The Heaviest Crown in America: The Quarterback’s Throne | Seth Wickersham (PT. 1)

In America, kings don’t wear crowns, they wear helmets. Being an NFL quarterback is the ultimate crown and it never comes free. Today, award-winning journalist Seth Wickersham joins Ryan to pull back the curtain on football’s most scrutinized position. They dive into why players can’t walk away, the intense loneliness at the top, and how the pressure can consume a player’s life. Seth Wickersham is a senior writer at ESPN and the New York Times bestselling author of It’s Better to Be Feared: The New England Patriots Dynasty and the Pursuit of Greatness https://www.thepaintedporch.com/products/its-better-to-be-feared-the-new-england-patriots-dynasty-and-the-pursuit-of-greatness?_pos=2&_sid=0d5097eba&_ss=r. Focusing primarily on longform enterprise and investigative work on the National Football League, Wickersham has been a finalist for the National Magazine Award for Reporting, and his stories have been anthologized in the Best American Magazine Writing, the Best American Sports Writing, and Next Wave: America’s New Generation of Great Literary Journalists, among others. Released in 2021, It’s Better to Be Feared https://www.thepaintedporch.com/products/its-better-to-be-feared-the-new-england-patriots-dynasty-and-the-pursuit-of-greatness?_pos=2&_sid=0d5097eba&_ss=r was named Nonfiction Book of the Year by Sports Illustrated and Best Sports Book by the National Sports Media Association. Follow Seth Wickersham: X https://x.com/sethwickersham?lang=en & Instagram: @Seth. Wickersham https://www.instagram.com/seth.wickersham/?hl=en 📚 Grab signed copies of It’s Better to Be Feared https://www.thepaintedporch.com/products/its-better-to-be-feared-the-new-england-patriots-dynasty-and-the-pursuit-of-greatness?_pos=2&_sid=0d5097eba&_ss=r and American Kings: A Biography of a Quarterback https://www.thepaintedporch.com/products/american-kings-a-biography-of-the-quarterback?_pos=1&_sid=efb24f02c&_ss=r at The Painted Porch | https://www.thepaintedporch.com https://www.thepaintedporch.com/products/its-better-to-be-feared-the-new-england-patriots-dynasty-and-the-pursuit-of-greatness?_pos=2&_sid=0d5097eba&_ss=r 🎙️ Listen to Seth Wickersham's first interview on The Daily Stoic Podcast: https://dailystoic.com/seth-wickersham/ 👉 Support the podcast and go deeper into Stoicism by subscribing to The Daily Stoic Premium https://dailystoic.supercast.com/ - unlock ad-free listening, early access, and bonus content: https://dailystoic.supercast.com/ 📖 Preorder the final book in Ryan Holiday's The Stoic Virtues Series: "Wisdom Takes Work": https://store.dailystoic.com/pages/wisdom-takes-work https://store.dailystoic.com/pages/wisdom-takes-work 🎙️ Follow The Daily Stoic Podcast on Instagram https://www.instagram.com/dailystoicpodcast/?hl=en: https://www.instagram.com/dailystoicpodcast 🎥 Watch top moments from The Daily Stoic Podcast https://www.youtube.com/@dailystoicpodcast on YouTube https://www.youtube.com/@dailystoicpodcast: https://www.youtube.com/@dailystoicpodcast ✉️ Want Stoic wisdom delivered to your inbox daily? Sign up for the FREE Daily Stoic email at https://dailystoic.com/dailyemail 🏛 Get Stoic inspired books, medallions, and prints to remember these lessons at the Daily Stoic Store: https://store.dailystoic.com/ 📱 Follow us: Instagram https://www.instagram.com/dailystoic/, Twitter https://twitter.com/dailystoic, YouTube https://www.youtube.com/@DailyStoic, TikTok https://www.tiktok.com/@daily_stoic?lang=en, and Facebook https://www.facebook.com/dailystoic See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

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

• 0:06Ryan Holiday?

