The Daily Stoic - Morgan Housel on Building Wealth and Happiness

Episode Date: July 30, 2022

Ryan talks to Morgan Housel about the real definition of wealth, the intricacies of building an audience as an author, the sacrifice required to gain success, and more.Morgan Housel is a partner at The Collaborative Fund. His book The Psychology of Money: Timeless lessons on wealth, greed, and happiness is a deep dive into the psychology of money and investing. Morgan is a two-time winner of the Best in Business Award from the Society of American Business Editors, winner of the New York Times Sidney Award, and a two-time finalist for the Gerald Loeb Award for Distinguished Business and Financial Journalism. He serves on the board of Markel and has presented at more than 100 conferences all over the globe.✉️ Want Stoic wisdom delivered to your inbox daily? Sign up for the FREE Daily Stoic email at https://dailystoic.com/dailyemail🏛 Get Stoic inspired books, medallions, and prints to remember these lessons at the Daily Stoic Store: https://store.dailystoic.com/📱 Follow us: Instagram, Twitter, YouTube, TikTok, and FacebookSee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Hey, prime members, you can listen to the Daily Stoic podcast early and add free on Amazon music. Download the app today. Welcome to the weekend edition of the Daily Stoic. Each weekday we bring you a meditation inspired by the ancient Stoics, something to help you live up to those four stoic virtues of courage, justice, temperance and wisdom. And then here on the weekend we take a deeper dive into those same topics. We interview stoic philosophers, we explore at length how these stoic ideas can be applied to our actual lives and the challenging issues of our time. Here on the weekend, when you have a little bit more space when things have slowed down, be sure to take some time to think, to go for a walk, to sit with your journal,

and most importantly, to prepare for what the week ahead may bring. Hi, I'm David Brown, the host of Wonderree's podcast business wars. And in our new season, Walmart must fight off target, the new discounter that's both savvy and fashion forward. Listen to business wars on Amazon music or wherever you get your podcasts. One of the tricky things about being ambitious or trying to be good at what you do is there's a inherent competitiveness, right? I want to be not just good at what I do.

That's like in my control, but that there's this part of you that wants to be better than other people, to beat other people, to get the most, to spend more weeks x, right? Anyone who attempts to master a profession there's a part of you that naturally gravitates towards comparison. Stokes would say comparison is dangerous, comparison is the thief of joy is the hero's vote puts it. But I think the other part of this that I have learned as a writer one of the what are the beauties of the profession that the sort of competitiveness and this tendency towards comparison misses is that we're actually not competing with each other by that, I mean me and my fellow authors.

What we're competing against is people not reading. And somebody reading my books doesn't take away from reading other books just as the success of someone else, a friend or a peer, their success doesn't take away from people reading my books. In fact, it makes them more likely to read my books. So I always, people sometimes will say, Brian, all of a day's books, why not read the original Stokes? I go, yeah, I know for a fact how many people I've driven to read the original Stokes because

of the success of my books. All of which is to say, it's taken some work, but you get to a place where when you see someone else's success, and Seneca talks about this, you want to get to a place where you're happy for them. You enjoy it. You're rooting for them. You hope they sell a bazillion cups. You hope they do really well.

And this is just bringing me to today's guest, Morgan Housel, who just has sold a metric ton of books and a very short amount of time, which is extremely difficult to do. His new book, The Psychology of Money, Timeless Lessons on Wealth, Green and Happiness, is a deep dive into the psychology of money, the difference between being rich and being wealthy, how we measure our success, the problem with comparison, as I was just saying, and much more. It sold nearly two million copies

and been translated into 46 languages. Just, he's on a hell of a run. And I actually first heard of Morgan because he is doing what I'm talking about, which is not being competitive and genuinely rooting for other people. He said some very nice things about me and my writing on Tim Ferriss's podcast. And I got a note from someone that I heard and I listened to that. And then I read the book. And so I was very excited to have this interview. Morgan is a two-time

winner of the Best in Business Award from the Society of American Business Editors. He's the winner of the New York Times Sydney Award and a two-time finalist for the Gerald Loeb Award for Distinguished Business and Financial Journalism. He serves on the board of Markle and has presented him more than a hundred conferences around the globe. He's also a partner at the Collaborative Fund, but I will say this. His book is really great.

It is really genuinely good. I loved reading this. His book is really great. It is really genuinely good. I loved reading it. I took a bunch of notes. I wish more writers would write in this style as we talk about in today's interview. I loved the stories. I loved that it was both general and specific. And I took a lot out of it. And I think it's a very apt for this crazy moment in economic history that we are in and I recommend it highly. We've had some trouble getting it at the Pain in Porch but I'm pretty sure we've got it in now.

Morgan was nice enough to help. So I recommend reading the psychology of money anywhere you get your books but if you wanna pick it up at the Pain in Porch, go for it and you can go to Morgan's website at morganhousel.com and follow him on Twitter at MorganHausel. Enjoy. Well, I love to the book, and I know you said some very nice words about me on Ferris'

podcast, which Christo, his editor, sent me, and I really appreciated it. All well deserved. I know many have said this to you, but what is equally impressive, not just the quality of your content, but is just the volume of what you put out is amazing. And I know your answer to that is like more professional writers should be writing more. Like your horizon will go do more, but it's impressive nonetheless. Well, no, I love the book and I think the reason your book is done so well and why it resonated. Like, if you think about like, if you're a nonfiction author and you're like, I'm going to write a book

in a certain space, the space you chose is probably the most competitive space that there is. Right. Like, because it's nonfiction, and then it's about money, and money is a universal thing. Most people are not good at it. And it's potentially a very lucrative niche, so people want to sort of crack that niche. And so for your book to come out of the gate, the way that it did, I think is probably, I don't think your average reader would appreciate just how hard a target that was. Like what you pulled off is very, very impressive.

To, I mean, to thank you and two things from this, every major publisher turned it down every single one. In fact, the agent that I had at the time, she had to fire me respectfully, because she said, I can't sell your book. And she said in 22 years, it was the first time that it ever happened. So I went out on my own, Haram and House who published it is a small brand. Right. Five people, the entire, the entire publisher is five people. They're the only ones who took it on. Look, I like them. They're great people. But I published with them

because they were the only people in the world who were willing to take it. And, and then our first print run was 5,000 copies. And even that, we were like, yeah, if it'd be great if it sold 5,000 copies, that'd be awesome. And then I remember like, we went to 10,000, it was like, this is crazy. And then 20,000, we were like, there's no way we can sell these,

maybe we'll give them away to schools. And then it just kept going from there, it's cool. What do you think they missed about the book that you saw? Like when I did the obstacles away, I've told the story before, but it wasn't quite like everyone rejected it. So I don't want to exaggerate the significance of the story. But when I went with Trust Me I'm Lying, there was a bidding war. Everyone was super excited about it. I sold it for at that, what was at that time? A lot of money and certainly a lot of money to me. But then when I went with my follow up,

they were like, will you take half or less than half? And that because it was like an obscure book about ancient philosophy, they didn't think would work. So what do you think they missed if everyone passed on a book that's since what, sold hundreds of thousands of copies? It's just about two million worldwide now. Wow, insane. That's with about two million worldwide now. Wow.

Insane. That's with all formats, audio, everything. If you lump it all together, it's 1.9. So what do you think they missed? I think, oh, I think there's two, there's a couple of things. One is, I don't think they missed anything because I think books are like seed stage startups where even if you do everything right, the odds are overwhelmingly that it's not going to work.

There are a lot of amazing books out there that never sold that much, because I think 90% of virality is luck. I'm making that figure out, but it's not 100%, but 90% is luck. And so I don't know if they missed anything. I think their feedback of like, same as your feedback, finance is really tough. This is like crowded space. A million people have tried to do this before. It didn't work.

