The Art and Obsession of Writing with Rich Cohen

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0:33Ryan Holiday: And Quo integrates with the tools your team already uses, HubSpot, Zapier, Claude, whatever. It helps you save time, stay organized, and spend less effort chasing down information between systems. Money is on the line. Always say hello with Quo. Try Quo for free. Plus, get 20 % off your first six months when you go to Quo.com slash DailyStoic. One of the reasons people think that they're not introspective people in the past is because it's hard to accept the reality of somebody that's not alive right now. It's just very hard to make them anything but kind of a character in your mind and not real.

1:11Most of the people in the past thought that they were doing the right thing.

1:14Ryan Holiday: Yes. So in order to judge them, it's not just that you're having more information and everything. You have to believe that you are doing the right thing right now. Rich is one of my favorite writers, so I was honored to have him on the show. He has just brought to life things that I didn't know about, things that I didn't know I wanted. He had this book called Tough Jews that I love. His father is fascinating, who he wrote a book about called The Adventures of Herbie Cohen, who wrote that book about negotiation. He wrote a book about youth hockey. He wrote a book about the Rolling Stones. He wrote a book about the Jewish resistance in World War II.

1:48Ryan Holiday: He created this show with Martin Scorsese and Mick Jagger called Vinyl on HBO. That's also incredible. I guess what I'm saying is this is one of my favorite authors. I've gotten so many stories from his books. I've learned so much from his books and I just loved this conversation. We dove into history and memory and writing and parenting and sports and grief. Great conversation. I think you're really going to like it. Let's get into it.

2:16Ryan Holiday: So I was thinking about a conversation you and I had like 10 years ago when I was working on obstacle. I just read The Fish That Ate the Whale. But we were talking about Zemuri, who is a fascinating figure. And you said something that I've been thinking about, which is like, you thought that he thought he would be appreciated by future generations. Yeah. Like they all thought history would judge them kindly or the future would be grateful to them. And of course, the exact opposite is true. How do you think about that? I think that the people that try to stretch themselves and go further than their time warrants or that it's typical for their time, then get blamed a lot of times because they're the ones we remember.

3:01Ryan Holiday: Yeah. So out of the millions and millions and millions and millions of people that lived in the past, there's only a couple of names that survived. Right. And a lot of times, you know, you'll find people that get blamed for even their very awkward reaching across lines that people haven't reached across. They left a record and they get blamed for their prejudices and for being stuck in their time. I think that Zemmuri basically entered, if you think about it, there was a football game going on and he entered the game. He didn't really think about the rules of the game, if the game was moral, immoral.

3:32He just was trying to compete in the game. The irony is that he started his own company that competed with United Fruit and was a much better company, a more moral, a cleaner company. But because of his success, he was ultimately forced to merge with United Fruit. And then he took on the legacy of this other company, which really wasn't his legacy. And that company itself has its own interesting past, which is more complicated. Everywhere you look, it's more complicated than you think.

3:58Ryan Holiday: But have you seen that clip? You know who Marc Andreessen is, the venture capitalist? It's a clip. He's on a podcast and they're talking about introspection. Have you seen this? The guy's like, you know, I've read all these biographies. None of the figures were introspective in any way. And Marc Andreessen, obviously very successful, sort of larger than life figure, goes, I'm not introspective at all. I never look inward. I never look back. I only look forward. And they're sort of, I think what they're trying to make the argument of, and it's not historically without basis, which is that like to be a great success, to be a world mover, to do huge things, you can't get caught up in these niceties about thinking about other people, thinking about moral questions.

4:41Ryan Holiday: Like, I think they're trying to say that today's generation is too conscientious and deliberative and not sort of bold and swaggering and ambitious enough. I'm not sure that's true, but it's an interesting argument that someone like Zemuri falls right in the middle of because he didn't strike me as a particularly introspective figure. Well, the thing about introspection is it leaves no evidence. Yes. You know what I mean? So you're judging based on what somebody did, not what they're thinking. Right. Which is a problem you always run into with nonfiction, which is I really don't really know what this person was thinking.

5:13There's no way to know. So you look for little hints of introspection. So the amount of charity Zamuri did, he set up this free school in South America. He did that shows a level of introspection. Plus, I think he saw himself one way. Yeah. You know, he was a member kind of of FDR's cabinet and all this stuff. And he saw himself as kind of with the good guys. And the values, he lived long enough that the values all changed. And all the things he did were suddenly judged not so good. So I think of him like a guy that's holding a hand of cards all night. And suddenly at dawn, all the cards change meaning.

5:47Suddenly the aces and the jacks are now like the twos and the threes. And the twos and the threes are like the aces and jacks. And it all turned around on him at the very end of his life. And it confused him. But one thing about people today, and this is what always drives me nuts, which is most of the people in the past thought that they were doing the right thing. Yes. So in order to judge them, it's not just that you're having more information and everything. You have to believe that you are doing the right thing right now. You have to believe that what you're doing, the things you're not even thinking of, won't be judged very harshly in 30 or 40 years by your grandkids.

6:24And the fact is, you try your best, but you don't really know how you're going to be judged. And it takes an incredible lack of humility and a sense of certainty to judge people about their actions, a lot of people about their actions in the past who were born into a particular time, lived in that particular time. And if they're lucky and they lived a long time, you know, live long enough to see that some of the things they thought were good were not going to look good in the long run.

6:48Ryan Holiday: Do you really think they were always doing their best though? Like, I was just reading this fascinating essay about Thomas Jefferson. And, you know, obviously Thomas Jefferson says all this world shattering and changing ideas about how we're all created equal and he condemns slavery and he understands the sort of moral rod of it. But they're sort of looking at some of the things that had been omitted from the history that actually was much more involved in running the slave plantations than people thought. And that the sort of big breakthrough for him, the pivot point and the change of his views, the essay is arguing, is when he starts to calculate the rate of return on the birth of new slaves.

7:21Ryan Holiday: And that this becomes, it's like the Upton Sinclair thing. It becomes very hard to understand something that your salary depends on you not understanding. It's like, He basically goes, he thinks slavery as this dying institution, this financially sort of inefficient industry. But then he starts to realize, oh, I'm making like a 4 % return a year just on the birth of new slaves. Right. And that it's this calculation that ultimately gets in the way of him doing what, say, Washington is able to do. So I don't know if it's true that they were all, that everyone was always doing their best. Well, you're talking about slavery, which is.

7:57I just mean generally. There's some things that are universal and they're always evil. Slavery, I would think, would be one of them. I think what's interesting about Thomas Jefferson was I think he was really introspective and he was a genius. Yeah. And he was smart enough to know that what he was doing was not defensible and would not be defended after his death. He understood all that and he wasn't willing to pay the price. So he was hoping that they were on a downward slope where it would slowly fade away. Would solve itself. Right. And that would allow him to escape and live his life the way he wanted to live and the way he wanted to live it.

8:26almost, you know, for his own sanity, maybe it would have been better to be a little stupider than he was. But he's sort of, you know, stupid people have the advantage of that. So I think that, you know, he's a really unique case because he sort of made America what America is. And built into that is the fact that he knew that he was engaged in something, an evil.

8:43Ryan Holiday: Yeah, it is. It is funny that the argument that they weren't introspective, because actually, when you really dig into the lives of the people, you find that they were quite introspective. There's all sorts of things that we sort of assume were cut and dried, but actually they went back and forth on, they tortured themselves without. And then also it seems like a silly argument to me because when I look at the flaws of those people, when I look at the most indefensible or the most egregious things they did, I see that as part and parcel of whatever that trait of not being introspective was. If they could have thought a little bit more, that probably would have been better.

9:24I mean, I think one of the reasons people think that they're not introspective people in the past is because it's hard to accept the reality of somebody that's not alive right now. It's just very hard to make them anything but kind of a character in your mind and not real. And what I meant by, you know, right now, I assume that Jefferson was involved in very evil behavior and knew it. And I think that the same is true today. You just don't know what, you know, it's not whatever it is that people are kind of letting themselves off the hook now by sort of sort of relegating it all to the past. Like now we have it figured out and now we're we got our heads on right.

10:02I just think that you run into this problem where it's very hard to understand what people were thinking in the past and what was going on. But I do think that people are basically the same. Yeah. And there might be some outliers. So I wrote this book, Murder in the Dollhouse, about this guy, Fotis Doulos, who killed his wife. I think that I came across him. I didn't understand him at all. He was an outlier, a murderer. But mostly, 99 % of people are basically the same. If you put them in the same situation, they'd behave the same way that the other people in that situation did. And as a writer, I think my whole premise is based on that, which is if I kind of feel something, most other people are going to feel the same way.

10:42If they were in my shoes, they'd feel the same way. And if I was in their shoes, I'd feel the same way. And that's also true with people like Sam Zemuri, even though he was incredibly talented, ambitious, smart, had a lot of energy, did all these things. He still, at the end of the day, wanted to do the right thing. And he still felt at some level that he wasn't doing the right thing, which is why he tried to make it right. Yes. You know, by a charity and everything else he did. And those things are appreciated. I mean, people are still benefiting from them. And I assume that with Thomas Jefferson, at some level, he was operating the same way.

