The Curse Of Success | Morgan Housel PT 1

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2:02Welcome 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.

2:52Hey, it's Ryan. Welcome to another episode of the Daily Stoic Podcast. I did it again. Well, actually, I think when I did this week's interview, my ankle was pretty severely messed up, and then I wasn't feeling any pain on it anymore, and I was back to running. I was taking it easy, but I was back to running, and I thought all was well. Then I was walking down the stairs of my house on Friday, and, oh, man, I rolled it so bad. I heard this pop and all these sounds started coming out of my mouth, which I was no longer in control of. And I just sort of couldn't stand and I'm on the ground. And then eventually my wife came on me and she's like, why are you laying on the ground shivering?

3:53And I think I went into shock. I rolled it. I sprained it. Maybe the worst I've ever sprained my ankle in my life. And I had a talk. I've taken the whole family to Kentucky to do this talk to the basketball and football teams. So, you know, immediate medical care was not a possibility. So wrapped it, flew, did the two talks, finished the dinner I was supposed to go to, went to urgent care. thankfully not broken but i am out of commission for quite a while it made me think so there's a story of epictetus where epictetus is being tortured by his master and uh he says i think you're gonna break my leg i think you're gonna break my leg the master keeps doing it and um you know he does break it and epictetus says see i told you and um i'm just not sure that's possible

4:50maybe there was also some screaming and cursing involved but I'm just not sure that was possible and so now I have the marathon of the recovery which for me is not running and I don't it's too cold to swim unless I drive all the way to Austin so try not to go too crazy I'm trying to keep busy, and I am. And I'm trying to learn a lesson from all this, which is that was my fault for not resting and recovering enough in the first place. You know, that's a painful lesson in more ways than one. Back to today's episode. One of my favorite authors, someone I've had on the podcast, I believe twice. I interviewed Morgan Housel, not just for the podcast back in 2022, and his wonderful book, Psychology of Money, but then he came on the Wealthy Stoic Challenge that we did our sort of course on what the Stokes can teach us about money and finance, about how to be wealthy in the truest sense of that word, not just being financially rich.

5:48And he was in town. And so I had him out to the studio and we did a big two-parter interview talking about the decisions we make, the idea that we're in control of life or not, how we choose our identity and what success can and can't do to people. Morgan is a fantastic author. His book, The Psychology of Money, is so popular in The Painted Porch, we are constantly running out. It's sold millions of copies all over the world. And his new book, Same as Ever, is actually published by my publisher, Portfolio, which is an imprint of Penguin Random House. It's been off to an incredible start. Also, he signed a bunch of them in the bookstore.

6:25His books have been translated in more than 50 languages. And he's a great writer. You can follow him at Morgan Housel on Instagram and Twitter. You can read his articles also over a collaborative fund. And you can grab signed copies of his book, Same as Ever in the Psychology of Money at the Painted Porch, or grab the audiobook or ebook or physical books anywhere books are sold. If you want to check out the Q &A with me and Morgan in the Wealthy Stoic Challenge, you can go to dailystoic.com slash wealthy. And I'll link to our episode from 2022 as well.

7:12we're still we're just finishing we still have to do a little construction it's so cool this was a barbershop wow was it so you bought this separately you bought the bookstore so there's three buildings and they're the same building it's like in new york you know where like someone will do like so but those two over there are connected so we did those and then this went uh on sale during the pandemic yeah and this had been in the the people that built it still owned it yeah like the family so it had been in they don't and it had been a barbershop since it opened in the 1880s like different barbershops obviously but that's incredible the guy the reason they sold it to us is they were like will you let the guy in the barbershop stay as long as he wants which we did and he had been he'd been in here since 1969 um and then he passed away and then we were like what we're gonna do with it and i was like it would be cool to keep it going and then i was like i don't want to own a barbershop so so the next door is the bookstore and your office yeah i'll show you the i'll show you the bookstore and the record store and then upstairs his offices yeah and then in the back is where we do like some of the daily stoic fulfillment and then all the e-commerce for the bookstore and then this is uh studio and figure out what to do in the front and then it's gonna be my wife's office and then like the production stuff do you work here every day or you work from home most days yeah yeah i don't like uh i don't really work from home anymore because i don't know but you when you start taking your kids to school it's like you're already leaving the house yeah so like leaving i just come here cool love it i didn't know you grew up where did you grow up tahoe you grew up in tahoe yep truck okay so i grew up in Sacramento.

8:49And then it's amazing. I actually, to make it more specific, then I grew up for half my childhood in Placerville. Okay. And then, and then Chucky after that. So I lived in, we were, we are in Placer County, technically on the very far edges. And then my parents had a little cabin on the West shore. So I would go to Homewood almost every weekend. Yeah. So cool. I'm sure that was probably the same time. Yeah. When I saw it in the book, I was like, wait, I would, I don't know why I thought you were like an East coast person or something. I don't know. I lived, So I live in Seattle now. Yeah. I moved there four years ago.

9:19Before that, my wife and I were in D.C. for eight years. Okay. That's probably right. But yeah, I wasn't thinking Lake Tahoe. And then this all probably, that we both grew up, I was snowboarding. It sounded like you were skiing. This sounds much fancier now than it was then. Because when I was growing up, you know, going to skiers, it was like$30 a day,$40 a day. Yes. Now it's like$250. I don't know how anyone does it. It's really sad that it went from you could be a lower middle class family, take your whole family skiing. Yeah. And now it's to take a family of five skiing for one day. Yeah. One day is probably$1 ,200.

9:55Yeah. A ski pass at Homewood for a kid was like$300 or$400. Yeah. And then you could go as many times as you wanted. Yes. So, yeah, it was a very middle class activity. I'm trying to think what an equivalent activity of it is now. I think a lot of that is for if you're in like competitive traveling soccer or lacrosse or whatever it is. Sure. Then it gets pricey. I'm actually going to Tahoe tomorrow with my son. Yeah. I'm going to go skiing with him. We're flying into Sacramento. And at Sierra Tahoe, which is my home mountain growing up. And when I was growing up in the 90s, a day ticket was 25 bucks.