  Welcome to the Daily Stoic Podcast where each weekday we bring you a meditation inspired by the ancient Stoics, a short passage of ancient wisdom designed to help you find strength and insight here in everyday life. And on Wednesdays, we talk to some of our fellow students of ancient philosophy, well-known and obscure, fascinating and powerful. With them, we discuss the strategies and habits that have helped them become who they are, and also to find peace and wisdom in their lives.

• 0:51Ryan Holiday?

  Hey, it's Ryan. Welcome to another episode of the Daily Stoic Podcast. This is more an American phenomenon than any other country, but if you have a kid picture themselves as a professional athlete, how many of them imagine themselves like in an instant, they're a quarterback in the fourth quarter, leading their team down the field, and they throw that pass? Right? That's, that's the dream. They're not, most of them are not imagining themselves as the center. They're not imagining themselves as a small forward on an NBA team. They're not

• 1:34Ryan Holiday?

  imagining themselves as a catcher on a baseball team. You know, a quarterback, it's the dream. I think it's interesting that among all the sports, right? It's one of the only ones where the head and face of the person is covered, and yet, the names, they are cultural touchstones. Steve Young, Warren Moon, Peyton Manning, John Elway, Tom Brady, Unitas.

• 2:04Ryan Holiday?

  Quarterback is where it's at. What that says about our culture, notwithstanding it is the thing that people aspire to, probably more than they aspire to be an astronaut these days, or a senator, or some other thing. I've been a fan of today's guest for a very long time. I had him on the podcast back in November of 21 to talk about his book, It's Better to Be Feared: The New England Patriots Dynasty and the Pursuit of Greatness. I'll link to that in the show notes if you want to check it out. The book and the conversation's obviously about sports a little bit, but I think ultimately a conversation about greatness.

• 2:46Ryan Holiday?

  How can you achieve and aspire to greatness without being Caesarified, to borrow Marcus Aurelius's turn, and the danger and the allure of wanting to do something of which the odds are so stacked against you? I was really excited that Seth came out to the studio to do this one in person, and I think you are really going to like it. And I think Seth can relate, and this certainly informs the book, to the idea of greatness and aspiration. As I pointed out to him, and he sort of shrugged it off, like, there aren't many sports writers whose names aren't known these days. I mean, sports used to be so popular, and writing about sports that sports writers themselves were famous, but there's a handful of them

• 3:31Ryan Holiday?

  who have broken through. I had another one on the podcast not too long ago, Wright Thompson, who is friends with Seth. But Seth Wickersham is one of the greats at what he does. And that's why I think ultimately this discussion of quarterbacks, this discussion of sports is ultimately a discussion about life, about mastery, about drive, about ambition, about greatness in all different forms. And we start this episode by talking about why someone would walk away from all that. One of the only times that anyone ever has done that, the Cincinnatus of football, if you will, Andrew Luck. Like I said, I think it makes

• 4:14Ryan Holiday?

  ultimately for a much deeper conversation. You don't have to like sports to do this. You don't have to like football to like this episode. I think you're going to get a lot out of it. He's a senior writer at ESPN, The New York Times bestselling author of It's Better to Be Feared. He mostly works in the long form medium, you know, not little, tiny, you know, guess who won this weekend kind of things, but primarily does long form investigative and narrative pieces. He's been a finalist for the National Magazine Award, and his stories have been anthologized in the Best American Magazine Writing, Best American Sports Writing, and many other places. It's Better to Be Feared was a nonfiction book of the year by Sports Illustrated. And you can follow him on Instagram and on Twitter,

• 4:58Ryan Holiday?

  seth.wickersham. You can grab signed copies of It's Better to Be Feared at the Painted Porch. They didn't have American Kings yet for us to have him sign. But it's a great book. You should definitely read it. I think you will really like this episode. And enjoy.

