a high watermark. So if we retire with a million dollars, we go, oh, I’m a millionaire. Like I did it. And then when you have to start drawing that down, it’s painful all the way down. So, there’s a couple of ways I think to overcome what is admittedly a pretty thorny problem.

The first is something called bucketing, which is kind of back to this naming it for purpose. There’s a psychological phenomenon known as mental accounting where the way that we label money materially impacts our willingness to save, spend and invest it. So something as simple as saying, here’s my principle, here’s my dividends, here’s my living money, here’s my vacation money, here’s my don’t touch it money, that can give us permission to spend it as we ought to.

Second powerful thing is to just automate the inflows and outflows so we don’t have to think about it. You wanna kind of minimize touches. And so if you can make a good decision once and kind of set it and forget it, that’s powerful. And then finally, kind of ripping off Stephen Covey here, he has this idea that effectively the only way that we can say no to something difficult is to have a bigger yes burning inside of us. And so we need that purpose again. We have to love our grandkids enough to spend that money on them, even though there’s some pain associated with taking it out, whatever the case may be. So, bucketing automation, purpose are all sort of powerful workarounds for what is a very complicated human tendency.

Brett McKay: Yeah. I think that’s, I mean, a lot of times the focus is on people who aren’t saving enough, which is a problem. That’s a problem. But then a lot of, I don’t think a lot of attention is given to people who save too much. ’cause that can become a problem. ’cause then you hit retirement or whatever. And like, as you said, there’s some people who have so much money saved away in retirement, they can’t even like draw it down by the time they…

Dr. Daniel Crosby: Yeah.

Brett McKay: So, they’re left over with a big chunk of money that yeah, they can pass on to their kids and grandkids, but then there’s gonna be like, it’s gonna be taxed. And it’s like, there’s all these other problems that come with that. So it’s, yeah, trying to figure out how to manage that nut you may have squirreled away during your working life. That can be tricky.

Dr. Daniel Crosby: It’s very tricky. And in a real sense, like every dollar that you die with, and look, I get it, you can’t probably, none of us knows when we’re gonna go specifically, but every dollar that you die with is a dollar that you weren’t able to spend in life on time with your kids, time with your loved ones, being generous, being kind, blessing the world. I mean, it’s in a real sense, it’s a missed opportunity. And there’s a great book called Die With Zero, which covers this very thing.

Brett McKay: Well, Daniel, this has been a great conversation. Where can people go and learn more about the book and your work?

Dr. Daniel Crosby: Yeah. The book is The Soul of Wealth. I hope people will go check it out. I’m active on Twitter at Daniel Crosby. I have my own podcast, Standard Deviations, and yeah, just Daniel Crosby, PhD on LinkedIn as well.

Brett McKay: Fantastic. Well, Daniel Crosby, thanks for your time. It’s been a pleasure.

Dr. Daniel Crosby: Thank you.

Brett McKay: My guest here is Dr. Daniel Crosby. He’s the author of the book, the Soul of Wealth. It’s available on amazon.com, at bookstores everywhere. Check out his podcast, standarddeviationspod.com where you get your podcast. Also, check out our show notes at aom.is/soulofwealth, where you find links to resources. We delve deeper into this topic.

Well, that wraps up another edition of the AOM podcast. Make sure to check out our website @artofmanliness.com, where you find our podcast archives. And while you’re there, sign up for our newsletter. We got a daily option and a weekly option. They’re both free. It’s the best way to stay on top of what’s going on at AOM. And if you haven’t done this already, I’d appreciate you take one minute to give review of the podcast on Spotify. It helps out a lot. If you’ve done that already, thank you. Please consider sharing the show with a friend or family member who you think will get something out of it. As always, thank you for the continued support. Until next time, is Brett McKay, podcast, but put what you’ve heard into action.

This article was originally published on The Art of Manliness.

Are leaders born or made? Judging by the 50 billion dollar leadership development industry, the answer is definitely the latter. From schools to workplaces, everyone is seen as a potential leader and expected to become one by undergoing leadership training.

My guest questions the assumptions underlying this phenomenon, which he calls “the leadership industrial complex,” and says that the cult of leadership, and its idea that everyone can and should become a leader, can create burnout and unhappiness.

Elias Aboujaoude is a Stanford professor of psychiatry and the author of A Leader’s Destiny: Why Psychology, Personality, and Character Make All the Difference. Today on the show, Elias describes the state of the leadership industrial complex, the mathematical impossibility it forwards that everyone can be a leader and no one is a follower, and the primary presumption it makes that leadership can be taught. Elias argues that, in fact, a lot of what makes for good leadership is innate and potentially unchangeable. We discuss the implications of this fact, and why it’s actually okay not to want to be a leader.

Resources Related to the Podcast

• AoM Podcast #838: Can Virtue Be Taught?
• AoM Article: Don’t Just Lead Well, Follow Well
• AoM Article: Are You a Strategist or an Operator?
• AoM Article: The Best Kind of Leader to Be

Connect With Elias Aboujaoude

• Elias’ website 
• Elias’ Stanford profile page

Listen to the Podcast! (And don’t forget to leave us a review!)

Listen to the episode on a separate page.

Download this episode.

Subscribe to the podcast in the media player of your choice.

Read the Transcript

Brett McKay: Brett McKay here, and welcome to another edition of the Art of Manliness podcast. Are leaders born or made? Judging by the $50 billion leadership development industry, the answer is definitely the latter. From schools to workplaces, everyone is seen as a potential leader and expected to become one by undergoing leadership training. My guest questions the assumptions underlying this phenomenon, which he calls the leadership industrial complex, and says that the cult of leadership and its idea that everyone can and should become a leader can create burnout and unhappiness. Elias Aboujaoude is a Stanford professor of psychiatry and the author of A Leader’s Destiny: Why Psychology, Personality, and Character Make All the Difference. Today on the show, Elias describes the state of the leadership industrial complex, mathematical impossibility [0:00:50.9] ____ that everyone can be a leader and known as a follower, and the primary presumption it makes that leadership can be taught.

Elias argues that, in fact, a lot of what makes for good leadership is innate and potentially unchangeable. We discuss the implications of this fact and why it’s actually okay not to want to be a leader. After the show is over, check out our show notes at aom.is/leadership. All right, Elias Aboujaoude, welcome to the show.

Elias Aboujaoude: Thank you very much.

Brett McKay: So you are a psychiatrist, and you’ve taken a deep dive into what could be called the cult of leadership in America. And what kickstarted this exploration of leadership development in the United States is you got a request to write a letter of recommendation for a medical student. So how did that request for a letter of recommendation lead you to exploring our country’s obsession with leadership and developing leaders?

Elias Aboujaoude: Indeed. So one of the best medical students I ever supervised, I’ll call him Tim, approached me for a letter of recommendation in support for his application to get into a skin cancer program. Tim had really shown exemplary performance on the wards where I supervised him.

So I wrote the most, probably the strongest letter of recommendation I had ever written. And in it, I praised his bedside manner, his clinical productivity, his conscientiousness, his research contributions, really the kinds of things that every program wants to see in an application and in a prospective applicant. To sort of make him feel better and hopefully less stressed out about this process, I shared the letter with him and I watched as he read it in my office. And I was surprised to see his facial expression sink into a deep depression and deep sadness. So for a second, I thought I had mistakenly given Tim another student’s evaluation, the evaluation of a student who had been failing the rotation, but it turned out I hadn’t. What was missing apparently from my letter is any mention of leadership qualities and leadership potential. And Tim was convinced that as strong and outstanding as the letter was, he wouldn’t get into any competitive program without a supervisor predicting a brilliant future for him as a leader.

So that got me thinking about how we’ve come to really prioritize leadership over any other quality in our medical field. But also as I started looking and exploring way beyond medicine, I started paying attention, for example, and noticing daycare centers with names like Future Leaders of America or Leadership Academy, the kinds of things that suggest that we’re planting this leadership seed and inculcating people into this cult of leadership, leadership literally with breast milk. And I started noticing also that college applicants now have an entire section where high school students are expected to talk about their leadership experience. Who wants a shy violinist or an introvert when you can get the president of five clubs kind of thing. So all this speaks to a real leadership obsession in our society, and it speaks to very high demand for all things leadership. Now, this demand is being met, met and then some, by what I’m calling in my book, a leadership industrial complex. There’s a $50 billion leadership industry that’s now available to really convince us that leadership is something that’s within reach for practically anyone.

All you have to do is take the right course or sign on the right executive coach. So it’s a very sort of unhealthy combination between this kind of demand and this kind of supply. And as I see it, it may explain the failures of leadership that we see every direction we look and on every front, whether political, corporate, academic, really everywhere and anywhere. We’ve created a system where we have so much product out there that the only way for leaders to stand out and actually make it to leadership positions is to be unscrupulous, to have traits that are closer to sort of the narcissistic or even the antisocial end of the spectrum. And we don’t want that in our leaders, but this is the system that we have created. And this is what this unhealthy balance between exuberant demand and exuberant supply has created.

Brett McKay: Yeah, that’s one of the big points you make in the book is there’s this paradox that we’re seeing in the past, maybe 50, 60 years, this emphasis on developing leaders. We’re going to develop leaders and very be systematic about it, take courses, but it seems like there’s a dearth of leadership despite all the leadership development we’re doing.

Elias Aboujaoude: Absolutely. This is the biggest, one of the biggest paradoxes of the leadership industry that there has never been more opportunities to develop and train leaders. And yet leaders have never performed worse than they are today. So, one way to look at this is to think, well, we need more training. We need the industry to be even bigger, but another way to look at it and the position that I take in my book is that the leadership industry and this approach to leadership is actually contributing to leadership failure.

Brett McKay: And another point you make too, is that this emphasis, overemphasis on leadership in college students, in your career, it could be leading to burnout and just feeling inadequate. Tim, he was disappointed that you didn’t talk about his leadership skills, but did Tim want to be a leader like personally?

Elias Aboujaoude: That’s the thing. Tim had no interest in being a leader. All he wanted to be is the best skin cancer doctor he could become. And that’s what he eventually became. But Tim was also convinced that without coming across as having leadership qualities, he had no chance of actually making it. When I touched base subsequently with Tim, a few years down the road, I found out that some leadership opportunities had actually come his way, but he was all too happy to ignore them and turn them down.

And yet in his application process, he felt forced to, if you will, pretend to be interested in leading. Otherwise, he wouldn’t have made it into the program that he was eventually accepted into.

Brett McKay: Yeah, I’ve encountered that too with letters of recommendation. So I mentor teenage boys at church and they’ll ask me sometimes to fill out letters of recommendations. And there’s always a thing on there about leadership, like what leadership skills does this person display? And some of these boys, they’re smart, they’re bright, but they’re not really leaders and they’re not really interested in leadership. But I feel like I got to come up with something because if I don’t, it’s not going to look good for them.

Elias Aboujaoude: It’s not going to look good. It’s going to count against them. And it speaks to a bigger problem in academia and in college and university life. Less than one in 10 students now major with a degree in the humanities. We’re shutting down English and history departments left and right. And yet there’s this curious rise of the leadership major and the leadership minor and leadership studies everywhere you look. So it’s a curious development and feeds into this cultural obsession and academic obsession with leadership that I was talking about.

Brett McKay: I want to talk about these courses, but before we do, when you’ve looked at the leadership industrial complex as a whole, what do they mean by leadership exactly? Because leadership can mean lots of different things. There’s lots of different definitions. So how is it described in the leadership industrial complex culture?

Elias Aboujaoude: What goes along with this leadership industrial complex, of course, is intense marketing. And to understand what leadership means to these programs, it’s interesting to look at the messaging and the marketing. So you’ll find words, really buzzwords like transformative, catalyst, a change driver, unleasher. You’ll be empowering people across many verticals and across many tipping points. You’ll almost certainly disrupt.

If I had the nickel for every time I came across the word disrupt in my leadership research, I’d be a very rich man. So these buzzwords add up to the leadership industrial complex’s definition of what a leader means today. And through these courses and through this coaching and through all this “development”, they sell the message that all these qualities and traits are perfectly teachable.

Brett McKay: So I mean, what skills or traits do they purport to teach would-be leaders?

Elias Aboujaoude: I don’t have a problem really with purporting to teach a skill. Where it becomes very problematic for me as a psychiatrist is where they start pretending or communicating that they can teach things like EQ, emotional intelligence, or even charisma, qualities and traits that are linked to personality. And if we know anything as mental health providers, as psychiatrists, as psychologists, is the difficulty changing people’s personalities.

People’s personality tends to be stubborn, not super malleable. If you want to make long lasting personality changes, it’s a long-term commitment that involves potentially years of psychotherapy. It’s not the kind of thing that you can pick up over a bootcamp or a weekend workshop. And yet this is the message that a lot of these trainings are selling. And this is the really misleading, no pun intended, notion that accompanies so much of the leadership industry’s offerings.

Brett McKay: Okay. So leadership in the leadership industrial complex, a lot of buzzwords, you’re a change maker, catalyst, disruptor. So it’s kind of an amorphous thing. It can kind of mean whatever and because it can mean anything you want, like you can create your content that you’re teaching however you want. Let’s dig into the actual content, these courses. I thought this was really interesting. You talk about what colleges and other businesses are doing to make money on leadership courses. You mentioned, I think you said a $50 billion industry overall?

Elias Aboujaoude: Yeah, it’s a $50 billion industry. And it’s an industry that’s been fully embraced by our top business schools, entities and institutions that know a thing or two about making money. And this has helped really transform this leadership development field into a full blown industrial complex. And when you check out something like Harvard’s program for leadership development, for example, you’ll be surprised to see that there’s an 800 number available for applicants to call. There’s an entire program advising team that’s waiting to take your call. You’ll also be, you might be surprised to see that really there’s no formal educational requirements to join. There’s this amorphous sort of leadership potential.

That’s pretty much the only requirement. The program is advertised to people at whatever role or career stage. Again, not really just meant for senior executives or folks already in the C-suite, but marketed as something that’s much more open and accessible than that. So the acceptance rate into it seems much higher than the 4.5% or so that undergraduates applying for Harvard usually face. What’s unquestionably exclusive though about the program is the price tag, $52,000 for the basic four modules of blended teaching. But if you want a lifelong Harvard email address, and if you want alumni status, then you can get that for an additional module and an additional $27,000. So strategies that to me feel very sort of marketing and business oriented in a way that to me fits uncomfortably within the educational model.

Another example that I talk about in the book is Wharton. Wharton is the premier, the oldest business school in the country. And I was checking out a program they have, a nine month, mostly self-based or largely self-based program called Global C-suite. And I read about it and then I wanted to close the window. And I had this very interesting pop-up show up offering me $1000 off the $20,000 tuition if I hurry up and apply in the next nine days. Again, marketing gimmicks and marketing strategies that have no place in education as I see it, yet this is what so much of the leadership industry and the leadership educational opportunities, this is the direction they take.

Brett McKay: Okay. So for $60,000, I could become a Harvard alum. I could put that on my CV. Yeah, that’s crazy. And then it’s not just colleges that are doing this. There’s also many businesses that offer leadership development courses as well.

Elias Aboujaoude: Oh, absolutely. If Harvard and Wharton are offering these kinds of opportunities, then you can imagine the Wild West out there and programs with names like Leadership Express Series or a workshop for $18.99 that promises to teach you how to become a charismatic leader. I mean, any number of such offerings that I review in my book.

Brett McKay: What’s the content of these courses? Like what exactly, when you sit down to through these modules, what are you learning?

Elias Aboujaoude: Well, a lot of the content is not research-based, certainly. There’s very little by way of long-term research results in terms of success that these programs can point to. There’s also a ton of mnemonics that I came across as I was researching. And this heavy reliance on mnemonics suggests that leadership is easy, literally as easy as ABC. One popular mnemonic is the so-called three Rs, three Rs.

But depending on which program or which professor of leadership or which coach you consult, the three Rs stand for different things. It could be reflections, resiliency, and relationships, but it could also be respect, recognize, and reward, and so on and so forth. So all this suggests a very sort of unscientific, make-it-up-as-you-go process that unfortunately takes up a lot of these offerings.

Brett McKay: Is there any research that’s been done on these leadership development programs that they actually work, like that people who go through them come out as better leaders? And how would you even measure that if you did research on that?

Elias Aboujaoude: Well, it’s not easy to measure, which highlights the need for good quality, large-scale, long-term research. And when you look for good quality, large-scale, long-term research that has assessed their success, there’s very, very little indeed that you can point to.

Brett McKay: Okay. And that’s interesting ’cause businesses are probably paying for their employees to go to these things. They don’t even know if it works or not.

Elias Aboujaoude: Oh, to the tune of $50 billion.

Brett McKay: Yeah. And what’s interesting too, you talk about how this is also creeping into middle schools and in high schools. I mean, I grew up in the ’90s, late ’90s. I was in high school then. And I saw that stuff. I was involved in student council, and we did this leadership development stuff. And typically, what it was like the school district was paying some organization to do the teaching.

Elias Aboujaoude: Yes. The leadership bug has fully infected our high school and college systems. And this is manifested in the place that leadership now takes up in college applications, but also it’s manifested in how so many schools seem to be changing their mission statements to emphasize leadership. Everybody wants to teach the future leaders of America. Nobody seems interested in teaching and informing the educated citizenry of the country.

And the downside, of course, of all this is the inferiority complex that it gives those who are not interested in leading, those who have the self-awareness to acknowledge that, so they’re not interested in pursuing leadership, who don’t succeed at leading. But there are real psychological consequences to that and a real inferiority complex that doesn’t get talked about as we send the message that all can be leaders and as we ignore the reality that the world also needs followers. And mathematically speaking, not everyone can be a leader.

Brett McKay: We’re going to take a quick break for a word from our sponsors.

And now back to the show. So the idea that everyone can and should be a leader and that everyone can develop into a leader with the right training is everywhere these days. And I think the big thing we need to talk about, and you mentioned this before, is that the whole idea and what the leadership development industry relies on is the assumption that leadership can be taught. And there are certain skills that can be taught and people can improve on a little bit body language, getting a little bit better with public speaking, getting better at strategy, but you talk about, if you actually look at the scientific research that’s been done on leadership, it suggests that a lot of leadership ability just comes down to inborn temperament. So what does the research say there about leadership ability and temperament?