10:31Yeah. And I was 175. Yeah. And granted, I think a lot of what's happened is most ski resorts used to be owned by families. And there were rich families that just owned it because it was cool. none of them made any money right now they're all owned by corporations and corporations were like well we got to make money so everyone just jacked up their prices by literally fourfold yeah we're getting a little far afield from what we should be talking about but i was thinking like you know everyone's talking about inflation and and there and then they talk about just brands jacking up prices i think it's also what brands have realized as you get more and more data you realize what the brands and big companies have realized is that there's a customer that is not price sensitive at all yeah and so just like the reason first class seats in an airplane become more and more expensive is that they'll essentially pay an unlimited amount for that thing and so it just jacks all the price instead because you can't do what's expensive for some people and cheap for some people yeah something like skiing it just has to be expensive for everyone and they just jack the price up because they know that that the people who are going to do it anyway are just going to do it regardless of what it costs.

11:32There's some people, if you have a$9 million house, you're not even thinking about what a ski lift ticket costs. So you just do it. There's a lot of those items too, where if the market is rich people, the inflation rate is very likely going to track the growth of their assets over time, not the general inflation rate. So what has the stock market gone up in the last 15 years? About 12 % per year. What is the inflation rate for skiing, education, those things that pandering to rich people, it's going to match that level, not the overall inflation rate. No, that's a really interesting way to think about it.

12:04Yeah. So if you have a middle-class hobby that's also aspirational, you're thinking about it, what it was to you then, but then as the difference in income inequality has gone up and up, that activity that used to be accessible to you is now insanely inaccessible. Yes, completely. It's sad. What do you feel like you learned doing something like that that's translated in your life? I mean, skiing. Like I think about, I got a lot of independence out of like the idea that my parents would just sort of let me go on a mountain all day and then be like, we'll see you at four o 'clock. There's not that many things that kids do like that anymore.

12:43It was great. And it also, we had a team and we were traveling around, but it's not a team sport. It's an individual sport. And it was, I think that was really good for me to just be like, you're on your own here. You can't rely on your teammates to make the goal. You're like, either you suck or you're good. And that's, it's all on you. And to learn that independence mixed with, as you just mentioned, like a lot of these races where we would go to like New Zealand in our summer, their winter, we were 15, 16, and technically our coaches were watching us, but they were at the bar. They were not.

13:12And so we were 15, 16 thrown into New Zealand or the middle of Colorado and just been like, go have some fun. And that level of independence was extraordinary. So I feel like we grew up very quickly doing that because we were not in high school. We were not being driven around by our parents. We were just wandering around by ourselves at that age. And so that level of independence was great. Although it almost killed you. It almost killed me. Yeah. So growing up in Squaw in Tahoe, one day it was February, 2001. And my two best friends, Brendan Allen and Brian Richman, we were skiing together as we had for since our childhood.

13:48And we would ski out of bounce, which is you duck under the ropes that say, do not cross, but that's amazing skiing. Out of bounds, there's no chairlift at the bottom. So we would hitchhike back. We would ski until it spit us out on this backcountry road and we'd hitchhike back. As we're doing this, this one day in February, 2001, the three of us are skiing down and we triggered a small avalanche. And it came up to our knees. It wasn't that big of a deal. You kind of just ride around. We were like, woo. We got to the bottom and we literally high-fived like, oh, just that avalanche, so cool. and we hitchhike back.

14:18We get back down to the bottom of the mountain and Brennan and Brian say, hey, let's go do it again. Like, let's go do that run again. For whatever reason, I said, I don't want to do it. I was like, I think hitchhiking freaked me out. I always thought we were going to be abducted. And so I said, hey, why don't, let's do this. You guys go do it again. And I will, like, rather than hitchhiking back, I'll drive my truck around, pick you up and we'll drive back. I said, great, parted ways. Brennan and Brian went skiing. I went to go get my truck so I could go pick them up. 20 minutes later, I go to where I'm going to meet them to pick them up and they weren't there.

14:49And I didn't think much of it. I thought that they probably had hitchhiked back and like, they just got tired of waiting for me. So they left. So I'd drive back down to our locker room at the mountain. I expected to find them there, but they weren't there either. And I still didn't think that much of it. Like people, we didn't have cell phones back then. And so people were comfortable being out of touch. The hours went on. And eventually later that afternoon, Brian's mom called me at home and she said, Hey, Brian never showed up for work today. Do you know where he is? And I told her, I said, we skied out of bounds.

15:18I was going to pick them up. They never showed up. Nobody's seen them since. And we put together that this was, there's a problem here. Several hours later, we got the police involved, missing persons report. We eventually got search and rescue involved. When search and rescue entered the out of bounds area where I told them we skied, they instantly found the fresh scars of a massive avalanche that had just occurred hours before. So search and rescue knows that this is, they understand what happened here. after about nine hours of searching the search dogs homed in on a spot in this avalanche debris field and rescuers found brennan and brian buried under six feet of snow and it didn't really dawn on me until a little while later like how close i was to going with them on that on that second and that if i did the odds that i would have died are 100 it was massive you can't outrun these things and then so like it's this weird thing of the most important decision i ever made in my entire life was this brainless, dumb decision to not go with them.

16:18And I didn't weigh the pros and cons. I didn't think it through. It was just like, oh, you guys go do it. I'm going to go do something else. And nothing else, no other decision I've ever made matters more than that. And I think everybody, including you, everybody has had one of those decisions, at least one of those, a brainless decision that literally saved your life. We should talk about that. But one of the things that's interesting to me is I think people have this, we were just talking about like what your parents you still allow you to do we have this sense that like parents are way too protective these days but i think it's also a reaction when you look back each generation looks back the things that their parents allowed them to do and you're like that's insane yeah why would you do that why would you allow your kids to be in a position where as idiots they could make stupid decisions that could potentially change the course of their life one direction or another and so on On the one hand, yeah, the world gets safer and safer because things get taken off the table.