Those all accurate. But it's accurate in seed state startups, too, where it's like, how many investors good, smart, the legendary VCs passed on Uber and passed on Google? Because the odds were stacked against them. So I think that's part of it. I also think, if I were to get cynical about this, I would say, I think there are a lot of big publishers that have not realized how quickly the content space has shifted in the

last five or 10 years. And then authors that have a social media presence and already have that audience that comes with them is a totally different world than a first time author as I was who did not have any audience that came with it. So in my mind, I knew I had spent 12 years building up an audience on my blog, and I knew that a lot of them were gonna buy the book, even if it sucked, but I think that's a harder pitch

to an established publisher who, even like they know the world has changed, but not as much as it has, I think it's different. See, I wondered if it was actually the opposite if, because the question that publishers tend to ask is, what's the platform of this book? They're less interested in how great an idea it is, how brilliant is the writing?

They're like, what's the platform? So, I wondered if they were the platforms too small. We don't think you can pull it off, but it sounds like that wasn't even the case. You know what I think it is? And I think like this is the reason my books have done well. I think this is the reason James clears books have done well. This is the reason your book did well. And almost invariably every book is a violation of this rule

and I think that's why most of them don't work. Which is I think people primarily learn via stories, right? They learn by stories, not by facts, not by charts, not by even these sort of long form like arguments, they learn by stories and not stories about the author but about like sort of bite sized anecdotes. The Greek word for this is a crayah. It's like a short story that has kind of a moral point to it

that teaches a larger lesson. And like most finance books are like, let me tell you how the markets work. They're not like, here's a bunch of memorable stories that will sort of triangulate for you and understanding of the market. Yeah, I totally agree. I could not agree more.

The best story wins. It's not the best idea. It's not the right idea. It's the best story that wins. Perfect example of this in a book is Bob Eiger's book, The Ride of a Lifetime. He's the CEO of Disney. And he's like, his book could have been like corporate management philosophies.

Anyway, so the couple thousand copies. Instead, the book starts with a story, a true story of a five-year-old kid being eaten by an alligator at a Disney World Hotel. That's how the book starts. And after you read that story, you're like, holy shit, I have to read the rest of this book.

You're never gonna forget it. James Clears book starts with him getting hit in the eye with a baseball and like nearly dying from it. And then you read that chapter and you're like, I have to read the best rest of this book. I cannot put it down after this. I remember because I read an early copy of that book and I was like, James, this story's incredible. It has nothing to do with what the book is.

Nothing. Like nothing. It's actually because James is such a genius at understanding how this stuff works, it's almost like so well done that it helps reveal how it's done. Like the fact that the story has nothing to do with habits or habit formations,

it's just a compelling story, is almost like the mask slipping a little bit and him accidentally revealing the power of what we're talking about. And it's like when, so I read James's book, I don't know, four years ago when it came out. And I probably remember, you know, five or six things about habits from that book. Yeah. Five or six, I have 250 pages, five or six things.

I remember everything about the baseball story to begin with, because I remember reading it in such wrapped attention at the beginning. Yeah. No, it has nothing to do with the book. It's hilarious. But I think that, like you said, that's best story wins. It's always like that.

But the problem is most business books start with like, like the problem, and that story happens to be very compelling because who gets almost killed while playing baseball. But the problem is most, and you'll hear publishers be like, I think you should start this book with a story. But the problem is most, and you'll hear publishers be like, I think you should start this book with a story. But the story is like, I was giving a speech

to a wrapped audience of insurance agents. And that's what it hurts. It's like the most boring, self-indulgent, like uninteresting story that you can imagine. Like obviously you're in the psychology of money, mostly sort of at the end where you kind of talk about your habits and you talk about your parents a little bit too, which is an interesting story.

But like 95% of the stories are about famous people or extreme examples at one end or the other that are very illustrative. You're not, it's not, this isn't your psychology of money. This is the overarching psychology of money. And I think that's another thing that people miss. They're so interested in themselves or they just default to talking about themselves. That if they had just, and I learned this from Robert Green, you go find a story of someone else that mirrors your experience and you tell that story and you put yourself in it, but you don't ever really have to say the word,

I or me or what I think. I forget who it was. The journalist is, the name is drawing a blank, but a famous financial journalist gave this advice one time that every, every article, every column should use the word I only once and it cannot be in the first sentence. Yeah. And that's, that's like, that's, but, but it, it should be used once. You, you, you should bring yourself into the story a little bit, but don't make it about you.

I was at a conference recently within the last couple of months, and I'm obviously won't say who it was, but someone was giving a presentation. And this was a professional presenter, like someone who, like an author who goes out and presents, and the entire presentation from start to finish was about this person. It was eye-eye, me, me, me. It was pretty good. It was a bad, but I remember thinking, I wanted was about this person. It was I, I, I, me, me, me.

It was pretty good. It wasn't bad, but I remember thinking, I wanted to tell this person, you could make it so much better if you use those takeaways and just took yourself out of it. People would like it way more if it wasn't me, me, me. Well, that's what ego does, right? Ego puts yourself unnecessarily at the center of things, which is like a grandizing for you, but you don't actually realize how vulnerable that makes you. Because first off, what if no one's ever heard of you? So you've already made the thing not that interesting. What if they don't like you, which I think about all the time?

Like I want to write a book that is vivid and exciting and illustrated and makes all the points I want to make, and that you could hate me as a person and still enjoy the book because I'm not making it about me. The problem is if the obstacle is the way it was filled with stories, first of all, it would be preposterous for me to be lecturing people on how to overcome obstacles based on my own experiences. But what if they just didn't find my experiences to be compelling, right? It's a weaker argument than like, let me go draw from the greatest or smartest people who have talked or thought about this thing. Chance, almost certainly that's going to resonate more with your average person than making it about yourself. Totally, it's always the case that a report from someone else

is gonna be so much more powerful than you. If you say, if you said, I, Ryan, and the best writer in the world, people are like, come on, but if I said it, if James Clear said it, if someone else said, Ryan Holiday is the best author in the world. They're like, oh, I gotta go buy his books now. That's like coming from someone else

just completely changes it. Well yeah, and like when you're telling this story, it's almost irresponsible to not, like, we know anchoring and framing is very important from a psychological standpoint, right? So like, if I'm telling you a story about overcoming obstacles and it's based on me and you haven't heard of me, I have to do a much better job than if I tell you a story about overcoming obstacles and it's based on me and you haven't heard of me. I have to do a much better job than if I tell you a story of someone you've heard of

or admire overcoming an obstacle because you already know the ending of the story which is that this person is impressive. I care about this person. I'm a fan of this person or conversely if you're a counter-programming you're like you're saying what not to do or you're saying how this person, or conversely if you're a counter-programming, you're saying what not to do, or you're saying how this person screwed up.

The point is, you wanna use a thousand years of history of that person to your advantage, or 50 years, or 70 years. It's easier to tell a story about Winston Churchill, or in your case, like a Warren Buffett or something, because people are like, oh yeah, I trust that Warren Buffett is a good example when it comes to money,

whereas this rant, like when you, when you, when people are like, oh, my friend Steve, and you're like, who the fuck is Steve? You're like, who are you? Right, I totally agree, totally agree. I've also had, this is similar related.

I'm sure you've had this experience. I've had this experience. When you speak at a conference, some conferences, the audiences know who you are. They've read your book and you get there and they're like, oh, read your book. They know you. Some conferences, you get there and they're like, who is this guy? And it is so much harder to be persuasive, even if it's the same presentation, the same story as the same examples. If they know you already and have a level of trust, those examples are so much more powerful

than if they're like, who's this guy on stage? I don't know who he is. Yes, no, that's exactly right. And you want to, I think it's better to assume they know nothing than to presume that they have been briefed, right? And you want to build a thing that's not dependent on you or them relating to you in some way. You want to build it around things that will stand the test of time.

I'm curious about you, because how many books have you written now? A 10? A dozen? I think it's 12, I don't actually know. A dozen. So, and I imagine there is substantial overlap. Like, people who bought your old books are are gonna buy your next book, not 100%. But so therefore, the people who are reading your books know you and probably know you pretty well. Does that change how you tell a story now that you don't have to introduce yourself? Well, I don't usually put myself in them at all.