Elias Aboujaoude: Yeah. So I talked earlier about how there’s very little long-term, long-term high quality research in terms of the success of leadership training. But there’s quite a bit long-term, high-quality research when it comes to people’s personalities and how people’s personalities evolve over time. And what this long-term, high quality research tells us is that personality is pretty sticky. I’ll just quickly mention a couple of studies. One involving a cohort of Harvard graduates who are assessed at age 22 and again at age 67, and you can imagine all the ups and downs and all the upheaval that can happen in a person’s life over the course of four decades or so.

And yet when this cohort was reassessed, the fundamental traits and their personalities were essentially unchanged. The fingerprint, their personality fingerprint was essentially the same. Another study looked at an even younger cohort, students aged 6 to 12 and assessed them on 39 personality traits and re-interviewed them again 40 years down the road. And what the researchers found was their personalities were essentially largely stable. So this is what a high quality long-term research from mental health and from psychology teaches us, and yet when you look at a lot of leadership offerings, there is this idea that we can teach you EQ and we can do it pretty easily. Now, nobody would dispute the importance of EQ in how leaders emerge and how leaders succeed. Up to 90% of leaders success has been attributed to EQ when other skills and when IQ is otherwise the same.

So the importance of EQ is pretty fundamental and pretty established. But the notion that you can teach EQ and transform EQ is highly problematic because EQ is pretty tightly linked to personality. And what the studies I mentioned about personality show is that it’s largely fixed over time.

Brett McKay: Okay. So yeah, when we typically think of a leader, with this idea, he’s charismatic, they take risk, they’re bold, they know how to manage people, they’re detail-orienting, and that kind of lines up with those big five personality traits, conscientiousness, extraversion, low on neuroticism. And let’s say you’re a person, you’re like, Okay, I’m kind of neurotic, I’m not very conscientious. I’m not a big risk taker. Can a course, a weekend course actually move the needle on that? And the answer looks like it’s probably not.

Elias Aboujaoude: The answer is probably not, because personality, again, is largely fixed and when psychoanalysis try to affect meaningful long-term personality changes, it was a year’s long endeavor, not for the commitment phobic. So to the extent that EQ is linked to personality and we know it is, it is not something that you can easily impart or teach.

Brett McKay: Yeah. And this idea of can leadership be taught, this reminds me, this goes back, this is like a couple of thousand year-old question. Like Plato is asking the same question. He was asking that can virtue be taught?

Elias Aboujaoude: Very interesting. Yes.

Brett McKay: Yeah. And he actually tried to figure it out. He actually had this theory that, yes, virtue can be taught. Like if you teach people about the good and they know the good, they’ll start conforming themselves to the good, then they’ll be good leaders. That was the idea. And then he had the chance to test it out. He got to go to Syracuse and be a teacher to this king guy who was having lots of problems and he was teaching him philosophy and teaching him about the forms and everything. And it ended in complete disaster. The guy did not change at all. And Plato was like, Okay, maybe this idea that I had that if you teach these philosopher kings to be good leaders, it’ll… Teach them the forms, they’ll become good leaders. It’ll work, and he actually had to take a step back and say, all right, that’s actually not gonna work. We have to try something else.

Elias Aboujaoude: Well, this is a vignette that clearly belongs in the book, Brett. Thank you for sharing that. You know what the Greeks were also interested in is charisma. In fact, the word charisma comes from a Greek root, that means a freely given gift like something that God endows you with or the gods endow you with. And again, it’s interesting how many people to this day when they try to define charisma will resort to religious sort of metaphors and religious terms. And yet this hasn’t stopped us from pretending we can easily teach it in a way that makes us look like we’re playing God.

Brett McKay: Okay. So a lot of these leadership attributes that we think of when it comes to a good leader, charisma, high EQ, lot of it is based in personality and a lot of that you can’t change. If you do change it, it’s gonna take a long time to do and you’re probably not gonna change it too much.

Elias Aboujaoude: Yes, indeed.

Brett McKay: So when companies or organizations are thinking about leadership, should it be less about leadership development and you know, this idea that you can develop anyone and everyone into a leader and more about leadership finding? Like is it better to focus on filtering for and selecting good leaders? Should that be the strategy?

Elias Aboujaoude: The subtitle of my book is Why Psychology Personality and Character Make All the Difference. And I think one shift that needs to happen for the health of our leadership culture is for us to start paying more attention to these things and ease up on the development, ease up on the steps and hacks and tips that supposedly guarantee good leadership. Basically go back to the basics and put psychology front and center where it belongs in leadership culture. And remember that there’s only so much planning and prepping and strategizing that one can do. And some of the most meaningful and significant leaderships that the world has seen, leadership found the leader not the other way around. So there’s a humbling message in this for leadership culture and it should be humbling for the leadership industry as well.

Brett McKay: Yeah. I think that’s a… Something that I’ve taken away as I’ve studied… I’ve read a lot of biographies of great leaders and one thing I have discovered is what made them great leaders is like, yeah, they rose up to the occasion, the leadership found them and they leaned into their unique personality. They weren’t trying to conform themselves to this ideal leader. That’s charismatic and bold and visionary. And even guys who weren’t that, like they were still good leaders. I mean, here’s an example. Patton and Eisenhower had kind of different personalities. Patton’s very bombastic, led from the front, was very flamboyant and that worked for him. He leaned into that. And Eisenhower was more of a like a people person. Like he did a lot of the, I’m gonna be in the background working on alliances. When you look at football coaches, I love watching how different football… American football coaches coach. You have some coaches who are very just high energy, just on the sidelines. Rah rah rah. And then you have those coaches who just arms folded, never say a word.

Elias Aboujaoude: Yes.

Brett McKay: And they’re winning football coaches.

Elias Aboujaoude: Yes, yes. I think you’re talking about people basically aligning with their psychology and leaning with their psychology and not pretending to be someone they’re not. Winston Churchill is another great example of a transformative, truly transformative and truly disruptive maybe figure who was found by leadership and rose to the occasion as opposed to self-consciously and deliberately in a step-by-step fashion strategized to reach the heights that he reached.

Brett McKay: Yeah. Another one, Abraham Lincoln. Like he was not your stereotypical leader. He had depression, he was severely depressed. He would just lay on the couch and read the book of Job and just be like, I’m the saddest guy in the whole world. But Lincoln was still one of the most eminent and effective leaders in history.

Elias Aboujaoude: Absolutely. Absolutely. So all this is to say that we lose by limiting the profile of who we support in rising to leadership positions the way we are doing right now.

Brett McKay: Well then, I wanna go back to this point you made that this everyone is a leader culture that we have can contribute to maybe burnout, depression, inferiority complex, amongst particularly young workers, young students. Flesh that out a bit more for them. How have you seen that manifest itself?

Elias Aboujaoude: When we live in a culture that only values leaders and when we are subjected to endless marketing that all that counts is leadership and that leadership is yours to have for just a little bit of training and little bit of development. Then those of us who don’t become leaders, either because they’re not interested or they’re not successful, can be left with an inferiority complex and be left thinking, well what is wrong with me when it should be so easy. Where did I go wrong? And that’s an unhealthy state psychologically speaking, and it’s totally unnecessary because the marketing itself that’s driving it and the leadership obsession that’s driving it are what’s faulty with society, not the individual who doesn’t become a leader or isn’t interested in pursuing leadership.

Brett McKay: Yeah. And it also sets people up if they do pursue leadership because they feel like they have to, to feel like, I actually hate this. I am not suited for this. I am miserable, but I gotta do this because I have to advance my career.

Elias Aboujaoude: Right. I got the position that supposedly is what matters in life, but I’m absolutely miserable leading.

Brett McKay: So I think the takeaways from what we’ve talked about are leadership development, probably not a thing. I mean there are certain skills you can develop a little, but as far as those ineffable qualities that we think of when it comes to leadership, that comes down to personality. And that’s either… It’s kind of either you’re born with it or you’re not. So maybe organizations of all kinds should focus more on leader finding, filtering and selecting instead of leader development. At the same time though, I think we can expand on our idea of what makes a good leader. It doesn’t have to be the stereotype. So maybe you don’t have those qualities of a stereotypical leader, but you can still be a good leader in your own way. But let’s say whether or not you do have potential for leadership, you’re just not interested in it. It’s not something you wanna do. What advice would you give someone who they’ve got the self-awareness to know that they’re not a good fit for leadership positions, but they still feel this pressure to get on that track to advance their career?

Elias Aboujaoude: Yeah. What I would tell them is to do what aligns with their psychology. Don’t tie your self-worth to leadership positions. It’s okay to be a leader, but it’s also okay not to be one. And certainly don’t look down on followers including yourself if you happen to be one.

Brett McKay: Okay. And that could be tough ’cause you’re just told from a young age, you gotta be a leader.

Elias Aboujaoude: It is tough and that’s why the change has to happen on many fronts. It has to happen at the level of parenting. It has to happen at the level of schools and universities and it has to happen at the corporate level. I mean, this is not an easy change to make, but it’s a necessary change to make to the extent that we need good leaders. And our approach to leadership today is almost guaranteed to leave us with unimpressive leaders.

Brett McKay: Yeah. But I feel like it just comes down to being okay with being a follower and that maybe will require reframing what it means to be a follower some, right? ‘Cause it has… The word has a lot of negative connotations and baggage. Being a follower doesn’t mean there’s something wrong with you or you’re deficient. You just have a different disposition or maybe you just different kinds of work. And actually this reminds me something we talked about on the site, this goes back to Patton and Eisenhower, is that some people are strategists and some people are operators, right? So like some people like to be the manager where they’re setting the agenda and other people they just like to be on the ground, in the field, doing the work. It’s like some people like to plan the action and some people just want to take the action. So it’s okay not to want to be a leader and just want to be an operator. That’s okay. Maybe you won’t get as much clout and money, but you’ll be happier.

Elias Aboujaoude: Absolutely. Leadership is not the only path to happiness and self-worth.

Brett McKay: I love it. Well, Elias, this has been a great conversation. Where can people go to learn more about the book and your work?

Elias Aboujaoude: Thank you very much. They can go to my personal website, eliasaboujaoude.com or find the book on Amazon or any of their favorite venues.

Brett McKay: Fantastic. Well, Elias Aboujaoude, thanks for your time. It’s been a pleasure.

Elias Aboujaoude: Thank you very much.

Brett McKay: My guest today was Dr. Elias Aboujaoude. He’s the author of the book, A Leaders Destiny. It’s available on amazon.com. You learn more information about his work at his website, eliasaboujaoude.com. Also, check out our show notes at AOM.is/leadership where you find links to resources we delve deeper into this topic.

Well, that wraps up another edition of the AOM podcast. Make sure to check out our website at artofmanliness.com where you find our podcast archives as well as thousands of articles that we’ve written over the years about pretty much anything you can think of. And if you haven’t done so already, I’d appreciate it if you take one minute to give us a review on Apple Podcast or Spotify. It helps out a lot. And if you’ve done that already, thank you. Please consider sharing the show with a friend or family member who you think will get something out of it. As always, thank you for the continued support. Until next time, it’s Brett McKay, reminding you to not only listen to AOM podcast, but put what you’ve heard into action.

This article was originally published on The Art of Manliness.

As you get older, you can start to feel like you’ll never achieve your dream or receive recognition for your contributions to a field, or that your best work is behind you.

Mo Rocca has compiled stories that demonstrate that you shouldn’t give up hope, and that no matter your age, the best may yet be to come.

Mo is a humorist, journalist, and the co-author of Roctogenarians: Late in Life Debuts, Comebacks, and Triumphs. Today on the show, Mo shares the stories and lessons of entrepreneurs, artists, actors, and more who achieved greatness or adulation in their twilight years or had a new spurt of creativity when they thought the well had run dry, including KFC founder Colonel Sanders, the artist Matisse, a couple of guys who didn’t receive their first war wounds until they were old enough to qualify for the senior citizen discount at Denny’s, and even a virile 90-year-old tortoise.

Resources Related to the Podcast

• AoM Podcast #849: Live Life in Crescendo
• Samuel Whittemore
• John L. Burns
• Frank Lloyd Wright’s Fallingwater
• Frank Lloyd Wright’s Guggenheim Museum
• Henri Matisse’s The Swimming Pool
• Documentary about Tyrus Wong
• Mr. Pickles the Tortoise

Connect With Mo Rocca

• Mo on X

Listen to the Podcast! (And don’t forget to leave us a review!)

Listen to the episode on a separate page.

Download this episode.

Subscribe to the podcast in the media player of your choice.

Read the Transcript

Brett McKay: Brett McKay here and welcome to another edition of the Art of Manliness podcast. As you get older, you can start to feel like you’ll never achieve your dream or receive recognition for your contributions to a field or that your best work is behind you. Mo Rocca has compiled stories that demonstrate that you shouldn’t give up hope and that no matter your age, the best may yet be to come. Mo is a humorist, journalist, and the co-author of Roctogenarians, late in life debuts, comebacks, and triumphs. Today in the show, Mo shares the stories and lessons of entrepreneurs, artists, actors, and more who achieved greatness or adulation in their twilight years or had a new spurt of creativity when they thought the well had run dry, including KFC founder, Colonel Sanders, the artist Matisse, a couple of guys who didn’t receive their first war wounds until they were old enough to qualify for the senior citizen discount at Denny’s, and even a virile 90-year-old tortoise. After the show’s over, check out our show notes at aom.is/lateinlife. All right, Mo Rocca, welcome to the show.

Mo Rocca: Thank you for having me, Brett.

Brett McKay: So you got a new book out called Roctogenarians, Late in Life Debuts, comebacks, and Triumphs. So you’re talking about people who in their elder years did some really cool stuff. And you talk about in the beginning of the book that you had an interview with Chance the Rapper that kickstarted the idea for this book. So how did Chance the Rapper get you thinking about old people who are doing cool things in the winter of their lives?

Mo Rocca: Well I think that there’s a meaning behind any joke you tell, whether it’s a traditional joke or even a jokey question. And I’m a panelist on Wait, Wait, Don’t Tell Me, which is NPR’s news comedy quiz show. I’ve been on it for a long time. And back in 2015, Chance the Rapper came on as a guest. And it was a really big crowd that turned out in Millennium Park in Chicago. And those of us on the show were kind of quizzing him on how you write a rap. And I thought, oh, here’s a hokey question I can ask him that’ll be an easy laugh. And I said, because at the time I was 46, I said, I’m 46. Is it too late for me to become a rapper? And it got a laugh, kind of an easy joke. But he looked at me dead on seriously. And without skipping a beat, he just said, I don’t know, some people might say it’s too soon for you to become a rapper. And people laughed and the conversation moved on. But I was kind of thunderstruck because I realized in that moment that I’d fallen into the trap of thinking of myself as kind of over the hill at 46.

And now I’m not suggesting that I’m going to become a rap star. But I think what he said to me had a lot of truth in it, which is that as you get older, you’re only gonna become more likely to have something meaningful to say, something to express creatively. And I’d fallen into that trap of thinking of life as kind of a series of sort of doors closing, of exits being shut off and of diminishing opportunities. And again, I was 46 and it’s kind of nuts. So my eyes were opened. And I was also kind of embarrassed that even though it was just a jokey question, that it came from a place of me thinking of myself as maybe past my prime.

Brett McKay: Yeah. I think a lot of us put those limitations on us because we have this idea in the culture that, okay, if you’re gonna be a great artist, you got to do it when you’re in your 20s. Or if you’re gonna start up a startup, you got to do it in your 20s or 30s. But you highlight a lot of great people who did some really amazing things in the second half of their life. So besides being on a panel for Wait, Wait, Don’t Tell Me, you’re also a correspondent for CBS Sunday Morning. So you get the opportunity to interview and spend time with people from all walks of life. And in your book, you talk about how you really, like you enjoy speaking to all these people, but you really enjoy speaking to the older ones. Why is that? What do you like about elderly people?

Mo Rocca: I think there are a few things at play. I think that older people tend to have better stories for one thing maybe simply because they’ve lived longer. But there’s also something that happens where people who are older generally are more comfortable in their skin. And I find that when I interview them, I have to go to them. They’re not playing up to me. So even if we’re talking about a movie that maybe they’ve been in, they’re not really overly eager to sell it to me. And that makes the conversation more interesting. I think they realize if you’re 80 and you’re in a movie, okay it’s cool, but it’s not high stakes. So they’re just kind of where they are and I had to come to them. I did this cooking series for about four years called My Grandmother’s Ravioli, where I went around the country learning to cook from grandmothers and grandfathers in their kitchen. And what I learned through doing that is that the older you get in general, the less you care about what other people think of you, which I think is where we all wanna be. And so it’s not a coincidence that my co-author John Greenberg and I could fill this book with stories of people accomplishing great things late in life, because I think as you get older, you’re more unfettered.

You’re more just willing to go for it. In my experience, I think younger people tend to crowdsource not only their decisions, but kind of who they are and their personalities. I know I did it. You try on different personalities. You’re figuring out who you are. But I think a lot of the qualities we ascribe to younger people about, oh, he really goes it alone or she really does it her way. They’re really more applicable to older people.

Brett McKay: Yeah, I’ve noticed that too. And I’ve noticed as well when I interact with older people, they lack self-consciousness, but in a good way. My grandfather passed away a couple years ago. He’s 100. And we were at the funeral and we were looking at photos of him from his life. And I was talking to my cousin. And I said Grandpa, he just didn’t seem like he was thinking too much about himself all that often. And he’s not the kind of guy that would need to download the Headspace app and meditate and figure out. It wasn’t like he wasn’t that he was shallow or anything and that he wasn’t curious, but he just wasn’t thinking about himself. And I find that incredibly refreshing in a culture where everyone’s just constantly thinking about themselves and where they stack up compared to everyone else.

Mo Rocca: God you know it’s so funny. I’m trying to think this is gonna be a little sloppy because I haven’t worked it out. But it’s almost like the camera is just shooting out, right? They’re not looking at the reversal shot. They’re not looking at the monitor, which would show you what the camera from the other side is looking at. They’re just outward facing. And I think it’s just easier to do, to just act, just like do stuff when you’re not hung up on how you look doing it.

Brett McKay: I agree. So let’s talk about some of these Rocktogenerians you highlight in the book. And you start off with one of the most famous Rocktogenerians of all time, Colonel Sanders of KFC fame. This guy is a global brand icon, but he didn’t start out that way. So what is the Colonel’s story? What was his life like before he became the colonel?