17:14But it's also because you have more – each generation, you have more and more data and horror stories about how easily it could go the other way. How fragile the world is and just hanging by a thread with everybody. It's not just true for individuals, but like the macro level too, how much the world hangs by a thread. I use a story in Same as Ever about during the Revolutionary War, during the Battle of Long Island, George Washington and his troops were cornered by the British. Yeah. And all the British had to do was sail up the East River in New York. They would have wiped them out. The war would have been over.

17:48No United States. Yeah. That didn't happen because the wind was not blowing in the right direction that night. Right. So they could not sail up the East River. And David McCullough, the great historian, was asked, he said, if the wind was blowing in the other direction that night, would there be a United States of America? Yeah. without hesitation, he says, no, never would have happened. So the entire existence of the country was just relied on which direction the winds were blowing on some random night in August, 1770, whatever it was. And so I think when you hear enough of those stories, you realize like how fragile all of this is.

18:19And then to me, this was kind of the core of same as ever. It's like, stop pretending that you think you can know what's going to happen next in the future. Because it all hangs by a thread in your individual life and at the macro level. Like the details of what's going to happen next at the macro level are completely unpredictable. I'm picking my kids up from school today and then doing our weekly routine, which is I take them over to Whole Foods. We get all our groceries for the week. Then we have dinner. It's one of their favorite things to do. It's one of my favorite things to do. And then my wife loves it because she doesn't have to take care of it.

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19:39You know, like a detour. So why would you ever take a tour when you could take a detour? Toyota Trucks.

19:53Yes. Yeah, it is weird, right? So there's sort of a paradox in the book, and I think in life, which is on the one hand, history is the same thing happening over and over and over again. Nothing changes, right? And then it's also true that each one of those historical events could have easily been something else. Like I think David McCullough said the one thing that you can't forget as a biographer, as a historian, is the people living those events didn't know how it was going to go. Yeah. And he said that it always could have been otherwise. Yes. And so that's the weird thing is that there's this sort of deterministic, like we're all just along for the ride-ness of life and history and fate.

20:38And then also this kind of both great man of history, like one person makes one decision and then also the wind or the elements or the football bounces one direction. And that changes the course of everything. Yeah. It's tough. There's a great book that I love. I think it's the greatest economic book ever written. It's called The Great Depression, A Diary. It was written by this bankruptcy attorney in the 1930s during the depression. And true to what you just said, when he's writing this diary in real time, he doesn't know that the Great Depression is going to end. And it was very common back then to think it would not end.

21:10And a lot of countries in Europe at this time embraced fascism in order to get out of that. And you have all these things like in the 1930s in America, good people like pondering in these diaries, like maybe fascism is the right way to go. Maybe that's the right thing to do because they didn't know what was going to happen next. And it's fascinating to read that relative to every other history book where the author knows how it ends. And that is going to color what they write in every single aspect. It was the same in World War II. Now we know that Japan surrendered in 1945. That was not a foregone conclusion.

21:44The United States was going to invade the Japanese mainlands in 1945. And there were estimates that could take years in addition to that and kill maybe half a million Americans in the process. So there's all these alternative histories that easily could have occurred. Yeah. So you have this, there's this kind of, it's a powerlessness and then also a very empowering idea that history can turn on a single decision. Your life can turn on a single decision. And then also the idea that you're in control is preposterous. Yes. I also think about like in our lifetimes, more modern, virtually everything that has occurred in the last, that's important, that's occurred in the last 25 years in America is tied to September 11th.

22:26Whether that was like monetary policy that led to the housing bubble or the wars in Iraq and Afghanistan that led to budget deficits, so many things tie back to that. Then you think, what if at Boston Logan Airport on that morning, the guy working at TSA security would have said, hey, you can't bring that box cutter on the flight. and just like wiped everything out. Everything from monetary policy to recessions to wars would have been different. Like there was not a single thing in America that would have been the same today if 9-11 did not have happened. Well, so Admiral McRaven was sitting in that chair yesterday morning and he was saying he was at the White House when Condoleezza Rice came out into the hallway to tell them that they'd made the decision to invade Iraq.

23:09And he was saying, you know, there wasn't any like music playing. like there was no sense that that was a dramatic pivotal moment like obviously it wasn't something anyone was taking lightly uh and they knew of course it was significant but he he was saying we were talking about it's like if that's a movie depending on when that movie's formed at the moment it's it's they probably would have thought it as this dramatic epic moment yeah and then now we understand it as a tragic foreboding moment. But in the moment, you don't know. You just think you're making a decision. It's just like a business decision that somebody whispered to each other in the White House.

23:47Yeah. And there's probably, if you've ever made a life-changing or what you think is a significant decision, there's just this sort of getting excitement of just like, we're going to do this thing. Do you know what I mean? It's the same decision. And I think this gives you a sense of history. It's the same decision your family made. It's the same energy your family had, are we going to buy this car? You know what I mean? Or are we going to move? Or should I take this job? And the people who are making the decisions at the level of like, are we going to invade this country? Or are we going to launch this bomb?

24:19Or are we going to put in place this, announce this economic policy? It's not that different. It is different, but it's not that different. It's just fucking people using imperfect information. trying to manage uncertainty. Yes. And that's like, yeah. And I feel like that, you're right. Like when I think about my wife and I's decision to have kids, to buy this house, to move to this city, most of those were more or less snap decisions in the moment. And I want to think that like, we thought these things out and planned alternative, like weighed the pros and cons. The truth is we didn't. It was like, all right, let's try this one.

