ESPN's Wright Thompson On What Makes Us Great… And Human

Ryan speaks with writer Wright Thompson about what drives an author to cover a topic, the similarity between writing and sports, their differing writing processes, and more. Wright Thompson is an author and journalist who covers the intersections of sports and culture. Thompson has written for ESPN.com and ESPN The Magazine on topics like auto racing, MMA, bullfighting and more. Thompson wrote The Cost of These Dreams and recently released the New York Times bestselling Pappyland: A Story of Family, Fine Bourbon, and the Things That Last. This episode is brought to you by Optimize, the membership that guides you on the path to living right. Optimize offers services like Philosopher Notes, six-page condensed reviews of insightful nonfiction books like Epictetus’s Discourses, Ryan’s The Obstacle Is the Way, and more. Members also get access to 101 video Master Classes, each one an intensive taught by experts about a particular topic. Visit optimize.me/dailystoic and get your first fourteen days free, plus 10% off your membership with discount code STOIC. This episode is also brought to you by the Jordan Harbinger Show. Jordan's podcast is one of the most interesting ones out there, with guests like Kobe Bryant, Mark Manson, Eric Schmidt, and more. Listen to one of Ryan's episodes right now (1, 2), and subscribe to the Jordan Harbinger Show today.***If you enjoyed this week’s podcast, we’d love for you to leave a review on Apple Podcasts. It helps with our visibility, and the more people listen to the podcast, the more we can invest into it and make it even better. Sign up for the Daily Stoic email: http://DailyStoic.com/signupFollow @DailyStoic:Twitter: https://twitter.com/dailystoicInstagram: https://www.instagram.com/dailystoic/Facebook: http://facebook.com/dailystoicYouTube: https://www.youtube.com/dailystoicFollow Wright Thompson:Homepage: https://wrightthompson.com/index.htmlInstagram: https://www.instagram.com/wrightthompsonbooksSee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info. 📢 Share | ⚙️ Manage Subscription

Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.

• 0:05Ryan Holiday?

  Welcome to The Daily Stoic, where each day we read a short passage designed to help you cultivate the strength, insight, wisdom necessary for living the good life. Each one of these passages is based on the 2,000-year-old philosophy that has guided some of history's greatest men and women. For more, you can visit us at dailystoic.com.

• 0:28Ryan Holiday?

  Hey, it's Ryan. Welcome to another episode of the Daily Stoic Podcast. My guest today is one of my favorite writers ever. I think one of the great sports writers of all time. I did a post on Instagram a couple of weeks ago where I just posted some of my favorite books about sports, and I had a copy of Wright Thompson's The Cost of These Dreams on there. And he sent me an Instagram message, which was a total surprise and unexpected. And I said, dude, you have to come on the podcast, please. And as it happens, he has a new book out called Pappy Land, which is an incredible book about this whiskey manufacturer who's really an obsessed craftsman, who is the best in the world at what he does. And of

• 1:11Ryan Holiday?

  course, in classic Wright Thompson style, it's not really about that at all. It's really about the human condition and the human experience, which we get into a whole bunch in the podcast. But his book, The Cost of These Dreams, is just incredible. There's a great profile of Bear Bryant's bodyguard in there, which you wouldn't think would be interesting, but is fascinating. He wrote the classic piece on Tiger Woods, which shaped the chapter in Stillness is the Key. He wrote two incredible profiles of Michael Jordan, which also influenced my chapters in Stillness is the Key. He has a chapter, a profile in the book about Ted Williams and his relationship with his daughter, which I wrote a bunch of emails about for The Daily Dad. And he wrote the classic profile on Urban Meyer, which

• 1:54Ryan Holiday?

  is also featured into a bunch of stuff we do over at Daily Dad as well. One of the best to ever do it at his thing. When I had Paul Kicks on the podcast a few months back, you definitely listened to that episode. I was talking to him about Wright, and he's just like, one of the best there is. Wright said the same thing about Paul Kicks. So it's a small world out there. The people who are true craftsmen are unfortunately quite rare. Any chance I get to talk to one, I'm gonna take. And we get into Stoic philosophy. We get into dealing with one's demons. We talk about...

• 2:28Ryan Holiday?

  Trying to detach from the results of things. And one of my favorite topics, how a great spouse keeps you sane and protects you from being at the mercy of said demons. So here's my interview with Wright Thompson. Check out his books, The Cost of These Dreams, and of course, the new one, Papu Land. Well, it's amazing to chat. I loved, I loved the new book. I love, I loved Cost of the, The Cost of These Dreams so much. So I thought we'd, we'd start there.

• 2:59Speaker 01

  Yeah.

• 3:01Ryan Holiday?

  That, I don't know, to me, that's just the perfect title for a book. It's the perfect expression. I went and I listened to the song, well, it's a drive-by trucker's song.

• 3:10Speaker 01

  Yes, it's a drive-by trucker's song called Angels in Fuselage.

• 3:14Ryan Holiday?

  What does that phrase mean to you? Like, why, I think I know why it resonated, but, but hit me with why that, that stuck with you.

• 3:23Speaker 01

  You know, that song has always lived inside of me in a really melancholy way, in the way that like really great music can, you know? I mean, I think the whole Bruce Springsteen album Darkness on the Edge of Town makes me feel a lot of those same things. But like, if you are really driven to do things and you don't really know why, I mean, you know, I think a lot of us who write for a living are a weird mixture of arrogance and insecurity that probably both come from some hole inside that we're trying to sort of understand the structure of before you can even start to fill it.

• 4:01Speaker 01

  And so that phrase to me, it always is like this reminder in the back of your, back of my head, certainly, to try to understand why you're doing the things you do and how that truth is different from the reasons you might tell people in public. You know, like, I love that thing when generals would come back to Rome, someone would sit in behind them and whisper, "All glory is fleeting." And the line lands to me a lot like that, you know, like adding up the cost of these dreams. Like, it's over now, you know, was it worth it? And so like, that line has resonated with me forever. And certainly in all these athletes I profile because nothing is ever for free.

• 4:45Speaker 01

  And so the, the combination of those two things is why I picked it.

• 4:48Ryan Holiday?