What I've done on the series that I'm working on now and I did this in stillness, and if I could rewrite you ego, I would change it. Like, ego is the enemy starts with a preface about me and then it's a book about ego, which was a note I got from my editor. And if I was doing it again, I would probably just move the preface to the epilogue.

What I like to do is I write the book totally self-contained, not dependent on me. I want the material to do the argument. And then I want to close the book with a story from me that illustrates sort of my own struggle or journey along those same lines. But I think if you're leading with you, it's setting a certain expectation for the whole process. I prefer to put sort of other stories or figures forward. The trickier thing for me with the books that I've written is not that I'm running out of characters,

it's that I really like certain characters and I have to be cognizant of not overusing them. And so it kind of has been a forcing function of like, I need to go read about cultures or ideas or times or errors in the world that I'm not really familiar with because like I can't talk about the Civil War anymore. Yeah, no, I feel like that is what I'll even with with with my book. I'm like, okay, I need to challenge myself to write a chapter without quoting Buff at 17 times. Yeah, and that was when I was Robert Green's research assistant's research assistant, he'd be like, I'm looking for a

story about X and I would go find him the story. And he would almost always toss like the first few that were the obvious ones that like if you imagine what a 20 year old is just pulling from my breadth of knowledge, it's not, I'm not going super deep. But yeah, that was helpful to me because like, there's always the story that you have on the tip of your tongue, the anecdote or the quote, and like sometimes that's the right one, but a lot of times that's just the easiest one. And if you force yourself to go find something better, it will probably, it's probably better. And the fact that it hasn't been used a thousand times, that's something I

think about too. There's quotes I really like, And I'm like, but this one's just been used to death. So they know that I'm getting it from the original source. They're going to think I'm getting this because it was popular on Instagram. And like, I just don't even want to deal with that implication. Yeah, it's tough. I do think that the more universal your stories are, it's not a finance story, it's not a finance takeaway, but it's just like, here's something that applies to so many other fields. There's endless examples of these things

that you can find from other fields, from people in other fields, people you've never heard of, stories you've never heard of. There's so much out there that applies to all these big, high-level ideas that we talk about. So one of the things I was thinking about with the book, and when I was reading your book, I have had a number of people on the podcast

that are very, very wealthy, like wealthiest people in the world. And I've always been, I've tried to get, like, I know what it's like to be successful, I know what it's like to not have to really think about money too much, but like, I couldn't go, I couldn't go buy Twitter or something Right like I couldn't like I couldn't I wouldn't I wouldn't fly up. I certainly I certainly don't own a private jet And I would I would only a handful of times of my life if I ever even been on one

But I am curious like what is it like to have so much money that you could do anything and everything you want? It's truly, truly life-changing money. I've tried to ask, like, successful, very successful people what that's like, because I'm, it's like, it'd be like talking to someone who's had a near-death experience. How could you communicate back what that's like? And I've always been, I don't know if it's, they don't wanna answer or they haven't really thought about it, but I've never actually really gotten anyone

to describe to me what it would be like to have a hundred million dollars or a billion dollars. Like what does that actually change about your life and your experience as a human being? Have you gotten any sense of that from people you've talked to? I think there's two things, two kind of common denominators that I think about a lot here.

One, I have the book right here. I'm sure you've read it as well by a friend Mark Manson about from Will Smith. He was written with Mark Manson. He has this quote in there that he's saying like, look, when he was broke and a nobody and he was depressed, he could say, I'm depressed because I need more money and more girls and more success. That's what's missing.

And then once he became rich and he had everything he could want and he was still depressed, he could no longer say, if only I had more money, it would be better. And therefore, it was like taking out this level of hope. He was like, when I was broke, I had hope that if I had more, I could, then I'll be happy. Once you have money, you're like, there's no more hope. You're like, if I'm depressed now, and I have all the money, nothing, there's then I'm really screwed.

I think that's one kind of like interesting quirk of this. Another is that I have this idea that, and you could pick whatever net worth you want for this, 10 million, 20 million, 100 million, that everything above it is actually a social liability. That if your net worth is 100 million, you're not going to be living a better life than it was if you had 50 million. Like the material difference is going to be either zero or it's not going to make any difference.

You're going to have a social liability in terms of family and friends and people coming and asking you for money, people expecting you to pay for this and do that. And I think that's, it's like the ultimate first world problem. But if you talk to a lot of these very wealthy people, it is a legitimate problem. How do I take care of my friends and family appropriately so that they feel that they are, you know, being taken care of, but I'm not spoiling them. How do I give my money away in a way that impacts society to a great degree? I think that social lie of the stress of that is very easy to overlook. Those are the two things that I think are easy for people like us and ordinary people to overlook about what it would be

like to have billions and billions of dollars, is it takes away your sense of hope of having more and the social liability, the downside of it that is so easy to ignore before you have it. It is weird, like if you spend time with someone, let's say they're like a billionaire. Their life is not, like, their life is utterly incomprehensible to someone making $30,000 a year, but their life is not, would be almost,

like you could take someone who's making $500,000 a year and drop them into a billionaire's life and there would be almost nothing that they're not familiar with, right? Like maybe flying private is like the one thing and that's someone who was quite wealthy was telling me like the only reason to make like insane amounts of money is to not fly commercial anymore. That's like the only thing that it really transformatively changes about your life.

Everything else, you're effectively still a regular person. And so that is a weird thing. If that's the case, why do people not stop at a certain level? It's an interesting question. It is. There's this other example that this is not something that I came up with, someone else pointed this out about a year ago.

Did you remember Tom, the guy who started MySpace? Of course, he had that picture. And then he sold MySpace. I think he got something in the tens of millions of dollars. And he went and lived his life. And he's on Instagram now and you look at his life. And like, all he's done for the last 20 years is like travel around the world with his girlfriend and he stays at like amazing hotels and Bali and goes for hikes.

And it's like the most amazing life. And then you look at Mark Zuckerberg, who did not sell early. He's now in the richest men in the world, of course. And his life by comparison kind of sucks. He's being hauled before Congress and he's being blamed for some of the biggest ills of society. You look at Tom versus Mark Zuckerberg and I think nine people out of 10,

including myself would be like, I'll take Tom's life. I will take the tens of millions and the calm cool life, versus 100 billion and have half the world hate me. But it's funny, like people, that seems like a choice that would never actually exist. But I remember my, because I think about this all the time, my dad was a police officer growing up

and he was a detective. And he did other stuff. He actually invested like in real estate. So we had like a kind of, I had kind of an interesting life where you were watching like public service life and also sort of somewhat entrepreneurial, small business life.

But I remember, I think about this all the time, he was a police detective and then you sort of go up, you're on this track and then people suggest you take these tests so you can be promoted. And he ends up being promoted to being a police sergeant. And the way it works, at least where we grew up, is like when you would get promoted to be a sergeant, you would sort of go back to the bottom

as far as the choice of jobs. So we went from being a bank robbery detective to being a sergeant who worked at the county jail. So he was in charge of people, but he worked at the jail, and it was like horrible hours. And I remember he was saying like, that he was like, they make movies about being detectives.

They don't make movies about this, right? And I, like, people think, oh yeah, if I was choosing between Tom and Mark, obviously you'd choose Tom. But then when you're like, hey, you have a great job as a salesperson and then they offer you a 25% raise to be a manager. Of course, you accept the management position

because it would be irresponsible and insane not to, even though it might actually translate to the same decrease in quality of life. Totally great. My brother is in this exact same position right now. He is a clinical lab scientist. He looks under a microscope to diagnose rare illnesses. It's like his dream.

He's a bio nerd. And then a year ago, he got promoted to manager. And now that he's manager, he spends 90% of his time in an office, like making the schedule for the next week and having to listen to the employees bitch that didn't get a big enough raise. And that's the exact opposite. He went into biology because he does not like dealing with that stuff.