24:54Well, that's the tricky thing. You know, Mark Manson's talked about that idea of like hell yes or hell no, or fuck yes or fuck no. And I think it's good. It's a good rubric if you're just like, do I want to have lunch with this person or do I want to go on this trip? People are going – like really minor things. But when I actually think about the decisions that changed my life, when I think about dropping out of college, I think about the decision to write my first book. When I think about this investment or that, like big things that I've done, the decision to do this bookstore, I was not. And anywhere close to fuck yes is the greatest idea.

25:26Totally. It's obviously going to work. And in fact, that kind of certainty is probably a sign that you're a maniac. You know what I mean? Like it's almost always, it's almost always 51, 49. Yes. My, I, I did not want to write psychology money and I put it off for years and years and years. And even when I finally signed a contract to do it and I had one year to write it, I basically started writing it 10 months into that process. It was just, it was just delayed, delayed. I didn't want to do it. And of course, looking back, it was the most meaningful thing I ever did in my career. and I did not want to do it.

25:59And then I can probably name a couple other things that I was so adamant that I wanted to do and were the right decisions. And in hindsight, I shouldn't have done. Right, I remember my agent had the idea for the Daily Stoic. I've had the idea for all of my books except for Daily Stoic. And my agent said, you know, here I'm thinking there should be this book of stoicism that people could start with. He had done a couple of daily books when he was a publisher. Like he did the Daily Drucker and a few other books. He's like, I think you should do it. And he's like, I think it'll be your bestselling book.

26:26Which wasn't, that's not how I make decisions about what I do or not. Like, was this going to be my best selling or most, you know, financially renumerative thing? But I was like, okay. Like, you know what I mean? Like, I didn't believe him in the sense, like, that seemed like hyperbole to me. And then in retrospect, it was true or close to true. Yeah. But what what happens then when you when you hear something like that or you make decisions like that, then you can take a really wicked lesson from that, which is that the prediction was correct. But in fact, the prediction and the outcome are two independent things.

27:05Yeah. There's some correlation there, but there's not necessary, not necessarily causation. And you can learn the wrong thing from having been, quote unquote, right. When you wrote Daily Stoic, in your mind, what did you think it was going to do in terms of sales and response? I mean, I think very – I can remember very vividly. I wrote the whole book. It's an unusual project to do to do a daily book because you're just doing a bunch of – you're not thinking about it as a book until later. You have to write – you're not like, what do I want to do on January 2nd? And then what's March 14th? You can't – that's weird.

27:38There's no correlation between the entry and the day at first. So first I just had to sit down and first I had to pick up like 366 quotes. Then I had to write 366 entries and then I arranged them and then I came up with themes. So it was kind of it wasn't until later that I even got a sense of like what the book was. But then I remember the day before I was supposed to submit it, I sent it to the editor that I work with, not at my publisher. And I was like, is this even good? I was like, should I do this? I was like, I don't know how I feel about it. Like, I feel weird about it. Like, I wasn't, because it was so different and it wasn't a style I was super familiar with.

28:22And I, so I, and he was like, I don't know. Like, he wasn't like, no, it's the best thing you've ever done. So there was what I remember from the writing to the up until publication. And then even like for a while after publication, I remember the ambiguity of it. Yeah. And I try to stay in the ambiguity of it because that's authentic and real and representative of where I was at the time. Not, okay, it spent two or 300 consecutive weeks on bestseller lists since, or it sold millions of copies since. And it became this whole other thing with the email and the videos and podcasts. I try to remember what I thought about it at the time because that's true.

29:07And what is true after is independent or it's a made up narrative that connects a different conception with a different impression now. because one, I think it's not honest, so I'd try not to do it that way. But two, it can bestow upon yourself a sense of prescience or brilliance or whatever that's not conducive to being right again in the future. Yeah, I think it's very true in venture capital as well, that the companies that make it and go on to be huge, at the time when the VC made that investment, it was not clear at all that this was gonna be a winner. And there were several companies in their portfolio that the VC was like, this company has got it and they go out of business.

29:55It's always the case. When Uber went out to raise money, I mean, it sounded like a joke. It's like most of these companies that do well sound like a joke when you pitch them at first. Uber is like, we think everyone should be a taxi driver and you're just going to get in a car with it. It sounds ridiculous when you go out to pitch it. Well, people do this. They go, oh, the first time I laid eyes on my wife or my husband, I knew that was the – And no, you had an, and look, there are some people and there's documentary evidence of it, which is, you know, that's unique and weird. But no, what you had was the same flash of attraction that humans have when they find people attractive.

30:29And then it evolved into what it is now. And you're finding a way to make that consistent as opposed to something that changed over time or grew into something. And I do think it's important as you think about your success that you tell yourself like the humblest version of that possible. Like with The Obstacle is the Way. When The Obstacle is the Way came out, first off, it didn't hit any bestseller list the week it came out. It probably sold three or 4 ,000 copies. No one was disappointed with it. Like I'm not, I don't want to present it like it was some, some failure, but like it was, you know like what most books do and then i had this idea that there was this thing called book bub which had come out then which is like an email that sends out a blast about deeply discounted ebooks every uh every day and it had just sort of come out and i a bunch of people i knew were using it and i was like let's wait a little bit and then let's let's discount the ebook let's do a pro a one-week promo where we discount the ebook from whatever they were 9.99 then to 1.99 And so the publisher did that, I don't know, two, three months into the thing.

31:44And I don't know why. No one's explained it to me since. But what happened was Amazon just like left it there. Like it just stayed at$199 or$290 at some deeply discounted price. And I remember going, are you going to ask Amazon to like, you know, increase it? And they were like, you know what's weird is like they're choosing to do this and they're paying the same – it's not a discounted royalty to you, so you shouldn't care. And I was like, okay. And it stayed that way for 11 months. Probably increased sales of the physical book too. Yeah, of course. So when you look at it, it's like it came out.