11:13Yeah.

11:13Ryan Holiday: I mean, that's what is so remarkable about philosophy and art and music is how they manage to capture emotional states or human experiences that reach across centuries or generations. And you're like, oh, I feel the exact same way. Because the fundamental problems haven't changed. They're still the same problems. Yeah. Still the same fears, still the same hopes. People have not changed. Right. Not in 2 ,000 years, maybe in 10 ,000 or 20 ,000. But even you look at cave paintings and you're like, there's something sort of fundamentally What this does is it gives you like a degree of humility, which is, it's like Ecclesiastes.

11:53Ryan Holiday: Yeah. That's my Stoics, you know, which is all these problems that you have now people have had not once before, but innumerable times before until it disappears until the event horizon, you know, and what you're dealing with has been dealt with and will be forgotten and will be dealt with again and again and again. Yeah. Yeah. And maybe the only thing we can do is practice a little introspection and try to share some of those lessons. I mean, some of the things are ones you can only learn from experience. But I think often you look at the sort of larger than life lives and you sort of go, okay, like at that level, if it doesn't solve it, you know, at that level, if it doesn't fill the hole or, you know, make them feel secure or good.

12:40Ryan Holiday: like why am I thinking that if I just accomplish enough or achieve enough or make my mark like deep enough it'll do it for me right because that's why sports are a good model if you ever played sports which is you don't play sports thinking you're going to change the game you're going to change the rules of the game you're going to solve the game and there will be no more reason to play a game anymore you're just thinking of that particular game and your particular teammates and that you want to do as well as you can mostly your first motivation is not to make a fool of yourself and to prove that you belong in the game, you know?

13:11And then if you get ambitious, you want to be good at the game. And that's basically what we got is, you know, what I feel like. My father just turned 93. You're making me think of my father. And he gave this, I taped it. He gave a little, he must've prepared it, but he said this thing. He said that he sees his kids and his grandkids as ambassadors he sends into the future past his death.

13:34Ryan Holiday: Yeah. And I think that there's something that's the best you can do. I mean, that was, he doesn't really, he's 93. He hasn't said a lot of things that I haven't heard before, you know, but I hadn't heard him say that before. And it was, uh, it's inspiring to think like you do what you, what you can do, what is in your power to do. You try to do the best you can and don't really worry about. Well, there's like different levels of that sort of multi-generational impact that people try to have. And then there's this for people trying to sort of bend the world to their will, trying to, you know, sort of make their dent in the universe.

14:05Ryan Holiday: The irony is how often those people like neglect the ambassadors that they're sending to the future that live at home. Yeah. Well, they don't, maybe don't think of them that way. Right. Right. You know, I mean, it's like, I, I want once wanted to write a book just about little brothers, a little, because I'm a little brother. Yeah. And when you're a little brother, you have humility usually. I mean, you can become very angry, I guess, but little brothers, because is when you arrive, it's already happening. The game is underway, you know? And so much of what your personality becomes depends on your birth order.

14:35So when you're a little brother, you have to figure out, or a little sister, I guess, the youngest sibling, you have to figure out how to fit in an existing paradigm. It gives you like a lot of humility and realizes that you're not inventing new tools. You're working with tools that are already there.

14:48Ryan Holiday: I thought about a line from one of your books two weeks ago. It's my son's like second to last lacrosse game. You have that great scene in Pee Wee's where you like go up to the coach and you're like, hey, my son needs more playing time or what's going on. And the coach is like, hey, let me ask you a question. Is he having fun? And then you're like, yeah. And he's like, what the fuck do you care? Right. You know? And my son had like basically played like 40 seconds in this whole game. Right. I was going to go up to him and be like, it's okay. Like, it's cool. And like before I could even say anything to like console him, he's like, hey, can I do lacrosse again next year?

15:22Ryan Holiday: And I was like, I mean, sure. Like, I thought you were going to be upset. And like, you didn't even know, I don't think, I don't think it computed for him that it wasn't good, like that it didn't go well. And then, so you just think about like, that is our, our sort of ambassador to the future is, is like our children, obviously, but then it's also these little lessons, hard one or otherwise. And we're either paying them forward in books or in, in art or in conversations. That is, that is the, we don't learn a lot and we don't change, but like there are little things here or there. Well, to me, the big lesson for Peewees was, so I've seen crazy sports parents.

15:59I judge them harshly. I make fun of them. I mock them and I don't like them. And then when my kid showed a little bit of talent for hockey, I became one of them immediately, instantly. And I couldn't, it was like a possession. It was like a kind of rabies of the soul. That's the big, which is when it's your kid, it's so deep. And when your kid does something well, there's nothing like it, man. It's like nothing. So it's the point is that just because you understand these things doesn't mean you won't spare yourself or others while going through them. And only later do you gain a little bit of perspective only because it's not happening.

16:34And I assume if it happened again, I would act the same way again. I would try not to. But it was like a big check on me, which is what I was valuing, which was not what my kid was valuing. My kid was valuing the experience. A lot of these even NHL players, when they're interviewed, they say their best moment in pro hockey was. Actually, there was a book about this guy, Derek Bougard, who played for the Rangers. A really good book. I'm forgetting the name of it. And he became a fighter in the NHL and he got CTE. And he has a tragic story. but in the book he says that his favorite moment in all of hockey playing in the nhl and everything was just driving to the games with his father wow that was it yeah you know and there was a really funny it's just sort of encapsulated which is there was a really funny meme or whatever going around among kids my kid's age which is it showed you how kids view the game like it was it was a kid tweeted basically when you've driven three hours to a hockey tournament and you suddenly realize you forgot your hockey bag and have to tell your father.

17:29Yeah. And that was actually retweeted by a bunch of guys in the NHL and stuff because everyone had that experience as having to buy all new equipment or something like that or borrow a bunch of equipment at the rink. But that's what they're thinking about.

17:42Ryan Holiday: I think about that one all the time that is attributed to the Sandlot and it feels so true, but it's actually not in the movie, The Sandlot. It's quoting the movie, but it's not real. But it says at some point there was the last time that you went outside with all your friends to play baseball and none of you realized it. And like, that's more what your kids are thinking about, like, because they still like it. They're still having fun with it. They're thinking about it as this thing they like to do. And our instinct is to sort of professionalize it or to raise the stakes of it. Well, it's funny because the funnest I ever had playing sports was an adult league softball team that played just with my friends.

18:20No coaches. We we got really bad. We won the championship. Then we went to college. Everybody came back, whatever they were, overweight, on drugs, not paying attention. And we went from a great team to a horrible team. And I got, everyone said I should make my father the coach. Okay. Cause my father looks a lot like, or looked a lot like Walter Matthau in the bad news bears here. So they call them, you know, butter maker, boiler maker. And my father took it super seriously and attempted to to do all this and we couldn't explain to him this is a joke man like you've just made us like you're having us one run wind sprints and you probably think of that memory as

18:59Ryan Holiday: well like it's probably time you enjoy getting to spend together oh yeah it's really really really funny my friends all talk about it he had us doing very advanced shifts that they now use computer models for because he grew up with the ted williams shift you know and we're like i'm not going to do it because i think it looks i'm not putting the shortstop in right field he's like why it'll work I'm like, because it looks stupid and it will be made fun of. That's another huge motivation in life, which is just not to get made fun of. So it's another great thing for me in a book is in the Tom Wolfe book, The Right Stuff, where he's got the astronauts sitting upside down in the capsule waiting for the blast off.

19:32And everybody's wondering what he's thinking. And all attention's focused on this guy. And they say what he's thinking is, I don't want to screw the pooch, man. Yeah. Just don't let me fuck up.

19:41Ryan Holiday: Dude, I just read this Tom Wolfe thing for the book that I'm researching right now. He wrote this weird sort of very new journalism piece about these two aircraft carrier pilots flying over Vietnam. It's called like Nick and Charlie Go Jousting or something. It's so incredible. I think I've heard of it. I mean, I'm sort of a Tom Wolfe fanatic. Yeah. It's weird that I've never read it. It must have been run in some like New York, in New York magazine. Yeah, some weird magazine that you've never heard of. And there's some reason probably why he didn't anthologize it. I know, but it was really good.

20:08Ryan Holiday: It was like exactly what I needed. But did you watch the Man in Full TV show? I watched part of it. wow that's so mad yeah i was so mad yeah well it's really hard because the better the book is usually the worst the movie is going to be because so much of what makes a book good is the voice yeah and there's no way to get the voice so they try to other ways to get the voice and they can't figure out what's missing it's why there's never been a good movie of on the road there'll never be a good movie of the great gatsby because they're all about the voice and when you're a reader, you get hypnotized by the voice of the writer.