He likes dealing with cells and molecules, and which is what now that he's quote unquote promoted, he doesn't get to do anymore. So now he's going back to working on the bench. He wants to be demoted to work on the bench because it was so much happier there. I think there probably is a lot of that. I think where you see a lot of this is with entrepreneurs where they are very good at building young companies and they're building good at building new products

and getting something off the ground. And then if they are lucky enough to be successful and that company grows, now they're the CEO of a company that has a thousand employees and that is a completely different, utterly different ball game than being a small garage entrepreneur building a product.

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Stoic. I'm sure you saw this as being an author, right? You see you write this book and suddenly it's successful and now you're diluted with requests to do things that are not being an author, right? You say, you write this book and suddenly it's successful and now you're deluded with requests to do things that are not being an author, right? Yes. To speak, to consult, maybe they're like, hey, I have this idea for a company that could take the idea, you know, all of a sudden, the reward for the success at the thing is not being able to do that thing anymore. Yes, I totally agree. And you have to get really good at saying no. Like what I like doing is reading and writing. And if the success for the book is going to take me away from that, then that's going to hurt the success of the next book. Jerry Seinfeld has a great story

about this is that he mentioned that the reason Seinfeld was so successful is because he and Larry David were so good at just observing society. They would go to a deli, go to the airport check-in counter and just watch people and come up with these jokes. And as he became successful and famous, they could not just go hang out at a deli. They would get moded because they were too famous. And he realized that the fame, that the success of the show was gonna take away from the success of the future show

because they could not observe society like normal people could anymore. And that was one of the reasons that he pulled the plug in 99. Was he was just like, I can see that the success was cannibalizing future success. Yeah, yeah, it's tough, especially if you like doing the thing, right?

Yes. But it's it's also hard when the thing you're being asked to do is quite lucrative. Yeah, it's it's it's it's tough. I think a lot of people fall for it. I imagine there are pro athletes. Dennis Rodman is probably one who was like so successful, so talented at basketball, but as he became rich, and then he was like, ah shit, I'm going to Vegas, I'm going, I'm going to go get some hookers. And it was like the success of his, of his basketball career took away from his basketball career, just cannibalized itself.

Well, the thing is, yeah, on the one, on the one side, you're besieged or just with distractions. On the other hand, that, that take you away from the pleasure of doing the thing. On the other hand, the thing is also very hard and not pleasurable, right? So like, would I rather give a talk in which I am paid a lot of money? And because it's art, I know it's gonna work because the materials work before,

I'm being celebrated and applauded and lauded for something. Or do I want to spend the day as I was doing this morning, in my office, with note cards on a thing that may or may not come together. So you're having to choose between the immediate gratification or the delayed gratification of, or not even delayed, but potential gratification from the unpleasant process of the craft itself, right? And it's like, do you want to go on the victory tour? Do you want to go back in the gym and work out? Most people would want to go on the victory tour. I'll tell you the polar extreme

opposite of that, though, is JD Salinger, the author who wrote the catcher in the rye, one of the most celebrated authors of the 20th century. And the brief story of his is he wrote the catcher in the rye. It was like the biggest book in the world sold to Zillion copies. He became a celebrity and he hated every single second of the celebrity. Yes. He hated it. And he got to such a degree that he eventually fell off the face of the planet.

And he went like 50 years where no one even saw him. No. Not only did he not write another public book, he did not, he bought a house in the middle of New Hampshire or something and no one ever saw him again. They're like two pictures of him from the last 50 years of his life. That's the most extreme example of it. And from what I understand of it, reading his biography, it was like, he loved the craft of writing. He loved making the story.

He loved becoming the characters of his story. He loved writing. And all of the other, the publishing bullshit, the advertising, the speaking, all of that, he just viewed as taking away from the craft of writing. And from what most people understand, I don't think we'll ever know, but he spent the last 50 years of his life writing these stories that will never be published. They're

just like in a vault that is, that is kid zone or something. Yeah, from what I, what I've read about Salinger was basically like he had horrible PTSD from, uh, from World War II. He fought in the Hurtken Forest. And then also clearly had some sort of, Also, clearly, it had some sort of like, I mean, he was like a statutory rapist basically. Like, he was super attracted to very young women. And something clearly broke in his brain as when he left to go to the war that he was like sort of in this weird repeating of a horrendous childhood trauma. And it didn't seem like it was fun to be JD Salinger or anyone in JD Salinger's orbit, including his family.

Totally agree. He was kind of a broken man after the war. But I think there's like a lot of very successful people. You know, I think most people who are very good at one thing tend to be very bad at another. Most skills tend to balance out. And Salinger was one of the best storytellers of all time, and probably always will be, and the flip side of that personality, that whatever allowed him to do that was kind of a broken man on the other side. You see, that was so many people though, who are very good at one thing. They're terrible at another buffet is like

that for sure. Well, that, to me, that's the interesting challenge. And then I think it goes to what you talk a lot about in the book, you're of definition of wealth to be extremely good at one thing and very very well compensated for it But then to be objectively terrible and miserable and essentially all the other facets of life seems to me to be a form of poverty like I would much rather trade like if you told me I could be 30% more successful, sell 30% more books, have 30% more money, or maybe even ratchet this number up even higher. Like, but if you told me like right now because of the choices I've made, I'm hitting some ceiling or plateau that I will never go beyond. And to get through it, I would have to trade my marriage, my relationship

with my kids, just sort of basic human decency in the case of like a salinger or whatever, right? Like, if you told me I had to become insanely unbalanced in these other ways, but I would for sure be compensated in these other ways. And it's usually not for certain. It's a gamble. But I wouldn't take that trade, I could turn down that trade without having to think about it. The people I really admire are super talented in what they do, but then are also more or less ordinary, regular human beings in the world. That seems to me to be the rarest of all the outcomes in life.

Yeah, it's like the more financial assets you have, for a lot of these cases, it piles on social debt. And Buffett, as I talked so much about in the book, he was like this as well. The part of the reason he was and is so successful is because since he's been 14 years old, there's been like no other thoughts have passed through his mind

than how do I value a business and how do I find the chief stocks and That singular focus came at the expense of his marriage his relationship with the children et cetera, et cetera So if you read the book the snowball which is like the definitive biography above it You do not come away from that book saying I Wish I had his life he it's amazing what he was able to accomplish, but there are so many aspects of his personal life where you're like, not great. I do not admire that in the slightest.

And I think a lot of that was because he was so successful, just nothing like there was zero balance in his life. Everything is just, how do I value a business? How do I find the chief stocks? That's the genius of Warren Buffett in a lot of ways is that he's managed to present himself as a kindly benevolent old man. Every time I remember I was talking to Shane Parish about this, so I'm sure you know, I was like, Shane, you never seem to present the fact that Warren Buffett is obviously also

a fucking shark who would tear your heart out to make six dollars if he thought he could get, you know, if he thought he could get one over on you, like, you do not become that profoundly wealthy and successful without a ruthless amorality and preference about a certain thing. That isn't to say that he's not also generous and kind and generally better than a lot of people in that class. But like that is a result of, it's like when people find out that Michael Jordan was like cruel to his opponents,

it's like, yeah, that's, it's not, that's what it takes. But that was right there on the surface. You just didn't wanna see it. Yeah, I mean, one other recent example of this is Ellen DeGeneres, who like, I look, I'm just going from what the headlines say. I have no idea what happened, but her persona has been like, I am the nicest, kindest, bubbliest, friendliest person in the world. And then you have all these stories from her staff that like, no, it's a shark tank in here. We get ripped to shreds for nothing.

But there's part of me that's like, yeah, it's a successful show. Of course, it's a shark tank. You can't have a successful show if it's every if it's just a bunch of kittens and rainbows sitting around. Of course, it has to be like that. So it's really hard to have one without the other. Bill Gates is probably another story of like, so I live in Seattle, Bill Melinda are like the king and queen of Seattle. And Bill Gates builds this incredible company, becomes a richest man in the world, gives

all the money away to cure malaria. It's just like, it's a story out of a fairy tale. And then last year, everything comes out. Like, no, actually Bill Melinder getting divorced and Bill cheated on her. And he has this relationship with Jeff Epstein and like all this stuff that it's gossip and I don't wanna get into it.