32:28It did like this and then it was kind of like this. And then there was this sort of spike from the e-book. And then it kind of just went like that. So what happened was an idea which is not super marketable, an obscure book about ancient philosophy or a book about an obscure school of ancient philosophy comes out and then it's subsidized by the biggest retailer in the world, which creates, which lowers the barrier to discovery and it gives that book a chance. So that's ultimately why everything I've done since had a better chance of succeeding because I got that thing. And so the lesson I try to take from The Obstacle is the Way is not I'm a genius.

33:11I wrote a book that popularized the school of philosophy and sold lots of copies. I go, actually, I wrote this book, and then I understood it had a certain barrier to entry. And then I proposed a unique marketing idea that happened to be far more lucky or successful than I could have ever imagined. And that's where the success comes from. That's where it came from, yeah. Yeah. I think in general, most book sales, particularly for big, big sellers, come from word of mouth. And therefore, like what you need to do early on is just get it in as many hands as you possibly can. And if it's a good book, as your books are, like any book that sells that much is a good book, but you get it into people's hands so that they can go recommend it to their friends.

33:50And it's just like a virus. If for every person who buys your book, if they recommend it to more than one other person, it's just going to go and go and go and go. And then, so I think like early on, it's just like waving your hands as much as you can, getting into as many hands, discounting it to$1.99 so those people can go recommend it to their friends and their siblings, whatnot. Well, I was just, I've just been very cognizant of it because I, when I was at American Apparel, what I ultimately realized is, so Dove, who's the founder of this company, the idea on its face is absurd, right? He's like, I'm going to make clothes in the US.

34:22They're not going to have branding on it. I'm going to run my own stores. I'm going to pay the workers a fair way. All these things that at each step of the way, people were like, that's a bad idea. That is economically impossible. That's not how we do things. And then it succeeded. And so what he took from that, what a lot of entrepreneurs take from that kind of success is, I know what I'm doing. I'm a genius. I saw what other people didn't see. And so that's the curse. That's why so many successful people fail to replicate that success. It's ego. It's hubris. It's this sort of narrative fallacy of I saw it.

35:03And so I am a seer. Yeah. And then that's what kills you. Almost the worst thing that can happen to you in investing is you're 19 years old. You open up a Robinhood account and you do really well. Yes. Because then you're like, I'm the next George Soros. I'm good at trading options on penny stocks. Yeah. It's the worst thing. It's the worst outcome you can have. Yeah. One of the best things you can have is you open up a Robinhood account and you lose half your money. And then you're like, okay, this can be dangerous. I need to figure out how this actually works because what I just did doesn't work.

35:31And it's this weird, and I think a lot of kids in 2021 who opened Robinhood's accounts and doubled their money in a month, day trading SPACs and whatnot. Yeah. That's like the worst thing you could possibly happen to them because every one of them thinks they know what they're doing at this point. Yeah. It's the same if you're genetically gifted in athletics early on, right? You think you're good as opposed to you have an advantage. You have an advantage. And so you don't actually develop the fundamental skill or the mastery of the specific sport, how it works. You don't develop the ability to see the love of the game.

36:10What you love is being great at the game. Yeah. Right? I was talking to Shaka Smart about this. And he was saying, you know, like he's the head coach at Marquette. He was at Texas. And he was saying that, you know, the athletes say stuff like, I don't love it anymore. and he's like what you don't love is uh what you love is being great at it you love being the best you never loved it you loved it being easy and and so if if you don't being successful early at something develops this sort of um false sense of what that thing is what it is whereas if you're bad at it for a while and you stick with it then you actually probably do love you're you're loving independent of the rewards, which is ultimately where you want to be with whatever you do.

36:56You do it because you like doing it. And then the fact that you're paid well for it or recognized for it or celebrated for it, that's like this little bonus. There's this quote from George Soros where somebody asked him, he says, George, how old were you when you learned that you love investing? And he says, love investing. He's like, I hate investing. I'm just good at it. And I think that's probably why he quit once he got rich enough too. Another thing on this topic that I always think about. So I grew up ski racing in Lake Tahoe. The two greatest ski racers from my era were Lindsey Vonn and Julia Mancuso.

37:27Both of them, by age five, you could tell where they were going. It was obvious. And by the time they were 10, it was like, they're gonna be the best in the world. They were a million miles ahead of everybody else. Another amazing skier from my era was Ted Ligeti, who up until he was about 18 years old, was good, not great. He was like a good regional skier. And then he became, by the time he was 25, the greatest giant slum skier to ever exist in history. And that, like, I always think about that. Like, did Julia and Lindsey have just an absolute natural talent? So the time they were five, it was just like, they were so good.

38:02And was Ted more just like hard work? He just figured it out. Sure. And like the different skills. And both of those are like really admirable skills. But it's, I remember from Julia and Lindsey, I remember always thinking, if you're going to be a good skier, it's obvious by the time you're five. Yeah. But then Ted just like completely broke that mold and showed like, no, you can become great 10 years into what you're doing. Yeah. Or that it's basically a crapshoot for everyone. Yeah. And if you're thinking it has to be a certain way, you're sort of missing the point. And I think Ted gave so many 18-year-olds hope that like, no, like I'm in ski racing for 10 years and I'm not that great.

38:38Sure. But that was true for Ted too. And he became the best in the world. One of the things you talk about in the book that I thought was really interesting that I don't think we talk enough about, especially people who write books for people who want to be successful, is that a good chunk of these people are like just maniacs. Like they're either fundamentally broken or wounded in some way, or that actually the success is a byproduct of some profound dysfunction and that you would not want to be these people at all. And in fact, they're not really these people. They can't help themselves. Yes.