Mo Rocca: Well, it may be a surprise to some people. He was a real person, Harland David Sanders. He was from Kentucky. He grew up very, very poor, had a seventh grade education from early on, was working to help support his family as a young man. At one point, he was a midwife. He did whatever he could. By the time he was in his middle age, he had a shell gas station/chicken and biscuits joint in the small town of Corbin, Kentucky. He was doing fine. He was getting by. But then in the 1950s, a highway cut through Kentucky. It bypassed his restaurant, kind of like what happens to the Bates Motel in the movie Psycho. This has a much happier ending. And the bottom fell out of his business. He had to sell it at a loss at auction. He was 66. He was living off of Social Security, $105 a month. He could have subsisted. He could have just continued on and probably survived in some way. Instead, he got in his car with two pressure cookers, a bucket of his secret recipe of 11 herbs and spices. And he drove from town to town to town, from restaurant to restaurant, cooking for people, hoping to hook them on his chicken.

And within eight years, he was the face of a Kentucky fried empire, over 800 outlets worldwide. And what I like about the story is it’s so forward moving. I mean, even him getting in that car, I mean, that’s the perfect Oscar montage, right? Like if it’s you did the Colonel Sanders biopic, but he just does what he has to. And he just gets in the car and he drives. And I think there’s something so significant about that. So this wasn’t, and there are in the book, this wasn’t an artist sort of pursuing something creative, which is wonderful. This was somebody who had to survive and just did what he had to do. And there’s something so bold about that. And it’s funny ’cause the story has been told a lot through the years in various ways, but it never gets old.

Brett McKay: Yeah, it doesn’t. And like you said, the way he built his business, he just drove around from town to town, trying to sell franchises with his recipe and it became a success. And eventually what happened is he’s able to sell the whole company for $2 million in 1964, which is about, I think it was about $20 million in today’s money, accounting for inflation. So that’s a lot of money. And then after his success, he lived a pretty modest life. Like he just did this stuff to make a living. It wasn’t anything more than that.

Mo Rocca: Yeah, it wasn’t like some big dream or something. This is this thing he had, this recipe, and he had to survive and he did live modestly. And he actually didn’t eat much chicken. He had a diet that he hoped would take him to 100. He made it to 86, but it involved eating sardines each morning. And I do think about that when I’m going food shopping and I look at the sardines now, I think of Harland David Sanders. But he testified in front of Congress about aged people and said a man will rust out sooner than he’ll wear out.

Brett McKay: So you also highlight some men who came out of retirement to fight in wars. And the first guy you talk about is Samuel Whittemore. This guy’s story is incredible. Tell us about Samuel Whittemore.

Mo Rocca: Well, this, I mean, I love these stories because I didn’t know them before. And when we dug into this, I said I wanted to include soldiers because what could be more counterintuitive for an older person to do? And so Samuel Whittemore, before we were the United States, he had served the crown in America as a royal dragoon, which just sounds really cool. He’d been in the French and Indian wars. But the Stamp Act of 1765 really converted him to a revolutionary. He was very fervently pro-independence by the time the American Revolution started with the Battles of Lexington and Concord in April of 1775. And on the very first day of battle, when Samuel Whittemore was already 78, he was there on the front lines. He picked off between one and three redcoats before he was shot in the face and had one of his cheeks blown off and then was stabbed in the head by a redcoat and left for dead.

He survived against all the odds and he lived another 18 years. So this guy, I mean, we put in the book that, I mean, Clint Eastwood, who was 78 when he was in Gran Torino, this would be the perfect biopic for him. It’s just an amazing story. And of course, Samuel Whittemore’s family did not want him doing this, but he felt so ardently pro-independence, he just couldn’t help himself. And he became a legend, understandably. I mean, really, half his face blown off and stabbed in the head and keeps going.

Brett McKay: That’s great. And you had the chance to talk to General Wesley Clark and you asked him about this guy. It’s like, why would he come out of retirement? He’s 78 years old. He’d just be sitting on the porch in his rocking chair. And his answer he gave you, it surprised you.

Mo Rocca: Yeah. Well, General Wesley Clark was unfamiliar with this story and with another story we tell, which is about John L. Burns, a 70-year-old veteran of Gettysburg who was, almost kind of spooky music here, born the year that Samuel Whittemore died as if passing the baton, or I guess in this case, the rifle. And John L. Burns became the only civilian known to have fought at Gettysburg and certainly is the only civilian with a monument to him at Gettysburg. And both those stories were unfamiliar to General Clark. And he said he could understand because when he, as a young man, had been injured in Vietnam, when he woke up the next morning and he looked around at other wounded soldiers, he immediately felt a sense of fraternity. He felt like that that was the initiation into this lifelong fraternity and service. And so everything changed with that injury for him. And he believes that the fighting spirit really intensifies with age.

The fervor only grows stronger. And that part, I mean, I was fascinated by it. And I suppose, yeah, I was surprised by it. And I was also, I have to brag here, happy that I could tell him these stories, which he was unfamiliar with.

Brett McKay: And yeah, that Burns guy, he was interesting. So he’s a civilian and the war was basically in his front yard at Gettysburg. And he’s like, well, I’m gonna go there, take my musket. They gave him a rifle and he saw action. When he became famous and he kind of, he didn’t handle fame very well. I think he kind of let it get to his head.

Mo Rocca: Yeah. I think he was apparently kind of blustery. I mean, one of the funny things, by the way, let’s just, I had to add is that he had fought as a very young man in the battle of, in the war of 1812. But by the time the Mexican-American war came along and he tried to enlist in 1846, he was already too old. So cut to 1863 and he’s really too old as far as the military goes. And he takes this kind of sinecure of a job as a constable and it happens to be in the town of Gettysburg. So the war wouldn’t let him go to it, but the war came to him in a sense. So, I mean, as luck would have it, he’s in this little town and the biggest conflict of the civil war happens to arrive on his doorstep. And so he grabs his very outdated uniform, his very outdated artillery. His wife is like, don’t do this. And he’s like, sorry, gotta go. And he eventually, it’s, I believe with a, I might have this wrong. It’s a Wisconsin or a Michigan militia. He manages to fight with them and he does indeed kill, I believe, three Confederates. And that night he’s sort of stranded. When the Confederates find him, he manages to convince them that he was just out and about looking for his wife, why he would be wearing that, who knows, but they let him go. And he meets Lincoln when Lincoln comes to Gettysburg later. And yeah, he becomes a real braggart, really blustery. Eventually he comes to dementia and is found wandering the streets of New York city and dies a few years later.

Brett McKay: So what’d you take from these guys?

Mo Rocca: I took, I was inspired by their sense of public service, their duty to country when they were fighting for a world that at best they’d enjoy for a few years. And I find that extremely powerful. People who put their butts on the line and these two guys did really, truly, I mean, put their lives on the line fighting for something that they believed in, which even if they were successful, they would only reap the rewards for a very short time. And that is extremely powerful. I mean, young soldiers, young civil rights activists, those people are heroic, of course, because oftentimes they end up losing what could have been long lives at a very early age. But there’s something in a very particular way that’s very, very profound, I think, about older people who dedicate themselves to public service and in this case, quite literally fighting for their country.

Brett McKay: So as you mentioned earlier, there’s this romantic idea that if you wanna do your best work as an artist, writer, painter, musician, you got to do it when you’re young. I think it comes from the romantic era with Keats and Byron. Like if you don’t get it before you’re 30, you’re hosed, you’re never gonna have a chance. But you highlight several artists who did some of their best work late in life. And I wanna talk about the architect, Frank Lloyd Wright, because I live in Tulsa, Oklahoma, so we’re not too far from the Price Tower, the only skyscraper that Frank Lloyd Wright did. So he experienced early success. He had some early success, but then his career kind of sputtered out. Tell us about that.

Mo Rocca: Well, I mean, Fallingwater, this home that he built for a department store family owners in Western Pennsylvania, not terribly far from Pittsburgh, quite literally on a stream, on a falls, built around the water and the rocks, integrating nature into it, put Frank Lloyd Wright on the cover of Time magazine, which then was a really big deal. So Frank Lloyd Wright was already a great innovator, seen, hailed as a great innovator and master by his middle age. But then the world of architecture moved on and he was seen as yesterday’s news, certainly as the international style came into vogue. And he was in his late 70s when he received the commission from the Guggenheim family for a new museum in New York. He was 84 when he submitted the design for it. And he had the leading artists of the day, those who would be exhibited in that structure, completely in opposition to him because they saw the design, which was actually a design that he resurrected from a Maryland car park, believe it or not, that was gonna be in the, I always mispronounce this, the Catoctin, I think I have it right mountains in Maryland, that hadn’t happened earlier. He had taken this design and he sort of pulled it out and refreshed it for the Guggenheim museum And these artists saw it and said, this is more about the architecture than our art. This is unsuitable for us, these curves.

These curved walls are not ideal for exhibiting our art. So he really was up against it. He had, the leading artists of the age saying, you’re past your prime. What you’re doing is wrong. He persevered. And that museum is as much a part of the environment of New York City and of Central Park. It sits on the edge of it, as Fallingwater is to Western Pennsylvania. So, I mean, I think it takes… Certainly Frank Lloyd Wright had an ego, but it takes a sense of self along with a great talent to push through this idea, Brett, that you’re talking about, that you basically have an era and that’s it. Frank Lloyd Wright was too much of an artist and believed too much of it, in himself to not push through that. And I think it’s that pushing through that I really admire in a lot of these people and people in life in general, who buck up against this idea that your time has passed gracefully bow out. Frank Lloyd Wright was not gonna allow that to happen to himself.

Brett McKay: Yeah. He even wrote a letter to all these artists who are saying, Hey, get out, stop this. He’s like, yeah, just take a hike, I’m gonna do it. You guys don’t know what you’re talking about.

Mo Rocca: Yeah.

Brett McKay: So you gotta harness a little bit of that grumpy old man to get your vision happening. So don’t sell yourself short, even if you’re old. You also talk about… Oh, go ahead.

Mo Rocca: Yeah. If I may interrupt for one sec. I also have to say that it’s funny because the cult of likability is so powerful, and as somebody who works in tv I understand how powerful it is. And in putting this book together, we did think, Frank Lloyd Wright isn’t very likable. So.

Brett McKay: Yeah.

Mo Rocca: So we actually debated it, but ultimately the willfulness, the sheer willfulness of Frank Lloyd Wright made the story irresistible.

Brett McKay: Yeah. He knew who he was. Like he was comfortable in his own skin, so maybe he was a bit of a curmudgeon. That’s okay. We’re gonna take a quick break for a word from our sponsors. And now back to the show. You highlight a few writers. One you highlight is Jorge Luis Borges, the Spanish author, who’s famous for his surreal mind bending short stories. But in his sixties, he started to lose his vision. So how did he turn losing his vision into an asset and begin a new phase in his career?

Mo Rocca: Yeah. Well this is in a section of the book called Loss into Gain. And it’s something that a few of the people have in common and latent life achievers, which is that whether by design or by instinct, they turn loss into gain, they look at endings as beginnings. And it’s almost as if obstacles force them to sort of become reborn. And it’s almost like, I don’t know, my mother has a real green thumb. And sometimes they see with this grapefruit tree that I… As a kid I planted and, and she keeps in her apartment still, 45 years later. She said, I’ve gotta cut this branch off so it’ll grow much stronger. And that’s sort of what I think about. But then the plant, will actually become healthier. Borges has had been known for what were called fictionese for short stories. So not the poetry that he became even more famous for later. But as he began losing his sight in the ’50s, it became harder for him to write. And so instead of just giving up altogether, he switched from these short stories to poetry to burs because this, he could compose and he could compose in his head while he was walking around. And so that’s what he did. So it opened up a whole new vein, a whole new avenue for him.

Brett McKay: And Borges talked about how he looked to other famous blind poets. Homer was supposed to be blind, and then Milton, Milton was blind and he did Paradise Lost.

Mo Rocca: Exactly. And then of course, Borges ended up writing about both of them in his own work.

Brett McKay: Yeah. And then another artist who, same sort of thing, he experienced a loss, but he turned into a gain. Matisse, my daughter’s got Matisse things in her, hanging up in her bedroom.

Mo Rocca: You know, I love this because Matisse was already hailed as a great modernist by his middle age. But in his ’70s, cancer robbed him of the ability to paint. He could no longer sit upright, he had to recline in a wheelchair or in a bed, but he was not content to just sort of sit around, receive visitors and sort of play a highlights reel of his greatest hits in his mind or to others. So instead he traded his paintbrush in for a giant pair of scissors and began cutting big shapes out of colored paper. Paper that had been painted. He still had assistance with him and he would have them pin these paper cutouts to the walls of his room. And I’m lucky enough to live in New York where MoMA, the Museum of Modern Art, has the swimming pool, one of the great paper cutout works of art remounted there.

And you can see up close lots of little pinholes because he was still very meticulous about where they were positioned. Move it this way, move it that, and move the pens with it. However, the work itself, and I think this is very significant, there’s something childlike about it, not childish, but childlike. The bright colors, the big shapes. And Matisse himself viewed the work as a second life for him and a kind of return to childhood because there was, he said, a lack of complication in the work. It was unburdened by too much thought. And I think a lot of these stories share that with the Matisse story, which is people returning to their childhoods in different ways. Sometimes literally like the writers Frank McCourt and Laura Ingalls Wilder writing about their childhoods sometimes with people going back to their childhood to finish something that they started like the Queen Rock and Roll Hall of Fame guitarist Brian May who had been studying astrophysics before he became a guitar… Before he joined Queen, returning at age 60 to complete his PhD in astrophysics. So there’s a lot of this sort of returning to a first love or just even a childlike outlook that is very powerful, I think.

Brett McKay: Yeah. And I think it’s inspiring too, these guys. They embrace the limitations that come with old age. Like it’s… I think we have a culture where we’re just constantly fighting against old age. Like we’re just doing all the exercising, taking supplements and doing Botox and peptides just to fight off old age. And I get it, I understand why people do it, but there’s something kind of unseemly about it as well at the same time.

Mo Rocca: Well, I think a lot of it ends up making people actually seem older. In a weird way, right?

Brett McKay: Yeah.

Mo Rocca: Like I think the people who embrace their age and their aging actually seem more energetic and youthful.

Brett McKay: I think so…

Mo Rocca: And certainly more at peace.

Brett McKay: Yeah. So find out how you can turn your limitations into assets like these guys. You also highlight several people in the book who did amazing work throughout their lives, but they weren’t recognized for it until they reached Elderhood. And one of these guys is Tyrus Wong. I never heard of this guy before until I read your book, but this guy’s an incredible story. What’s Tyrus story?

Mo Rocca: Well, we wanted to include people who didn’t necessarily accomplish great things in late life, but were acknowledged before they died. It’s sort of the reverse Van Gogh, like, you know, van Gogh great artist, dies very young, largely unrecognized in his time. And to me, there’s something very sad about that. You wish that some people that died young and were recognized later could kind of come back from the dead just so that they could be like, wow, people really did actually appreciate what I did. These stories, there are three that are like the opposite of that, including Tyrus Wong who lived until 106, and towards the very end of his life finally received recognition. Tyrus Wong had grown up extremely poor in China, so poor that in his village they had to hang the poultry on ropes from the ceiling so that the rats couldn’t get to them on the dirt floor.

When he was eight years old, his father took him to America. He never saw his mother and sister again. He was for a month on Angel Island where immigrants would come in in California and near Los Angeles was separated from his father for a month, which alone would’ve been traumatic, right? You leave your mother and your sister and you’re just with your father and then you’re separated for a month. The father then got a job as a laborer, but saw talent in his young son and earned the money to send his son Tyrus to the Otis Art Institute in Pasadena. And he quickly excelled there. As a young man. He was actually exhibited at the Art Institute in Chicago, and he made his way to Walt Disney to Buena Vista Studios. And there he worked on the movie Bambi. Disney had already had a big success in feature films with Snow White and the Seven to Dwarfs.

But Bambi had a completely different look. Instead of clear, bright lines, people will remember that it’s much more evocative of the forest and the moisture. And that was due to Tyrus Wong who was doing backgrounds. And Walt Disney himself was so impressed that Tyrus had sort of combined the Impressionists whom he’d studied with the brush work of the Song Dynasty of the Chinese Song Dynasty. So everything was much more impressionistic. There weren’t clear stark lines. It was a completely different look. However, he was never… First of all, he never even met Walt Disney himself. He ended up getting laid off from Disney after a strike by animators, even though he himself had not been striking. And he just went on without ever having received recognition for the look of what became a blockbuster. He ended up then continuing his art at different studios and then making kites by all accounts, he had a very, very happy life with his wife and his two daughters.

In his 80s though, close to 90, suddenly Disney made him a legend and a whole cascade of honors followed, including a documentary. And he died at 106 and he had been working very, very late in life. But his story, and two others in this section of the book have one thing in common, very, very long marriages that they credited with getting them through very rough patches in life. Tyrus Wong was married, I believe, for 58 years. And if you’re gonna continue pursuing something certainly like art and you’re not gonna be really recognized, you are gonna need somebody. I think these stories tell us who is gonna be your champion in life and is gonna help you get through those downturns.

Brett McKay: I imagine too, it helped having another way to, I don’t know, feel good, like another mission in life. If the only thing he had going in his life was his work, didn’t have family, well if your work didn’t work out like you’re hosed, you don’t have another, another thing to fall back on.

Mo Rocca: I think that’s right and I think you can even see it in the photographs of Tyrus Wong. You can see, first of all, when he talks about his wife and how taking care of her as she went into a slow decline and died years before he did, was the most important work of his life. And he means it. And yeah, it’s a beautiful story. And actually one of my colleagues, Tracy Smith, who was a correspondent at Sunday morning, actually interviewed him before he died. And that’s how I learned about the story. And you just, you can just feel the love coming off the guy.

Brett McKay: Another person you highlight that worked tirelessly to build a career but didn’t experience success in recognition till later life was the actress Estelle Getty, better known as Sophia from the Golden Girls. She had dreamed of being an actor from a young age. And she took steps to make that happen, but it didn’t really happen for a long time. Tell us about her career.

Mo Rocca: Well, you can’t do a book like this and not include at least one Golden Girl.

Brett McKay: That’s right.

Mo Rocca: I think the book would’ve been banned or something if they hadn’t. So she was the one, all four were pretty great. But Estelle Getty was such an interesting story and she played, as you pointed, she played the mother Sophia on The Golden Girls, a hilarious character. But the other three Golden Girls had all had big careers from early on. And, I think it’s fair to say they’d really put their career center and good for them. Estelle Getty had actually wanted to act from a very early age. She grew up in the lower East side of New York. Her father, who was working class, would take the family to the Academy of Music when she was just a kid to see vaudeville and early talkies.