20:41Ryan Holiday: And the rhythms of the speech and the descriptions. And yeah, the books that make good movies are dependent on plot. If you have a clever plot or something like that, or if they take a classic and kind of completely rip it up and start over. So we'll see about the Odyssey this summer, I guess. But the Odyssey is different anyway. But it's also got an incredible plot, right? Yeah, sorry. I'm saying the Odyssey is different. It's not about the, it can't be about the voice because it's been translated and blah, blah, blah, blah, blah, blah. So Tom Wolfe, no one's figured out. I guess the movie, The Right Stuff is pretty good.

21:09Ryan Holiday: Yeah. But again, it's because it's a very action-packed story. Right. And because Philip Kaufman, who was a director, was a great director, underrated director, I think. And he understood that what he could do was just about images. So he has an image at the beginning of that, you know, movie where you have Sam Shepard, like the coolest guy of all time, riding through, it could be a Western, it could be a John Ford movie, riding on a horse through the brush, you know could be John Wayne in the searchers and he comes over a rise and there's the plane that's going to break the sound barrier just with the flames coming out of the tail and it's this moment of the cowboy and the rocket and you realize it's the same guys and it's the same moment of every era just it's it's the archetypes just on a new horse right and the pilot is the cowboy yes right on and and that's all registered subconsciously in a moment with an image and that's what movies can do.

22:02And so that's why I think that that was actually a good movie.

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24:30So how could you ever make a good movie of the moviegoer?

24:35Ryan Holiday: Yeah, that's like some adaptation level. It's got to be something completely different. It's all internal. and it's all the voice and it's all the detachment that he feels from his own life. He is a detached person. Well, Confederacy of Dunces is funny. So you could potentially get to the dialogue and the absurdity of, you know, you have the hot dog vendor eating all the hot dogs and making fun of everyone. A comedic actor could probably make hay of that in a good way. Like, I think you could probably do it. But making a good movie of the moviegoer might be genuinely impossible because it is, It's about the alienation.

25:12Ryan Holiday: It's about the weirdness. It's about the aimlessness. And there's not a good movie of The Catcher in the Rye either for the same reason. And I sometimes say that Walker Percy's The Movie Goer is Catcher in the Rye for adults. Yeah. Well, they're very, I'd say they're both for adults, you know? Yeah. But I'm just saying, instead of being a 17-year-old who's alienated, it's a 31-year-old who's alienated. Yeah. Yeah. And by the way, I'm just making me think like maybe the best that I think of off the top of my head of movie adaption is No Country for Old Men, which I understand was written originally as a script, I think.

25:46And then he adapted it the other way. That's why there's another really great book by James Salter called Solo Faces. You ever read that book?

25:53Ryan Holiday: I am on a huge James Salter kick right now. And I was just thinking when you were talking about great books that got butchered, did you read The Hunters? Yes. And that was a Robert Mitchum movie. Yeah. But it's like not about, there's nothing from the book in the movie other than it's about fighter pilots in Korea. Because they want the IP and they can sort of slap this thing underneath it. Yeah. But Solo Faces started as a screenplay for Robert Redford and he rejected it. Right. And it's great, man. And it's, I had a really good friend growing up who died really young and he kind of had gone off and lived that kind of life.

26:27Yeah. And I never really knew what happened to him after like early twenties. He died like in his early thirties. Yeah. And I felt like reading that book, I was reading about his life, which is a power of that, of his writing and his voice.

26:40Ryan Holiday: I loved The Hunters. I loved Burning the Days, which I think was an incredible memoir. And then I just read Light Years, which is the one about like a marriage falling apart. I haven't, I don't know if I've actually read Solo Faces. Well, his famous book, you know, is A Sport in a Pastime. Yeah. Which is very dirty. Yeah. Yeah. Somebody came up to me once at the gym and I was reading it. I just was on page one and they started talking about it. Like later I had to rethink what that conversation was really about. That's like not a book you should be reading in public. I didn't know. Yeah. Yeah.

27:11I was in my twenties and I was at the gym. Yeah. Reading it. But, you know, and also short stories. Yeah. I think somebody, when I turned like 22 or 23, somebody gave me his book of short stories, Dusk. Yeah. Which there's this thing that old European novels have, like, I mean, like the Camus era that capture something about how strange it is to be in a city that you don't live in that I've never read an American novel capture it in the same way until James Salter. So he clearly must've been hugely influenced by those books.

27:40Ryan Holiday: Yeah. You know, so when you read Dusk, like a story like American Express or something, just what it's like to be young and in a place that you have no reason for being. Yeah. Yeah. I thought when I was rereading the hunters, I thought of it as like these fighter pilots, it's the same story. Like these guys are just desperate to make their mark. They all want to make ACE. They're, they're a Silicon Valley entrepreneur. They're a cowboy. They're a, they're a, an athlete. They're just whatever that thing is that you think, if I just achieve some, some semblance of immortality, I I will matter. I will be important.

28:13Ryan Holiday: If I can be the best in the world at this thing, that just, I think he just captures that sort of timeless human drive. But it's always fascinating when someone does it in like a profession or a domain that you don't expect to see that. Yeah. And he changes how you see the world. Yeah. I mean, you can't really see, and he's, it's really about competition. It's like the same as sports. And the fact that he himself was like this pilot adds to it. But he was very introspective, probably so introspective that it inhibited his career in the Air Force, which is ultimately he left the Air Force. And I think that it is good sometimes for certain things to be not so introspective, to be it's a huge advantage to be a little dumb.

29:01And I say that as somebody who considers himself a little dumb, takes me a little long to get things. I'm a little slow about a lot of things. I have to reverse engineer him to understand what's happening. Sometimes somebody, I was talking about this this morning. Sometimes if somebody were to come up to me and say, nice to see you. And shake my hand, but stab me in the back with the left hand. I will come away thinking, oh, it was nice to see him. That is a nice person. He said, nice to see me. It'll take me years to realize I've been shanked. Yeah. You know? That's funny.

29:28Ryan Holiday: I thought the interesting part of Burning the Days is where he talks about, because he flew with Buzz Aldrin and Ed White. When they land on the moon, when they go into space, he's like fucking pissed. Right. And you go, oh, yes. Like from the outside, these are selfless public servants who are motivated by duty and honor and country. And they are. But they also want to be the best in the world. And the people they're flying with are their are their buddies and their wingmen and their compatriots. And then they're also competition to be number one. I mean, it's like everybody's in that situation where the person you're friends with is also your competition.

30:06And if that person succeeds, you don't succeed. Yeah. And when they succeed, you have to pretend like you're happy for them. Yes. You know, and that's just something that we've learned to do. And especially in a book like James Salters, because it's about the Cold War and what's good for the West and good for America. So there's this other level of self-sacrifice. But he feels like he's made a terrible mistake. Yeah. Because he was on the path.

30:30Ryan Holiday: Yeah. You know, I have a friend when my son was playing hockey, I have a friend who said, oh, so he's on the path. He was a very this guy's a great hockey player. Yeah. And I'm like, what frickin path? You know, and he's like talking about the NHL path, which my son was never on. I've never known anybody on, but just said he kind of saw it that way, which is what's the goal here? Yeah. You know? Yeah. The goal is in the case of me and all the people I know, adult hockey on Tuesday nights. That's the goal, you know? Right. But so there are people that see the goal as the goal. But it is interesting how much in common the people on the path, whether they're trying to be a fighter pilot or a Navy SEAL or a professional basketball player or, you know, a billionaire or a senator, like the path is the path is the path.

31:16Ryan Holiday: And all these kind of elite domains, it's not just like the same path, but it's the same personality type in there too. Yeah. And I'm a writer, so I don't have that. I don't understand that. I'm fascinated by it. It's human nature, you know, but of course you have in that league in as a magazine writer and as an author. No. And it probably is a TV writer also. Like it's very kind of you to say that. Thank you very much. It's very true. I mean, that's the funny thing is it doesn't feel that way sometimes to the person, but all you have to think about is like how many people would literally kill someone to have what you have.

31:48Ryan Holiday: And that's a sense of where you are on the path. Do you know what I mean? Like, like, I mean, thank you. That's, I mean, but I, but I'm not, I'm so focused on, you know, what a great story is and watching these other people. I do. I guess there have been times where I think about, like, where I am in the whole blah, blah, blah, blah, blah. But I also know that the writers from 20 years ago that were considered great are forgotten and the writers that were forgotten are considered great. And one of the great examples for me is like the painter Chardin, who he when he painted his paint little scenes, they were kept like in people's kitchens.

32:25so they could look at food while they ate, you know? Yeah. And in the main rooms in the museums were the giant pictures of Napoleon on horseback. Yeah. And now you go to like the Met in New York and it's reversed, man. Those big giant paintings in Napoleon are out by the elevators and the Chardin paintings are in the main room. Yeah. And so you can't really know in the long run how any of it's going to turn out.

32:47Ryan Holiday: Well, also it doesn't make a fucking difference to either of those painters. No. Because they're both, like it evened out for both of them And the fact that one is now here and one is here is totally irrelevant to either of them. So you think, would you rather be successful in the long run or have a much better life? And you think probably the much better life. Or would you just, what it ultimately comes down to is like who enjoyed doing the thing the most and didn't torture themselves so fucking much. Like Salter, who we're just talking about, was like a great writer and, you know, maybe at his peak, although he did make some money from some movie stuff, was considered a writer's writer.