  Yeah, writing is a weird profession because you're, a great writer is as driven and ambitious as the kinds of people you're talking about in your book, whether it's Jordan, or Ali, or Tiger, or Bear Bryant. But then we kind of have a foot in the insanity, but then we're also a little bit outside the insanity, observing it and observing ourselves at the same time. So it's this weird thing where you get it, but then you're also sort of haunted and horrified by it at the same time?

• 5:22Speaker 01

  It's interesting because, I mean, look, I don't believe, for instance, that Aaron Rodgers wants to be a great quarterback any more than I want to be a great writer. Do you know what I mean? Like, I fundamentally don't believe that the public nature of something, I don't think I want to be a great writer any more than the guy who built my house wants to be a great contractor. You know, I think, so I think people are driven in really personal and complex ways. I mean, the fact that they do it in public is very interesting and certainly amps up all of these forces. And if you're, you know, if ambition, if we sort of can

• 6:05Speaker 01

  agree that ambition almost always flows from some need, then having to chase that ambition in public like that just cranks up all of this stuff to 10. You know, it's funny, like, you know, I made the mistake of reading some like online book reviews, and I was like, you know, I was talking to my wife, I'm like, who the, like, what gives them the right to say this? And she sort of looked at me, she goes, well, what do you think all those athletes you write about think? And I just went, oh shit.

• 6:36Ryan Holiday?

  Right.

• 6:36Speaker 01

  You know, like, oh, uh, oh, I'm a total hypocrite. But it is interesting, the public nature with which these athletes chase their jobs becomes an obstacle for them to overcome, a companion for them to walk with. You know, I have a story coming out in a week or so on Archie Manning. And it is basically about how 50 years ago, his life split in two, and he had to learn to get to know this total stranger. Archie Manning, all capital letters. And it's a story about his evolving understanding of who that person is and what, where that person intersects with the actual him and where that person doesn't.

• 7:18Speaker 01

  And so, I mean, I think, you know, for all of these athletes chasing these deeply personal dreams in public, you know, they certainly are doing things that most of us can relate to a little, but not really.

• 7:32Ryan Holiday?

  And one of the weird things about sports, which I both am deeply envious of and then feel must be an immense curse that, that we don't have to bear, is that it's such a measurable experience, right? So like, I think your book is amazing. I think it's one of the best sports books ever written, but there's no demonstrable way that the, the books in your category are ranked. You know, my books, they've, they've sold well, they've, they've, they've been reviewed pretty well, they've, they've hit this list, but not this list. It, I, I have the ability to sort of define my success. I have much more autonomy over my definition of success, whereas Aaron Rodgers, as great

• 8:13Ryan Holiday?

  as he is, you know, has to look at Tom Brady in a way that's so much more measurable and in your face and mathematical than the rest of us. And I gotta think that, you know, even with Tiger Woods, I think it's in your piece, but it's like Tiger Woods is like, I play for the hardware. Like the fact that it's like a trophy, a thing you get if you have the score that's higher than someone else's score is very artificial. And so that way it's probably a relief from the vagaries of life, but then it's also a thing that you can never quite get.

• 8:52Speaker 01

  I've certainly thought about that. And I've also, you know, I don't have an answer, but I've also wondered if the, you know, if the inverse is true, you know, like if the stats are a protection against imposter syndrome. You know, like, like if Aaron Rodgers can be like, I've won X Super Bowls and thrown for Y yards and Z touchdowns. And so you put a book out in the world and some people like it and some people love it. And, you know, if you were both arrogant and insecure, you are suspicious of the praise and give too much credence to the criticism. And so I've always wondered if, if the tangible nature of success and the fact, I would love for there to be a scoreboard on the wall. Just let me know if I won or lost.

• 9:34Ryan Holiday?

  Yeah.

• 9:35Speaker 01

  And, you know, I think the other thing you, you know, I wrote about Dale Murphy one time, the old Atlanta Braves, two-time MVP. And I just came away thinking, that's the happiest ex-athlete I've ever met. Because he, you know, there's that great Updike quote, "The mask eats the face." And he is one of the few professional athletes who was, you know, beloved and very, very famous at the time when the Atlanta Braves were on the Superstation every day. And he set about intentionally killing the avatar of Dale Murphy, number three, when he stopped playing. And so, you know, when you're around him, it's hard to remember he was even a star. Like, he has been so successful in killing

• 10:17Speaker 01

  all that was fake and nurturing all that was real. So, you know, when you go back to your question about, you know, you talk about Brady's hardware. I mean, when you look at Tom Brady right now, and I don't know the answer, I'm posing a question, I have no idea of the answer. When you look at Tom Brady right now, who has six Super Bowls, and you look at Peyton Manning right now, who has two, who seems happier?

• 10:39Ryan Holiday?

  That's the ultimate question. I mean, I had, I had, and, and I think your, your, your pieces, you know, certainly illustrate the idea of the sort of the haunted, tortured athlete to some degree, right? Your, your famous Tiger Woods profile and, and your... Your Jordan profile and I had Manu Ginobili on the podcast a few months ago, who I've gotten to know over the last couple of years. And what I think so fascinating about someone like him is like, well, there you have a guy with four rings who doesn't seem to be tortured, who seem to have enjoyed his experience and seems to be a sane individual. And that's actually something that I struggle with in my own life. It's like, I almost feel like

• 11:24Ryan Holiday?

  the ultimate ambition is to be really great at what you do and not be turned into a monster in the process.

• 11:32Speaker 01

  I had to reread my new book, Pappy Land, about, I don't know, two weeks ago, trying to find an excerpt for someone. And that's a weird experience to read it. And there's this line in there, or there's something in there, and we'll get to this later. I don't want to sort of veer off cost of these dreams until you're ready. But like, there was something in there I wrote about, the whole point of success is that it is an asset for you to trade for something. And so what do you trade? Do you trade it for a real life? Do you trade it for one more hand at the table? Do you blow it? I mean, if you look at any success as a fragile set of chips at a blackjack table, like, you know, I mean, like, I think

• 12:17Speaker 01

  about that all the time. And so people like Ginobili, there, like, there are a lot of guys like this who you meet, you're like, that dude's just happy. You know, Charles Barkley just seems happy. And so, you know, I mean, I find people like that to be, I mean, I don't know if seductive is the right word, but there's something about that life that I find I want. And I think the reason I want it so much, and I'm so interested in it, is that I just don't have it yet. Do you know what I mean? Like, there's some inner thing that Manu Ginobili has that I don't have. And, you know, I would love to spend time around him just to try to see it. You know, one of the things I loved about Julian

• 12:59Speaker 01

  Van Winkle was that because his bourbon has to sit in barrels for 15, 20, 23 years, he has to live a sort of long game that I don't.