She had gone to the Catskills to wait tables and try her hand at standup comedy. She married when she was 23. She had two sons. And raising a family just made it impossible for her to pursue her career full-time, at least at that time. She did take whatever small parts in plays she could get, by the time she was in her 50s, she joked that she was just getting parts as mothers, as Irish mothers, Jewish mothers, Italian mothers. She once said she played everyone’s mother except Attila, the Hun’s mother. And when her kids went off to college in the ’70s, she kind of turned her focus back and said, I’m not done yet. And she was in her 50s by this point and she did something I think that’s really, really pivotal here that characterizes a lot of these latent life achievers.

She went to see a play off Broadway by a then unknown playwright named Harvey Fierstein. And she liked it and she went backstage and she basically forced herself on the playwright. She said to him, I want you to write a part for me. And I think he was so taken aback and charmed that he did it. He wrote apart for her as the mother in what became Torch Song Trilogy, which was a very, very big play on Broadway, very important in the eighties. And that became her Broadway debut. And I think she eventually did it in a touring company in Los Angeles. And that’s how she got noticed. But I think it was that kind of proactivity of saying, Hey, I’m really good. You need to write something for me instead of being sort of coy about it. And so she was 62 when she was cast in the Golden Girls as the mother. She had never been on network television before and she became arguably one of the funniest characters of the last 40 years, 50 years on a sitcom.

Brett McKay: Yeah and I think the lesson there is sometimes you’ve just gotta put it on the line and ask for what you want. ‘Cause it could change the whole course of your life. What happened to Getty’s career after Golden Girls?

Mo Rocca: She did all sorts of movies. I’m not sure how Stop or My Mom Will Shoot you became such a funny joke maybe because the title’s so ridiculous and it’s with her and Sylvester Stallone. But she continued working. She eventually had dementia and, by the end of her run on the Golden Girls, she was having a lot of trouble. Partly it was nerves remembering lines, but she made it work. But I mean, it’s weird to put it this way, but she really deserved it after living the life she had and never giving up on this dream. It really was the ending that she deserved.

Brett McKay: Another actor that you talk about that had late in life success. And when he showed up in the book, it’s like, no, that’s not right. This guy has always been famous. Morgan Freeman. It’s hard to believe that he was a late in life success ’cause You just think Morgan Freeman has always been a big star, but he wasn’t. What was his early career like?

Mo Rocca: Well, I was sort of familiar with Morgan Freeman from having interviewed Rita Moreno back in 2013. And it forced me happily to revisit the Electric Company, a show I loved growing up. I was not a Sesame Street person, I was an electric company person. And Rita Moreno and Morgan Freeman had been on it together, but they had had opposite career trajectories. She had already been a star from West Side Story. And she had taken this role on a PBS show because she’d moved to New York with her husband and daughter and thought, all right, I’m in my 40s, which at that time was considered old for actresses. I mean, it’s ridiculous, but she thought this will be a nice job as I raise my daughter. Morgan Freeman was also on the show about the same age, actually, I think. Is he a little bit older? I think they’re about the same age.

And he had been struggling for a long time and he didn’t love being on the electric company. And there was actually some tension between them. They ultimately became very good friends and remained close. But, so their stories were sort of intertwined and doing this book, you know, it was interesting to learn about how Morgan Freeman had come up. He served a stint in the Air Force. He went to LA to become an actor, but he always had integrity. He had quit a job with the San Francisco Opera that included what he felt was a denigrating stereotype of an American Indian. He had walked out of a television commercial audition because there was a part called the Jew actually called the Jew. So he had a real moral backbone from the beginning, even when he was struggling, really struggling.

And he said, there was a great possibility he could have ended up homeless because he was putting everything he could into acting and if it hadn’t succeeded, things would’ve looked really bad. So he really struggled. And on electric company, he was frustrated and Rita Moreno said, look, we didn’t know how much talent this guy had. It was then after that that he made his feature film debut when he was well into his 40s. It was in the Robert Redford movie Brubaker. And then in his early 50s, he had an Oscar nomination for a movie called Street Smart. But then he had a real banner year that included both Glory, which he’s co-staring with Denzel Washington in Driving Miss Daisy, when he was 52, although he was playing a 60-year-old then. But it’s very funny because an interviewer once asked him about the struggle of being an older actor.

And he said, I can’t tell you about the struggle of being an older actor. I can tell you about the struggle of being a younger actor. And I think he… There are actors out there, I think Angela Lansbury was, even though she had been a success early on, but there are actors who grow into their roles, who somehow they’re meant for real success later because, maybe because in the case of Morgan Freeman, that great voice and that gravitas he had, I mean, you can’t play God when you’re in your 20s.

Brett McKay: Right.

Mo Rocca: And no one has played god like Morgan Freeman or sounded like it. Since he turned 60, he’s been in 80 movies. I mean, that is the opposite of what we think of as a Hollywood career.

Brett McKay: Yeah. Like Clint Eastwood had, I mean, he was a big star when he was young, but I’m always amazed that he’s kept on producing and acting even in his 70s, 80s, and 90s.

Mo Rocca: Well, I think Clint Eastwood and actually I’m not bragging here as a college kid, I got to meet Clint Eastwood and my god what star wattage, but Clint Eastwood is amazing because to be this international film star known for Dirty Harry and Spaghetti Westerns and then just say, no, I wanna make movies and I wanna make good movies. And we forget now but there were so many naysayers early on, and Clint Eastwood has made so many different kinds of movies and I mean, talk about somebody who is not concerned with what other people think of him and just does it and has continued to grow. And like we were talking about before, just not respecting this idea, this artificial idea that you have a sort of an arc that you kind of have to observe that you do one thing and then when you’ve peaked, that’s kind of it. And no, I mean, it’s amazing.

Brett McKay: So we gotta talk about Mr. Pickles. Why did Mr. Pickles end up on the octogenarian list.

Mo Rocca: Well, we wanted to… John and I wanted to include personal milestones and because, not to make them all career or even creative or entrepreneurial, or sports, late in life achievement, but personal ones like marriage and parenthood. And Mr. Pickles is a Houston Zoo tortoise, I say is because he’s expected to live for many more years, like most radiated tortoises. And he became a first time father at 90. And, you were impressed by Al Pacino fathering a kid at 83. He was just a kid in comparison with Mr. Pickles. Mr. Pickles has, by the way, the three kids are named Jalapeno, Dale and Gherkin. Lucky he’s gonna live a long time. He could have a lot more kids. He could become the Nick Cannon of tortoises.

Brett McKay: Yeah. He’ll get to meet his grandkids too. So are there any, we’ve talked about some lessons you’ve learned from all these people we’ve talked about, but are there any through lines you found in these stories? Any overarching takeaways that you found while writing this book?

Mo Rocca: Yeah, and I’ve mentioned some of them, but I think the first one will sound, I think really obvious, but these are people who are very much in it. They’re not fixated on the past, that’s for sure. And this is what surprised me. They’re not fretting about the future. I always thought, even as I got into this project, I thought the less time you have on the other side, the more frenetic you’re gonna become about Oh my God, time is… And while there certainly is an urgency to many of these stories, there’s nothing frantic or fretful about them. So they’re neither fixated on the past, nor fretting about their future. They’re very present minded and in it, they’re very in it, which is where I think we all wanna be, which is why we should spend… And this is a note to myself, spend a lot less time on social media. So you can really be in it and not distracted. I think, as I said, these are people who were not overly concerned with what other people would think. And I think another one of these patterns is kind of a return to an early love to unfinished business.

Brett McKay: I love that. Well, Mo, this has been a great conversation. Thanks so much time. It’s been a pleasure.

Mo Rocca: Brett, thank you very much.

Brett McKay: My guest today is Mo Rocca. He’s the co-author of the book, Roctogenarians. It’s available on amazon.com and bookstores everywhere. Check out our show notes at aom.is/lateinlife where you can find links to resources. We can delve deeper into this topic. Well, that wraps up another edition of the AOM podcast. Make sure to check out our website @artofmanliness.com, where you’ll find our podcast archives. And while you’re there, sign up for a newsletter. You have a daily option and a weekly option through both three. It’s the best way to stay on top of what’s going on at AOM. And if you haven’t done so already, I’d appreciate if you take one minute to give us a review on the podcast or Spotify helps out a lot. And if you’ve done that already, thank you. Please consider sharing the show with a friend or family member you would think get something out of it. As always, thank you for the continued support. And until next time, this is Brett McKay, the Art of Manliness podcast, but put what you’ve heard into action.

This article was originally published on The Art of Manliness.

You have a relationship with family, with friends, with a romantic partner. You may not have thought about it this way, but you also have a relationship with your job — a quite serious one, in fact; after all, you spend a third of your life working.

Just like the relationship you have with your significant other, there are ups and downs with your relationship with your job. It can start out with exciting honeymoon feelings, but along the way, you can end up drifting apart from your job, lose interest in it, or not feel appreciated. And there can come a time when you start wondering if you and your job should part ways.

Here to help you figure out if you should break up with your job is Tessa West, a professor of psychology and the author of Job Therapy: Finding Work That Works for You. Tessa interviewed thousands of people who have recently switched jobs or undergone career changes and found that there are five forms that job dissatisfaction typically takes. Today on the show, Tessa shares those five job dissatisfaction profiles, and how to know when you need to try to move into a new role within your company, or move on altogether and even change careers.

Resources Related to the Podcast

• Tessa‘s previous appearance on the AoM podcast: Episode #834 — The 7 Types of Work Jerks (And How to Deal With Them)
• AoM Article: 30+ Questions to Ask Yourself Before Leaving a Job
• AoM Podcast #578: Figuring Out If You Should Change Careers (And How to Do It)

Connect With Tessa West

• Tessa‘s website
• Tessa‘s research lab

Listen to the Podcast! (And don’t forget to leave us a review!)

Listen to the episode on a separate page.

Download this episode.

Subscribe to the podcast in the media player of your choice.

Read the Transcript

Brett McKay: Brett McKay here, and welcome to another edition of The Art of Manliness Podcast. You have a relationship with family, with friends, with a romantic partner. You may not have thought about it this way, but you also have a relationship with your job, a quite serious one, in fact. After all, you spend a third of your life working. Just like the relationship you have with your significant other, there are ups and downs with your relationship with your job. It can start out with exciting honeymoon feelings, but along the way, you end up drifting apart from your job, lose interest in it, or not feel appreciated. And there can come a time when you start wondering if you and your job should part ways. Here to help you figure out if you should break up with your job is Tessa West, Professor of Psychology and the author of Job Therapy: Finding Work That Works for You. Tessa interviewed thousands of people who recently switched jobs or undergone career changes and found that there are five forms that job dissatisfaction typically takes. Today on the show, Tessa shares those five job dissatisfaction profiles and how to know when you need to try to move into a new role within your company or move on altogether and even change careers. After the show’s over, check out our show notes at aom.is/jobtherapy.

All right, Tessa West, welcome back to the show.

Tessa West: Thank you again for having me.

Brett McKay: So we had you on last time to discuss your book, Jerks at Work, and how to deal with those jerks you sometimes encounter at the office. You had a new book out called Job Therapy, where you dig into our relationship with our job. And I think a lot of people typically don’t think about having a relationship with their work. A job is just something you do. What got you thinking about work in terms of a relationship?

Tessa West: Yeah, this is a great question. I think a bunch of different things, but just to kind of give you a little bit of background, I’ve been teaching a close relationships class at New York University now for 15 years. And so I’ve been thinking about how we go from the kind of initial attraction stage, so the first date, which is a lot like a first interview, all the way through that stage where we get a little bit itchy and we start drifting apart from our partner, the ambivalence, those feelings we have that are a little bit complicated, the emotional ups and downs, and all the way through the end of a relationship when we decide to break up.

And what I noticed in the past couple years is that there’s just been kind of this shift in how we talk about work using these relational concepts. And so every time I taught, and this was last semester, we would talk about what can go wrong on a first date. And at the same time in my consulting and in my research, studying the workplace, people were asking me the same types of questions about interviews. And when they were trying to process whether they should break up with a job that they’ve been committed to for a long time, they would ask me questions about identity loss, like this hole in my heart, how am I gonna fill it? And that’s the same language we’re using around marriages.

And so, I started to kind of see these two worlds I live in converging and these concepts starting to overlap in ways that I think most of us had never really thought of before. And that’s really when I decided to adopt a relational perspective to think about your career as just another thing that you have a relationship with, much like a person.

Brett McKay: So, a lot of people are unhappy with their current jobs, but they’re unhappy for different reasons. If you ask five different people why they don’t like their job or their career, they might give you five different reasons. And you took a deep dive to find out what are the top reasons people are unhappy at work. So, you did this massive survey. What did you discover?

Tessa West: I think most of us, if you ask someone why, they don’t truly know. And so, you kind of have to ask more indirectly about how they’re feeling. And so, what I found was that a big chunk of people, especially those who’ve been working for a really long time, they have a crisis of identity. They used to love this thing. And the thing is, tends to treat them very well. The career does. But they don’t feel as strongly identified with it as they used to. And there’s a lot of shame and guilt that goes along with that. So, that is the crisis of identity person. Kind of in a similar vein is the person who’s drifted apart from their job. And this is the person who’s pretty nostalgic about what that job used to look like. It could be that the whole industry has changed. Maybe it’s just this company. But it’s a little bit like waking up and looking at your spouse in bed and thinking, who are you? I don’t recognize this person anymore. And for those people, they really have to dig deep to understand kind of what is the source of that drifting apart. Is it really just the job or is it also them?

And then the third is the person who’s stretched too thin. And I actually wrote this chapter for everybody. I think we all know what it feels like to be juggling multiple roles or tasks or to be task switching all the time that we’re not getting anything done. And so, those individuals tend to have taken a few missteps along the way in terms of absorbing roles or taking on what I call high visibility roles that they think will get them a raise or promotion, get them on the map, so to speak. But they end up just kind of being all over the place or interrupting themselves constantly at work.

And then the last two chapters are for people who are not getting the love back from their careers. So there’s the runner up. We all probably, if you’ve worked long enough, you know what it feels like to get passed up for raises and promotions. And you don’t really know why. There’s a huge kind of gap there between their understanding of what they’re doing wrong and what leaders think they should be doing instead. And then the underappreciated star, the person who gets a lot of nice Slack messages or emails, but the real rewards aren’t coming and they’re often kind of dangled in front of them in some sort of like hypothetical future, if you stick here long enough, you’ll get that president job in a year and then eventually the C-suite and once we have enough money, you’ll get that bonus. And so, they really have to figure out if they can get compensated better elsewhere and how much organizations actually even really care about hiring stars. So, those last two chapters are really about trying to get the love from that relationship with your career back that you are feeling towards it.

Brett McKay: Okay. So, these are the top five. We got the crisis of identity, the drifted apart, the stretch too thin, the runner up, the underappreciated star. We’re gonna dig into each of these here in the conversation. But you also found before we talk about these five different types of dissatisfaction profiles, you also talk about there might be a lot of job dissatisfaction that just comes up from like daily stressors that we tend to overlook with a job. It’s not even that you don’t identify with your job anymore or you feel like you’re stretched too thin. It’s just the other stuff that we overlook when it comes to having a job that might be causing us dissatisfaction. What sorts of stressors are those?

Tessa West: Yeah. I think most of us experience a lot of low-level stress at work, but we don’t actually see how it kind of builds up and affects our happiness at work or our engagement or these kind of like bigger picture things. And I think what I did for this chapter was I ran a simple study where I asked people in the morning, what do you think is gonna stress you out today? What your biggest stressor is gonna be? And then I asked them again to do it in the evening, what actually stress you out? And there’s not a ton of overlap. And I think it’s because anticipated stressors tend to be big things. They tend to be things like a presentation I have to give, a meeting I’m really nervous about.

What people reported are what I would call like certainty-based stressors, thing that they can anticipate and then plan for. And because you can plan for those things, you actually don’t end up experiencing that much stress. You put some steps in place to make sure you can handle the thing. We call this a challenge response in health psychology. But what ends up actually stressing people out are pretty small things. And many of them, we tell ourselves we can’t anticipate, but we actually can if we’re a little bit more strategic. A commute that ran too long. Your parking space has been taken up. Your boss putting a last minute deadline on your calendar. Someone interrupting you at work. Those things that we don’t really see coming in the morning, but they end up being additive and really stressing us out.

But kind of ironically, what I found is that even for those things, if you ask someone if they’ve experienced it before, they’ll tell you, oh yeah, I experienced this all the time. They just don’t encode it as a stressful thing. And so they don’t think about it again and they don’t plan for it. But most of the time, we’ve had that last minute meeting put on our calendar. We’ve had that commute go long. We’ve had our parking space stolen and so forth. So if we just kind of keep track of these things, we can actually do a much better job of mitigating their effects on us.

Brett McKay: And what that can do, I think a lot of people, they might experience those sort of daily stressors, mundane stressors. They think, well, I just hate my career. I hate my job. Well, it might not… Maybe your career and job’s fine. You just got to take care of those things like the job or career you have right now. It’ll be great.

Tessa West: Yeah. I think we tend to catastrophize a little bit when we’ve had an accumulation of small stressors. It’s a little like anyone who’s been a parent and they have a kid who misses a nap and they just lose it completely and cry over everything. I think there’s an adult version of that, which is an accumulation of small daily stressors. They affect our health. They affect our sleep. And that in turn affects our ability to cognitively function, to regulate our emotions at work, to handle difficulties that come flying at us. And I think that we do dramatically underestimate the effects of those low-level things. And then we catastrophize and tell ourselves, oh my gosh, this job just isn’t a good fit for me. I feel really miserable right now. But because we haven’t identified the source, we attribute it to something big and existential. And that’s where I think your first step is just to keep track of those low-level things to try to correct for those before you get into the deep kind of psychological issues you might be experiencing.

Brett McKay: Okay. So let’s dig into those deep psychological issues. Let’s say you took care of all those stressors and you’re still not feeling happy with your job. Your book is designed to help you figure out why you might not be unhappy, why you might be unhappy with your job or career. And that first one you said is the crisis of identity. And this is someone who starts a job or career. It’s a good fit initially. They enjoy it at the beginning. They actually get really good at their career job, but then they start having second thoughts. So what are some signs that the crisis of identity is the reason you’re unhappy with your job?