But it's like, it's so easy. There's no perfect story out there, whether it's Buffett or Bill Gates or Ellen, whatever it is. Like, that level of success requires a degree of sacrifice and sacrifice sometimes comes back to bite you in the ass. I think is what this comes down to. So, I have a psychology of money thing. This is a first world problem, but I thought you of all people might be able to help me with it. So, here's what will happen. this is an example, this happened yesterday. All right, so there's a concern I wanna go to in September

that I'm planning on going to. And then I got an offer to do a talk on that same day, right? Yeah. That just came in and I don't need to talk about what my speaking fee is, but it's like an obscene amount of money that like ordinarily, like just a handful of years ago in my life, I would have been like, that is a good years income, right? And that is certainly above the median income for a huge

percentage of society. So putting that on the record for context. Now, I have this tricky thing where, okay, I was planning on doing nothing on this day, but something I enjoyed. But now I have this offer to do this other thing on this day. So obviously, if I had never known about the offer, I wouldn't have felt like I was missing out on anything, it would have been a wonderful day.

But as soon as the number comes in, it feels like if I say no, I am costing myself that much money. It's not that I'm getting back to neutral, but the amount is now, I'm literally lighting that amount of money on fire, it actually feels like I am spending that amount of money. In this case, it'd be like the concert tickets were $100. Actually now they're $100 plus the speaking fee, even though that's objectively rationally not the case. How can one tweak this psychology so I am not trapped by what randomly comes in my inbox?

I don't know if there is a good way to do this because what you're just talking about is opportunity costs. What is the concert and it's gonna cost you your speaking fee? I've had something very similar recently where two groups were gonna hire me for a talk on the same day. Obviously, I can't be in two cities at once to have to choose one or the other.

And now instead of, it feels like I made X, it actually feels like I lost because I couldn't make two X if I could be in both cities. I don't think there's a good way to get around that per se. I'm a victim of that as much as anyone. The thing that I think about that is relevant to you and I in our particular fields is that most authors like us don't stick around for 30 or 40 years.

And if you think that you are in the spotlight right now, that probably is not gonna last for 30 years. And one takeaway from that as a guy in his 30s who hopefully your life expectancy is another 50 or 60 years, you might wanna crank as hard as you can right now on the assumption that you're probably not gonna be making this kind of money in your 60s.

That might be the case, I might be wrong about that. But odds are, for both you and I and James Clear and all these other, it's probably not going to be like that. That's what I think about in terms of like, I am willing to make sacrifices right now, because I assume that I am not going to have these opportunities 20 years from now. And I don't want to look back 20 years from now and say, I wish I would have done that. But how do you balance that with, I also don't want to look back 20 years and say, all I did was work.

I should have gone to the damn concert. I wish I had the memories from that. To me, the things that I try not to sacrifice is like, times with my kids doing the fun things. Like a concert, in my view, I could be like, I'm okay leaving that. If it was, hey, I'm gonna go speak at this event, but I have to miss my kids first day of kindergarten.

I'd be like, no, that's a line for me. A concert I would probably do. So do the talk, Ryan. Go do the talk. Yeah, a good line I heard is like rest at the end, not in the middle, which I think makes sense, except that is, that may, you know, what we do,

yes, relevance is a thing that's always sort of, relevance is a thing that's always sort of, relevance is a thing that's out of your control but it's not as if you are an athlete where you can physically only do this thing for 10 years, right? So so there's also this tension between are you trying to get it now? Or are you trying to build something sustainable and and? or are you trying to build something sustainable and steady, right? So that's the other, that doesn't really apply to this talk, because there's one talk or another.

But there is kind of this idea of like, you gotta do all of it now, but that may cut, there's also a hidden opportunity cause to you are out there picking up money, not working on your craft, not working on your relationships, not working on your relationships, not cold experiencing the world, like Seinfeld is talking about.

And then of course your career was short lived. You wasted the prime moments of your career when you could have been preparing and stretching out the prime of your career. So here's my question for you, because when I think about that problem for myself, I want to stretch out my career, I would love it if I can keep writing books like this for another 30, 40, 50 years for the rest of my life.

Great. Let's do it. So then when I think about that, I'm like, okay, I shouldn't slow down the cadence of the next book. If I want to stay relevant forever, I don't want to saturate things. So let's wait five years for my next book. But you trick me if I'm wrong. You publish roughly once a year. Yeah. So how do you balance that? Like, I don't want to saturate

with what I so admire about you, which is your, your volume. So I, this somewhat happened accidentally. So the obstacles away came out and it didn't do amazing. It probably sold 60,000 copies its first year, which is not great as compared to most books, but nowhere near what one would have expected for how it's gone on to do. So I had sold a sequel because I was like, well, I had to, but I wasn't sitting around or resting on my laurels, because there were no laurels, right?

Like, I was, I was busy on the next book because I was still trying to prove the, the series or the, the style of books. And then so when that came out, then it sort of created, not a precedent, but it just, it was a different way of doing things. It wasn't like you or James or you, this book comes out. It's this monster hit and you're like, I don't want to, I don't want to slow this down. I'm going to, you know, just, I'm going to wait. But I think there is a certain amount of, you can feel like you're the center of the

universe when you're not. So like, yeah, I'm not saturating the market because like the vast majority of people who read the first book don't even know that the other books exist. It's actually the opposite. You, I, someone told me that once in fiction, it's, it's often the second or third book in a series that makes the series explode.

Um, the first, it's not that the first book is huge and then people are hotly anticipating the second and hotly anticipating the third. It's that that the first book is huge and then people are hotly anticipating the second and hotly anticipating the third. It's that a critical mass builds with by the third or fourth book that then people shearing the marketing about the fourth book go and start at book one, right? So, no, that's interesting. I was thinking, I've been thinking much more about like I just make lots of stuff and any one of those things can be an entry point into my world. I'm not like this book is for the people who read the other book.

I think about it differently. That's just because now that you say that, I think that was true for me. I forget which one of your books was the first I read, but after I read it, I went back and bought the earlier ones. So that's totally true. The other example of this, that I, someone I look up to as I think the greatest contemporary writer, Michael Lewis, and his style of doing this, he writes a book roughly every four or five years, and then he disappears.

He's not on social media, he does one or two podcasts when the book comes out, and then after that, you don't hear a single peep from him until the next book comes out. It's like, it's very different from what you and I and James do where we're always waving our hands on social media. And I, like, sometimes I wonder,

does Michael Lewis have a better shot at being relevant for 50 years? Because just at the very moment, you start to forget about him, he comes out with another book. But then he does it, he's not in your life until the next book comes out. Raising kids can be one of the greatest rewards of a parent's life. But come on, someday, parenting is unbearable.

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traditional media. So they have a level of notoriety and fame and a base that like contemporary writer doesn't have. So I see them as not that they're antiquated, but they are like grandfathered in to the environment that we're in. And it's just really hard to compare yourself to the, it's really hard to emulate their strategy because I honestly haven't seen very many people do it since or after them. Yeah, obviously when you're at that level of fame and success, like it doesn't matter what Michael Lewis's next book is about, a million people are going to buy it. It could be, it could be a terrible book that's about a crazy topic and it would do it. The back cover of his last book, that's on the pandemic, there's one phrase quote.

And the quote I'm paraphrasing if the quote is, Michael Lewis could write the history of the stapler and I would read it. And that's who he is. I would read it. So that's a completely different level of success. But I'm often astounded like the, like in music, it's different for authors, but the number of like massive musicians

who then fell off the face of the planet and you never heard from again. You know, go back to the late 90s, the Backstreet Boys, you know, a different genre of music, but like they were the biggest thing in the world. They were a massive selling out Madison Square Garden. The biggest like, he did not get bigger in the match. And then just like poof gone, no one here.

Some of them ever again. Well, I mean, they're probably, it's different than books. They probably still make 50 to 80 million dollars a year to a ring. So it depends on like what your definition of shearing about them is. But there's an interesting thing that Marx really says meditation is where he's talking about like who has heard he is like there's five good emperors, right? He's the fifth of the five and it's like I can name Marcus. I can name Antoninus. I could name Hadrian and then Trajan and then I like already by five like I you know, I'm forgetting who it was, right? Yeah. And that's how that tends to go.