• 13:11Speaker 01

  You know, and so I found that to be really seductive. And, you know, you meet athletes sometime who are like that, you know? I mean, Archie Manning seems, when you're around him, he just seems happy. He doesn't complain. He's really good with fans who approach like, you're just like, I want some of what he's got. And I'm sure that's true for Janobli.

• 13:34Ryan Holiday?

  I was thinking about this when you mentioned Manning and you were telling me you just, you just had another kid. I was reading a book a few months ago. I think it's called My First Coach, which is all about quarterbacks and their relationship with their fathers. And there's a scene in that book about Archie Manning where he talks about, I forget what team he got traded to from the Saints. But, but he talked about one of the reasons he retired is that he saw that Eli was just sort of much more introverted than his other kids. And that, that the relationship wasn't as natural. And then he said, one of the reasons I retired, even though maybe I could have, there was a chance that one of those last couple of seasons could have turned into something. Was he, he was, he walked away from the game because he wanted to be home and he wanted to spend more time with his son.

• 14:18Ryan Holiday?

  Cause he wanted to have the same relationship with Eli that he had with Peyton. And I'm forgetting the name of his other son. And I just thought, wow, that, that, yeah, that may actually be the greatest thing that you've ever done. Like to, that is almost a form of more elusive greatness than had you won the Super Bowl that you, you probably wanted more than anything in the world.

• 14:42Speaker 01

  One of the things that's so interesting about viewing the long arc of someone's life. As what it really is, which is a series of choices that, you know, especially like in the context of this conversation, which is sort of, you know, we're circling all around the idea of character. You know, lowercase c. I mean, they're very, it seems to me that there are very few chances in life. Where you were faced with the decision to prove whether you're the thing that you say you are, or whether you're full of shit. And the problem is, is no one tells you which decision is that, you know, like one of the things Michael Jordan said to me that was so interesting was that it was all coming at me so fast that I wasn't even really making

• 15:27Speaker 01

  decisions, you know, it was almost like sort of just deflecting. And, you know, those years of those high speed reactive deflections become who you are. And these things become muscle memory. And when you're flying that high and that fast, whether you're Tom Brady or Michael Jordan or Tiger Woods or Peyton Manning or Eli Manning, you, everything is happening so fast that no one stops and shakes you and says, this is one of those moments. And so when you see someone like Archie or like Dale Murphy, who arrives at this moment and makes the right decision, it's really something.

• 16:08Ryan Holiday?

  I'm sure you watched The Last Dance. And actually, I read a piece you wrote sort of afterwards. So I'm sure you saw it. But there, there was that scene in the, in, in the documentary where the Bulls have just beaten the Jazz at home. You know, it's probably the last, it's the, it's the, the sort of final disappointment of Karl Malone's, you know, sort of never quite getting there. And there's that scene where Karl Malone runs out of the stadium, you know, through the tunnels outside the stadium, onto the Bulls bus. And you don't know what is he gonna, is he gonna punch Michael Jordan in the face, you know, is he gonna, what, what is he gonna do? And he, he just wants to shake his hand and congratulate him. And you're like, again, that actually may be a greater accomplishment.

• 16:53Speaker 01

  Much greater.

• 16:53Ryan Holiday?

  Than winning the champion. I've certainly fewer people have done it.

• 16:57Speaker 01

  No, it's like those are the moments. You are who you are, you know? I mean, I find that's like, you know, after Urban Meyer won his first national championship at Florida, he had this beautiful celebration with his father and a bunch of friends and coaches and they're sitting around cracking beers. After he won the second straight national championship, the confetti is still falling. He runs from the field. I think they're at the football stadium in Phoenix. I think it was the Fiesta Bowl and he runs from the field through the confetti, past his celebrating players, runs into the locker room, into the coach's locker room, shuts the door, locks

• 17:41Speaker 01

  it and starts calling recruits. I mean, the confetti has not all been released and so you just realize-

• 17:49Ryan Holiday?

  Character is fate.

• 17:50Speaker 01

  Yes, like 100%. I mean, Michael Jordan said something to me that was so interesting that he was like, you know, I spent my whole life crafting myself into this perfect being for one purpose and I did that at the expense of all sorts of other things that I might have been. Different kind of father I might have been, husband I might have been, friend I might have been. And now that it's over, I have turned myself into this person with these traits and those traits are not only useless in my new life, they are the thing that is standing between me and enjoying all of the things that that person I created

• 18:29Speaker 01

  purchased. And it just like my head exploded because I was like, one, the self-awareness of that, like I don't have that, you know? I mean, and two, just you realize what the work of the rest of his life was. And so when we see these people who do these things in public, particularly musicians and athletes, who I think we have different relationships with than we do with movie stars and TV people, but like, you know, just dealing with the cost- Of the person they had to be to become the, to get the things they wanted is often as much work as the thing itself, it seems like to me.

• 19:08Ryan Holiday?

  There's a tragic element to it in, you know, Michael Jordan can articulate that. I can even articulate, like, I can think back to my childhood, my relationship with my parents, the thing I wanted from my, from my mother, my father, what clearly like what they saw as success. And then I went out and did that thing. And I can, like, I can articulate it. I can see it. But in, in the sense, you're, you're also kind of powerless to stop it. You know, you're, you're, it's like Michael Jordan can say that, but then doing it is doing even the slightest thing about it is almost impossible.

• 19:46Speaker 01

  It, it's almost impossible for me and you. I mean, imagine what it would be like for that.

• 19:51Ryan Holiday?

  Yeah.

• 19:52Speaker 01

  You know, I mean, like,

• 19:54Ryan Holiday?

  Right.

• 19:54Speaker 01

  I, I like to think that if I had a billion dollars.

• 19:56Ryan Holiday?

  When you have a billion reasons not to do anything.

• 19:58Speaker 01

  Yeah. If I had a billion dollars in a Gulfstream, I mean, I wouldn't be doing this right now, except that I probably would. But you know what I mean? Like, that's the, that's the thing.

• 20:09Ryan Holiday?

  Yeah.