33:23Ryan Holiday: but you do get the sense that he felt somewhat tortured and inadequate as a writer. Like it, I'm not sure he always had the best time, you know? Yes. And so... By the way, I knew somebody, a person that was involved in his career who was kind of making fun of his lack of success, which is unbelievable to me. Right. But then the fact that he's been slowly, subsequently vindicated and that his stars are writing, again, it doesn't matter. Like he's not able to, you can't dine out on your posture. This is how I always think about it. Like, think about it like a band. Yeah. Okay. What do most people want from a new record?

34:00Although records aren't the thing they were when they want a slightly different version of the record they already like.

34:05Ryan Holiday: Yeah. Okay. So if you come to them with something new, they're going to freaking hate it. Yeah. Until they learn how to listen to it. The record itself has to teach the people how to listen to it. So the best records usually get hammered by most critics and they don't sell. they sell over a period of 20 years as people figure out how to listen to them yeah it's hard to be ahead of your time it means that you're not of the time right which is now and all that you'll get resistance from everybody from agents from editors who don't want you to do this thing whereas you know that this is the thing you got to do right so it takes a like a lot of confidence to do that and james salter did that for years you know and he finally at the end of his life He started to be recognized, like you say.

34:49And by then he was old. Yeah. You know, he wanted what he wanted when he was young, which was to be an ace. He writes about being an ace. Yeah. Shooting down three Migs. Five. Five Migs. Sorry, I messed it up. And he didn't get it. He got one and a half. Yeah. In Korea.

35:04Ryan Holiday: Yes. And then when he became a writer, he wanted the same thing. Yeah. You know, and again, he shot down one and a half Migs. Totally. Totally. Except that's really fucking hard. Like as time passes, in a way you're just like, you did it. You were in the league. Right. You know, like you were one of a small number of people to ever do this thing. Yeah. Obviously what he couldn't anticipate is almost no one shoots down planes anymore. That's not how, like by the time Vietnam comes along, planes don't fight each other in the air anymore. It's just not, it's not. I know. Well, that's the other thing, which is the language that you live your life in becomes unintelligible to the generations that follow.

35:46Ryan Holiday: Yes. You know, so like a lot of my career was about magazine writing and a kind of magazine writing that doesn't really exist anymore. Yeah. You know, I mean, it's writing, it's writing is writing. But like the Tom Wolfe stories, where would he write those? Some of them he would sell here and there, but it'd be fucking TikTok videos. Yeah. So we're like looking at his accomplishment. But to people that are growing up now, it doesn't matter. and it wouldn't even make sense. It's like a different language. Yeah, and look, that happens not just in sort of art or whatever. Like I was the director of marketing at American Apparel, which was at one point a very cool job.

36:19Ryan Holiday: And I thought at that time when I was walking away to be a writer, I would be like, well, it's like, hey, I was the whatever at Apple. Now people don't, the company doesn't even exist. It went bankrupt twice. And it might come back around as like a sort of a retro company at some point in the future. But like, if you think that that this thing is going to have staying power or matter, like the meaning changes. So, like, you're making me think of like my father. Go back to my father. He was a pretty high level executive at Sears. Yeah. You say people that now they're like they have this idea of this old, tired store at the mall.

36:56Kmart or something. Yeah. But at the time, you're like, no, Sears was like Sears gave Muddy Waters his first guitar, man. You could order a house from Sears. Right. Sears was like Amazon.

37:05Ryan Holiday: Yeah, being an executive at OpenAI. It's like the biggest company in the world. Yeah, exactly. And then so there's a ticking clock on all this stuff and to attach your value or your identity to it is a fragile thing. Well, it's funny because there's like one of the things that made me want to be a writer was it was all about that voice was freshman year in high school. In a class, I got, I think a dean. OK, so that class, which is English, tended up making me want to be a writer. Yeah, because she had we had to read a book of short stories. And I read the Hemingway story in our time. And from the first line of that story, it was like made you feel something different than you ever felt before.

37:47The lesson in that story is the guy says you should never love anything you can lose. Okay, but that's what life is. I mean, there's no way that always, that you can lose everything.

38:00Ryan Holiday: But what you fell in love with, the way those words worked and the feeling it evokes, like magazines can go away. Right. But that, the doing the thing can't. That's what I mean. It's like, if you look back and you're like, hey, I'm proud of the things I wrote. I'm proud of my growth as a writer I'm I'm proud of who I was in this industry or whatever then then you can have a pretty good go of it right um but if you're like no no I need to be one of the guys I need to have won the great prizes I need to get the best slots that's something you can lose yeah but but by the way so like if you're like have a slightly less optimistic turn of mind you worry that people now aren't reading okay so and it's not just like my career who cares about my career.

38:45It's really bad because the kind of illiterate mind is a different kind of mind. You process the world differently. It's like slow cooked food, man. You need to take time for things to register, to understand them, to see them. And it's scary that the people that ultimately will judge are people that don't really, you're doing something that they're never going to notice because they're not reading other. It's like when you're writing, you're coming, you're trying to be like the best writer there is. You have the great advantage of You don't need school or any of that because it's all available to you in books.

39:16Right. And you find the writers that speak to you and you're basically operating on a sentence level. That's the whole thing. Yeah. And then you're being read by people who don't know about a sentence or care about a sentence or you're in a speech. You know what I mean? And that's.

39:28Ryan Holiday: But that's the point is like it has to light you up. And then, you know, if a fraction of the audience appreciates everything that goes into it, great. If the rest of the people just appreciate the final product, great. I'm struck by this and I want to come back to the movie goer but I'm also struck by the devaluing of of not just writing and really good writing but the thinking that goes into really good writing and I've been talking about this probably too much for people but it's like like what we're talking about here is obviously interesting and I think we've spent some time thinking about it clearly but like this is nothing compared to what you and I might sit down and write about this exact topic like I think people people go like oh I heard them talking about this on a podcast there's also an audio book about those are the same thing.

40:14Ryan Holiday: And it's like, no, no, like Joan Didion had this great line that she said, writing is a hostile act, that like you're having to like, you're like mounting this invasion. You're like attacking this other person and trying to replace their thinking and their narrative and their sense of the world with the one you made up. She was such a genius. Do you know this was her table? No. Yeah, this is the table she put her to wrote at this table. What's his name? Could have died at this table. John Gregory. Dunn. Yeah. I always think of that scene where he just collapses at the, very scary. Yeah. So, but yeah.

40:47So what I'd say is like people have an idea, I think, that you think of something, you have an idea.

40:53Ryan Holiday: Yeah. And then you write it. Yes. But in fact, all the thinking happens while you're writing. It doesn't make sense until you write. It's like a different part of your brain turns on. Yeah. And you have access to a different part of your brain, which is when we're talking about ambition and career and all that doesn't get to that, which is the main thing, which is the actual writing. itself, it's like... It's otherworldly. It's this magical thing. But then also that's step one of the process. And then the other process, like in music of the producing and the re-recording and the mixing and all the stuff that goes into it at...

41:28Ryan Holiday: These books are not first drafts of these books. These are so many drafts down the road. And so that refining and that improving and rereading it and realizing, oh, I missed this or I made this assumption here. like how much thinking and craft and deliberation goes into what the finished product of a thing that you've read. Well, also like just speaking of Joan Didion's hostile act, okay, which is to put it at a very personal level. Yeah. So, and this goes back to James Salter too, which is he said, I think in his last book, he has a quote from himself, which is weird. That is right. Slightly, slight, slight van glory.

42:03If you're quoting yourself, just say it again. Like I don't, it bothers me. Well, I remember once when I got, when I was a kid, I got the John Cougar Mellencamp record, Scarecrow. And he had a quote on the dust jacket that said, there's nothing more sad nor beautiful than watching generations change hands. And it said, John Cougar Mellencamp.

42:19Ryan Holiday: Yeah, just, you don't need that second part. It's yours. So, but anyway, he said, like, only that which is written down has a chance to last. Something like that. Yeah. Which is, by the way, he doesn't say it will last. He says it has a chance to last. But like I wrote my third book was about growing up and my best friend growing up and all that. It's a memoir about growing up. And you realize that as you're writing it, you're basically taking a bunch of memories and replacing them. Yeah. Because writing is never the same. It's just a translation of what you feel. And that's what I'm going to remember.

42:50So when you write something down, you kind of freeze it and you lose everything else in a way you preserve, but you also destroy without really meaning to. So it's like a very serious, you know, thing. And that's what you can even replace people's memories of their own lives. And that's, I think what she's like. So you write about your father. He reads it. Yeah. That's what he remembers as happening. Yeah. You know, except maybe not my father, who's a helpfully hostile reader. But, you know, there's different versions. But you can see that there's it's it's a very intense thing where you kind of save, preserve and destroy while preserving, which is probably maybe what all.

43:26That's a famous line.