Tessa West: So I think there’s two things that you need to do. I give you kind of this checklist of, is your career identity a central part of who you are? And a lot of people who are having a crisis of identity still say yes to that question. Things like when I think about, for me, when I think about being a professor, that’s really important to how I see myself. It’s central to my self-esteem. So you wanna measure that and you wanna measure it over time because I think we have days in which we feel highly identified with our work and days when we feel less identified. You wanna measure how stable that so-called identity centrality is over time.

But the second core piece is what we call identity satisfaction. And so you can be really identified with your career. It can be a core piece of who you see yourself as a person and hate it at the same time. Hate the fact that your self-esteem is yoked to this thing, that this thing doesn’t bring you happiness. And I think a lot of people having a crisis of identity kind of fall into that dangerous quadrant of high centrality and low satisfaction. We see this a lot in healthcare with burnout and things like that. And that can create a lot of ambivalence in people where you sort of love and hate your job at the same exact time. And that to me is the big warning sign. Not that you hate your job consistently, but that you feel like it’s a core piece of you and you’re not happy with it. And you kind of love and hate it on and off, often within the same day. In relationship science, this kind of heightened sense of ambivalence tends to be what predicts when people break up. Not so much just consistently being negative, but feeling really kind of angsty inside when you think about your career.

Brett McKay: Yeah. Your crisis of identity, that high centrality, low satisfaction. It’s like your job’s your frenemy. You love it and hate it. We’ve had podcast guests talking about that. That’s like the worst type of relationship you wanna have with somebody.

Tessa West: Yeah. It is the biggest predictor of getting into an on-again, off-again relationship. If you don’t actually sort of resolve that identity centrality and you start kind of exploring new identities before you leave, that’s really key. Otherwise, it’s just like breaking up with your ex and getting back together because you have nothing to kind of fill the void. The same thing can happen at work.

Brett McKay: Give us some more concrete examples of what it would look like if you had high career identity centrality. You think of yourself as ex-profession, but low satisfaction. What contributes to that low satisfaction?

Tessa West: It’s a lot of intermittent reinforcement at work, I think, that really does that, that puts you in that unique quadrant. It is your boss reinforcing you in a way that is difficult to predict. You don’t know when you’re going to get a pat on the back or told you’re great. You don’t know when you’re gonna get ignored or told you’re doing poorly. It’s a very unpredictable reinforcement schedule. We know from behavioral science that that’s the best way to keep people yoked to something that they don’t actually love. And so if you are getting reinforced, but if you keep track of that reinforcement, and by reinforcement, I just mean anything from a bonus or raise, those are big forms of reinforcement, to small ones like people recognizing your contributions at work. If you can’t predict when you’re gonna be positively reinforced for what you’re doing at work, then you’re gonna get really strongly pulled into that pattern where you have a hard time letting go.

In fact, reinforcement, it works on monkeys, it works on rats, it works on humans in relationships. I think it actually makes you more identified with something than even just getting positively reinforced consistently does. There’s something about the uncertainty, the lack of predictability that really keeps people tethered to these things that they don’t love. I think that’s where it gets a little bit scary.

Brett McKay: Okay. So if your identity centrality is high and your identity satisfaction is low, that might be an instance where your career is fine. Your chosen career is great. You just need to find maybe another place to do that career.

Tessa West: Yes. I think the biggest mistake people make is they act on that identity satisfaction and think they should just completely pivot to something new. And then they realize a little bit into that journey that, oh, wait, I actually missed my old thing. Well, you need to measure your centrality around that old career before you make that pivot. So if you have that low satisfaction, before you pivot, you wanna make sure that that identity centrality is consistently low for a period of time. And so you’re absolutely right. If you find high centrality, identity centrality consistently for a while, a couple of weeks, a couple of months or whatever, then you probably are just more in a place where you wanna stick with your career, but you need to find it elsewhere.

Brett McKay: Okay. What happens if you have low identity centrality with your career? Let’s say you’re a professor and at the beginning of your career, you think or you feel like this is what I was meant to do. I enjoy doing this. I enjoy being professor. But then 10 years later, you’re just not feeling it anymore. It doesn’t seem like that’s what you’re supposed to be doing. How do you go about trying to figure out what your next career is? How do you go about making that big change from professor to something else?

Tessa West: Yeah. I think the first step you wanna do, and this scares people, but I think before you quit your job, is you actually need to start dating new identities. And I probably take this metaphor too far. But you need to actually try on new identities, develop a clear sense of what your future identity is going to look like before you make any moves. And the only real way to do that, it isn’t by reading company websites or taking extra courses. It’s by networking and having 15, 20-minute conversations with people in new careers where you can do things like tell the difference between two things that sound similar but are actually super different or learn the hidden curriculum around what it really takes to succeed or learn jargon, which I know gets a bad reputation, but we use it anyway.

So really kind of exploring these new careers to develop just a clear sense of what your future identity looks like or could potentially be before you ever take that next step. I think too many of us are attempted to quit, take some time off, take some extra courses, apply for jobs before we do that whole developing the new identity thing. We think we can’t develop an identity around a career we haven’t jumped into or haven’t tried yet, but I actually don’t think that’s true at all. I think you can actually start to understand what that identity would look like should you be in it by doing this networking. I think that’s a really important kind of in-between step people need to do.

Brett McKay: Yeah, so before you quit, talk to a bunch of people who are in that career you’re thinking about. I think another thing you could do too is do some moonlighting. Maybe you wanna be a writer. Well, try moonlighting as a writer while you still have your job or you’re like, oh, I hate my corporate job. I wanna become a pool cleaning guy. Start cleaning pools and see what it’s like. Do it on the weekends, for example.

Tessa West: Yeah, you have to try it out. I meet all kinds of people who think a career would be a good fit for them because they think really big picture in terms of it. Someone wants to be a nurse who I talk to because she cares about helping people and she really wanted to just do that. But when she got trained as a nurse during COVID, so very, very little hands-on training, but then she kind of realized she hated the sight of blood and cleaning up poop, which turns out to be like 80% of your job as a nurse. And those just kind of like what is the day in the life actually look like is something that you can’t know unless you actually kind of try the job on a little bit and try it. And I think the moonlighting piece is really important. I think people are afraid to do that or they feel like they don’t have the time or the mental resources to do it, but you’re not gonna know how that new job feels, whether it fits you, unless you actually sample it a little bit first.

Brett McKay: Yeah. People can have this problem even at the start of their careers. I went to law school. I thought I wanted to be a lawyer since I was in high school because my idea of being a lawyer was like watching Matlock and law and order. And then I went to law school and I had to do my internship and I did my first internship at a big firm. I hated it. I absolutely, like I just did not suit my personality. So yeah, that can happen at the beginning. So I think I would have been better served before going to law school. Like I didn’t know any attorneys too. I just thought, I had no clue what it meant to be a lawyer. I think it would have been better served to maybe talk to a bunch of lawyers, maybe like in high school or college work there for the summer to see what it was like. That would have been helpful.

Tessa West: I think, yeah, I would add another piece of advice, which is like when you’re doing this, the temptation is to find a bunch of people who kind of know each other and network that way. So, you find a lawyer and then you ask that lawyer for another lawyer you can talk to and we call that snowball sampling. It’s a great way to network. But when you do that, you get a lot of overlapping information about a career ’cause those people have things in common with each other that might not actually reflect what it’s gonna look like for you. So you wanna actually network with people who don’t know each other, who don’t have completely shared histories or even work in the same organization. ‘Cause you wanna look for that kind of signal in the noise across all these diverse people to understand what that career could really look like. I think one big misstep people do is they talk to 10 people, all of whom have the same boss or work for the same organization and then they overgeneralize those 10 people’s experiences to what that career would look like for them. And then there’s just nothing in common. And I think you really have to really broaden your network in that early stage, talk to a litigator for you but also maybe someone who works for the county. All kinds of law just to get a little bit of sense of the heterogeneity of that career.

Brett McKay: And then when you’re talking to people you have this great question to ask to really get information you otherwise wouldn’t get to really figure out what it’s like to have this career. And the question is, before I started this job nobody told me that… And then have the person finish because then you might learn some things that you probably didn’t know and wouldn’t have even known to ask.

Tessa West: Yeah, I think I love this question. It’s based on this NPR really funny thing they did of, I must have missed that day where people talk about late knowledge that they accumulated. And I gave this survey to a bunch of people and I got like really wild answers. All kinds of things from like weird hidden norms. Like I didn’t know that I had to bring chocolate once a week to the boss to, I didn’t realize that as part of my job running this art gallery, I had to lift heavy boxes and most of the things people reported were extra roles and responsibilities that they were assumed to do that was normative to do but they were not hired to do. And I think that’s one of the main reasons why we actually drift apart from our job or have an identity crisis is because of this sort of like lack of role clarity, being asked to do random stuff that has nothing to do with the job. So you wanna get a sense of what weird randomness you might encounter should you take on this career. And I think the answers will surprise you and people are always a little bit surprised when they get asked that question, but they come up with like pretty interesting and creative answers. So that was kind of one of the more fun things I did for this book.

Brett McKay: Okay. So with crisis of identity, you wanna look at your identity centrality, identity satisfaction. So if you are still, you still have a high identity centrality with your career, but low satisfaction, maybe you don’t jump careers completely, you just find another place where you can get that satisfaction again, then if your identity centrality is low. So maybe you started your career thinking yourself as a lawyer, professor, teacher, et cetera, and you’re not feeling that anymore, that’s when you might think about jumping ships to different career. But before you do that network, ask around, figure out what it’s like with these new careers, you’re dating other careers and maybe even moonlight. We’re gonna take a quick break for a word from sponsors.

And now back to the show. Let’s talk about that second reason you’ve found that people are dissatisfied with the work and that’s when they’ve drifted apart from their job. What does that look like and how do you know that’s your dissatisfaction profile?

Tessa West: So the drifted apart person tends to think about what their career used to look like. So their happiness is anchored on the past and they’ll use very nostalgic language. I really loved it when we all worked under the same roof and now we’re hybrid. They will often… I gave people a checklist of a bunch of items. They’ll often check off a whole bunch of things that have changed at work. And the most common are the people you work with. So relationships, who your boss is who’s on your team, whether that best friend from work is still there and they recognize that a whole bunch of little things have changed but they often have a very difficult time seeing how all of these things have led to them just feeling on we at work, feeling bored and not interested and no longer motivated.

I think what’s fascinating is a lot of us tend to think that some big picture change like a restructure or a round of layoffs is what led to these things. But even the leaders I surveyed said that it’s very hard to draw those associations. So we’re left with a million kind of death by a thousand paper cuts at work, a million little things that have changed but no sense of how they all kind of work together to lead us to feel this way. And then coupled with that is a bit of an underestimation of how much we’ve changed at work, how much maybe our preferences have also changed that have contributed to this feeling. So we know we’re unhappy, we think we still like this career but we’re not quite sure why. And that’s where a lot of the soul searching goes.

Brett McKay: So what are some questions you can ask yourself to figure out whether you need to jump ship to a different career? Maybe you just gotta change things with your current career?

Tessa West: I think for the drifted apart, the main mystery here is if one type of change will happen in the workplace, is it gonna trickle down to affect a type of change that they really don’t enjoy? And whether that’s industry-wide or not. And I think for them is this a new career issue or is it just my job really comes down to has the whole industry changed? And a lot of people who feel drifted apart at work who are nostalgic for their old job really think it’s just their workplace. They think very locally about the changes, but often once they start networking and exploring things they actually realize there’s been kind of this just massive evolution of the whole entire industry and often in ways that they don’t totally anticipate.

So, one person I talked to was a school psychologist and that used to involve a lot of therapy and now it’s just testing. And why has that happened? Well there’s been some state regulations around what a school psychologist can and can’t do that has just fundamentally altered the nature of that career. It doesn’t matter what school district you’re in, you’re just gonna be doing testing all day long. People who feel it and just kind of a very much in the moment way have had AI introduced into the workplace or things like new software programs that they have to use. And so they don’t actually understand how widespread these changes are and that’s really what they have to first decide is, are there so many changes to this whole industry that I no longer recognize it and I need something completely different or is it just my place has gotten weird and different and I could actually kind of find what I used to have somewhere else.

Brett McKay: Gotcha. Yeah, I think that’s interesting. The idea of industry-wide changes causing you to drift apart. You’ve been seeing a lot of this, going back to education, a lot of teachers are quitting teaching and you ask them why and they just say, Well it’s just the profession of teaching, particularly in public schools has changed dramatically. We had to do different things like this is not the thing I signed up for when I became a teacher.

Tessa West: Yeah, there’s a huge emphasis on state testing performance and so now they all have to just spend so much time doing test prep, very little flexibility in curriculum. There’s a lot of kind of like top down direction giving of what you can and can’t teach. So teachers who really value creativity feel stifled in the classrooms. So they’re looking for jobs in which they can like kind of do that piece of it elsewhere. But I think for them the struggle is often, well where can I actually do that? Who does value that piece of me? That kind of creative curriculum building piece and then how kind of fungible is that skill into a new career and how can I talk that new career into believing me that this skill has utility in that job? And so learning kind of how to transfer skills is super important for people like that, for people like those teachers.

Brett McKay: Okay. So if you feel like you drifted apart, you need to figure out whether this is just happening at your particular job or if this is a larger thing and if it’s a larger thing that may suggest you need to jump ship to a different career pivot.

Tessa West: Yeah, absolutely. And I think you also wanna document your own changes. I talk about in the book about framing this not in terms of what you used to love and now hate but in terms of your preferences for specific types of work to kind of pull the emotions out of it a little bit. I used to prefer X and now I prefer Y. So that when you network you can kind of anchor those conversations around whether that type of task you’re interested in that preference is reflected in what people are doing in that other job.

Brett McKay: Gotcha. Alright, so the third reason people might feel unhappy about their work is the stretched too thin. And you said earlier you think a lot of people, even if they’re pretty happy with their career job, a lot of people might be experiencing this. So what are some signs that you are the stretch too thin dissatisfaction profile?

Tessa West: One of the main things is you have a really hard time rank ordering the importance of your roles at work. So, I kind of talked a little bit about like there’s two issues, there’s the role stuff, what you’re doing, what your actual job is and then how you work. The role thing I think is a real problem. I think we have our assigned roles, the roles that we’re paid to do. And then we have most of us spend like 8-10 hours a week on roles that we weren’t assigned to do, many of which we’re not even paid to do. And you need to ask yourself the question, write out all your roles at work rank order them in terms of most to least important and importance in terms of what you care about, but also importance in terms of what matters for promotion and raises and so forth.

And if you have a hard time with that rank ordering list, you probably actually have no idea what roles you should be focusing on. I think, a lot of us work in places where it’s normative to take on the role of somebody else when they’re out or if they’ve been laid off, there’s a lot of role absorption going on. But one thing that people also do is they volunteer for roles that they think will make them visible. Things like running an employee resource group or a conference committee, these kind of community building roles that are helpful but your performance on those roles are rarely discussed by leaders during promotion decisions.

And so you feel good and you get a lot of pats on the back and everyone loves you for taking these things on, but they don’t actually matter as much as you think you do. So I think you really wanna sort of critically evaluate your own roles. And then the second piece is how you actually work. Are you switching tasks so often you’re getting nothing done. And I think most of us are used to task switching. Most of us are also not very good at preventing ourselves from interrupting ourselves. And so most of those interruptions are so called self interruptions.

And so kind of figuring out what your pattern is there of like how you can actually just be more productive at work by interrupting yourself or having others interrupt you more strategically so that when you jump back into something you can actually kind of have a much more systematic workflow. I talked to neuroscientists for this chapter because a lot of why we feel stretched too thin actually comes down to the memories we form at work and our ability to kind of start where we left off has to do with how good we were at encoding what we did in the first place. And when we interrupt ourselves a lot, we don’t encode those memories of what we are working on and that makes it very hard for us to pick up. So I think there’s some little things you can do, some strategic things you can do to kind of reduce that mental load of task switching.

Brett McKay: So if this is your dissatisfaction profile, there’s actually a lot of things you can do with your current job to maybe remedy. You can talk to your boss about the distractions or the multiple roles and maybe you can reduce some of that but it might reach a point where it’s just expected that you do these multiple roles and you realize you’re not gonna be able to do the work that you want to do, well. That might nudge you to look for another job.

Tessa West: Yeah, I think one thing that happens a lot is organizations talk out of both sides of their mouth. They say that they’re really good at promoting people internally into leadership positions, but at the same time they ask everyone to do all the things at once and they’re not very strategic about how they get you to prioritize roles and then they kind of like shift the narrative on you like, well the reason why you weren’t promoted is because you weren’t good at prioritizing your work. What they don’t realize is that maybe the middle manager is asking 15 people to do all of these different jobs at once. And so if your own leader manager can’t help you with that task of just prioritizing your roles most important to least important and they keep telling you that there’s a tie between one and two and five and six, then that’s probably a red flag that they don’t even know, what this should look like. And they’re not even sure about people who’ve been successfully promoted and how they prioritize their own roles. So, you can make that list and go out into the world and talk to hiring managers with your role prioritization and during interviews ask them point blank how are you gonna help me stick to kind of this rank ordering of roles when people start nudging me to do additional work. Like what process do you have in place to sort of protect me to insulate me from that role creepage that a lot of us are feeling at work. And I think that’s a fair question to ask.

Brett McKay: And as you were talking it reminded me it might be useful too if you’re feeling stretched too thin to do a broader view of the, your career landscape. ‘Cause you might find, Okay, I’m feeling stretched too thin at this particular company or organization. Maybe if I just go somewhere else and keep the same career, you might find the same problem because industry-wide, they’re asking these people who have this career to do multiple roles no matter where you go. So you might have to do some more investigation like talk to your friend who lives in Nebraska or different states. Are you seeing the same sort of thing in your career? Like if you’re a teacher, are they having you do this, this, this, this? And if it’s like, Yes, and it’s like well maybe this is all over the place, maybe I have to go to a different career.