39:10I mean, that's true. The most stunning example is Elon Musk, where it's like he has achieved some of the greatest success of any entrepreneur. He's going to Mars, he's building cars and whatnot. But the same personality characteristics that let him do that also have these negative sides that people hate. His views on Twitter, his manners, whatever you want to call it. But that's all the same personality. And I think what people want is they're like, no, we want Elon to be the crazy engineer, but we want him to be nice and civil and polite. And you're like, no, that doesn't exist. It's the same person.

39:43Bill Gates was the same. Walt Disney was the same. Steve Jobs was the same. They're all maniacs at their core. That's why they were successful. And there's this other element that comes from it. So you could say like, if you read Steve Jobs' biography, he was an absolute devil of a boss. You did not want to work for him. But that was why he was successful. So you can't separate those things. And I think a big takeaway from this is like, be careful when you are admiring someone. If you're like, I want to be an engineer like Elon Musk. Well, you're like, well, the only reason he was able to do that is because he's also has this kind of a jerk side that's attached to it.

40:14And you can't separate that. Well, also that it's not a choice. Do you know what I mean? It's like saying, I want to be like someone that's seven foot tall, or I want to be like someone that has cancer. Like, you know what I mean? Like, these are not things that they had anything to do with. And in fact, it's on net probably more negative than positive. Yes. I also think if you take someone like Mark Zuckerberg or Elon Musk, if they, let's just say that Mark Zuckerberg inherited a billion dollars when he was 18, hypothetically, that would not have slowed him down at all. I think he still would have been as successful as he was.

40:46They were not motivated by money. They were like, I have to build this product. I have to go out and do this. And I think a lot of those people, even today, when they're worth a hundred billion dollars or more, they wake up every morning terrified. And like, I have so many problems I need to go solve and I have to do it. Musk gave this interview like a month ago where he was like, you might think you want to be me, the richest man in the world, but you don't. Like it's a mess inside of this head. You do not want to be inside of this head. And I think it's true for all of them. Yeah. There's a Wright Thompson profile of Michael Jordan.

41:16It's called Michael Jordan at 50. And it's one of the most haunting, incredible pieces of journalism you'll ever read. And it's basically at this point, I think Michael Jordan is still, Michael Jordan is basically just the GM of the Hornets or the owner slash GM of the Hornets. And you would expect he's got the greatest life in the world. He's made his greatest basketball player of all time, biggest shoe brand, owns a basketball team, can do whatever he wants. But he's sort of just haunted by this ability, the sense that he can't do the one thing he's meant to do, which is play basketball. and that he had the thing, the part that made him great, but also made him a maniac was this competitiveness, this need to win at everything.

42:02And he says something to Ray Thompson, like you get this gift and it makes you great, but you can't turn it off. Yeah. Right. And that it's all, it sounds like something that would be in like a Shakespearean play or in a fable by Aesop where the gift is, comes with the inability to not utilize the gift or not maximize the gift. So it's actually a curse. Yeah. And he just can't not be competitive. And so, yeah, when you're a professional basketball player at 26, being competitive is an asset, right? Because it makes you better. You compete for a living. But now you're a 50-year-old billionaire who should be enjoying everything that you have.

42:48But you can't because all you're doing is comparing yourself to other people. and impotent to express the competitiveness that you feel in a reality or a world where you don't have the ability to be what you want to be. Yeah. I think that's especially true in sports where you can't do it forever. Warren Buffett's been investing for 75 years. You can do that forever. But what was it like when Kobe retired, when Jordan retired, when LeBron is going to retire someday? What do they do the next morning? I imagine that is a sense of torture, waking up and saying, and then realizing you can't be doing what you were born to do.

43:27Yeah. That's got to be a really tough thing. Well, but the problem is you weren't born to do it. Do you know what I mean? Like the amount of therapy and work you have to do as a person to go, I'm not born to do anything. I don't have to do anything. There is, do you know what I mean? Yeah. So the asset is not just the genetic ability or the blessing is the genetic ability and the skill and all the stuff. And then the curse is the belief, what we make up, which is like to be worthwhile as a person. I have to maximize the skill. That's it. And you don't. I mean, it's good too and it feels good too, but you don't.

44:11You don't have to do anything. I really admire athletes and business people and authors who quit while they're ahead. Yeah. And it seems like a weird thing to admire, but I really like people who are like, I'm at the top of my game and I have so much more potential in front of me, but I'm going to pass the baton to somebody else and I'm going to go spend more time with my family, whatever it be. Like, I think that's so admirable to do. And it shows that like they're in control of that demon inside of their head that I think probably people like Jordan and Kobe and LeBron are not in control of it.

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47:46Well, you realize that that's a rarer thing, right? So being, you know, 0.001 % in your profession is a very rare thing. And then among those people, like people who are considered great or not even great, just or a goat, like just people who are considered elite at their thing, how many of them have the ability to turn it up or down intentionally and more rarely turn it down or walk away or feel good or be enough or have happiness inside it? That is the far rarer thing. There's, you know, ultimately there's lots of people who become generals, who become billionaires, who become, you know, MVPs or champions or bestsellers.

48:33Like ultimately it feels rare because at any one moment there's not that many people doing it. But every year there's more of those people. So cumulatively lots of people have done it through history. how many of them have had some semblance of control over it and themselves while they did it. That is the rarer thing. It's like the 0.001 of the 0.001. Like they're already in the 0.001 by their talent, but then only 0.001 of them will be able to like take control over the demon and say, I want to quit while I can. Yeah. I mean, look, so you sold millions of books, right? You put out a book and first off to write a book is a rare thing, right?

49:11Then to write a book that sells. It's a rare thing. Then to write a book that sort of reaches escape velocity, right? Which you've done, I've done. That's a rare thing. And then for how many people can that be, what percentage of those people does it not become this sort of thing that either they're always trying to surpass, right? Or this thing that they're trying to do more and more of. for how many of them are they just like, that's what I did. And I keep doing it because I love doing it, but it's not, it's not a great burden in some way. It's actually, it's surprisingly rare thing. It's hard work.