• 20:09Speaker 01

  It's like, when is, what is enough? And what does that look like? That's a really interesting thing that I think a lot of people face. And like, like, what is enough?

• 20:18Ryan Holiday?

  Well, that's the, that's the Tiger Woods thing, right? And, and I mean, I, I, I wrote about this in my, in my, my last book, Stillness. You know, his father, I'm sure you know this, I probably got it from your article, but you know, his father called enough the E word, right? It's like when you've had enough, either had enough, or you're full, or you're done, just say it. And, and I, I thought it was so revealing, almost Freudian, that, that enough, that they called it the E word, like it was a curse word, like it would be bad to ever be full. That struck me as almost Shakespearean.

• 20:52Speaker 01

  Well, you know, it's interesting. There's like, for a long time, you know, the, so this is the second time I've mentioned this, the song Darkness on the Edge of Town, which is on that album I referenced earlier, you know, he has this line, like, I'll be on that hill with everything I got. I'll be on that hill because I can't stop. Lives on the line, dreams are won and lost. I'll be on that hill and I'll pay the cost, I think is what it is. And like, You find these mantras that you use to sustain yourself on the climb when you need to sacrifice and to be willing to push harder than other people are willing to push. And then those same mantras that get you somewhere are almost always the mantras that

• 21:33Speaker 01

  either A, will stop you from enjoying everything you gained on that climb, that will B, probably be the seeds that lead to the sort of tree of your self destruction, or most likely C, both.

• 21:47Ryan Holiday?

  Well, you brought up Urban Meyer and I actually wrote this line down. I pulled up my copy before we talked and I actually just wrote in the margins, I just wrote the word like, "Jesus Christ" next to your sentence. But I thought it was a perfect encapsulation of the tragic element of that ambition. You said, "Like any man who destroys himself running towards a finish line that doesn't exist." It's like, "I'll be happy if I get this. I'll feel good if I get this. Dad will be proud of me if X." And you get there and it's nothing. It feels like nothing.

• 22:22Speaker 01

  And it's so interesting, you know, like, I don't know if you've ever heard David DeVal talk about, all he wanted in his life was to win a major championship. And he was for a long time, the best player to never win a major. Then he wins the British Open and he wakes up in the morning and he understands that nothing is different. And he hasn't won a golf, he hasn't won a golf tournament since. I mean, you know, it does become interesting, like, the meta levels of the fact that we're having this conversation to me, the meta levels to me are, I'm selling a lot of books. I want to sell more books. I mean, part of me is proud of it and I want it to reach eyeballs. But another part of me is just, you know, I'm on a treadmill. This is what you do. And in the book that I'm actively

• 23:07Speaker 01

  out here saying, selling, I write about how I need to not do that. And so like, do you know what I mean? Like, Jesus Christ. I mean, like, how unself-aware could a human being be? And so, I mean, that's how these things connect in my head, is that, you know, these things are always a walk. They're never a destination, hopefully.

• 23:29Ryan Holiday?

  No, I mean, so I wrote in my, in my book, Ego is the Enemy, I had a chapter about how the effort has to be enough. You have to detach from the external results. You can't think about, you have to, you have to focus on what you control, not on the external results, because the external results are not in your control. And I even talked, I talked about John Kennedy Tool, right? John Kennedy Tool writes A Confederacy of Dunces. It's a brilliant book. It gets rejected. He kills himself. It wins the Pulitzer Prize posthumously. Nothing has changed, right? It's the same, the same fucking book. And if nothing illustrates the hollowness of the publishing industry or critics, it's, it's that. And so I wrote that and I feel it and I know it. And that book comes out and it, it sells enough copies, it should have debuted in the number

• 24:13Ryan Holiday?

  one slot on the Wall Street Journalist. And I open up the, you know, it comes out on the Friday after the release and it's, it's not there. Like not, not like, not at the number one slot. Like it's not there. And it was like, what happened? And, and it turned, it turned out my, my, I won't say who, someone at my publisher had switched without discussing it with anyone, something they thought would, would be helpful. They'd switched the category that the book was put in what they called BISAC, like it's the, the sort of categorization. So this, this technical decision disqualifies it from the number one spot. Instead, it hits zero spots. And so it's like, you know it, but then you have to do it in that moment.

• 24:55Ryan Holiday?

  And everything in you rebels against doing it in that moment. And then, you know, I mean, I've, I've had that experience so many times. You, you, you know it, you write about it, you feel it, you practice it. But then to do it in the moment, for, yeah, for, for Jordan, it's turning down a, a chance to win a competition with someone. For Tiger Woods, it's putting family above X, Y, or Z. You know, we all have that thing. And then it's, can you do it in the moments that count? That's really, I guess that's really what philosophy and this stuff is about.

• 25:29Speaker 01

  Well, I mean, in some ways, I think the study of philosophy, it seems abstract when you're on a college campus, but when you're grown up and you start reading. Thomas Aquinas, or Thomas Martin, who I love. I write about Thomas Martin a lot.

• 25:42Ryan Holiday?

  Me too.

• 25:43Speaker 01

  Will Campbell, if you've ever read Brother Do a Dragonfly. I mean, the real point of reading philosophy is to develop some sort of like ethical muscle memory. So when we're in that moment, like Jordan was talking about, where things are flying at you, and you're just making decisions, you're not going to make all the right ones. You're not always going to be the person that you want to be, but that doesn't mean, you have to understand that you're going to fail at that, but that if you have thought about this a lot during calm moments, then you stand a better chance of making the right call during moments of chaos or stress than if you hadn't done that. I mean, like, you know, I'm sitting here

• 26:23Speaker 01

  looking at my desk right now, and on it, I have the bubble gum cigar I got when my first daughter was born. I have a picture of my wife and I. I have the bound volume of Esquire magazine from January to June 1986, which had Richard Ben Kramer's famous Ted Williams story in it, which was always sort of a thing I longed to achieve. I have my signed copy of Willie Morris's North Toward Home, and I have the pocket Thomas Martin, which is just beat to death. And so hopefully, by just picking that thing up and reading it from time to time when I'm bored, some of that shit's gonna seep in, I hope.

• 27:00Ryan Holiday?