43:27Ryan Holiday: You know, we tell ourselves stories in order to live. People think that's like this beautiful meditation on the role of creativity and art in humanity. And she's saying, no, no, we fucking lie to ourselves so we can live with ourselves. I mean, that seems obvious to me what she's talking about, which is you have to see the whole idea like now about sort of, let's say, destroying the American myth. Yeah. OK. If you destroy the American myth, which I happen to love and grew up with and everything else, it's not like it's replaced by the truth. No. It's just replaced by another myth. which might not be helpful, actually.

44:02Yeah. I mean, the myth that we have, there's some things about it are helpful. The myth that we'd replace it with might be less true and might be unhelpful. Yeah. You know, so you got to be careful about destroying a myth kind of thing. It's like taking someone's legs out.

44:15Ryan Holiday: Well, I've said this also before, but I think a city we both love, which is New Orleans, you take down the Robert E. Lee statue. Yeah. Great. Now there's just a column there for eight years or however long it's been. like um it's like you know what it's like it's like uh you know remember those stories create your own story your own create your own statue imagine your own statue i imagine my friend mark on that statue being celebrating the time he drank 17 shots at fat harry's but i mean that would almost that would be better than an empty like like deciding hey we're going to turn this into an art like actually we're going to say i want you to envision your own thing there that is replacing it the problem is what we do with these myths we have this tendency in in american culture to point someone out as shitty or hypocritical or contradictory or whatever.

45:03Ryan Holiday: And then they destroy the myth of Lance Armstrong. And then they have to go so far down the list to find the actual winner that they're just like, nobody won the Tour de France. Right. And so then you're like, okay, but now who are we supposed to say was the greatest in that era? And there you need, I mean, that's in the Bible, you know, when David, King David gives his eulogy for Saul and his son, Jonathan, he says, oh, how the mighty have fallen. It's about these mighty figures of yore, you need them. And they make life kind of interesting, you know, but it's sort of, if you think about it, I'm a little older than you, I'm a bunch older than you maybe.

45:41And, um, I grew up, I was born in 1968. So I grew up with the constant threat of the permanent record. Okay. The permanent record was you do this in this class Your file. Yeah. Yeah. It's going in your permanent record. And I always expected someday I would find my permanent record when, say, in third grade, rather than engage in cleanup, he jumped out the window and ran home, which I did. Yeah. You know, or he threw a firework and whatever. And then I got older and I realized, oh, the permanent record's a lie, man. There's no permanent record. I'm free. I'm absolutely free. Right. And then now, because of all the technology, there's a freaking permanent record.

46:17There actually is a permanent record. And it's kind of, you got to be able to forget. You know, you got to be able to like leave your past behind you, even like Hemingway going back to Hemingway. Hemingway wrote his first book about people in Michigan near Traverse City, Petoskey, Michigan, where he spent his summers, like kind of a rich kid spending his summers at a country cottage. And he took all those stories and he wrote them up. And he was so hated that he couldn't go back to Petoskey for like 50 years. Now Petoskey has a bookstore just with his books, but he couldn't go back. and he would not have done that in the age of facebook or instagram or anything because he would have heard from all those people yeah you know what i mean no no totally i also think um

46:59Ryan Holiday: i think about this with my kids like how many things i got temporarily into when i was younger yeah and there wasn't an algorithm keeping a record of what i liked yeah and then feeding me more of that thing over and over and over again until that became who i like like i i do also gives you a completely distorted view of the world yeah yeah of course but i i just even mean And like, it's hard to go down rabbit holes and then entirely abandon them. Yeah. In a world where the algorithm is incentivized to, and so stupid in a way, that it can't understand that you have fleeting and changing interests.

47:32Ryan Holiday: I mean, basically, there should be a button. You can press it. It forgets everything about you. Yeah. Like, turn limits on the algorithm. Yeah. Just like, forget everything you know about me. Yeah. I want to start. I don't like what I like. I'd like to start over. You know? So like a year ago, I hurt my foot. and I was searching for stuff about I could do about my foot. And now I'm like, I'd like to see a movie about, uh, what's a good Western I could see that go, well, someone with your foot condition. Exactly. Yeah. No. And like you at least have a whole lifetime of experience, but if you're like 17, these things like, that's like 40 % of what it knows about you is that period where you got really into Goss music or something.

48:11Ryan Holiday: And now it's like, it won't let you grow out of the thing. No, it's crippling. All right. So why is The Movie Goer one of the greatest novels ever written? Well, I'll give you my experience with Walker Percy, which was I went to Tulane and I had like a bit of culture shock when I first got there. Just as simple as the way things smelled, the way things looked, the lack of, you know, I loved in Chicago when it was time to put on your jean jacket and that was gone. Yeah. There were drunken people roaming around on the street. That was unusual. I was just completely like, where am I? What's going on?

48:43It's another world. Yeah. And I found at the Tulane bookstore, for whatever reason, no one, I picked up the book by Walker Percy Lancelot, which is, you know, and it blew me away. Like it's what writing is for, which is it named and described things I had felt, but I had never articulated. And it gave me a way to understand what was happening and in the world, in my life and where I was. Yeah. And then I went, read everything by Walker Percy and the moviegoer is sort of the book. Yes. And I think it's that. I mean, it's good that I came upon it. I didn't get the Grand Canyon the first run out.

49:18I got some smaller feature, which was Lancelot. Because that's what he does, which is he takes something you feel but have never put into words and think you're the only one who feels it. And he puts it in language so you can understand, one, you're not alone. You're not unusual. And two, you can understand what's happening. And it gives you the sense that only books can do this. which is he can take the inchoate you know and actually put it into words uh make it a real thing and that's what to me what walker percy did and i just recently read that book again and of course like a great book i pick up a million things that i didn't even notice the first time

49:58Ryan Holiday: around even though i've not the first time around the fifth time around i don't think the first handful of times i saw him so much as a veteran struggling to readjust to normal modern life yeah like i didn't i didn't sort of see that i mean he's a korea there's a don draper element to him that you don't really think about but that was common yes so like my father was during the korean war and everything that was just that was something everybody did right but that doesn't mean it wasn't incredibly no no it was it was it was it was presented as just life yeah whereas now it's very notable because it's unusual yeah i mean it was you know i don't know what the percentage of people who went into the, it was a huge, it was a pretty much a good part of life.

50:42So, I mean, I think that, and then the terminology, PTSD and the way you would treat it. Sure. And there were, you know, just a lot of people that had gone through this big experience when they were young and they were trying to deal with it. Yeah. Trying to recover from it or whatever you want to say. Even when I was a kid, the movies, I was talking about this, every movie had like a Vietnam veteran character who was just wandering around the fringes scaring the crap out of kids. They were scared about backfires and just a weirdo. Yeah. And by the way, so I, it seemed like the Vietnam War was ancient history to me.

51:16Yeah. You know, but it wasn't really. No. I mean, in 1978, when I was 10, that was just a few years before. Sure. But it was sort of quickly covered over, you know, we moved into a different era and it wasn't really talked about. And the only hint of it you got was these movies. I'm thinking of the movie specifically The River's Edge, which scared the crap out of me. I don't know if you remember that movie with no oh it's i'm not even gonna describe it but it's crispin glover and keanu reeves and i saw it when i was a kid and it scared the crap out of me obviously the idea of

51:44Ryan Holiday: certification in the novel is like one of my favorites i remember i read that book sum that up for me again so like he's in a movie theater and like when he things from his actual life appear in the movie like i think the scene is he's in that movie theater and then that movie theater is in the movie that they're watching like i remember i read that that certification thing was so funny. I was like, oh, that is a great thing. Like there is something like you go to New York and people are like, I want to go on the sex in the city tour. Like I want to see like the, the, the establishing shots from a movie, from a TV show that I liked, even though it's like, I can go to museums.

52:19Ryan Holiday: I could see historical buildings. We want to see the stuff that we've seen on TV. Well, you remind me of a couple of things. One is when my son, who's now an adult was like four, we went into the supermarket and there was some product, like a Clorox type product. And he went crazy as if he'd seen like George Harrison or something. He's like, they're from a commercial. Yeah, he'd seen it on TV. It was like a celebrity to him. The other thing is I grew up in Glencoe, Illinois, a suburb of Chicago. And John Hughes filmed all those movies there. And I feel like at my high school, which was Nutriar High School in Winnetka.

52:50And so that was our life, man. Our life was made valid by the fact that the Glencoe Beach was in Ferris Bueller. Right. And the Home Alone House was in Winnetka. And Nutriar West was in Uncle Buck. You know? so i understood it it made us feel seen like it was real i remember i read this in in walker

53:12Ryan Holiday: percy's the movie goer i was like oh that's such an interesting concept and then i'm watching the first season of true detective and my storage unit in new orleans is like the storage unit they go to where he has all this stuff and i'm like this is it and it's like it should like i have no attachment to this storage unit in chelmette or whatever and i'm just like there it is like so there's something about like a novel that captures or explains a thing that didn't have a name before yeah you're just like that's fucking yeah it's got a couple little and he's there's other there are other everydayness he says that word the everything you're like yeah that is i'm stuck in the everydayness of life yeah and i think no i think it's probably not that book it might be confederacy dunces that gave me a lifelong fear of buses where i spent a lot of time because in the fact that in the movie goer he loves his car because it's it's basically resistant to malaise.