Tessa West: Yeah, absolutely. And I think, some people can handle that sort of milling things at once. Some people are really good at boundaries. Others are yes people and they’re people pleasers and if you are a people pleaser and you have a hard time saying no or you care a lot about your team liking you, then you know your achilles heel at work is gonna be taking on the extra work of people taking on those extra roles. And another kind of interesting thing I learned when writing this book is that a lot of times when we are taking on extra work of people, it’s not because there’s a free writer problem in our teams where people are just sort of offloading. Often this happens in well structured teams that don’t have a free writer problem where people are actually getting credit for their work. What they don’t realize is when you get credit for doing something someone else is paid to do, even if people verbally recognize it, it’s very hard to kind of integrate that information into a promotion decision. Rarely will a boss say, Yeah, this person was amazing, they took on the work of everybody else on the team. I think we should promote them because it makes them look like a bad boss. It makes them look disorganized. And so doing work that someone else is technically paid for, even if you get credit for it in the moment, rarely translates to an actual promotion opportunity. And I think people don’t understand that disconnect. That is pretty common.

Brett McKay: Okay. So the next reason, the fourth reason that people might be unhappy with their job is they feel like they can’t get ahead in their career because they never get promoted or get a raise. They’re just overlooked all the time. I mean you call this the runner-up. Why are some people consistently runner-ups in their career?

Tessa West: There’s a couple sort of really difficult answers to that question. The first one is that they have less status than they think they do. And this is a hard pill to swallow, this idea that maybe people don’t respect you, admire you, they don’t care about your contributions as much as they need to in order for you to get promoted. And I asked people, were you given an explicit reason why you weren’t promoted and most weren’t, but they had some kind of sense that low status might be at play. I asked people who make promotion decisions why people weren’t get promoted. They kind of said the same thing, no one was really told they don’t have status, but that’s kind of the reason that’s… It’s implied but never actually said. And then among those who successfully get promoted, they’re like, Oh yeah, absolutely. It’s because I was told that I have status. So the only people who are actually sure that status matters are those who are successfully promoted. ‘Cause it’s easy to tell someone when they have status. It’s very hard to tell them when they don’t. And I talk a lot about in my book of like how to read status, which is this kind of complex topic around things like if you write an email to the boss, how quickly does the boss reply versus if someone else does, is it quicker or slower? Status is often conveyed very indirectly through these subtle ways. When you contribute to a meeting, does your contribution stick?

Do people build on it or do they always switch topics? And this kind of like soft nebulous construct is one of the main reasons why people keep going up for promotions and not succeeding because they don’t have as much status as they think they have and they don’t, they’re never told that and they have a really hard time correcting for that. So I think, that’s kind of one of the trickier things that you have to learn about yourself. One of the more kind of threatening, stressful ones, some of the kind of more obvious ones are things like you’ve missed a couple key roles along the way. So you’ve got maybe a battlefield promotion. You were hired into a position of leadership that you really didn’t have the experience for, but you missed one or two things in the past. And whoever’s making decisions now really cares about those one or two things. And they can even feel a little bit arbitrary, but they’re gonna die on this hill of we’re not promoting someone without those things. I think those are a couple things. And then there’s the like scary not within your own hands problem. Like, my boss actually doesn’t have enough status to promote me. My boss loves me, but when that person walks into the room, no one listens to who they think should get promoted because they’re not a big enough deal. They don’t have enough tenure at this company. So those are the three main categories of reasons I found that people really struggle.

Brett McKay: Okay. So you have to become more status savvy if this is your problem and you talk about again like status, you said it’s very subtle. You have to pay attention to how people respond to you, how quickly they respond to you, to emails, et cetera. Because you don’t want to ask, Hey, do I have status? Do you guys think I have high status? ‘Cause everyone’s like, what the heck, you weirdo? You don’t ask that question.

Tessa West: Yeah, I know it’s a totally weird question. Yeah.

Brett McKay: But you can ask a question to your boss or maybe your coworkers like, do you think my contributions have an impact? And if the answer’s no, hopefully they’ll give you that honest feedback.

Tessa West: You’re even smaller than that. Say you bring three ideas to a meeting and none of the ideas stick, and they don’t end up being any of the ideas written on the whiteboard. You can talk to your boss or your team members and say, can you maybe give me some insight into why you think those ideas weren’t the ones we went with, or in what ways it was presenting these ideas maybe not ideal. So the smaller, the more specific and behavioral you can get and the kind of the more immediate after the thing, the better. And I think a lot of people in client-facing jobs have this problem where they don’t know why clients don’t prefer them. They prefer someone else over them. And they walk out of that client meeting and think, I thought that went really well. And then they find out, okay, well we got the job but the client doesn’t ever wanna talk to you again. And they don’t… No one really explains to them why that was the case. And it could be something like they interrupted too often or they talked for too long or they were too loud. It could be little things like that that accumulate over time that if you don’t get corrected, you just end up kind of hitting your head against a wall constantly ’cause you can’t move forward.

Brett McKay: So what are some solutions, you mentioned just asking for feedback, figuring out like what you need to do to advance in your job. Let’s say you do those things. How do you make sure your contributions get recognized?

Tessa West: I think that you need to do a lot of work ahead of time to figure out whose voices get heard and why. Kind of one of the more fascinating findings from my work on status is that, it’s not always the person who makes the most persuasive argument. It’s the person who organizes the team ahead of time and says things like, let’s all go around the room and share one idea. And so people have some instincts of what gives them status, and those instincts are talk a lot, come with the most persuasive arguments and interrupt people, those are dominance things. Those aren’t actual prestige things. And so you kind of need to learn how to figure out where your expertise lies, stay in your lane with that expertise and minimize the amount of jocking you do for status in groups.

Nothing loses status quicker than trying to take it from another person in the actual meeting by verbally dominating that person. That is a losing strategy that I see people try over and over again. It’s a very heavy hand in strategy. You gotta kind of do your work behind the scenes, and that includes kind of networking with other high status people who aren’t in your role, so you know who you need to actually impress, who actually matters in this meeting. And so subtle things, subtle leadership behaviors that actually show you care more about the team than the individual is a huge way to gain status. I did a lot of work, a lot of research looking at what’s called a status jolt in the workplace. So this happens when all of a sudden we have our team, we know who has status, we know who doesn’t, and then something happens to the organization to kind of throw a wrench in it, a merger, or we’re now all on Zoom or whatever the thing is.

The people who try to cling to their old status with selfish behavior, by trying to outperform others, not sharing information, not being helpful, they lose their status the quickest. And so clinging to old status is also a way you can lose status in a new team. You need to actually be pretty helpful and not so Machiavellian if you want to actually gain status after jolt like that. So focus more kind of on helping behavior and on transparency around process and around kind of soft leadership. Those are the best ways to actually gain status at work, not by being heavy-handed and loud and interrupting people or even being the most persuasive in the room.

Brett McKay: Let’s say you do all this stuff, you try to do a better job of managing your status at your current job, but you do it and nothing’s coming from, you’re still getting overlooked. So I think it can happen ’cause you’re kind of, people kind of put you in a box. It’s like, well this is Bill. Bill is just this way, even though…

Tessa West: Yep. We know Bill.

Brett McKay: We know Bill, but like even though Bill’s been doing some great stuff, some great moves to make contributions, it’s like well, it’s Bill, he’s just not gonna get a promotion. When do you realize like I’ve reached my limit here. Like people aren’t gonna give me a promotion. Like how do you decide I gotta jump ship?

Tessa West: I love that question. It’s like, at what point is your status, your old status so stuck to you that impression formation change is impossible. Like everyone’s just decided who you are. It’s a bit of like manifest destiny problem. Like you cannot override that impression that people have of you. It’s too difficult. I do think if you’re stuck in that position, and it doesn’t matter what you do, then a learned helplessness is gonna set in and you’re gonna figure out it doesn’t matter if I actually improve here, nobody cares because they are anchoring their judgments on my past behavior. I really do think that’s when you have to consider leaving. If you are getting pretty hard evidence that no matter what you do here, you can never correct for your mistakes of the past. It’s a little like I have cheated on my husband five times, he’s never gonna believe me ever again. Then I think you are kind of stuck.

And we know from the impression formation literature that it’s really hard to override those impressions once we have them of someone. And so I don’t wanna be Pollyannish about this and say you cannot fix your status. You can override those impressions, especially if you’ve been at a place for a while and it becomes kind of impossible, then you might need to actually make a career change. And when you do that, you might have to take a step down before you can take a step up again. You might have to eat a little slice of humble pie to kind of make a move up. You might have to downgrade a bit in order to do that somewhere else.

Brett McKay: All right, so the final one is the underappreciated star. This is someone who’s underpaid and undervalued, compared to what they bring to the workplace. How do you know if you’re an underappreciated star?

Tessa West: I think the kind of first thing that you need to question is, are you actually a star? And I give people a few things you can do to figure out if you have a skill that you are both the best at and is rare at work and both need to be true. If you’re really good at something that everybody can do, then you’re probably not a star. And then the under-appreciation part also takes a little bit of interrogating. So I think most underappreciated stars are told they’re great, but they’re not shown that they’re great in any kind of compensation way that they care about. And it doesn’t have to be money, it can be other perks, whatever the thing is. It’s a lot of promising future compensation. And we see this in small organizations and new startups that don’t have a lot of money or resources to give out. They will bring in a star and they will promise them the world if they just stick around long enough. So if you’re getting a lot of these kind of hypothetical future promises, I’ve worked for organizations that weren’t publicly traded but they promised me stock once they were in which they made up a number to estimate what that number would look like. Those kinds of things tend to be the forms of under-appreciation that people who are at the top of their game experience.

Brett McKay: One factor that contributes to people becoming under-appreciated stars I thought was really incisive is that many companies and organizations are just looking for good enough when hiring. Tell us about this finding.

Tessa West: Yeah, I’m a little cynical about the whole star business, partly because I think most companies don’t actually want a whole bunch of stars. They might not even be able to afford one star. I think a lot of people who are really, really good are in the 99th percentile. They get compensated exponentially more than someone who say the 90th percentile. And so if salaries don’t go up in a linear way, starhood increases. They go up exponentially and it’s often not worth it to pay these stars. And a lot of places who have hired people like this, who have hired so-called geniuses or kind of the more dark version of that as a super chicken that will kind of peck the eyes out of all the other stars to be number one, they find that this is a mistake and that it’s actually better to hire people who are pretty good, who have decent skills, but they don’t have the price tag, they don’t have the expectations of being treated like they’re fancy that come with the true stars, that come with the person who is the CEO at the fortune 100 company or whatever. And I think you need to figure out whether there’s even a market for your starhood. And most places, they can’t afford you and they’re not actually that interested in bringing someone in who is so, so much more powerful than everybody else. There’s a psychological distance that you’ll create should you come to that place.

Brett McKay: Yeah, I imagine this good enough problem is gonna become even worse with the introduction of AI into companies, ’cause like AI can do a lot of the stuff at… It’s starting to be able to do a lot of stuff at white collar jobs. It’s not great, but it’s good enough.

Tessa West: Totally.

Brett McKay: And so companies are like, well instead of paying a human being with all these advanced degrees $100,000 a year to do this job, we’ll just use AI that costs us $20,000 a year.

Tessa West: Oh, absolutely. And I’m seeing this… Any kind of job in psychology where you’re hired as like a consultant to kind of import and export knowledge from science and make it palatable to the masses. So go summarize these 15 academic articles and make a PowerPoint presentation, explaining what growth mindset is. Those people used to make like one 150K, coming out with a PhD in psychology. Now, they make 0K because AI chatbot GPT can do that in five seconds. It’s a little janky. Sure. But someone can take five minutes to kind of make it pretty, add the human touch to it. And so there are just these whole white collar careers that are just being rapidly shrunk, and anyone who used to kind of be good at summarizing things, no longer has a job. And I do think we’re seeing kind of more and more of this good enough problem. Even cropping up a pretty sophisticated levels like coding and things like that, which we used to just really rely on well-trained computer scientists to do, AI does that just as well, if not better.

Brett McKay: Yeah. The thing you have to start thinking about is, well, how can I take that skill that can now be done by AI? How can I take that to the next level, like higher level? What can AI not do and maybe AI can’t make those bigger connections? I don’t know, I’m just kind of shooting off the hip here.

Tessa West: Yeah, I could tell you the jobs AI can’t do that people are really desperate for is anything in hospitality, in healthcare, any human interfacing jobs where you have to actually talk to people. So not like back office jobs where you can chat with your Bank of America app or whatever, but anything that involves like a complex human interaction of any form. And whether that means making a salad or talking to a client or giving someone a shot in the arm, those are the jobs that people are really distrustful of AI. Even like ironically, things that AI could be better at, like radiology and reading scans, there’s a complete distrust. I have a paper on like the trust of this kind of machine stuff. There’s a distrust when there’s no human eyes on it. And so ironically, even some of these things that AI is getting better at, people still wanna hire people for as kind of the last stop. And I think anything like that, if you’re a new career person listening to this, human interfacing stuff where people wanna talk to another human being, those are the jobs you need to start looking into.

Brett McKay: Well, Tessa, this has been a great conversation. Where can people go to learn more about the book and your work?

Tessa West: So you can go to tessawestauthor.com to take the quizzes from Job Therapy and from Jerks at Work as well. If you wanna read about my research, you can go to tessawestlab.com.

Brett McKay: Fantastic. Well, Tessa West, thanks for your time. It’s been a pleasure.

Tessa West: Thank you so much.

Brett McKay: My guest today was Dr. Tessa West. She’s the author of the book, Job Therapy. It’s available on amazon.com and at bookstores everywhere. You find more information about her work at her website, tessawestauthor.com. Also, check out our show notes at aom.is/jobtherapy, where you can find links to resources, where we delve deeper into this topic.

Well, that wraps up another edition of the AOM podcast. Make sure to check out our website at artofmanliness.com, where you can find our podcast archives, as well as thousands of articles that we’ve written over the years about pretty much anything you can think of. And if you’ve done so already, I’d appreciate you to take one minute to give us a review on apple podcast or Spotify, it helps out a lot. And if you’ve done that already, thank you. Please consider sharing the show with a friend or a family member you think will get something out of it. As always, thank you for the continued support. Until next time, it’s Brett McKay reminding you to listen to the AOM podcast, and put what you’ve heard into action.

This article was originally published on The Art of Manliness.

Businesses and individuals often feel overwhelmed and stretched — that they can’t get done all the work they need to. The solution they frequently turn to is finding a new app to use or hiring more employees to spread the load.

But my guest would say that you can steal back hours of productive time simply by using the tools and teams you have now, if you learn to use them in a more efficient way.

Nick Sonnenberg is the founder and CEO of Leverage, an efficiency consulting business and the author of Come Up for Air: How Teams Can Leverage Systems and Tools to Stop Drowning in Work. Today on the show, Nick explains how people spend almost 60% of their time doing work about work, and why hiring more people can actually make the problem worse rather than better. He then shares his “CPR Business Efficiency Framework,” and how making changes in how you communicate, plan, and manage resources can open up hours of time. We talk about how to organize your communication channels so your work day isn’t taken up by what Nick calls “The Scavenger Hunt,” one of the most underutilized tools for taming your inbox, how to stop wasting time on meetings, and tiny changes that will add up to many hours saved each year. Along the way, we talk about how some of these tactics can save you time in your personal life as well.

Resources Related to the Podcast

This article was originally published on The Art of Manliness.

Jim VandeHei didn’t have an auspicious start in life. His high school guidance counselor told him he wasn’t cut out for college, and he went on to confirm her assessment, getting a 1.4 GPA at the University of Wisconsin-Oshkosh and spending more time drinking beer than planning his career.

Eventually, though, Jim turned things around for himself, going on to co-found two of the biggest modern media outlets, Politico and Axios.

Jim shares how he started moving up the rungs of success and building a better life for himself in his new book Just the Good Stuff: No-BS Secrets to Success (No Matter What Life Throws at You). Today on the show, Jim shares the real-world lessons he’s learned in his career. We discuss the importance of matching passion to opportunity, making your own luck, surrounding yourself with the right people, keeping the buckets of your happiness matrix filled, understanding the difference between wartime and peacetime leadership, harnessing the energy of healthy revenge, and more.

Connect With Jim VandeHei

• Jim at Axios

Listen to the Podcast! (And don’t forget to leave us a review!)

Listen to the episode on a separate page.

Download this episode.

Subscribe to the podcast in the media player of your choice.

Read the Transcript

Brett McKay: Brett McKay here, and welcome to another edition of the Art of Manliness Podcast.

Jim VandeHei didn’t have an auspicious start in life. His high school guidance counselor told him he wasn’t cut out for college, and he went on to confirm her assessment, getting a 1.4 GPA at the University of Wisconsin-Oshkosh and spending more time drinking beer than planning his career. Eventually, though, Jim turned things around for himself, going on to co-found two of the biggest modern media outlets, Politico and Axios. Jim shares how he started moving up the rungs of success and building a better life for himself in his new book, Just the Good Stuff: No-BS Secrets to Success No Matter What Life Throws at You.

Today on the show, Jim shares the real-world lessons he’s learned in his career. We discuss the importance of matching passion to opportunity, making your own luck, surrounding yourself with the right people, keeping the buckets of your happiness matrix filled, understanding the difference between wartime and peacetime leadership, harnessing the energy of healthy revenge, and more. After the show is over, check out our show notes at aom.is/goodstuff.

Jim VandeHei, welcome to the show.

Jim VandeHei: Great to be here. Thanks for having me.

Brett McKay: So, you are a journalist and you’re also the co-founder of Politico and also Axios. But you got a new book out called Just the Good Stuff, and it’s an advice book, an advice book about family, career, and life in general. So why did a journalist and media operator decide to write a life advice book?

Jim VandeHei: Yeah, I never thought I would. [chuckle] But I’ve started and I’ve run two big media companies, so Politico and Axios, as you’ve mentioned. And I guess what’s unique is I was a journalist for most of my life before becoming an entrepreneur. So, when I became an entrepreneur, I became a CEO. I took very close notes, usually of all the things that I was screwing up or that other people were screwing up around me, to learn how to do things better. And so I kept these notes, I started writing a column, the feedback to it was very positive. And so I wrote this book ’cause if you met me when I was 20, smoking Camels and drinking and getting crappy grades, you never would have said, “Oh, that dude from Oshkosh is gonna go start a couple of companies, interview presidents, write a book.” And I think I have some obligation to sort of give back, especially to people who might be thinking about career changes or thinking about how do they make the next big move or how do they navigate a difficult situation. So I hope people find it as a really handy user’s guide to life.