  Yeah. And I was thinking about that recently myself, where it's like, maybe this goes to the sports idea. It's like, you don't have to be perfect. Just more often than not, you have to be able to hit that shot, you know? And, and it's like, can, you don't have to win every game. You just have to win enough games to sort of stay ahead of 500, basically. And I think that's almost a, maybe a kinder way to think about it. Instead of expecting perfection, can you just... You know, can you just do it pretty consistently?

• 27:32Speaker 01

  Yeah, I mean, it's it's also not being precious with it or with the idea of you. I mean, I love that Samuel L. Jackson is in the greatest movies of our generation. And he'll, you know, do the Capital One commercial and I guarantee you he's laughing his ass off on his Gulfstream on the way to the Med aboard his 260 foot yacht. Do you know what I mean? Like, like Samuel L. Jackson looks like someone who's happy, you know? And so like,

• 28:02Ryan Holiday?

  Sure.

• 28:02Speaker 01

  It is interesting how it's one, it's a volume game, probably be a volume shooter, you know?

• 28:11Speaker 01

  But yeah, not expecting perfection from yourself is vital. And it's something that's very, very hard for athletes. My mom used to say, study for 100 and you'll make a 90. And, you know, that that sort of thing seeps in.

• 28:28Ryan Holiday?

  There's a great Seneca line. He says, what progress have I made? I have begun to be a better friend to myself. And that struck me as a theme in a lot of your profiles, whether it's, you know, Ted Williams or Tiger Woods or Michael Jordan is just how almost heinously hard these people were on themselves. And that that was the the real cost of the dream is that it it wasn't fun. Like, when I watched the Michael Jordan Hall of Fame speech, I don't feel envious. I feel sadness for him.

• 29:07Ryan Holiday?

  Like, it seemed like, oh, the cost of being this great, the the cost of being great, the way he was great, meant that he couldn't enjoy this moment.

• 29:18Speaker 01

  And like, what's so interesting too is, you know, you have people like Michael Jordan, who are doing these very Personal things in very public ways. And so like, you know, I think there are two things in Michael Jordan's public athletic life that are deeply tied to how he feels about the loss of his father. One of them is quitting basketball and going to play baseball, which is, seems like a cry for help and a wandering and a stumbling through the dark. And then, you know, he just did this NASCAR team. And, I mean, I teared up a little when I heard about it because I know him really well. And when Michael Jordan closes his eyes and imagines his father, his father was a mechanic in the military, and they grew up way out in the country, he sees a guy out in the driveway, working

• 30:03Speaker 01

  on an engine of a car on blocks. And so the fact that Michael Jordan has a NASCAR team, like, all I could think about was what a healthy tribute that was to James Jordan. Almost as healthy as quitting basketball to play baseball was unhealthy. And so like, in those two things, you see the arc of someone's personal growth, doing it in a very, very public way. It's like what we were talking about at the beginning. I mean, it's, you know, it's, it's, it's the challenge of athletes and musicians, songwriters, is that they're doing this very personal intimate thing, in a very public way, and opening themselves

• 30:45Speaker 01

  up, not just to critics, but to fans. You know, they, their avatar doesn't belong to them anymore. And that yet their avatar is the vehicle that they're trying to use to deal with this deeply personal shit. And so it's no wonder, you know, I mean, Diego Maradona died last week. I mean, that guy didn't stand a fucking chance.

• 31:06Ryan Holiday?

  You have that quote in the Tiger Woods piece that I think about all the time. And I forget who said, I'm sure you know who's, who said it. I think it was anonymous, but it was like, mirror, mirror on the wall, we become like daddy after all.

• 31:19Speaker 01

  Oh, and that wasn't anonymous. That was the first director of the Tiger Woods Foundation. Mirror, mirror on the wall, we turn out like daddy after all. You know, it's like, uh, that's, Jesus Christ, you know? Wow. I mean, that's not what you want someone saying about you. But I mean, no, that's brutal in its efficiency.

• 31:42Ryan Holiday?

  Yeah, no, it's it's a it's like encapsulating the human generations of the human experience in one ridiculous dismissive rhyme. And you're just like, oh, man, that is, that is our destiny in such a and and all the good we've done is us managing to overcome it. And all the horrible things we've done in some ways is us not managing to overcome it.

• 32:08Speaker 01

  I listened to that new Dixie Chicks album when it came, the Chicks album when it came out, and they had this line just in a chorus. It was like, blah, blah, blah, blah, blah, blah, repeating all the mistakes of your father. I'm just like, whoa, holy shit. Like, boy, that is a non iron to the head. Or, you know, I mean, like, it is, it's let's take, let's take all of human existence and sum it up into nine words about your deepest insecurities.

• 32:35Ryan Holiday?

  And and I think one way that I've found that I've been able to combat that, however lucky I've been able to do it, or whatever success I've managed to have, is something that I also loved in Cost of These Dreams, although I guess for some people could be the exact opposite. But you you talked about your relationship with your wife in the intro of that book. And you were talking about sort of her being your corner man, or that that's how she saw herself. And I related to that. But it's like, it's they're they're a corner man, in the sense that they're encouraging you to get back out there. But they're also there telling me when you have to throw in the towel, or what you're doing wrong. There, I think that one of the, one of the ways we combat our natural inclination

• 33:16Ryan Holiday?

  to repeat the patterns of the past is by bringing in a totally disinterested observer with their own familial issues, who looks at your stuff and just says, like, what the fuck are you doing? That's the most insane logic I've ever heard. Why are you repeating this pattern over and over again? And that's like, that's what my wife does, at least.