54:02Ryan Holiday: Yes. Yes. Yeah, totally. You know, so, and I always think about that when I, you know, get anything, which is this thing going to be covered in malaise in a couple of years, you know, what's this going to look like on a Sunday afternoon? Yeah. And that's like a very Walker Percy. He's got a line in there in one of his, might not, I don't think it's in the movie where he says, how do you make it through a Wednesday? Yeah. And it's weird to have this person. I think one of the other things that's great about that book is like, it feels so modern, Like it's so capturing perfectly the modern moment.

54:32Ryan Holiday: And then you're like checking and you're like 1962 or whatever. Dude, I'll tell you, I had this experience in college. It just shows how stupid I am. It was an introductory philosophy class. And we read a Kierkegaard book called like On the Current Situation or I forget. It's something like that. And it's like 60, 70 pages. And I just connected to it very deeply. And he asked us to guess when it was written. And I said, I thought it was written like maybe five, six years ago. Right. That's incredible. I mean, when that happens, that's like, I mean, that's my experience. You read Marx's meditations.

55:06Ryan Holiday: You're like, this cannot be from a God King 2000 years ago. Like how could he possibly think so much of what we are dealing with has to do with whatever the current technology is or the current political scene or the current this or that. But it's not. Yeah. All that stuff's just an expression of the deep thing, which doesn't change. Yeah. The malaise, the everydayness. Yeah. The alienation. They say that every day your business is late to AI, you fall two days behind. One of the things we've been talking about at our staff meetings at Daily Stoic is how can we use AI to maximize efficiency? And how can we make sure that it's buying us time to do the things that only humans can do?

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56:22Ryan Holiday: It automatically surfaces custom insights throughout your day. AI agents work alongside to help you solve problems and handle routine work. And anytime you have a question, you just ask, just like having a conversation with a colleague. NetSuite is customized for a wide variety of industries, so it supports the way your business truly works. Whether that company earns millions or even hundreds of millions of dollars, it's time for NetSuite Next. For the first time ever, you can try NetSuite Next for free. If your revenues are at least in the seven figures, go to netsuite.ai. It's built for every industry, ready for every boardroom.

56:56netsuite.ai.

57:00Ryan Holiday: This is the busy season, right? More calls, more customers, more chances that something can slip through the cracks. Staying ahead means having the right system, not just working harder. And that's why today's episode is brought to you by Quo, Q-U-O, the business phone system built so that you never miss a call. It is the number one rated business phone system on G2, trusted by over 90 ,000 businesses who rely on it to stay reachable and look professional every day. All your calls, texts, and voicemails live in one place so anyone on your team can pick up the conversation, see the full history, and respond fast.

57:34Ryan Holiday: And quote, integrates with the tools your team already uses, HubSpot, Zapier, Claude, whatever. And it helps you save time, stay organized, and spend less effort chasing down information between systems. Money is on the line. Always say hello with Quo. Try Quo for free. Plus, get 20 % off your first six months when you go to Quo.com slash Daily Stoic. Quo.com slash Daily Stoic. And Walker Percy had another thing I love where he's talking about re-entry, that life is about re-entry. Yeah, yes. And I think about that every time I'm coming out of a book, like re-entry into normal life where I'm no longer living in this fantasy world.

58:14Well, I think that Walker Percy thought that his books would change the world in some way.

58:22Ryan Holiday: Yeah, he saw himself as this kind of philosopher evangelist. I think he was depressed that it didn't have the impact he thought it did, but it did. Yeah. Because that's the thing about a book. Look at me. Me and you are here sitting. He died. I remember when he died because I was in college. Yeah. I actually got a book signed by him. Because he was at Loyola when you were at the end? The book Thanatos Syndrome came out and it stood in line at the bookstore that's not there anymore. I forget what it's called in New Orleans. And he signed it and he was, you know, whatever. But I think he thought that he would, you know, he would become a national figure.

58:55He would change the world and all this stuff. And he didn't see that happen. But it did. Yeah. It just happened inside the brains and the heads and sensibilities of thousands and thousands and thousands of people who he helped figure out how to get through life. Yeah.

59:10Ryan Holiday: To go to our point about competition, I got to imagine when he surprise wins the National Book Award, Shelby Foote was both happy and fucking pissed. Right. And then when Shelby Foote became a celebrity in a way that Walker Percy never was through the Ken Burns documentary, probably the exact same feeling. Well, do you know the story? You must know the story about how he won the National Book Award. Yeah. Wasn't it A.J. Liebling like gave it to his wife or something? Yeah. Well, Gene Stafford, I think. I think what happened is Liebling was writing the book about Earl Long in Louisiana. He was writing a New Yorker article.

59:44So he said, I want to read everything to his publisher. Give me everything you have about New Orleans. And the moviegoer had just come out published by Knopf. And so they gave him that book.

59:55Ryan Holiday: And Knopf didn't really like the book, I don't think. Well, they let him go. Yeah. And by the way, this summer, I bought a first edition of the movie published by Knopf. I'm never like into, like I don't save things. There were too many great things I had that were destroyed by somebody in my family or given away by my mom for me to think I'm not going to start collecting things now. It's too late. I've already lost. I had a complete uncut sheet of 1974 Topps baseball cards from the factory and that got given away. So I'm like, I lost that. There's no point, man. But I did. I was very excited to get this first edition of this Knopf.

1:00:27But anyway, he read it and he basically said, this really has nothing to do with what I'm writing about, but this is a great book. And he gave it to his wife and he won the National Book Award, even though he hadn't been nominated. Right. okay which is by the way similar to hemingway i don't know if you know this story about hemingway which is hemingway uh one of his stories was published and they gave it the best american short stories like the best story of the year like in 1920 whatever even though it wasn't like nominated it wasn't listed they did because it was so outstanding it was so freaking great and the story with hemingway is he had all these short stories and his wife at the time you know this story?

1:01:06She lost them all? She lost them on the train, which he always thought was intentional. It was some kind of Freudian attempt to kill him. Yeah. You know, the only story that survives from that earlier batch, it's like an earlier era. It's like the ancient aliens, man. The only one to survive was the one that won Best American Short Stories because it was out with, you know, being considered.

1:01:24Ryan Holiday: I told that story when I updated The Obstacle is the Way because there's this great letter that Hemingway writes to Ezra Pound after. And he's like, I know you're going to tell me it's all for the best whatever and he's like and i know but i'm not there yet yeah and i think that's such a great way of putting it because like you do know that the devastating breakup or the bankruptcy or the what you know this is what humans do we're going to derive meaning from this we're going to learn from it it's it's going to be in retrospect part of the trajectory that we couldn't have anticipated but but in the moment yeah you're like don't tell me this is all for the best Well, it's interesting because I think the story that survived is My Old Man, which is about Jocky's son telling the story of his father's decline.

1:02:10And it's different. Yeah. It's not as severe. It's not as harsh, you know, and that's editing. But another, I don't know if you've had this experience where you lose something and you got to rewrite it. And it is good because basically that's editing, you know, and what's kind of really freaky and also reassuring and also a little bit depressing. is sometimes you rewrite something and you find the original and it's pretty close to the same.

1:02:35Ryan Holiday: Yes. I had a weird similar experience. So I read Fish and the Whale when it came out, this hardcover, and then I reread it a couple years ago. And I was going through, it was fascinating to me to see how I marked several of the same passages. Yeah. And took an almost identical note. Yeah. It makes you feel like a machine. Or just like, but it's not like I remembered that that passage was meaningful to me. It's just, It struck me, the same note hit me 10 years apart. But it's reassuring because you know it's real. Yes. It's not just because you had a big lunch. You know what I mean? Yeah. Or whatever, you're hungover or something.

1:03:12There's something real about it. And same with the writing. So like one example, I mentioned On the Road earlier, a book that I really like and is often derided, but I really like it. By the way, one of the great audio books of all time is David Carradine reading On the Road. I don't know if you ever. So, but anyway, the thing is always, Truman Capote famously said, that's not writing, it's typing. Because he would say he just wrote one draft and all that. But if you read about Jack Kerouac, he kept writing the same stories over and over again. And every time he wrote them, he was honing them.

1:03:41That was all, that was, those were rewrites.

1:03:43Ryan Holiday: Well, the myth is that he wrote that in 24 hours on some drug binge or whatever. But it was actually like, yeah, meticulously edited and rewritten for like months and months and months after. But even before he wrote that version, he'd written those stories. Oh, and somebody who writes the same stories again and again and again. I know that every time you go back over the same ground, you kind of like the story becomes tighter and you hone it and you realize what about it makes it work. Yeah. And that thing, by the way, that he wrote the books famously on kind of computer paper and it's like a holy scroll.

1:04:14Yeah. Actually, one of the weirdest story assignments I ever had for a magazine was to write about Jim Ursa. Remember Jim Ursa? He owned the Colts. Oh, yeah. He died just a couple of years ago.