49:58Yeah. It's tough. Paul Graham's idea of keep your identity small is really important. Anytime in life where you say, I am a blank, whatever it is, I am a Republican. I'm a bestselling author. I am a blank. You are tying yourself to that, to something that may not last. And if it doesn't last, then your identity is broken once it's gone. That's a tough. The other thing I'd read recently from Arthur Brooks, which I thought was interesting was don't keep your trophies on display because those are your past successes. And if you are literally walking into your office every day and being like, I used to be great.

50:29This trophy shows I used to be good. And then if you, then it prevents you from moving on to some other phase of your life. It's a reminder of what you used to be. And that can be a tough thing for people. I don't know if I totally agree with that because I could see a world where you're like, I did it. I feel good. That's the recognition of having done it. Yeah. And then a version where you're like, it's Jeff is it's day one. It's always day one. That's also a way to keep yourself from never feeling like you did it, which you did do it. It's not day one. The company has been around for 15 years.

51:01Pat yourself on the back. Do you know what I mean? Yeah. And so I can see a world where. I can see both ends of it. I do think there probably are people in sports, whatever it be, who are haunted by their trophies as a reminder of the body that they used to have, the skill that they used to have that they don't anymore. It's a first world. I mean, I remember the first time I was like profiled in something or the first time I hit a bestseller list. And then also like, you know, like a publisher will send you something or, you know, you'll like someone has a gift, we'll we'll get it framed and you go like i did it you know like and then and and it's cool and then what happens is if you keep doing it if you keep doing good work then you get more of them and then you're like now i just have a lot of this shit yeah right and what do you what are you supposed to do with it because you you don't want to get rid of it because it feels like it means something um but it it it doesn't and it's just like another framed thing that only has significance to you.

51:59And so to me, it kind of the, the, as I've done this now a long time, the accumulation of like mementos or commemorations, it, it, it, it's kind of the physical embodiment of the baggage that the ego picks up, you know? Um, and, and, and the stuff is just kind of rattling around physically when you move, but then also mentally in your head. And yeah, it's not super conducive to just like being present and being content and just being a person in the world. I think choosing your identity is really important too. I consider the core of my identity to be father, husband and not author. And I think I would be okay at some point in the future, not in the near future, but at some point being like, I'm done writing books.

52:44That was like, I'm not an author. That's not core to my identity. It's a thing that I did that I'm proud of and I like doing it. I'm glad I did it. but my identity is father, husband. And like, that's the core of who I am. So I think no matter what you do, I think like everyone has their identity, but like choose what you want to be very carefully. I think if you tie yourself to things that you either don't want to or can't do indefinitely, you're setting yourself up for some phase of misery. Cheryl Strayed once made this distinction between writing and publishing, which I think is really important.

53:16So if you're, and then my friend Austin Kleon has talked about this, like, you know, are you the noun or the verb? And so if your identity is the verb, that's great because you can keep doing it professionally or not, right? If your identity is that you love basketball, well, you can play basketball a long time. If your identity is NBA all-star - I win championships. Yeah. That is much less in your control. And I think with Stoics, the whole point of Stoicism is like, where are you in relation to things that you control versus things that you don't control? And so, yeah, sure, look, the identity of a basketball player can get taken away by an accident, but that's more rare.

53:57And also there's still ways you can relate to the game. You can still be a dude in basketball, whether you're playing or not, right? Because you can participate in the universe of the thing. But if you have associated your identity or your self-worth with the recognition for the thing. That you're getting it. Yeah, that's really cool. But let's say, I'm not saying this is going to happen, but let's say in 30 years you're writing books and they're selling 2 ,000 copies. Nobody's paying attention. Would you still enjoy writing it? Well, that's the question. Do I like writing? Do I write because it brings me some sort of satisfaction or relief?

54:37does it help me figure things out? For the most part, yes. I mean, would I write differently if no one was reading? Probably a little bit. If it was just a diary entry. Yeah, I would, but I also journal every day, right? I have been sitting down and trying to arrange words in an order that makes sense to me since I was in my room in high school, right? It's always done something for me. It's done different things for me in different ways and at different times. But yeah, fundamentally, I like doing the thing. And there's probably some universe where if you're selling 2000 copies, you're telling yourself, oh, it's going to be appreciated.

55:14Like I'm sure the mind finds a way to rationalize that it's different. But I do think I would still be doing it. And one of the things I think about when I make decisions, I go, one of the benefits of this profession is that you can do it forever. It's like investing. It's not like music or like sports where the public is judging you harder as you age, right? Or the environment is harder to keep up as you age. I could literally do this till I die. So I've tried to make better decisions about how I can be more sustainable in what I do with the idea that I do want to do it for a long time. I mean, at that rate, you're on track to write roughly 17 ,000 books.

55:52Yeah, it would be probably two. But I actually think about that. When I open an academics book for example and there's like 500 you know it's like other also by books it's like yeah i go these can't all be good you know what i mean and so so i was like at this pace i'm gonna be that person fiction is probably an exception to that i think there are people who've written 50 fiction books james patterson uh john grisham that can all be great sure you need to do deep research and be some sort of expert on your topic hard to write 50 non-fiction books that are all great yeah yeah yeah and so i was like okay i should probably slow down a little bit and so i i i do think about it that way.

56:28So now you're at one a year instead of two a year, whatever it be. Yeah, probably. I took an extra year on this one I'm doing right now. But yeah, that is the question. Do you do it because you love it or do you love what the thing brings you? Yeah. You and I have talked about J.D. Salinger before. And my understanding, I might be getting some of this wrong, but he was a very mentally disturbed person. A lot of it was PTSD and alcoholism, but he was, you know, all kinds of, all, all, all, all, all kinds of brokenness. Um, my understanding is he was, you know, one of the bestselling published authors, but then after he got kind of sick and just like went off the reservation, got sick of the industry, he kept writing for himself.