• 33:37Speaker 01

  I mean, it's interesting. Do you know what, when that book, when the Cost of These Dreams came out and hit the New York Times Best Seller list, my wife got me a present. And she got me one of those metal things with a rubber handle made by Everlast that corner men use. Let you know she's paying attention. And I mean, you know, Yeah. It's interesting in that, you know, I mean, in a lot of ways, the voice of Pappy Land, which I struggled with, was born out of writing the intro to that book. You know, the intro to the book was late, the intro to The Cost of These Dreams. Like, I just didn't know what to say. And we went over to visit my mom in Clarkstown, Mississippi, where I'm from. And we'd been out to Moon Lake the night before and had this

• 34:19Speaker 01

  great dinner. And I woke up and I went to this coffee shop downtown Clarkstown, this little bitty town where I grew up. And it just came out. And in some ways, doing that unlocked the voice of Pappy Land, because like, I was really struggling. You know, I kept going up to visit Julian Van Winkle, and I loved the conversations we were having about bourbon. But he was dealing with a lot of stuff in his life, you know, coming up with a succession plan for his business, bourbon business. You know, he had a cancer fight. My wife and I were trying and failing over and over again to have a child. You know, we had a miscarriage in Paris that was like, a nightmare. And it was just, you

• 35:00Speaker 01

  know, I found that the conversations I was having with Julian about life were more important to me than the conversations I was having with him about bourbon. And yet, I had sold this book about bourbon. And so, I just couldn't abide the best version of the story, being the one I experienced, but couldn't figure out how to pass on to readers. And so, when I wrote that intro to that book, I found the voice. I mean, it would be interesting if you read that and then read Pappy Land. It could be the intro to Pappy Land. And so, like, Yeah. It's funny, I'd never really thought about this till right now. But like, writing that unlocked this book, which I had, you know, I was really, really late. I mean, you

• 35:43Speaker 01

  know, it was due before Cost of These Dreams came out. I just couldn't write it. And like, you've been through this, like, just to be real crass, I'd already spent the money. Like, do you know what I mean? Like, I had to give him a book. Yeah. And I couldn't figure out how to do it. And so, understanding how this book flow, how this book in a lot of ways, was trying to answer the questions I posed in the intro to Cost of These Dreams, unlocked it for me.

• 36:08Ryan Holiday?

  Hey, it's Ryan. Got a quick message from one of our sponsors and then we'll get right back to the show. Stay tuned. Yeah, there's a humility that comes from realizing that often your best writing or best work comes when you're the least in control and in some ways, being the least intentional about what you were doing. Like, you like to think you're in the driver's seat and then you have these moments, like Steven Pressfield sort of talks about the muses. If you haven't read The War of Art, you would love it. He's amazing. Steven Pressfield wrote The Legend of Bagger Vance and Gates of Fire. But, you know, he talks about that this stuff doesn't come from you. It comes from some magical place, whether it's the gods or the subconscious or

• 36:50Ryan Holiday?

  whatever. You think you're in the driver's seat and then every once in a while, there's like a crack and you actually see, you're like, oh, I have nothing to do with this. I'm just sort of a vehicle for this stuff. Maybe I shouldn't, I shouldn't let this go to my head and I shouldn't grip the wheel so tight.

• 37:09Speaker 01

  You know, both of those things are necessary. Shouldn't let it go to my head. You know, it was interesting. You know, I've been feeling pretty good about myself the last couple of weeks. And then I went on my dear friend Scott Van Pelt's television show last night. And almost immediately, you could see the Amazon, you've done that before, even though we lied, say we don't look at the Amazon number. I mean, almost immediately, you could see it starting to climb. And it just hit me like, I'm selling books right now. And these books have nothing to do with me or the way anyone feels about me. This is a reflection of a gift that my friend Scott and his producer, Mike McQuaid, who's also a dear friend of mine, that they have given me. You know what I mean? That they are using

• 37:53Speaker 01

  their thing in this moment as an act of agape, or whatever you want to call it. And like, it really hit me that like, that the only emotion that isn't laced with at least some toxicity is gratitude. And, but we have to, you know, I constantly have to remind myself that like, you know, there are a lot of people involved in everything that we would call, quote unquote, a success.

• 38:20Ryan Holiday?

  Yeah, I had an experience with my book, The Obstacle is the Way, which is my first book that really, really popped. And when I, when I sort of really trace it back down to what that sort of breakthrough moment was, it was like the Amazon algorithm, like, Accidentally discounted it, but didn't like change the royalty. It was this whole, it was like a loss leading discount that a billion dollar behemoth accidentally sent my way and that put in motion these other things. You're just sort of like this, this has nothing to do with me. This is the universe doing its thing. And this time I'm the beneficiary of it, but oftentimes you're the victim of it.

• 39:00Ryan Holiday?

  And you, you sort of can't, you can't take either of those too, too close to your identity.

• 39:10Speaker 01

  That's so hard. I mean, especially.

• 39:12Ryan Holiday?

  Of course.

• 39:13Speaker 01

  Especially now with like how virtual, you know, I mean, you know, is there, is there a more toxic word in the English language than brand? You know, I mean, like, like, but it, you know, it's hard to tell now where the avatar stops and you start. These are the philosophical questions of our time, you know? I mean, I would love, I would love Seneca to be on fucking Twitter.

• 39:39Ryan Holiday?

  He might not be Seneca if he was forced to be on Twitter. That, that may be, that may be the.

• 39:45Speaker 01

  Oh, yeah.

• 39:46Ryan Holiday?

  Reason we had wisdom. I, what I loved about Papu Land, I was curious if you agree. It, it's sort of, I, cause I, I don't, I don't drink, so I don't like, not only do I not drink, even if I did drink, I have like the palate of a child. So I couldn't appreciate, you know, good whiskey versus mediocre whiskey. There's an element of it though, where it's like you're reading the book and you're like, oh, craft is craft is craft. Like whether it's golf or writing or whiskey or fixing cars. You, you either, you either get what craft is and you dedicate your life to it, or you're, you're one of those people that doesn't understand why this is so important to you.

• 40:25Speaker 01

  First of all, craft is craft and zen is butts in seats. You know, I mean, like zen is not some magical thing. Zen is the, is the ability to do something over and over and over until you're great at it, whether it's making whiskey or it's like John McPhee's birch bark canoe maker. You know, one, even if you don't drink. You know, I mean, the Wall Street Journal review of this was basically like, it's barely a book about bourbon, and that's right. I mean, it, you know, it's, it's more about, it's more about craft, and it's more about why, it's about what we owe, like, what do you owe your ancestors? And so, like, a lot of people don't know this, but, but Julian,

• 41:08Speaker 01

  his grandfather started this really famous distillery, and then his father lost it. And so Julian was left to pick up the pieces and kept making whiskey, losing, look, he borrowed so much money to keep this thing alive, starting in 1981, that this year, they are finally paying the loans off. I mean, this is one of the most famous products and valuable brands in the world, and 2021 is the first year in the black. And so, when you talk to him, you realize that, you know, you hear all these, you know, you see bulletin boards and shit where people follow your dreams, believe in your dreams, your dreams will come true. And like, that is deeply toxic, because it is the pursuit of the dream

• 41:51Speaker 01

  that is where character and identity is found. And that's certainly shown in Julian, because I came to realize that he wasn't burning through all this money and then borrowing more and borrowing and borrowing and fighting, because he believed that one day, suddenly people would realize he made the best bourbon in the world. It was because he owed something to his father and his grandfather, and was going to die honorably. I mean, whatever you know, cliche you want to use it, go down with the ship, you know, be carried off on your shield. Like, it was never about success. It was always about failing with honor. And that's when this, the book was born, really, in my head. When I sort of understood, okay,

• 42:33Speaker 01

  this is about inheritance, and this is about the journey and not the destination.