And so he's like, you know, who remembers the name of Vespassian? You know, he's sort of pointing out how these one's very famous names become unfamiliar. And you can do a version of this on Spotify. So if you're like, give me the best of the, there's a playlist on Spotify that's like, best of the 2010s. And you'll have heard of

pretty much every song. It will be unusual that a song will come on that playlist. You'll be like, I've never heard this before, right? Then if you do best of the the the the odds, you'll probably have heard of most, but there will be some that you missed. Then you do 90s and then, you know, it's more. And then 80, and by the time you get to like, you know, 80s, let's say, you're like, shit, I've never heard of this song. And then you look it up and it was like a number one hit for 30 weeks, right? And so how much of that is just our age? Like, like you and I were too young to know the hits in the 80s. Well, that's what I mean is that sort of generationally, like we tend to think like success is success forever or fame is fame forever, but there is a very quick expiration date on these things, a very strong half life, right? And that it very quickly, your accomplishments

and success start to get sort of covered up in ignored and forgotten. And I think this is a like for people who are who measure their wealth based on yeah where I rank according to these other people or what have I done or how well liked I am like it's a losing battle. Like your wealth has to be based I think on what it gets you in life. And by that, I don't mean like pleasures. I mean, like, what does it get you day to day? Like, to me, the definition of wealth is autonomy. How much control do you have over your life? And you find like a lot of very successful people are quite poor in that regard. Totally. I'm curious for you in that regard, I know you used to work

at American Apparel. When did you become fully autonomous, full-time writer, no external salary? So I intended to leave in 2011. I called and I said, hey, I'm gonna write this book about media, I gotta go. And they basically said, whoa, whoa, we like can't afford to lose you. Can we, can we keep you on? They're like, you can keep your health, your health benefits,

everything. You can work remotely. We'll just pay you like half what you were making. So that was pretty tempting for me. So I accepted that. So I, I wrote, trust me, I'm lying while I still had a small salary. I wrote growth hacker while I still had a small salary. And then Dove was fired from American Apparel. And there was this whole thing which I wrote about. You know, that happened the day that I ended the book tour for the obstacle is the way. So I did another like three or four years. Was it was it hard to let go of the stability of a salary? It, what actually happened, I remember it quite vividly is that I, so I got called back to American repair when they fired Dev as a consultant. They paid me a lot of money to sort of come in as they

were trying to do the company. And I remember I was, I was staying in an Airbnb and so over like I didn't have kids yet. I was with my now wife, but we weren't married. And I remember I was on a run around the Sovereign Reservoir. And my phone did the 10 minutes, you know, you have an appointment thing, you know, the buzz, like when you have a calendar reminder. And it was like, I have a staff meeting. And I was like, wait, like I've written multiple best selling books, which was my dream. I've gotten paid a more money than I thought to do those things. And I'm

cutting short this thing I like doing to go to a fucking staff meeting. Like this is not, I was like, this is not success. I was like, this is the whole point of becoming an author was to not have to do bullshit like this. And that was sort of the beginning of the, I equipped for other reasons. But that, that was like, oh, I've, I, I allowed myself to get drawn back in right when I had gotten away. And now, and now I know you sit on the other side of the table and you're a small business owner. What is that is, but that's a level of responsibility and time suck I would imagine that is almost worse than being a full-time employee in some regards, right? It is, but I try to make decisions like when I do stuff like that, people often go like, okay, so you own a bookstore that must be like so much work, but I only do the things if I can set them up in a way that I can opt out

of most of the stuff that you would typically do, if that makes sense. So like, I really think about, like sort of what is the 80, 20 of this thing? What are the things that most people are doing that you don't actually have to, like I'll give you a really easy example. We don't accept cash at the bookstore,

because if you accept cash, you have to worry about getting robbed, you have to worry about your employees stealing from you. You have to go to the bank to deposit cash, right? You have to have cash on, like all, and so it's like by not doing that, I eliminated like five other things that I would have to worry about.

So I really do, when I do stuff like that, I think about, you know, what will this actually require me to do? And I'm only interested in it if I can limit that. So that my time to spend writing is still protected. Do you think now that you have a level of financial independence that you didn't have before you were a best sign author? Has it made you happier? Has it made-selling author. Has it made you happier? Has it made you less stressed?

Has it made you more focused? What, like if you compare Ryan Holiday today to 2010 and before, what's it up to you? That's a good question. One of the things I think a lot about, I really like Remiets work in this regard, is like, you know, you sort of pick up these scripts from how you grew up, right? And you talk know, you sort of pick up these scripts from how you grew

up, right? And you talk about your parents' sort of financial act. Like my parents were very much of the sort of like millionaire next door mold of like, you know, you save a lot, you invest a lot, and eventually ultimately you'll have a lot towards the end of your life, right? And so they were, I don't want to say stingy with money, but money was always seen as something scarce rather than abundant, even though now, they're like living the high life, right? And so I think as I've become successful, one of the

things that I've had to deal with my wife, too, is like, how do you update your perception of what a small or a large amount of money is and update your decisions accordingly? Because you can end up being very stupid and make yourself very unhappy for problems that you have more than enough money to solve. Do you know what I mean? Yeah, totally. So, I would say I'm happier, but it's still, I'm still in the process of updating. And the pandemic is weird because it's created

this kind of like bubble period where you like things were really scarce or things were scary and potentially uncertain. Then there was this sort of wild period of the markets doing what they did. And then also my books have continued. So kind of in this process of coming out of it and having to adjust and make decisions that are updated for the new reality that maybe I put off for a while. Yeah, yeah.

I'm curious, as your career progresses, have you become more of a saver, more of a spender? Like how is earning more money changed? progressives, have you become more of a saver, more of a spender? How is earning more money changed? How you allocate the money that you and your wife earned? Yeah, more of a spender in the sense that the savings kind of happens automatically or intuitively. We just naturally live below our means

also because the amount we're earning seems to keep going up. But which is a very good problem to have obviously, but like having to adjust for like, it's actually too expensive for me to do this myself. Yeah, right? Yeah. So having, and like, I'll never, I would have preferred not to be a small business

in the sense that like, I just, I don't have stuff, but I've had to, if I want to keep doing what I'm doing, I've had to scale what I do. And that is certainly been an adjustment. Yeah, no, that's great, that makes sense. Yeah, it's weird too, because like, with philosophy, and this is going back to Senaqa, this is the thing that Stokes have talked about, it's like,

it shouldn't be, it seems like something that shouldn't be financially rewarding, like Senaqa is Rome's richest man. And actually, he's such a prominent money lender that he sets off a rebellion in the colony of Britain because he puts out all these super high-interest loans. But he says, it's fine for a philosopher to be rich, provided their money's not stained in blood. But there is something strange. There is something strange or surreal about writing about an obscure school of philosophy and then selling millions of books about it. Like, it's a weird adjustment.

Even the bookstore, like, the bookstore I open, because I was like, I think it'll be fun to open a bookstore and my plan was, if this doesn't lose obscene amounts of money, it will be successful. And then it's actually been successful. And then you're like, it's not, it's like great. Now this is a weird

thing I have to adjust to. Yeah, yeah, that's interesting. Yeah, do you, like, how, so what has changed financially in the last two or three years for you? Like, or do you, like, is, is, are things pretty stable for how you invest your money, how you spend your money, or have there been big changes? Yeah, I've been able to take bigger swings at stuff I wanted to do with the bookstore. I was like, I'll just buy this building. And then I'll figure it out.