• 5:19Speaker 01

  I remember I saw, you know, your books in Sean Payton's office.

• 5:22Ryan Holiday?

  Yeah, I know. Yeah, that's been cool. I met him once. So I spoke, I spoke at the NFL owners meeting, like five, no, seven, six, seven years ago.

• 5:30Speaker 01

  Okay.

• 5:31Ryan Holiday?

  That was like the weirdest room that I've ever talked to. You're like, okay, it's 32 billionaires.

• 5:36Speaker 01

  Yeah.

• 5:37Ryan Holiday?

  Plus their families, plus every GM.

• 5:39Speaker 01

  Yeah.

• 5:40Ryan Holiday?

  Plus every coach.

• 5:41Speaker 01

  Yeah.

• 5:41Ryan Holiday?

  And like, it's still like a work conference. It was, it was a strange, it was a strange room.

• 5:47Speaker 01

  I mean, those are my, those are, that's my beat, you know?

• 5:49Ryan Holiday?

  Yeah, yeah, it was, it was interesting.

• 5:51Speaker 01

  The boardroom.

• 5:52Ryan Holiday?

  Yeah. And I guess they do it, what, like twice a year or something like that?

• 5:56Speaker 01

  They do more, but they only do the big one like once a year.

• 6:00Ryan Holiday?

  Yeah. And then it was like, on the other hand, like, like every other conference. There's something equalizing about it. It's like they're there, they had badges. You know, they're sitting there, they're like, they like some of the speakers, not some of the other speakers. And then there was like, there was like a get together after, you know? And then like, I remember I went up to Belichick after. And like, he was like-

• 6:19Speaker 01

  Because you probably knew him from-

• 6:21Ryan Holiday?

  Well, he knew my work.

• 6:22Speaker 01

  Yeah.

• 6:22Ryan Holiday?

  We'd never met, but like, it was like clear that his then girlfriend, not the, from this one.

• 6:28Speaker 01

  Yeah.

• 6:28Ryan Holiday?

  But was like, no, you have to go for a little bit. I want to talk to people, you know? Like, like, he probably wanted to be in his room, like watching a film. She was like, can we do something? You know, it was like, so it's just very weird to see the kind of like human element. And it's like-

• 6:40Speaker 01

  Totally.

• 6:41Ryan Holiday?

  Some of them are friends, some of them hate each other.

• 6:43Speaker 01

  They're all like in a, they're all in a, in an arranged marriage that none of them want to get divorced from.

• 6:48Ryan Holiday?

  Yes.

• 6:48Speaker 01

  But they all kind of secretly hate each other.

• 6:50Ryan Holiday?

  Yeah. And, and like even the, the inequality amongst them. It's like,

• 6:54Speaker 01

  Yeah.

• 6:54Ryan Holiday?

  You have Stan Kronke, who I, I've gotten to know a little bit and he's like, he owns like five sports teams.

• 6:59Speaker 01

  Yeah.

• 6:59Ryan Holiday?

  And then you have someone who like their great grandparents bought the team for a hundred dollars.

• 7:04Speaker 01

  Totally.

• 7:04Ryan Holiday?

  And that's the only, that's the entirety of the family wealth. And so like, then just, just like that there's social dynamics, even like to the outside, they're all the same. They're all the one percent they all, and you're like, actually no, there's like cliques and groups and totally different approaches and.

• 7:20Speaker 01

  Well, and they, the ones who bought their team remind the ones subtly all the time that they inherited theirs.

• 7:28Ryan Holiday?

  Oh, right.

• 7:28Speaker 01

  Which is a really interesting like class dynamic.

• 7:31Ryan Holiday?

  Yeah.

• 7:32Speaker 01

  And you have situations where like the Bears, you know, they have like 40 some McCaskey's who own the team.

• 7:38Ryan Holiday?

  Yeah.

• 7:39Speaker 01

  They limited how many of them could be on the field before a game because there's so many.