Brett McKay: No, and the way you wrote it, the format, it follows that Axio style. You get to the point. It’s nicely organized. It’s easy to read. So I really like that as well. And as you said, you’ve had a lot of professional success and personal success as well. But you mentioned there, you started off life pretty mediocre, and you kind of admit that. You admit that in the book. You’re like, “Yeah, I was kind of a screw-up.” Yeah.

Jim VandeHei: Yeah.

Brett McKay: So what were you like as a high schooler and college student?

Jim VandeHei: I grew up in a small town in Wisconsin. I was like a normal small-town Wisconsin kid. Like I drank, I misbehaved. I occasionally went to school. I got crappy grades. Graduated the bottom third of my high school class. Could barely get into college. Had to go to a two-year college to get into four-year college. Four years took me 5.5 years. At one point, I was on academic probation with a sterling 1.491 grade point average. So it really wasn’t until I found journalism and politics and really got excited about a potential path that I really got my head out of my butt and started thinking about how to go get a career and how to go do stuff that I might be good at. And so, it took me a little while to get there, but I moved out to DC, became a journalist, turned out, a lot of the things that I did when I was misbehaving actually helped me as a journalist. Used to gamble a lot, play poker, teaches you how to deal with people. I used to go to dive bars, so I could deal with people from any kind of walk of life. And I was curious, I love to ask questions, love to talk. And those things worked awesome as a reporter. And in Washington, where it was kind of a lot of elite kids from Harvard and other hotshot schools, I didn’t know any better. So I just kind of stirred up mischief, wrote stories, and ended up being pretty good at it.

Brett McKay: So was that the thing that got you out of your passive mode when you were a kid, just finding something you were passionate about?

Jim VandeHei: A hundred percent. The minute I found something that, like, “Oh, I’m a good writer, I like politics,” and I learned that I could get paid for it, I became obsessed with it. And I think that’s true for most of us. The moment you can match a passion with an opportunity, you’re gonna be on fire naturally. The advice I always give young people now or even old people is, do something you would do for free. Like, I love what I do. I love writing. I love leading. I love starting companies. I love covering presidents. I love writing about AI. I would do this for free if it weren’t my job, but I get paid to do it. So when you can do that, I think really magical things can happen. And it doesn’t just have to be at work; it could be in a relationship or personal hobbies that you have, but I think that’s the good stuff of life.

Brett McKay: How did you discover politics and journalism?

Jim VandeHei: It’s funny. I didn’t even really realize I was that into politics until I was… I would come home, I’d go out to a kegger, and I would come home drunk at 2:00 in the morning. And I would sit and watch C-SPAN hearings on the Agriculture Committee or on a health bill. I was just fascinated by it. I was fascinated that I could watch this. I was fascinated about how a bill became a law. I was fascinating about how people use power, how they communicate. And so that got me hooked on politics. And then when I was trying to figure out what to do, I figured out I was a pretty good writer, and I went to a newspaper and asked ’em, “Hey, I know a lot about sports. Could I ever be a sports reporter?” I was dumb enough to do that, having not even taken a journalism class. And the guy I happened to go to was nice enough to be humored by it. “I’ll give you a writing test.” And I did the writing test, and he’s like, “That’s actually pretty good. I’ll give you a job.” And so I covered high school sports, and it was kind of off to the races from there. And I’d say most of my career has been these kind of serendipitous things that are either courage or luck or some mix of the two that have put me on a course to do things I just didn’t think I would otherwise be able to do.

Brett McKay: Yeah, you got a chapter on luck. What role do you think luck plays in success in life in general?

Jim VandeHei: A ton. That’s why I don’t… I hate these people who are like, “Oh, look how damn smart I am,” and “Look at me.” Yeah, you might be smart, I might be smart, but if other people aren’t putting you in positions to have opportunity, you might just be a smart person who had no success or no accomplishment. And so, I think being ready for those moments of luck is really, really important. I think now especially, I think a lot about my health, my diet, my mindset, my morals, my relationships, to make sure that when luck comes, I’m really ready to pounce on it. But yeah, again, going back to college, so I take a class. I start to take a journalism class, and I say, “You know what? I don’t know if I just wanna do sports.” I literally picked up a piece of paper of every newspaper in the State of Wisconsin. I’m like, “I’ll just call every one of them and ask if I can work this summer, and I’ll work doing something else at night. I’ll do it for free.” So I called, and Brillion News was one of the top ones on there.

I happened to call a guy, Zane Zander, who answers the phone, who runs the paper, and he’s like, “Hey, could you come here today?” And I’m like, “What?” So I drove. It’s only an hour away, so I drove up there. And the guy is like… I explained to him I’ve not really taken any classes. I’m a good writer. I like journalism. He goes, “I don’t care.” He goes, “Well, you run my newspaper.” And I’m like, “Dude, I’ve never really done anything. You really shouldn’t hire me to run your newspaper.” He’s like, “Yeah, well, my editor just told me he’s quitting if I don’t give him three months off to go to Finland.” He goes, “I’ll teach you in one week how to run a newspaper.” And I said, “Okay,” and he gave me a pay package. I’ll never forget this, $300 a week, which was a lot back then, and a place. He had a cabin on a lake filled with largemouth bass. He says, “You can live here. And part of your pay comp is I’m gonna let you have a car that I’ll rent for you, and I’ll always have your refrigerator full of beer.” It was like the best executive package I could possibly have dreamed of. And I ran a newspaper for three months and learned more in three months there than I probably learned in five years of college.

Brett McKay: So, the trick there getting more lucky is just putting yourself out there, I guess.

Jim VandeHei: Yes, for sure. I think you make your own luck. The more you put yourself out there, the more you put yourself in uncomfortable situations, the more you ask questions, the more people you get to know, you just vastly increase your odds of luck coming your way. If you just sit there passively eating Doritos in your couch, you’re probably not gonna make a whole hell of a lot of luck for yourself. So, there’s a combination of effort into really making luck this magical thing.

Brett McKay: So you had a chapter on constructing greatness, and you used Tom Brady, famous quarterback, as an example of someone who did that. What can we learn from Tom Brady about constructing greatness?

Jim VandeHei: Yeah, I used him in that chapter, ’cause Sally Jenkins is a pretty well-known sports writer at the Washington Post, and she had this quote that really stuck with me about how Tom Brady constructed greatness. And he basically was this very mediocre athlete coming out of Michigan. There was nothing that said to anyone that he was gonna be the greatest quarterback of all time. And he willed it into existence. He constructed it, and he did it through what he put into his body, how he treated his body, how he treated his mind, his preparation, his work ethic. And really stuck with me, because I think we all control more than we think we can control. I think so often people just feel like, “Oh, whatever, serendipity,” or “Man, life just dealt me a bad hand.”

Well, no, that’s not true. You actually control every moment, like what you’re gonna eat, what you’re gonna drink, are you gonna work out, are you gonna have a healthy relationship, are you gonna compliment somebody, are you gonna accept a compliment? All day, it’s just a series of things. Just keep track of it, and one day, just write down all the different things that you could control and the decisions that you made. And you could realize, “Man, there’s a lot that we control.” And when you start to realize that you look at life through that lens, you can construct your own greatness. You can have, “Hey, this is where I wanna go. These are the things that I would need to do to be the type of person that I want to be or to achieve whatever goal I’m trying to achieve.” And it just takes on a life of its own once you do it. Like, yes, we’re not gonna be Tom Brady. We’re not gonna be Michael Jordan, but we could probably be a hell of a lot more than we are right now if you adapt that mindset.

Brett McKay: How did you start doing that in your own life?

Jim VandeHei: It was really an evolution. When I was young, in my 20s, I just enjoyed being a reporter, even to my young 30s. Then I had this idea to start Politico, and I became an entrepreneur. And then I realized, “Oh, my God, I might be… I’m actually a pretty good leader. I never thought of myself as a leader,” but I’ve got pretty good morals, values, and I’m confident enough to make decisions. And so I taught myself how to be a CEO. And I just learned that with each of these things that I never thought I could do, once I did them, it opened my mind to the possibility, “Well, wait a second. There’s probably other aspects of my life that I could change. Why can’t I be a runner?” I hadn’t run in years, so I ran a quarter mile, then I started running half marathons. Or why can’t I go from being unhealthy and eating pizza and cheeseburgers all day to somebody who’s really thinking about, what do I put into my body and how does it make me feel and how is it gonna affect my ability to perform long term?

And so I became, I’d say, almost addicted to that now, this idea that there’s things that I can do to keep making myself better at the things that I care about. I wanna be a really good fly fisherman. I’m getting pretty good. I wanna be a golfer. I suck, but at one point, hopefully I’ll be decent at golf. I love to conquer different sort of workout things. I’m really into core power now. I’m not naturally flexible, so it took me a long time to get flexible, but now I’m more flexible. So I just… Your mind, it almost becomes a drug, but like a healthy drug.

Brett McKay: So you got several chapters in the book about avoiding jerks, a-holes, in life and in business. Why so many chapters on that topic?

Jim VandeHei: Probably ‘çause we meet too many jerks and a-holes. [chuckle] Because I hate it. I’ve had so many interesting professional experiences where the job was great, but then you’re working next to a person who just sucks the life out of you. Who’s either bitching and moaning all the time or gossiping or being competitive in a super unhealthy way. And I just realized, “You know what? Just like I can control what I eat or I could control whether I work out or I could control my job, I control who I’m around.” I can decide that if someone’s a jerk, I don’t have to have them in my life. I can either freeze them out, not pay attention to them, or get away from them, whether it’s in a personal relationship or in a professional relationship.

And so by the time we started Axios, which was seven years ago, and now we have about 550 people, the first thing we put on a piece of paper is we’re never again gonna work with people we don’t like. That doesn’t mean we’re not gonna work with super high-achieving, ambitious people, which we do, but they’re gonna be good people. And if they’re not good people, no matter how talented they are, we’re gonna fire them. ‘Cause we don’t wanna be around bad people. And guess what? We’re 550 people and I don’t have any bad people around me.

So once you’ve proved to yourself that you can do that and you tell others to do the same, you can have a pretty magical work experience. And if you think about it, for your listeners who are in a place where they’re dealing with a jerk or they’re in a business or a company culture that they don’t like, they don’t feel it’s on the level, just think about all that negative energy. Think about how many hours of the day you spend either complaining about it or thinking about it or trying to do something about it. It’s all a waste of energy. I wanna design my life in a way where 90%, 95%, 98% of my time, I’m doing things I’m good at with people that I like. That’s gonna make a difference. And when you take on that mindset that that is something that is attainable, it’s not attainable everyday, it’s attainable a lot more often than people think.

Brett McKay: Did you have any moments in your career where you kept working with somebody, you kept a hire that was super… They were a jerk. They were just a complete jerk, but they were extremely competent at what they did, but that ended up biting you in the butt?

Jim VandeHei: Yeah. That was my weakness when I started Politico. I was enamored with people who were brilliant, and I overlooked the fact that they were bad people, that they were cancerous, that they were either… They’re mean, they’re narcissistic, whatever it was. And I had one person in particular who I put into a position of power, and a brilliant person, but just not a good leader, not a good effect on other people’s human psyche. And what happens is people start to hold me accountable for that. They’re like, “Jim, you’re the leader. You’re supposed to protect us. Why would you allow someone like that to bedevil me? That’s just not right.” And they’re right: I was wrong. I made a mistake, and I had done that several times. And I decided after seeing that that I don’t ever wanna do it again. That I’m not gonna make the deal with the devil. I’m not going to take extreme talent that comes with a baggage of bad values. And I jettisoned it. I stopped doing it.

But yeah, for a long time, I made that mistake. And I’d say, almost everything, I think I’m a pretty good leader now. It sounds a little cocky, but I think I am. But it’s only because I was so bad at it at the beginning, ’cause I’d never been a leader. I didn’t know how to hire people. I didn’t know how to create a culture. I didn’t know how to get rid of jerks. I didn’t know how to figure out a diverse set of people who complement the skillset I have. I just knew once… I knew I could outwork anybody. That’s basically what I knew. I could work as hard or harder than anyone. No one was gonna outwork me. Well, that’s not really a great leadership style.

Brett McKay: How do you hire to filter out the jerks? Do you have any criteria or heuristics you use?

Jim VandeHei: For sure. We’ve gotten quite good at it. And part of it is like a screening process of one really trying to talk to people who aren’t on the list of people that they tell you to talk to for character witness, try to find people who really work with them. And were they a good colleague? Do people like them? Do they light up when you say that person’s name? When you’re interviewing the person, some red flags are, if they say anything bad about somebody else, that’s a disqualifier. You just don’t want people who talk crap about their current or previous employers. And then the other red flag is people who say, “I, I, I,” who just seem to be very self-focused, taking credit for things that you probably know were a group effort. That’s another big one. And then being very clear with people. I say all the time, “Listen, you might be the most talented person, but if you’re a bad person, I’m telling you, we’ll fire you. And you’ve got to do a gut check before you come here. If you’ve had problems in the past being narcissistic or being self-focused or not being able to put the cause above your own selfish ambitions, we will reject you.” And so you do those things, and some people smuggle themselves across the border on this one, but most don’t.

Brett McKay: Yeah, and what do you do find one, I imagine you just fire quickly?

Jim VandeHei: Yeah. Yeah.

Brett McKay: Yeah.

Jim VandeHei: The minute you know you got a problem, you gotta get rid of it. And again, it’s hard. It’s a human being. We’re not cold, and it’s never easy to fire somebody. But I don’t really find it that hard firing people anymore, especially if I’m telling people along the way, “Here are the things that you’re doing that you gotta change, or you can’t work here.” The problem with firing is when you’re not being direct with people, you’re not giving them blunt feedback, you’re not giving them an opportunity to change. There should never… By the time you fire someone, they should know when they’re coming through my office door, they’re here to get fired. They’ve had enough conversations with me. I’ve been crystal clear with them. They know they haven’t improved, and they know the end is here.

Brett McKay: Besides avoiding jerks, you got a list of different types of losers you want to avoid. Who are these losers you’re talking about?

Jim VandeHei: Well, you want to avoid people who are super self-focused. You want to avoid people who are blaming other people. You wanna avoid people who don’t sort of carry their weight. So, obviously, I spit on the ball there with the loser thing, but it’s just like it’s people that are just drags in life. They’re not honest. They’re indirect. Hate people who are indirect in terms of like you know that they’re mad about something, but they can’t tell you what they’re mad about. You know that they’re unhappy with you, but they won’t explain why. And so, it’s really trying to find people who are high-achieving. You should never be apologetic about trying to find people from the right gene pool, people who are just super-duper spectacularly talented at what they do. You should never be apologetic for that. But you gotta find people who are… They’re life-enhancing. They’re fun to work with. They lift you up. They make you feel better about yourself. They make others feel better about themselves. There’s a humility to them, even if they’re exceptionally talented. And I’ve been lucky. I’ve been around a lot of those people, and that’s rubbed off on me in a very positive way. And I like good people. I love good people.

Brett McKay: Yeah, you have the list here. They’re all W’s. You want to avoid whiners, whisperers, weasels, wannabes, and wunderkinds, which you define as someone who brags about their own credentials or brain power. They say they’re smarter or better than someone else when deep down, they fear they’re not.

Jim VandeHei: Yeah, those are pretty good five W’s. And yeah, no one wants to be around people who are whining or whispering gossip. It’s just not fun. Life’s too short for that kind of crap.

Brett McKay: Yeah, so if you see some of those things in yourself, maybe you gotta do a gut check and be like, “Ah, I gotta be less of a mope, less of a whiner.”

Jim VandeHei: For sure. And if you’re surrounding yourself with people like that, you gotta be like, “Man, is that rubbing off on me?” You really are. Think about you sitting at work for eight hours with a group of people. Don’t kid yourself. You might be the strongest person in the world, that stuff rubs off on you, good and bad.

Brett McKay: We’re going to take a quick break for a word from our sponsors. And now back to the show.

Well, speaking of the stuff rubbing off on you at work, your job can be incredibly stressful, incredibly intense. How do you avoid bringing that stuff home?

Jim VandeHei: Yeah, it goes to controlling the parts of my life that I can control. I’m probably got a little bit of a screw loose, so I don’t think people have to take it maybe as far as I do, but I’m super religious about what I put into my body. I really try to be careful with drinking, even though I love drinking, but I try to curtail it. I work out every day. I very rarely miss a day. I try to have a lot of diversity in the type of workouts that I do. I try to have a lot of really good relationships. I’ve been married 23 years. My wife’s my best friend. I’ve got three kids. I have this thing I write about in the book called my happiness matrix, which my wife has always given me crap about, but it is my way of keeping real. I think of my happiness matrix as these buckets. I have my faith, my family, my work, my friendships, my hobbies, my health. And if I’m off or if I’m stressed or if I’m tired, usually it’s because one of those buckets is empty.

Like I’m not been paying enough attention to my parents, or I haven’t had meaningful one-on-one time with my kids, or I haven’t been as healthy at night as I should be. And it’s just a good way for me to keep inventory of the things that I know make me feel good about myself and help me perform better, ’cause it is. We run a company, and we also have a family, and I wrote a book, and we do TV. There’s a lot that we do, and I love doing it, but it could be terribly stressful. I don’t find it stressful; I find it very energizing, but if I didn’t do those other things, if I didn’t have my faith and my mind in the right place, I don’t know how I’d do it. I think I would be grumpy and I’d be worn out and worn down and bitter, and I just don’t wanna be that way.

Brett McKay: All right, so just focus on making sure you’re filling up all the buckets in your happiness matrix. But what do you do… Let’s say you had a really crappy day. Something happened at the office and there’s all these fires to put out, and then you’re going home and you’re just in this pissy mood. Do you do anything to decompress so you don’t take that out on your family?

Jim VandeHei: Yeah, work out, a hundred percent. I’m super into core power right now, which is basically high-intensity yoga with weights in a hot room. You sweat, but you’re also working quite hard. And something like that for an hour where I’m pounding for an hour and I’m sweating and I can’t think about anything other than the moment, I find that to be extremely therapeutic. Extremely therapeutic. Or then after that, come home and just watch something stupid that doesn’t require a whole lot of intellectual engagement, or do it with my wife, or whatever, just do something. ‘Cause in the old days, I would just come home and have a couple of martinis, which is like that helps, too, but then it sets me back the next day, so it’s always a trade-off.

Brett McKay: Your business is online, and it’s the news business, so it’s constantly going on. Do you set hard boundaries where you’re like, “When I’m at home, I’m not gonna check my phone, I’m not gonna see what’s going on”? Do you do that?