• 42:38Ryan Holiday?

  Why I hear that from people that go, oh, I want to write a book. And I go, oh, they don't. You know, it's, it's, I have to, right? Like, it's, it has to be, and that's where the cost of these dreams comes in. It has to be like, almost a compulsion. It has to be coming from some profoundly deep. Place in your soul where you can't not do it. That's the only way you do anything that matters, I feel like.

• 43:03Speaker 01

  Well, I mean, it's, I would say that's why there's so many false starts on Pappy Land, because I didn't have to tell a story about bourbon. But ultimately, I had to tell a story about family inheritance and home. You know, there's, and I went to see Springsteen's Broadway show and he said this thing that was, I was like, holy fucking shit. He was like, you can either be an ancestor to your children or a ghost. You know, and an ancestor propels them to chase their own thing and to carry you around as armor and flag. And a ghost wraps their shit so tightly around your kid's ankles that it drags them down. And I just, you know, that was another one of those things that helped unlock it. And so, you know, I think you're totally right. If you want to write a book, don't.

• 43:45Speaker 01

  Because it ultimately, before it's going to come out, it, it, it, it's going to stay underground and build and build pressure till it demands to come out.

• 43:55Ryan Holiday?

  That's a beautiful line about from Springsteen. Holy shit, I might have, I might have to steal that. That's, that's amazing.

• 44:01Speaker 01

  It's unbelievable. I mean, I was at the Broadway show in New York because I'm a grossly overpaid sportswriter. And so I just paid and bought the ticket. And I was sitting in there and I was with my friend Seth and we both really like Springsteen. And that left me feeling hollow. Like, have you ever heard wind blow through a pipe or someone like blow through a gun barrel? You know, it's that sort of whistling hollow sound? That's how I felt inside when he said that. And I was just like, oh shit. So, yeah, I mean, you know, those things coalesced in my subconscious until the book just demanded to come out like it came out.

• 44:38Ryan Holiday?

  I love the subtitle of the book, the, the idea about things that last. I did a book about that myself a while ago. I'm fascinated by work that stands the test of time. And I was reading, I read like these poems to my son before he goes to bed. And I was reading Longfellow's A Psalm of Life. And, and And he has that line, which I guess is a Latin saying about how life is short, but art is long. There is an element, I think, you maybe the Stoics would say philosophically, it's unhealthy, but it's also beautiful that, you know, creating great art or great whiskey or, you know, coming back when you're down 28 to three in the Super Bowl. There's a,

• 45:20Ryan Holiday?

  there's an element of like, that's what the denial of death gets you, right? There's this idea that it that for this brief moment, we can reach that kind of sublime place as, as Longfellow says, you know, leave a footprint in the sand of time. There's just that that you can get there for like a fleeting second and do something and it endures. I think that's what motivates the craftsman.

• 45:44Speaker 01

  I mean, craft stands the test of time because it's a table and it either works or it doesn't. You know, art is tricky. I mean, there's a, if you haven't read it, there is a fabulous essay in the current New Yorker about William Faulkner. And it is basically a book review about this book that was written about how Faulkner was so progressive and anti racist in his novels and yet was so sort of paternal and racist

• 46:14Speaker 01

  in his personal life and how these two contradictions say something interesting. I mean, even the most famous artists have to understand that art doesn't belong to the artist. You know, art belongs to the world in which it is put. And there's no way to know how it will be received generation after generation, or how it will fall from favor and return and how it will be, you know, beautiful and intellectual and then in the next generation might be seen as schlock and merch and then might find its way back. And so like, you know, the lesson I think of the craftsman is that it's the craft that matters, not the thing produced with the craft. Do you know what I mean? Like it's,

• 46:56Speaker 01

  you know, when you're in the ground, it's, it's, it's, I mean, God, it's such a cliche, but it really is the journey, you know? I mean, like, and I don't, we all know that. I mean, living it is something different entirely, but it really is. I mean, when you talk about Julian Van Winkle making whiskey, you know, they put whiskey into barrels this year that he will never live to see be put in bottles. And so. You know, if that's the case, then what are you doing it for? And I mean, you know, that certainly propelled the book.

• 47:30Ryan Holiday?

  That's true.

• 47:33Ryan Holiday?

  No, that's true. There's a great line from Marcus Rilke that I love where he says, you know, like, "People who are out for posthumous fame, forget that people in the future will be just as stupid as the people around now." And I think about that as a writer.

• 47:47Speaker 01

  That's great.

• 47:49Ryan Holiday?

  Which is great, you know, given the idea that this emperor 2,000 years ago wrote a book that people still read. I just love like the perfectness of that. But at the same time, I think it is the journey. But like, I think one of the things that writers miss especially, like, I had two sort of formative moments as a writer. Robert Greene, who is my mentor, he said, you know, "A book has to be either extremely practical or extremely entertaining." And my editor said to me on my first book, you know, sort of describing what I wanted it to be. And she said, "It's not what a book is, it's what a book does." So at your point about craft is a table, like, a book has to fucking do a thing for someone and that's how it endures.

• 48:32Ryan Holiday?

  And the whiskey, it's not some beautiful expression of whatever. It's also like, does it do the fucking, does it do the fucking job?

• 48:43Speaker 01

  That is 100%.

• 48:44Ryan Holiday?

  And what is the job?

• 48:45Speaker 01

  Well, that's what becomes interesting because the job,

• 48:51Speaker 01

  the job is never what you think it's gonna be. I mean, like, you know, I've written a lot of stories for ESPN and the one I get stopped about most of all in airports, for instance, is one I wrote about my father. And I was just trying to use my megaphone so that I could tell his story loudly enough so that some piece of him wouldn't die.