Right? As opposed to having to start much smaller. Or like, I'm just gonna hire three or four people and we'll solve this problem. As opposed to, I'm pretty good at white knuckling things and my wife's very good at white knuckling things and the decision to like not do that has taken a, you know, has taken some deliberation. I actually have a story about this in the new book that I just finished, But like Harry Belafonte, the activist and

actor, he calls Martin Luther King one day and Martin Luther King is gone. And so he Coretta Scott King answers the phone. And they're like, he's trying to get some information from her about, you know, something they're working on. And she's like, keep having to put the phone down, right? She's like, got to take the dinner out of the oven. She's got to answer the door. The kids need something blah, blah, blah. And finally, Harry Bell of Hunter is like, I, I, please, I hope this isn't too forward, but he's like, you know, do you have any help, you know? And she's like, no, Martin won't allow it. Like Martin, it's not, Martin had made money and was the head of a huge organization,

but it felt incongruent for him as a minister to have a staff. But Harry Belafonte was like, all right, he's like, this ends now, he's like, I'm hiring a staff for you and I will pay for it and Martin has no saying it. He's like, I can't have this person whom the fate of millions of people's freedom depends on, worried if there's milk in the fridge, right? That can't happen.

And so I think one of the big adjustments is having to be bringing people on, because it's not just, I talked to Cal Newport about this, it's not just like there's a lot Newport about this, it's not just like, there's a lot to manage, but once you're successful, it actually becomes harder to do what you do because the expectations are now against you, right? So to even stay in the same place, you have to invest more and do more and create more. Like Steph Curry, who just won the NBA Finals yesterday, is not the same player he was five years ago.

He had to raise his game significantly and that isn't free. Yeah, that's good. I like it. Yeah. One of the questions Tim Ferris asked me early on, this is right when I was starting my first company, he said something like, what do you spend your money on?

And I was like, what do you mean? He's like, do you collect baseball cars? Do you have a speedboat? Like, do you have a drug habit? Like, do you like to travel? He's like, what do you spend your money on? And I was like, nothing. You know, I was like, I don't really have anything.

And he's like, so you should be aware of that when you go out and try to earn money. His point was like, if you don't need the money or even enjoy having the money, make sure you make financial decisions accordingly, right? Like so many people, they don't care about money. And yet if you looked at the decisions they made in their life, the primary determining factor was, does this help me make more money?

Yes. No, I feel like my wife and I kind of fall into that bucket as well. You know, our income went up substantially with the book, but our spending didn't, the increase in what we spend is so marginal. And we live in the same house and drive the same car. And it's just like, they really didn't change anything. We've from that saved and invested every cent that we made from the book and speaking and stuff. And that's fine with me, because what I want more than anything is independence.

I want financial independence, just like, so if this all implodes tomorrow, like we're totally fine, the kids are fine, everything's all good, but there has to be some end to that. At some point you have to say, okay, like I'm independent now, and now I can go out and do what I wanna do.

But I feel like reaching some degree of that has probably made me a little bit calmer. I don't think it would be happier, but it's like, I don't know if I worry as much about career risk as I did two or three years ago, but that's very different from saying, are you happier? No. As it, as a major life better, like, no, no, it's, it really hasn't changed that much. And in some ways, that can be a little bit, not depressing, but just a little,

it's just eye opening to be like, oh, once you, once you gain the thing that you wanted, it probably doesn't feel as good as you thought it would. Or, or, or, well, maybe it still feels good, but good in a very different way than you thought. A lot of people, when they chase happiness, it's like, happiness is always a fleeting emotion. The example I use is like, if I told you the funniest joke in the world, you've never heard a funny or joke. You are going to laugh for 30 seconds, and then you stop laughing.

And if I tell you that joke every day, you're going to be like, okay, I get it. It's not that funny anymore. It's like, it's a fleeting emotion, even if it's the that joke every day, you're gonna be like, okay, I get it, it's not that funny anymore. Like, it's a fleeting emotion, even if it's the best joke in the world, and I think happiness is the same. If you find it, it's fleeting. It's something that you'll be happy for an hour, and then it kind of fades away a little bit. And the best you can hope for, therefore, is contentment.

Just get to a point where you're like, I'm good. I don't mind my desires are not that great anymore. I think that's the best you can aspire to. And when you gain some level of financial independence, you really realize that. It's like, no, it doesn't make me happier. It just made me a little bit more content. It should make you creatively, more free.

And if it doesn't, then you fucked up, right? So like you're asking me about having a job. One of the benefits, like when my publisher offered me what was not as much money as I would have hoped for the obstacles the way, I was like, sure, whatever, right? Like I had a day job. Like all my expenses were paid for, right? Like I didn't need to think about all I was thinking about is the thing you probably asked yourself with this book, which is like, will it get published or not?

That was the, that's the main hurdle. And so as soon as they were like, we are offering you a deal. I was like, whatever, whatever it is, I'll take, right? And so I have thought about that. Like one of the, one of the decisions I made has my book started to work as far as like investing is I was like, okay, I'm very dependent like on my brain making stuff. So I wanna have sources of income that would eventually get me to a place

where I could do whatever I want creatively and not have to think of it. So I invested a lot in real estate, but specifically like real estate that would pay like rents that would create a cash flow that would allow me to do whatever I wanted creatively, right? So like, yeah. And it took a while and it's probably there.

It's definitely there. But then the same, the irony is the same thing happens, right? You're like, once I do this, I will feel good. And you get there and then you realize there's no parade. There's no moment where it magically feels different. It's just another fact. And then the human brain goes, well, if I did that, can I do five times that? It just becomes this endless moving goalpost.

But the security of that is nice and I'm glad that I did that. Yeah, and I agree. I think having young kids really keeps you centered too, because no matter how much money you make, the kids don't think any different of you. It's like they don't care. They could care less how many books you sold or what your what your IRS, tax returns says they're like, hey, like I'm I need more toys and I'm hungry and I'm cold and they have their basic needs and they could care less how many books you sold, which is actually

a great thing that when there are external people like, oh, I love your book, it's great. And then you come home and your kids could care less. It's a great humbling anchor in your life. I just wrote an email about this for daily dad when, when, uh, which I do every day. Uh, David Letterman was quitting, uh, his show, he was the king of late night, you know, he's making 30, 40 million dollars a year. People would literally kill to have that job. He's quitting. And he goes to his son who was like 10 or 11 because he had kids, he had a kid late.

And he was like, uh, I think his son's name's Harry. He's like, Harry, I'm giving up the show. Our lives are gonna change, right? And his son goes, well, I still be able to watch cartoon network. And he was like, I think so. I think it's gonna work. And you realize like, oh, they, they're like,

you tell yourself I'm doing this for my family. And your family does not give a shit. Pass and care. The most basic of levels. I remember this really interesting interview with Michael Dell's son, Michael Dell, of course, one of the richest. I know, I have the world. And his son, at one point, I think the interview, he was probably like a middle teenager,

15, 16 years, something, years old, something like that. And the question was along the lines of like, what is it like to grow up as one of the richest families in the world? And his, his answer paraphrasing was like, it's all I've ever known. I've never known anything different than this life of mansions and private jets. So it doesn't feel like anything to me. It just feels like a complete baseline. Yeah. And I thought that was such an astute answer because the life that the typical middle-class

American lives right now would have seen incomprehensible to John D. Rockefeller 130 years ago. Like in Rockefeller's age, like the research man in history, he did not have adville. He didn't have penicillin. He didn't have sunscreen. He didn't have any of these, like absolute basics, not even like I tech, he had nothing. And so I think that just like, it's the same from the kids.

It's like, that's all they know. Like all David Letterman's son knew, and son knew was like, I like the cartoon network. That's all that matter to him at that point. It's all he knows. Well, and then you realize that also, I think the implication there is that the richest kids are the kids who have a relationship with their parents,

who have time with their parents. The kid doesn't care whether you made 30 or $35 million. It's incomprehensible to them. By the way, it's incomprehensible to you also accepting that it's some competition you're in with other people, right? You hear like NFL players, you're like, I have to be the highest paid tight end in the NFL, even though the difference between $132 million contract and $136 million contract are utterly indistinguishable from each other, especially over 11 years or whatever it is

in the guarantees, you're really in this competition and these are all symbols that don't mean anything. Your kid would trade in two seconds, 95% of that to have you at their baseball games. Are you talking about earlier to have you for? Are you gonna miss the first day of kindergarten for this opportunity? Like that's, and if you can't,

like if you're like, no, I have to do it. How rich are you actually? Totally, it's like lifestyle debt. It's like a unique form of poverty when you have no control over your schedule. And some of the richest, most successful people in the world have no control over their schedule. There's a great story from Muhammad Alierean who used to be the CEO of PIMPCO, giant financial company.