1:04:23Ryan Holiday: He's a drug addict. Yeah, he's the only guy I ever interviewed who fell asleep while he was talking. Creating a very awkward social situation. I'm like, what do I do? Do I wake him up? Do I quietly leave? Or just wait. Right. Anyway, he bought that scroll. Oh. Yeah, he was a weird collector of stuff, right? Yeah, and he would hire musicians, big deal musicians, to come to his studio to play with him. And he would record. I mean, he was kind of nuts. Yeah. And he was another guy who went to my same high school. And his father is super interesting because his father is the one who moved the Baltimore Colts to Indianapolis in the middle of the night.

1:04:59Anyway, he got to see that scroll, which is amazing because it's at the University of Indiana, along with like a first folio of Shakespeare and an early edition of the Bible. It's a crazy collection that he gave it to. But it makes you think like there is something about the physical object that we kind of lose when everything's on computers. Right. You know, so we're talking about ambition. so the nature of Jack Kerouac's ambition is captured somehow in the mania of that scroll and the fact that he did I always heard took a lot of Benzedrine to write a bunch of stories he'd been telling for years and years and years and the Benzedrine was about the art right you know what I mean and I always think about it like you can't really cheat in art like you would test him give him a drug test if you're in the major leagues and say those home runs don't count but they count Yes.

1:05:51Even if he took all the Benzedrine or whatever in the world, the home runs still count in the book. Yeah.

1:05:56Ryan Holiday: Yeah, there is something too about, was it Hemingway where he wrote this book and then he just cut the first two chapters? Yeah. Is that in The Sun Also Rises? No, that's, yeah, I think it's funny because my friend David Lipsky, who's a really great writer, he always talks about that, which is he opened The Sun Arises with a joke about the boxer, I think Benny Leonard. And he had Fitzgerald read it. And Fitzgerald said, oh, that's an old joke. Everybody knows, get rid of that joke. So he cut the beginning. So it has this very stark modernist beginning, which hadn't been the beginning. And then Hemingway found out later that he had heard the joke from the same person Fitzgerald heard the joke from.

1:06:42It wasn't an old joke, it was just they both had the same friends.

1:06:45Ryan Holiday: Yes, yes, yes, yes. But there's something about like that that's all gone and yet it's it's there it's there it's it's under it and there's something powerful about that i mean that's his idea about the iceberg and all that which he put it but it's true that like for me i don't know how you write your books but my first drafts are like like the first draft of the fish that ate the whale was probably like 130 000 words and the book is probably like 65 ,000 words. So that's the kind of thing where it's good to be a little stupid because I've done that with basically every book I've ever written, except for the first couple of books, maybe.

1:07:22If you're aware of that at the time, you realize half of what I'm working, I'm throwing out. So all today's effort is just nothing. I'm throwing it all out. But of course, you can't think of that when you're writing or you go freaking nuts. But the truth is, it's like censoring people for stuff they say online, okay? Which is maybe they shouldn't be saying it online, but you got to go through the bad stuff to get to the good stuff. Like you have nine bad ideas and one good idea. And then in the book, you just go with the good idea and get rid of the bad ideas. You have to write all the boring parts to get to the interesting parts.

1:07:53Ryan Holiday: You know, it's right. You can't think about it because I'm on the project I'm working on now. It's like, oh, I want to say this. And then so that requires, I don't know, a week of research, find all this stuff. And then I'm trying not to think about the fact that my editor is probably going to tell me to cut it at some point. And like, I have to remember though, it's not actually lost. Like even if this paragraph gets distilled down into three words, that's a tag on the end of a sentence or whatever. I earned it. And it is there informing my understanding of the subject and the person and all that.

1:08:22Well, ideally for me, if it's working, you want to be right on the edge.

1:08:26Ryan Holiday: Yeah. Okay. But the only way to find the edge is to go over the edge as Townes Van Zandt taught us. I don't know if you know that story, but do you know that story? No. Which is he wanted that he was on a balcony at a party and he wanted to see how far he could lean back without falling off the balcony and he realized the only way to really know is to fall off the balcony, which he then did. I was thinking there's a great passage in Hunter S. Thompson's Hell's Angels where he says something very similar about going over the edge on a motorcycle. Oh yeah, I remember. I just read that recently too.

1:08:51So basically what I try to do is like, because you get those people in your head, like your editor or imaginary editor, what's going to, so I, each day I try to write something that I think will make my wife guffaw or recoil in disgust.

1:09:08Ryan Holiday: Yeah. You know, try to get a reaction, you know, like get red on the mood ring. Yeah. So it's just a good exercise as a way to keep pushing yourself to what is uncomfortable to say. Yeah. You know, and the idea is, you know, most of the writing happens in the rewriting anyway. Yeah. So I think the weird thing about a writer is it's like you're like a sculptor, but you got to like create the block of marble and then carve the statue out of what you created. But the first whole part of it is creating the block of marble. Right. I ended up putting in this paragraph of writing about the spider pilot.

1:09:37Ryan Holiday: And I was like, I found every single pilot from his graduating class that died in an accident and how they died. And so that was like a lot. I had to go through newspaper article after newspaper article and read obituaries and find their gravestones. I'm writing all this stuff. And it's like, I'm imagining this on the page, just getting an X through it. Yeah. And yet I'm informed by the fact that this guy would have been aware of this graveyard of these ghosts following him. Right. Do you know what I mean? Yeah. But so a couple of things. One is that kind of thing could be great. Yeah. It could stay in.

1:10:14It could be great. It's like, do you ever read the Ian Frazier book, Family? No. It's a great book. He's a great writer. He's one of the best writers. And he's got this whole chapter, which was excerpted, I think, in The Atlantic, where he goes through... every kid in every house on the street that he grew up in and says what happened to them and it's like a x-ray of a society of an american society it's like you know so that that could be like that i'm saying like don't be so quick to throw it out because it could be it's like when you're talking about the fates of a lot of different people you're talking about a picture of a whole generation yeah the second thing is this is like a danger when you're a non-fiction writer and you're doing research and you find something really cool yes it's very hard to cut I'm going through that right now.

1:10:58So it's like you're like the dog with the bone. You want to show everybody the bone you got. And it's really hard to cut, man, because it's like I got something no one else got. And now I'm just going to act like that didn't happen. It's like when I'm watching a lot of NHL right now and you see an incredible play, but nothing results from it. You're like, that's just gone. There's no statistical record. They're not going to show it in a highlight, but it's the best pass I've seen all season. And that's kind of like the research that you end up cutting. There's 10 pages that you cut down to a sentence.

1:11:25Ryan Holiday: And that's why I think about that Hemingway thing, because he does, he just cuts the chapter's whole cloth. But none of the other chapters could have been written without those chapters. It's not like he wrote the book, then he wrote two prologue chapters and then cut two prologue chapters. It's like, that's the scaffolding. And then you remove the scaffolding in the building's stands. I mean, all that's still there. It's like the ghost of it is still there. And even if you don't read it, you can still feel it. And that's what I mean. Like you got to go through the bad to get to the good. Like, not that it's bad, but that, you know, behind the story that you're reading is this other story that you feel.

1:12:02Yes. And a lot of times you're writing sentences in support of or at the culmination of sentences that you've cut. So literally it's there in the sentence structure. You can feel it. Right. I mean, that's all like the nitty gritty of it. And it's and it's really interesting. I really believe in. If you can take a hundred and twenty thousand word book and cut it to sixty thousand words, ideally, whatever power was in that is concentrated.

1:12:29Ryan Holiday: it's there's no fat there's nothing extraneous and it's all concentrated yeah so i think there was a hemingway quote because talking about hemingway where he talked about wanting to concentrate everything boil it down to as few sentences as possible and he said the only writer that he'd read that was better at that than him was isaac babble and that's another huge writer for me which is like red cavalry stories and if you ever read any of that stuff it's so freaking intense have you looked at the alternate endings for a farewell to arms no i've heard about them I bought a copy of that book in an airport in Norway that like they were clearly trying to like add stuff.

1:13:02Ryan Holiday: So they just they included all the different paragraphs that he did and like different. There's like ending number. It's got like 30 endings. It's like ending number one, two, three. And you realize just how many directions he tried. I'm assuming that was published after he died because he would have just never stopped vomiting. Yeah. But you can tell like, yeah, it's it's like he's he's riffing all these different notes. and trying it. And then he goes with one that's really good. But some of them are close to being as good or better. The ending is so great. Yeah. But I think that - There's just more.

1:13:35Ryan Holiday: Like you can tell how he boiled it down to the essence and all this other stuff is there. Right. But it wouldn't be there had he not tried these other ways in. I mean, okay, first of all, you make me think of two, you keep making me think of two things. For some reason, everything you say makes me think of two things. I'm like Jimmy two times. Yeah. So the first is, again, Ian Frazier, he writes about, I think his story about Brooklyn, he writes about seeing a page of a book on the beach, like at Coney Island or something. And he picks it up and it's a page from Anna Karenina. Yeah. And just a random page.