57:08He just never published it, but he kept writing maybe every day, just loving putting words together. And that's like, that is really fascinating to me that he, like, he's an example of just someone who loved writing but got sick of writing for other people. Just wanted to tell some stories. It seemed like he hated his family. And you know what I mean? It was this escape from reality, which is probably not healthy. I just read this book called Furious Hours, which is sort of a true crime book, but it's also about Harper Lee, who wrote To Kill a Mockingbird. And she was going to write her next book about this murder case in Alabama where this preacher was killing everyone close to him for insurance money.

57:48It was just like wicked insane case, not far from where she grew up. And the writer's just talking about this sort of crippling perfectionism that besets Harper Lee, plus probably some alcoholism. Plus she had this weird like aversion to paying taxes. And she was like afraid if she made more money, she'd have to pay more taxes, which is again - That's a tough mindset. Something people should never think about. As the Stokes say, you pay your taxes gladly. um but but it the curse of being so successful right out of the gate prevent it sucks from her the love of being able to do the thing and to do the thing not always at your best right like the the curse of perfectionism says that this is the standard and anything below the standard is worthless yeah and that's not true she if if to kill a mockingbird is one of the great novels of all time, something half as good is still really good.

58:46And so part of doing anything sustainably is being kind enough to yourself to not expect you to be anything other than a human being. Yeah. I mean, if you think about the authors who have written 30 or 50 books, John Grisham, James Patterson, there's a very clear hierarchy in there, whether it is sales or just your own opinion. If you've read all John Grisham's books, you're like, some are amazing, some were duds. Yes. That's true for everybody. I'm sure with you, you don't have to name them, but there's a hierarchy within your own books, within your own head. Yeah. And maybe it doesn't correlate with the sales.

59:22It might correlate with your own view of it. James Clear and I were talking about this recently too, that like, yeah, if you write a lot, there's going to be a natural hierarchy and you just have to put up with that, that some books are going to sell better than others. You're going to be prouder of some than others. And that's just a reality of what you're doing. You can't write smash hit after smash hit after smash hit that are of equal quality, of equal reception of equal sales. Well, I bet it's, I mean, it's probably hard for him. James is already a perfectionist, right? And just putting out his first book was very hard for him.

59:52Like it took longer than it was supposed to. It took longer than he probably wanted to. And I know sort of right up until the last minute he was tweaking, like that's how he, so for it to then come out and set an impossible bar. Like I heard when someone go, they're like, that song wasn't a hit. They were like, it was a freak, right? Right. And and there's actually that seems like it's dismissive, but there's actually a lot of freedom in that. So to go that book or that project or that company that I did, that wasn't a hit. That wasn't a success. That was a freak. Yeah. Is a way to free yourself of the impossible expectations and burden of what you did the first time and to go, OK, I'm just doing it again.

1:00:35And there's zero chance that we'll even approach where I was before. Yeah. But it's still worth it. doing. And so I can imagine following up something like Atomic Habits. It's like impossible. And so you can't. You can't try to. I've been lucky in that a lot of my books popped in many cases well after they'd come out and I was already on to the next thing. So what they represented or the success they had it it not only um was a a conclusion slow in coming um it it was it wasn't even something i was thinking about because like i had a contractual delivery date that was more important which is also what someone like john grisham does john grisham and i've worked with his agent before and actually i did the marketing on one of his books many years ago he's like i start a book in I forget what it is exactly, but it's like, I start a book in June and I turn it into the publisher in August and it comes out in March and that's my life.

1:01:35That's just what he does. And so when you're like, some are great, some are not, it's like, it lined up in 2016 and in 2017, it didn't. And then 2018, 2019, 2020, he was on fire. But it's a process that is independent of him as a person or as his identity as a person. And that is how he is able to do what I think would otherwise be crippling or you'd be too self-conscious about. Yeah. I know F. Scott Fitzgerald is another great author who was just mentally crippled at his own success too. And I think there's a lot of like that early success, having it early on. And if you have the kind of personality that you're like, nothing short of what I did the first time is going to be good enough.

1:02:21A lot of founders fall for this too. If you're a first time founder and your first company is a big success and then you're like, I'm going to start another company. The odds are never in your favor. Even if you are successful the first time, your second company is probably not going to work no matter who the founder is, no matter what you're doing. That's always the case. And I think it ruins a lot of them. It gets back to like big success early on, either early on in your age or the first time you do something can be like a hidden curse. It's a very first world problem to have, but it is kind of a hidden curse to have.

1:03:06Thanks so much for listening. If you could rate this podcast and leave a review on iTunes, that would mean so much to us and it would really help the show. We appreciate it. I'll see you next episode.

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1:04:36That's why I don't begrudge them when they appear on the shows that I listen to. But again, as a person who has to pay a podcast producer and has to pay for equipment and for the studio and the building that the studio is in, it's a lot to keep something like the Daily Stoic going. So if you want to support a show but not listen to ads, well, we have partnered with Supercast to bring you an ad-free version of Daily Stoic. We're calling it Daily Stoic Premium. And with Premium, you can listen to every episode of the Daily Stoic podcast completely ad-free. No interruptions, just the ideas, just the messages, just the conversations you came here for.

1:05:20and you can also get early access to episodes before they're available to the public. And we're going to have a bunch of exclusive bonus content and extended interviews in there just for Daily Stoic Premium members as well. If you want to remove distractions, go deeper into Stoicism and support the work we do here. Well, it takes less than a minute to sign up for Daily Stoic Premium, and we are offering a limited time discount of 20 % off your first year. Just go to dailystoic.com slash premium to sign up right now or click the link in the show descriptions to make those ads go away.