• 49:16Speaker 01

  And, and, and yet what it does, like the number of people who said they were sort of quietly or, you know, like in a cold estrangement with their father or with their son and how reading that story made them realize that they were acting like idiots. Dude, I mean, I bet I've heard that from 10 people and like, nobody's gonna remember this stuff, really. I mean, I'm a sports writer. Let's just be honest about it. And maybe they'll remember a couple of the pieces. But the fact that there are like 10 relationships that were repaired because there was some unintended side effect of this thing I did very selfishly, like that just lets you know that like, the world is going to decide

• 49:59Speaker 01

  the use of something. And no, you're exactly right. I mean, all of these things are out of our control.

• 50:06Ryan Holiday?

  Yeah, it's, uh, it, it, it's, the, all the best sports writing is really at the core, not about sports. It's about what it teaches us about what it means to be human, which is probably a great definition of, of art in general. Like, the, the painting is not the, the painting of squares. It's what does it make the person looking at it feel?

• 50:27Speaker 01

  Well, it is, it, yes. I mean, it's interesting in that art, art always is a prism, not a object. I mean, it's always a way of seeing either the world or yourself, you know, and, uh, you know, things move us in ways that we don't understand. Like, you know, that Van Gogh painting of the, that has a lot of orange in it, that it's his room at Arles, I think I'm pronouncing that correctly. I love that painting. I can't really tell you why, except that it emotionally affects me. And one day, maybe I'll figure out why. And like, but it, it's not really important that I know why, you know?

• 51:12Ryan Holiday?

  Yeah, music is a, is a hard one, but for, I, I remember when I was researching the book, you would find all these, these sort of great songwriters, whether it's Metallica or Max Martin, they were like, no, you, you, you put the song on, you, you, you take the demo, you put it in the car, you put the roof down and you drive up PCH. And how does it, does it work? You're like, oh, even music has a job, right? Music isn't just, you know, me doing what I want to do. It's, does it, does it heighten the experience in this way? That, that's the, the job. And I think it can be really easy to be self-indulgent, but you gotta, does it, does it do the job?

• 51:55Ryan Holiday?

  And if it does the job, boom. It doesn't really matter how you do the job. There's lots of ways, but it's gotta do the job.

• 52:03Speaker 01

  Well, I mean, and when art goes wrong, it is very often because the artist has forgotten that they are not doing something for themselves, but are in essence, doing a job for someone else. They're building someone a table and the table better hold shit.

• 52:18Ryan Holiday?

  Yeah, I forget who said it. They're like, the one thing all bad art has in common is that it's like a poem to the self or some, you know, that it's, it's, it's about you, not about the universal we or, or whatever.

• 52:31Speaker 01

  That's really interesting. I mean, one of the things I think that art is also trying to do, I mean, as a corollary to that, is try to see what pieces, what is a universal we? You know, I mean, like what are, you know, my editor used to say, all great stories need to be on some level about the human experience, about the condition of being alive on the planet now. And I find that, uh, like I've always found that to be like a, a jumping off. When I'm talking about that in a story, it has a chance of success. And when I'm not, you know, it is very easy for things to slide into being merch.

• 53:10Ryan Holiday?

  Yeah, like I, I think the, the, one of the great, greatest novels of all time, certainly I think the best southern novel is The Moviegoer and, and you know, Walker Percy's just

• 53:20Speaker 01

  Of course.

• 53:21Ryan Holiday?

  Here, here you have a guy who has this weird malaise and, and experience and it's on the one hand totally about that, but on the other hand, it becomes about the experience we all go through, which is like trying to find some shred of meaning in a world that feels devoid of meaning. And I think it, the weird part is that's probably why the second person doesn't work too much in novels, although I, my act, I, I love Lancelot, which is his, Walker Percy's second person novel. It's that if it's too on the nose, if it feels like it's about you, there's something strange about it. But if it's about someone else that you see yourself in, that's when it works.

• 54:02Speaker 01

  Well, and

• 54:03Ryan Holiday?

  So Tiger, if, if you're like, you're like Tiger Woods, you'd be like, no. But if you just show me Tiger Woods, warts and all, it, I go, I'm like Tiger Woods.

• 54:13Speaker 01

  Well, it's interesting that we, again, back to the thing we started at the very beginning, like, I don't fundamentally believe that, you know, somebody who is going about something anonymously cares less about their job or craft than Tiger Woods does. And so what you realize through doing these stories is that, you know, fundamentally, all human beings are the same, whether you're Tiger Woods, Michael Jordan, whether you're Julian Van Winkle, whether you're me or you or anyone listening. I mean, you know, wants and needs are primal and I mean, that's food chain shit. And so like, you do start to see that, you know, everyone is connected in that way.

• 54:56Ryan Holiday?

  Totally. And I, that, to me, that's the most stoic idea of all, that people are people, we've always been people, we always will be people. And whether the emperor or the lowest part of the totem pole, you're struggling with the same things. And, and people were struggling with it 2,000 years ago, they were struggling with it 200 years ago, and they'll be struggling with it 20,000 years from now if we're still around.

• 55:18Speaker 01

  Well, that's the, you know, that, that the mark, the, the arc of the moral universe is long, is what the truest thing anyone's ever said. Because, you know, We it's interesting that like, you know, if you read a history of the 30 years war, and you replace every mention of the word printing press with the word the internet, it's a pretty good description of the planet today. And you just start to realize like, oh, we're idiots. We're just doing the same shit over and over and over again.

• 55:49Ryan Holiday?

  Yeah, or you read John Barry's book, The Great Influenza.

• 55:52Speaker 01

  Yeah.

• 55:52Ryan Holiday?

  And you're like, fuck, literally 100 years have passed and nothing has changed.

• 55:56Speaker 01

  Not a single thing.

• 56:00Ryan Holiday?

  Well, right. Thank you so much. I loved both books. You're one of my favorite writers. It was an honor to do this and we'll have to do it again because I feel like we got another couple hours of stuff to kick around.

• 56:11Speaker 01

  I could do this forever, man. Anytime you want to. This is really interesting.

• 56:14Ryan Holiday?

  All right, man. Thanks.

• 56:18Speaker 02

  Don't forget to subscribe to this podcast on iTunes or your favorite podcast app. And if you don't get the Daily Stoic email, go to dailystoic.com/email.