1:14:05And he writes that in a great book, every page is great. Mm-hmm. Okay. So I always heard, you'll see how this is connected, that the movie Breathless, you know, the John Luca Darden movie? Yeah. It's a great movie, French New Wave. And he turned it in and it was kind of semi-conventional. And it was like, let's say three hours long or something. This story might not be true, but it's what I'm using it because it's useful as a writer to think about. So the studio said this story, it has to be 120 minutes or 90 minutes or whatever. And you have to cut. And he couldn't do it. He just couldn't bring him.

1:14:40He couldn't do it. So he gave it to an editor friend and said, you make the cuts. And the editor cut at random. I'll take 10 minutes off here, 10 minutes off here. And it became, this movie's famous for its jump cuts. Scenes start with no explanation. They start in the middle. And it turns out to be this kind of revolution in how movies are told. Yeah. And it's movie telling. And it works because the movie is so great. Right. That every page is great. Like Anna Karenina. You could pick Anna Karenina up at random and start reading it. And you wouldn't really need much more than that. Right. You know?

1:15:09So my point is that Hemingway, like in cutting the beginning of Sun Also Rises, even if he started five pages after that, it would have been great.

1:15:18Ryan Holiday: Right. Right. And probably still be great even if you left the two pages. Yeah. Or the two chapters. It would have been a very funny joke about Benny Leonard. Yeah. The joke, which I heard is, how do you beat Benny Leonard? He's such a smart fighter. And the guy says, yeah, he's such a smart fighter. He's thinking all the time. And all the time he's thinking, I'm hitting him in the face. Yeah. Also, though, there is something powerful about like, there's something about Hemingway where you think, and I found this on anything that you do that short. the reader thinks that they're reading quickly and finish and they finish it in one sitting or two things or whatever because it's so fucking good and it's it's because it's short yeah you know what i mean like yeah they're like oh i burned through that book it was incredible and it's like you burn through that book because it's half the length of a normal right that's why you finish it on an airplane because it was finishable on an airplane right like and and so there is something just powerful about being shortened to the point yeah well that's that first story um in another country, which by the way, that book begins.

1:16:19This was a sentence. The first sentence got me. It's something like, I'm quoting from my memory, in the fall, the war was always there, but we did not go to it anymore. Okay. That's fricking Walker Percy. That's detachment. That means the entire society is engaged in a war and he's been injured out of it.

1:16:35Ryan Holiday: And they've been going to it over and over and over again. And now he's not. Right. He's with the few other people who are, and by the way, another thing, Hemingway is another person who's a prisoner of his myth, which is people have this idea about what he is and it's not what he is at all. Like it's not what his writing is at all. And in that story is the soldiers about how all the other story soldiers were war heroes and he was a pretend war hero. And when they figured out he was a pretend war hero, like his medals were a joke. He had all these medals, but all they said was he showed up. Yeah.

1:17:04Basically. And there's another guy, the only guy he can be friends with is a guy who was injured before he got to see battle. So he doesn't know if he would be a hero or not. So he could be friends with him. So, but it's, it's super, super interesting. And you also mentioned And Hunter Thompson, who I think I did the last interview with Hunter Thompson. Did you know that? No. So, you know, I was at Rolling Stone and Hunter had left Rolling Stone. He was in a kind of a fight with Jan Wenner, who owned Rolling Stone. And Hunter was writing for Vanity Fair, which I also was writing for. Yeah. And Jan, I always thought, wanted to get Hunter in the magazine one way or the other.

1:17:37So he asked me to go out and profile Hunter as he is today. So I went out to Woody Creek, I went out to Aspen. And Hunter was sort of like suspicious because Jan had sent me. I always think it's like in Apocalypse Now, he's like, you're a messenger boy sent by a grossly clerk to collect the bill, you know? But I spent like about a week with him and it was not long before he killed himself. I felt like this was a guy that the myth of him had become so great that it prevented him from functioning.

1:18:01Ryan Holiday: Yeah. You know, because he felt like he wasn't selfish enough. He felt like he kind of had to entertain people. And Hemingway writes about this too, about people showing up in Cuba and wanting him to be Hemingway and demanding he go out and get drunk with them and go fishing with them. And he just needed to write. And I really felt that way about Hunter too. So my point is that when you get down to what makes Hunter great, it's great. He was a great, great writer whose writing has been obscured by all the sort of fans who want something else from him, which is drugs or something. I always thought the drugs were a weird way to give him complete liberty in writing nonfiction.

1:18:35Ryan Holiday: Well, I think the drugs ultimately destroy him and the work. I'm forgetting the name of that. I have it in there. Did you read that Tim DeVeney book about Hunter S. Thompson? It's about him as a political thinker, like a political journalist. And then you're like, you think about him as the fear and loathing in Las Vegas guy, not the guy writing the best, most insightful political commentary, both sort of about America as a whole and the current political landscape of that era. Right. And that he was an astute sort of observer and critic of fascism, the American version of fascism. And then you think back and you're like, oh, yeah, where does he go in, like, not only is Fear and Loathing in Las Vegas about sort of the emptiness of the American dream, but he goes to that FBI convention.

1:19:19Ryan Holiday: Yeah, that's yeah. And he's like sort of perfectly caricaturizing that sort of figure of American authority in that time. Those are the people that are, you know, the stooges of J. Edgar Hoover and spying on Martin Luther King Jr. And, you know, he had the magazine that he could write that would let him do whatever he wanted. And that's sort of the sadness about the death of magazines in some way. But the thing is like Hunter Thompson, like you're saying, the drugs kind of destroyed him. Like he felt like he had to deliver Hunter Thompson. Yeah. So like a lot of his great things, there's like the first two pages are all the Hunter Thompson stuff.

1:19:56And then he just gets into writing.

1:19:57Ryan Holiday: Yes. And that's where cutting like the jump cuts is good. Like the cut the first three pages or whatever. Yeah. For me, the book that I like, the first book is the best, which is the Hell's Angels. Incredible book. and incredible and it's you see where tom wolf must have been hugely influenced by him because they were shared work they shared material he gave tom wolf all the stuff the reporting that became electric kool-aid acid test he gave him the tapes to the hell's angels and at ken kesey's i did reread that recently they asked me if i would write a forward to it and i was like no i was like i'm not remotely qualified to write a forward to a tom tom yeah uh book that seemed insane um but rereading that it just made because i know a lot of the people in the sort of psychedelic space now that are like but now it's like all official and it's about research and healing or whatever and you're just like this is the same fucking bullshit clown show as it was you know then yeah the book held up amazingly well but no there's a sentence in in hell's angels where he goes myths and legends die hard in america because they prove to the average person that the tyranny of the rat race is not yet final.

1:21:07Ryan Holiday: And then you're like, oh, that's first off an incredible line. And then it explains like, why are the Hells Angels famous? Why tough Jews? Why do we hold up the mafia? Like, why do drug dealers and the storylines and the arcs and the characters we love in rap music? Like, these are horrible people doing horrible things that if they were in your neighborhood or you knew them, you'd be like - Or you were sitting next to them on a six hour flight. Yeah, you would want nothing to do with them. These are bad people doing bad things. But from a distance, you know, why do they feel, why did we celebrate those, you know, John Dillinger and stuff?

1:21:42Ryan Holiday: It's because it's like, oh, there's an untraditional path. Well, it's because they represent kind of an underground. Yeah. Which is everybody's kind of broken into the system and there's no other way. And here's another way. Yeah. And it sort of suggests just knowing it's going on gives you a sense at a distance, like you say, of kind of freedom. Yeah. That somebody's not doing it that way. Yeah. It's beautiful from far away. If you look close. Yeah. It's hideous. Also, a lot of the gangsters, like, because you mentioned tough Jews, they were really, they wanted the status quo. They're all about the status quo because they're getting rich off the status quo.

1:22:13Yeah. It's interesting, like the Hell's Angels, because that's more pure. Yeah. Because that's not, I mean, it becomes a money making thing, but it starts out as like, and it's again, a PTSD thing. Yeah. Which is all these guys that come back from World War II, I think originally, and they don't, they're not quite ready to be Don Draper or whatever. They're not ready to have a nine to five job.

1:22:30Ryan Holiday: Well, before that, World War I, it's the same, like you watch Boardwalk Empire and you're like, oh, it's the same. Well, that's Hemingway too. I mean, that's the whole thing. It's all, they're all veterans trying to get over what happened. But I think like the Hunter S. Thompson is and the Tom Wolfe is, they just, they're kind of opposed to whatever's happening. Yeah. Which gives them a way to get some distance and to recognize it. So like to me, like the idea of being a writer, the whole idea is to be outside and to see it from a distance and describe it. And so much of like a lot of writing now feels like it's all about being inside.

1:23:01Yeah. Which is exactly where you don't want to be, man. Is it like it's much easier life, better way to be inside. But you got to try to get outside. And by the way, you write about things and you think you have one opinion and then you write about them and your opinion changes by writing about them.

1:23:17Ryan Holiday: Yeah. If you want to go next door, I got something I want to show you. Yeah. Some book stuff.

1:23:51Thank you.

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