Jim VandeHei: No, I suck at that. I really do. I’m really bad at that work-life balance thing. ‘Cause I really do like it. I’m always curious what’s going on. I’ve basically integrated work into my life, which allows me to travel a lot, or I can go fishing and come back and engage really heavy for a couple of hours, go out and fish for another hour or two. And so, I’m not great at just shutting off. But at the same time, I think I do enough stuff to offset it. And I try definitely, if I’m with my kids, my wife, my parents, friends, I try to be very focused and present in that moment. But then the minute that’s done, I’m checking my phone, I’m doing a call, I’m listening to a podcast. I definitely am not great on the discipline around that.

Brett McKay: So you talk about that, the skill of quitting is something you need to learn. So why is quitting an important skill?

Jim VandeHei: Because I think there’s a stigma attached to quitting, but sometimes quitting is the best thing you can do. If you’re in a bad relationship, quit it. You have a bad habit, quit it. But I mainly talk about it at work where, listen, it happened to me. I started Politico. I’m 10 years in. It was seven years in, really, ’cause it was a three-year ordeal. I didn’t get along with a guy who bankrolled the company. We had different values, and it was starting to suck the life out of me. I went from 80% or 90% of my time doing things I enjoy with people I enjoyed to spending 70% of my time trying to clean up other people’s messes, and I hated it. And my wife was just like, “You gotta quit. You just gotta quit. Even though you created the company, get the hell out of there. This is no way to live.” And I quit, and I started another company and created that more in the image of the company that I wanted the first one to be.

And sometimes you have to do that. You have to quit managers. You have to quit companies. You have to quit relationships to give yourself a chance to reset on things that make you feel a lot better about yourself. And I think maybe it’s ’cause I’m getting old. I’m 53. I think you start to think about your own mortality, but it’s not that long, man. We just don’t have that long of a run on earth. And I just want every single day or week or month to be better than the ones before it. You wanna make a difference, you want to be around people that you love and admire and that love and admire you. And if you could stack your life that way, you can extract a lot of joy. And then when the bad parts of life hit you, and they do hit you, man, they hit you hard, but if you’ve kind of fortified yourself for it, you’ll be all right. We’ll persevere.

Brett McKay: Any advice to people who, they feel like they gotta quit something and it could be a job, it could be a business, but on the surface, it’s a success, but they’re miserable. How do you go about quitting something that is a success? Like Politico, that was a success. Everyone knows what Politico is. Did it take you a while to finally get the gumption to stop that?

Jim VandeHei: Yeah. It was one of the hardest things I’ve ever done. It’s like I had to leave my baby. Like I literally there, I was there at birth. I birthed the damn thing, and here I had to quit it, ’cause I didn’t really own it. I had shadow equity, someone else owned the company. But we are incompatible. And the way you do it is you just have to have that hard conversation with yourself. Are you mostly unhappy? If you’re not, we should all be trying to spend 80%, 90% of our time in a good place, in a good head space. And if you find yourself at work with a manager or a job or a company where most of the time, you’re demoralized and you’re angry or you’re bitter or you’re just bored, you gotta get out. That’s the universe telling you it’s time to move on. Not everybody can. Sometimes we’ve got these obligations in life to take care of other people, but I think more often than people realize, you have agency, man. You wanna quit, you can quit. You can go find something else. And the truth is, we all worry way too much about what other people think about our success. People are really… They’re too busy. They’re focused on their own life, they don’t give a hoot about yours. And so, you gotta live up to your measurements, stick to yourself, not what you think other people are expecting of you.

Brett McKay: We had Annie Duke on the podcast a while back ago to talk about her book, When to Quit. Annie Duke, famous poker player. She’s a psychologist now. And one of the bits of advice was if you’re trying to figure out whether you should quit something, is you want a quitting coach. And that’s basically someone you can talk to, third party, that can talk to you through all the different factors about why you should quit or maybe you shouldn’t. It sounds like your wife might have been a quitting coach for you.

Jim VandeHei: Yeah. I think we all have to have, whether it’s a quitting coach, but I’d say a life coach. You just need… I’m lucky. I’ve got about half dozen people in my life who really know me, know the good, the bad, the ugly, care about me and will be blunt to me. Obviously, my wife is at the top of that list. And you’ve got to be able to have those conversations with people. I think, let’s be honest, especially for dudes, it’s hard. It’s hard for us to open up. It’s hard for us to have even the word “intimate relationship,” with another guy. You’re like, “Whoa, what’s that?” But you gotta have that. You have to have these friendships that go a level deeper. You have to force yourself to really get to know at least a small group of people so that you have somebody to call you out or to tell you, “Man, now’s the time to go. Now’s the time to quit.” Or “Man, you shouldn’t have done that. You look like a real jerk. You are a jerk. You got to apologize.” You need those people in your life. And it doesn’t need to be six people, but you need at least one. And I would argue, you need a couple as an insurance policy.

Brett McKay: So you have a chapter called Excellence Over Success. What do you mean by that?

Jim VandeHei: Yeah, it’s interesting. It’s from right in the chapter around this coach, Messiah University, which recruited one of my sons to play soccer, Christian university in Pennsylvania. And I went to listen to him talk to the team, and I realized he spent two hours and he never talked about soccer. And he has… I think he’s the winningest coach in the history of soccer, certainly the current winningest coach. And he talks about it’s not about trying to be undefeated, which they often are or close to it; it’s about each person being excellent. Really having a measure for yourself, for your team, to truly be awesome, which is different than success, ’cause you could be awesome at something, you could truly achieve excellence, but you might fail. But I would rather achieve excellence, know I gave every single thing I had, know that I maxed out on my ability and failed than to have a success that I really wasn’t that responsible for and I kinda lucked into it and really it was somebody else. And I think really striving for excellence, and really, again, it goes to excellence is measured by you. When we start measuring ourselves against other people or magazine pictures or other folks who are doing what we’re doing, you have lost.

You have to say, “Okay, who am I? What am I capable of? How can I exceed my current expectation of myself?” I’m not a naturally gifted athlete, and I’ve really had to force myself to become pretty good at working out, but one of the things at 53 I try to do is, every year, I try to be able to lift a little bit more than I lifted the year before. And it’s probably in my own psychotic way, I think I’m trying to reverse ageing or something. But if you think about that, and yes, I’m not gonna be benching 250 or 300, but can I lift a little bit more each year so far? I can. And that’s measuring me against me. It’s not me against my nephew or my son or my friend. And I just think it’s a healthier place for us to be.

Brett McKay: I love this idea in theory, but how do you balance pursuing excellence but also the need to deliver the goods and get paid? Take like a writer. Writer writes excellent stuff, but it doesn’t get noticed and they’re not getting paid. You gotta make a living. So have you had a struggle with that at all?

Jim VandeHei: Listen, at the end of the day, we have basic needs we need to meet. And so there might be areas that you want to pursue excellence in that you can’t monetize or they become a distraction or they become a hindrance to you doing the basics of life. I’m never advocating for anyone to abdicate the responsibilities of life, but I just think when you’re looking at success, success is often in the eye of other beholders, whereas excellence, I think, is something you can see and that you can feel and that you can measure. And that doesn’t mean you’re trying to be Wordsworth or you’re trying to be Michael Jordan; it’s you trying to just be a little bit better than you were before, establishing your own level of excellence. And I do think you can apply that to most situations. Even if you said, “Okay, I have to just be a regular writer to provide,” well, how can you be the very best version of the writer that you have to be to put food on the table, and how can you be better next month than you are this month? That’s always possible. Always possible. Otherwise, I just think maybe not everyone’s wired the same way, but just the idea of stagnating just sounds so boring.

Brett McKay: So you have a hire at Axios named Kathleen Halpin. And you say if you wanna have success in your career, you need to be like Kathleen. What did she do in her career that made her stand out?

Jim VandeHei: She was a young woman who worked for us in the early days of Axios, and she just had a personality where she stood out. And she ended up going to business school, and I ended up talking to her a little bit and ended up writing a chapter about her, because she was one of these people who, it’s a great lesson for early in work. She was 23 or something like that. And she just was the kind of person who was in first, left last. No matter what the job was, get someone coffee or do a research paper or help strategize a new product, raising her hand, enthusiastically throwing herself into it. Always made people feel better about themselves. Was naturally a funny person. So like lit up a room. And I just think it’s such a great lesson for those people. I think the book, in some ways, is really good for college grads, is just realizing that, just go in there and the basic values of life. Work harder than other people. Be honest. Try to have a little bit of humility. Those things make such a difference. And they’re simple things that all of us are capable of. And she really exemplified them.

Brett McKay: Yeah. Yeah, so volunteer. I love that. Raise your hand for every little task. Sometimes when you’re at a job, you’re like, “Ah, that’s donkey work, I’m not gonna do that.” No. You should do that, ’cause you don’t know what you’re gonna learn by doing what you think is a donkey job.

Jim VandeHei: Or who you’re doing it for. Maybe that person you just did a research thing for that you didn’t have to turns out to be the person who hires you and promotes you and pays you more than you ever thought was possible. Or maybe that person goes on to be CEO of the company. You never know. It’s again, throwing yourself out there, taking advantage of opportunities, increasing your chance for luck, because you’ve put yourself in these situations that other people aren’t putting themselves in. And it makes you stand out.

Brett McKay: You talk about how you encourage your kids to play poker, an actual play-for-money poker. People would be like, “That’s bad parenting advice. Why would you tell your kids to play poker?”

Jim VandeHei: One, I love poker. Because I think you learn so much about humanity at the poker table. You learn so much about risk-taking and calibrating risk-taking. You learn so much about bantering conversation. You learn so much about reading people. How are they gambling? Are they reckless? Are they careful? Do they have some weird twitch? You get a feel for the rhythm of numbers, the rhythm of momentum. And so, I look at the poker table and I just think back, “Man, I learned a lot by gambling a lot.” And I’m not advocating to gamble recklessly or anything like that, but I’m saying, there’s just something about it that teaches you about people. Most jobs are people. People are people. No AI, no robot. They’re not going to replace our species. And we’re a complicated, nuanced, idiosyncratic species, and so being at a poker table or being at a bar or being just in a place where you gotta read people and you gotta start to sharpen your emotional intelligence and combine that with some actual intelligence, that’s where you start to really sharpen your repertoire.

Brett McKay: So I’m sure people have heard, there’s these poker games that go on in Washington, DC with journalists and politicians. Is that a real thing?

Jim VandeHei: It is. I played in a bunch. I don’t know how much they still do. I don’t know of any going on right now. But yeah, I used to… Man, before 9/11, they’ve really locked down the Capitol since then, but I used to grab a 12-pack of beer, walk into the Capitol late at night, sit in a congressman’s office, and there’d be six, eight, 10 people playing poker. Not like high-stakes; just playing like for fun and playing for a little bit of money. But I used to do it all the time. There’s a couple of games we used to play in right off Capitol Hill where some congressmen and journalists would play. And I love it. I love to banter more than anything else and just being around and talking smack and playing cards. It’s not a bad thing to do.

Brett McKay: Yeah, I know when Harry Truman was Vice President, that’s all he did, pretty much. He just played poker.

Jim VandeHei: [chuckle] Just played poker. Not a bad way to spend your time.

Brett McKay: No. Yeah. All right. You talk about in a career, there’s a difference between wartime leadership and peacetime leadership. What do you mean by that?

Jim VandeHei: Yeah. I think about it a lot in terms of starting a company. Like when you’re starting a company or you’re trying to radically change a company, it’s wartime. And during wartime, you’re not really worried about casualties, you’re not worried about niceties; you are in survival mode. Meaning, you’re willing to break things, do it in a sloppy way, take risks you might not otherwise take, be a little maniacal, because it’s life or death. And to be honest, I always have found myself to be a better wartime leader than a peacetime leader. I thrive in that environment. I love the energy. I love the high stakes. I love kind of being creative on the fly. That’s different than once your company’s five, six years in or you work for an adult company and you’re a peacetime leader, which now, when you’re a peacetime leader, you’ve got a little bit of stability and your job is to manage the success you have. It’s to create processes. It’s to find people who are good institutional managers, as opposed to kinda radical, risk-taking cowboys and cowgirls.

So, it’s a totally different mentality. And you gotta be comfortable that you might be good at one and not the other. And I think I know I’m a very good wartime leader. Now I’m kind of a mix. There’s a little bit of war and a little bit of peace. Peace is harder for me. It requires like I don’t care that much about process and I don’t really like the status quo; I like change. And so there’s always a tug of war inside of me internally. There’s probably a tug of war for any of us, anybody listening who’s in a position of leadership, but just realize there’s different attributes in different people that you need around you in moments like that.

Brett McKay: During the online content business, is artificial intelligence causing you to shift back into wartime leadership mode?

Jim VandeHei: For sure. Mainly because you can just see… Like media is a tough business to begin with, but just the nature of how we get information and how we run companies is gonna change profoundly. I think AI… We’ll look back and artificial intelligence will be as big of a deal as the creation of the internet. I really believe that. I just think it’s gonna fundamentally change the nature of how we live, how we do our jobs, and for me, in running a media company, how people get information. And so, it’s my job to sort of get back into that wartime mindset, which means, “Okay, what does this mean? How is it gonna disrupt my business? How do we make changes to make sure that the humans that we hire can do things that no machine could replicate? How do we think of this technology not as a threat, but as an asset? How do I use the improvements that we’re starting to see with these large language models and integrate ’em into the work that we’re doing?” And I love that stuff. It worries me sometimes that it might make my job harder or the industry more complicated, but I like the dynamism of having to solve a problem that’s evolving, that’s new in real time without the real obvious, no one really knows which direction to go. I find that exhilarating.

Brett McKay: Yeah, so imagine you’re trying new things that you otherwise wouldn’t have tried maybe five years ago.

Jim VandeHei: For sure. And really trying to think about, “Okay,” I always try to think about, “Okay, let’s assume that AI is even better than people think it’s gonna be. Then what would that mean for information consumption?” And for me, as somebody who runs a media company who has hundreds of journalists, the thing that I know no robot will do is they’re never gonna be a subject matter expert that has human sources, that can capture the nuance of human conversation and break news and tell people things that they did not know. So, I’m very much reorienting our company around that. I want more of those people, and we’ll use machines to make those people stronger, but the machine is not a threat to those people and therefore to us.

And every business is going through this or will go through this. And media is just a harder business in general. It’s a complicated business, but it’s also a very public, fun, interesting, dynamic business. And so, this is just… People who don’t pay attention to AI are nuts. Crazy. Basically, you know the world’s about to change. You’re getting a preview of it in real time through OpenAI, Anthropic, Google, Amazon, Character AI, you name it. Pay attention to what they’re doing, ’cause that is the future, and it’s going to affect you. And we all have an obligation to be smart about the world around us and get smart about the world around you and control your own destiny and make the decisions on your terms, as opposed to having them imposed by some damn robot.

Brett McKay: So you got a chapter on healthy revenge. What is healthy revenge?

Jim VandeHei: I got a little revenge freak in me. It could become all-consuming. Like someone screws you and you wanna get back at them. And for me, healthy revenge is like give yourself a little bit of revenge. And maybe that revenge is just being a better company or showing that the person who screwed you over that you’re gonna do better than them. And so, don’t say you’re not gonna have any revenge or you’re not gonna think about it at all, but don’t allow revenge to be the thing that just animates your activities and consumes your mind. There’s a lot of research out there that that really pollutes your mind, pollutes your decision-making capabilities. So, having a little bit, thinking about it a tiny bit, using that energy that comes from it to just be better at what you do, that’s a way to have a little bit of healthy revenge.

Brett McKay: I like that, because I think sometimes we’re a little too down on revenge. We’re always telling ourselves, “You gotta be stoic, just let things go.” There’s that quote, “The best revenge is to not be like the person who wronged you.” But sometimes I think it’s nice to try to outdo the other person who wronged you. And I think as long as you keep it within healthy parameters, having a little bit of a chip on your shoulder can be an animating force. So, you also have a chapter about a Wall Street Journal reporter named David Rogers and what he taught you about quiet greatness. Tell us about that.

Jim VandeHei: So David, thank God he’s still alive, he lives here outside of DC, I still see him, try to see him every month or two for lunch. He was my mentor at the Wall Street Journal, and he was on Capitol Hill covering Congress. He was a legend, he is… Very few people would dispute he’s probably the best congressional reporter of our generation. But he wasn’t on TV and he wasn’t writing books and pounding his chest; he just was quietly way better than anybody else, did way more homework than anyone else, understood the institution so well that members of Congress would routinely call him to ask him, “What are the rules of the House? What is the history of this legislation?” He was just encyclopedic. And what he taught me was, you’re never going to really be excellent at anything if you don’t really have a real-deal mastery of your subject. He really taught me to do the hard work, to master the craft or master the beat in that case that I was on. And he was tough, man. He was a tough guy. He was gruff. He could be brutal in his assessments of my work. But he cared. And despite the gruff exterior, he was a sweetheart of a guy and has become one of my best friends and mentors and really changed my life. It was hard, but it was just a big, big reason I think I am who I am today.

Brett McKay: I think that’s really one of the best pieces of life advice: Just find yourself a great mentor. They’re worth their weight in gold. Well, Jim, this has been a great conversation. Where can people go to learn more about the book and your work?

Jim VandeHei: You can get it on Amazon, just the good stuff, if you’re looking for the book. Axios.com is where I write and the company that I run. It’s all about getting people smarter faster on topics like politics, business, AI, media. Check it out, it’s free. Most of the products are free. The idea is to help you better understand the world. So, I appreciate conversations like this. I appreciate all the work that you do.

Brett McKay: Well, thanks so much, Jim. I really appreciate that. It’s been a pleasure.

Jim VandeHei: Take care. Thank you.

Brett McKay: My guest today is Jim VandeHei. He’s the author of the book, Just the Good Stuff. It’s available on amazon.com and bookstores everywhere. Check out our show notes at aom.is/goodstuff, where you can find links to resources and we delve deeper into this topic.

Well, that wraps up another edition of the AOM Podcast. Make sure to check out our website at artofmanliness.com, where you can find our podcast archives as well as thousands of articles that we’ve written over the years about pretty much anything you’d think of. And while you’re there, sign up for our email newsletter. It’s completely free, and there’s both the daily and weekly option. As always, thank you for the continuous support. Until next time, it’s Brett McKay, reminding you to not only listen to AOM Podcast, but put what you’ve heard into action.

This article was originally published on The Art of Manliness.