At the time, it was public. His annual income was over 200 million per year, one of the highest paid people in the world, making dynastic fortunes every year. And at one point, his daughter came to him. His daughter was like 10 years old or something like that, with a list of all of her major life events that he had missed. Yeah. So he comes to her to him with a list that says,

you missed my birthday, you missed my soccer game, you missed XYZ, and she presented that list to him. And he said it's just like it stopped him in his tracks, and he retired soon after that. He obviously had more than enough money. There comes a point where it's just like, this thing that I'm so proud of and I work so hard to achieve has so many downsides and embedded debt within it that is so easy to overlook until it's actually in the face. And thankfully, he recognized that when his daughter was

10. I imagine there are a lot of people who realize that when their kids are 50 and they have no relationship with their parents anymore. We're looking down upon their parents or don't know anything about their parents because they had no relationship with them. That is what I would give up anything to avoid that. And thankfully you and I have jobs where it's like, I travel a lot, you travel a lot, but we were from home. Like I'm around with my kids all day long. Totally different if you're the kind of job where it's like you go to the office at 6 a.m.

and you come home at 11 p.m. that's a totally different game and the things that you are striving for and aspiring for to make your kids life better. That's the irony of it is like you're doing this to better your family. Or you tell yourself, you tell yourself. You tell yourself, that's what it is.

But it comes at the expense of it. I think it's so difficult to find that balance for people. Well, it's difficult, but it's also not that difficult because you tell yourself you're doing it for them as they are repeatedly telling you, you're not doing it for me. I would like this. And you're like, no. And it's always interesting, you you hear those for people like family first, blah, blah, blah. And then you're like, why are you at this conference? I know why I'm at this conference. I'm not worth $100 million, right?

Like why are you here? And you're like, there's this Sennaka talking about one of the sort of Boogie men of Rome, this general named Marius. And he says, Marius commanded armies, but ambitious command, ambition commanded Marius, right? A, a, a, a, a, a, a, a, a, a, a, a, a, a, a, a, a, a, a, a, a, a, a, a, a, a, a, a, a, a, a, a, a, a, a, a, a, a, a, a, a, a, a, a, a, a, a, a, a, a, a, a, a, a, a, a, a, a, a, a, a, a, a, a, a, a, a, a, a, a, a, a, a, a, a, a, a, a, a, a, a, a, a, a, a, a, a, a, a, a, a, a, a, a, a, a, a, a, a, a, a, a, a, a, a, a, a, a, a, a, a, a, a, a, a, a, a, a, a, a, a, a, a, a, a, a, a, a, a, a, a, a, a, a, a, a, a, a, a, a, a, a, a, a, a, a, a, a, a, a, a, a, a, a, a, a, a, a, a, a, a, a, a, a, a, a, a, a, a, a, a, a, a, a, a, a, a, a, a, a, a, a, a, a, a, a, a, a, a, a, a, a, a, a, a, a, a, a, a, a, a, a, a, a, a, a, a, a, a, a, a, a, a, a, a, a, a, a, Woods being a great example of this, not just driven to win beyond any normal measure, but also pulled by this addiction, this compulsion that ultimately ends up destroying not just his family life, but his reputation.

And then also cuts off prematurely that run of greatness. The craziest example that I know of this, I write about this in the book, is that if you go back to the 1980s, Bernie made off before his Ponzi scheme began. Before he started the fraud, he was earning something like $30 million a year from the legitimate side of his business. He was a market maker on Wall Street, very successful. It was not a fraud. It was all legitimate.

And despite that, he was literally one of the most successful businessmen in the world in the 80s. And despite that, he wanted more so badly that he started the fraud that ruined everything. And there's this great quote from Buffett, which I know I'm a broken record quote, but he says, if you risk what you need in order to gain what you do not need. That's the definition of foolish. Risking what you need to gain what you do not need. That's the craziest thing you can do. And I think made off, of course, is the most extreme example. And he's a sociopath. But all of us have a little bit of that in us that like if we're lucky enough to have a rising income and a rising net worth, but our expectations grow by more than that, then we're never

going to be satisfied with what we have. And I think, I think Buffon does fall into that, that category. And it's, it's always just astounding to watch when there's never enough. No, enough is the enough is the richest place to be, right? There's a Epicurus line. He says, enough is never enough for whom enough is too little. Right. Like it's great. If you and then there's the famous Kervana get story, but you know, I have what he doesn't have. What is that? Enough. It's that. And everyone who hears that story is like,

Oh, great. I love it. It's so accurate. It's so smart. It's a great story because it is so obviously right. There's no debate that what he says is you're like, yeah, that's the key. But how many people after hearing that story will be like, cool, I'm gonna take back my career. I'm gonna tamp down on my ambition. Virtually nobody.

That's the back to the Will Smith book that I'm reading right now. He has this point where he's like, being the star of the next blockbuster movie was not an achievement, it was an addiction. It was a full addiction. And it wasn't like, oh, look what I've achieved. My next movie, like I achieved so much,

I'm so proud of myself. It was just achieving that. That was the baseline just to keep himself from being miserable. And once it turns from an ambition to an addiction, I think that's where you've crossed the line until like, this is all a net loss for you. Yeah, like Robert Green summarizes both the law of human nature, which is like that we deny there is such a thing as human nature. I would say the summation of the psychology

of money is that turning down money is one of the hardest things to do in the world. So difficult. And the irony of me writing that in the book is that the book led to opportunities that I should not have done. But I did. That's the irony. I'm becoming a little bit better at it,

but you talk about this too. Do you go to the concert or do you do the talk? I'm dealing with that as well. And the irony of it is I have that opportunity because of the book where I told you that you should not be doing this. So that's where human nature comes into it. I do feel like the majority of the book

was not me, it's not like I've mastered these skills, and let me tell you about it. I'm like, these are the flaws that I've noticed in myself and in my way, in my family, in my parents, in my friends, in my family, that have impacted me in negative ways. And rather than saying, I've mastered this and let me teach you, it's just like here's

a reflection of the faults that I've noticed in myself. Perfect man. Well look, this is awesome. I love the book and I hope we can get together sometime. This has been fun. Thanks Ryan. Being able to control your anger is a difficult but worthwhile goal. We'll take time and effort, won't be free, but by changing your perspective and developing techniques to control your temper, we'll ultimately be achievable in life changing.

So take the first step on the path to a calmer and more fulfilling future. Check out Taming Your Temper, the 10-Day Stoic Guide to controlling your anger. With the first step on the path to a calmer and more fulfilling future, check out Taiming your Tempor, the 10-day Stoic Guide to controlling your anger, you can just go to dailystoic.com slash anger. If you go back to the 1980s, Bernie made off before his Ponzi scheme began. Before he started the fraud, he was earning something like $30 million a year from the legitimate side of his business. He was a market maker on Wall Street, very successful. It was not a fraud.

It was all legitimate. And despite that, he wanted more so badly that he started the fraud that ruined everything. And I think all of us have a little bit of that in us that like if we're lucky enough to have a rising income and a rising net worth, but our expectations grow by more than that, then we're never going to be satisfied with what we have. And it's always just astounding to watch when there's never enough. No, enough is the enough is the richest place to be, right? There's an epicurus line that says, enough is never enough for whom enough is too little, right? Like it's great. If you and then

there's the famous Kervonigit story, but I have what he doesn't have, what is that? Enough. Hey, prime members, you can listen to the Daily Stoke early and ad-free on Amazon Music, download the Amazon Music app today, or you can listen early and ad-free on Amazon Music, download the Amazon Music app today, or you can listen early and ad-free with Wondery Plus in Apple podcasts.