• 7:43Ryan Holiday?

  There's not enough tickets.

• 7:44Speaker 01

  Yeah. It's like, it became, it became a problem. Like there's too many people. So when do you write?

• 7:49Ryan Holiday?

  In the mornings.

• 7:50Speaker 01

  What's your schedule?

• 7:52Ryan Holiday?

  Uh, like I dropped my kids off, I dropped my kids off at camp this morning, came here, I wrote for an hour. Then we had a staff meeting, then I have this, I might do a little bit of writing in the afternoon. And then we have like a book club for the bookstore this afternoon. That's my day. I don't have to do any like reporting though. So I don't have to like spend a lot of time like on the phone. Do you know what? Like my writing is like, if I'm sitting there, I'm writing, you know, like.

• 8:13Speaker 01

  But that's a whole different mental exercise and mental gymnastics. Cause it may not require the travel, but like, one thing I've realized about books and Wright Thompson and I kind of realized it at the same time is that they're all essays. All the good ones are essays, whether they're reported essays or not.

• 8:28Ryan Holiday?

  Sure.

• 8:29Speaker 01

  They have to be, you know? And so you have to be constantly on that thinking level. And that's a hard place to get to.

• 8:36Ryan Holiday?

  Yeah. I've likened it, it's like, you know, sometimes like you close your laptop and then you come back to a couple of hours later and it's like burning hot. Somehow didn't shut down. That's what your brain is like when you're mid, like when you're in the middle of, there's a part on a book where you like, you've gotten it.

• 8:50Speaker 01

  Yeah.

• 8:51Ryan Holiday?

  You're like, oh, I'm actually going to finish this. Like it's, it's going to come together. That part's fun.

• 8:55Speaker 01

  Yeah.

• 8:55Ryan Holiday?

  But it's the, it's the whole, like the first. Maybe like two thirds, maybe a little bit more than the first two thirds where you're just like, it could fall apart at any moment and you could come up short at any moment. You know, maybe it's like in sports where it's like, oh shit, I think we're basically an insurmountable lead if we just don't fuck this up.

• 9:14Speaker 01

  Yeah.

• 9:14Ryan Holiday?

  We're gonna walk away with this and that kind of pre-celebration energy.

• 9:17Speaker 01

  Could be the Falcons, could not, you know, who knows?

• 9:20Ryan Holiday?

  Not that, I'm talking like in the fourth, like in an NBA game, it's the fourth quarter, it's like two minutes left and you're up by like 15.

• 9:26Speaker 01

  Yeah.

• 9:26Ryan Holiday?

  Oh, okay, as long as we, we'd have to do a lot wrong in a row. So as long as we just don't fuck it up.

• 9:32Speaker 01

  Yeah.

• 9:32Ryan Holiday?

  We got this, that's a good feeling, but most of it, it's nail biter the whole way.

• 9:36Speaker 01

  I grew up in Alaska and I do a lot of extreme skiing with some of my buddies and it reminds me a little bit what you're saying of that, where it's like the first 20%, you're like.

• 9:46Ryan Holiday?

  Yes.

• 9:46Speaker 01

  This is hit or miss.

• 9:47Ryan Holiday?

  Yeah.

• 9:48Speaker 01

  Like we might be, you know, sledding down, you know, who knows? And then once you get to a point and you're like, okay.

• 9:53Ryan Holiday?

  You can look up, you're like, I've made it a good chunk, the hard part of it's behind me. Again, it's not that it's easy from here, but like, I, I'm pretty sure I have this. That's a good, that's a good feeling.

• 10:04Speaker 01

  Yeah.

• 10:05Ryan Holiday?

  There's a thing in, that entrepreneurs talk about, so you get like the first bump of your media attention, that's really exciting. And then it's like the, you immediately go into what's called the trough of despair. And that, like, you spend most of a book in the trough of despair, just like, what did I sign up for? Am I literally capable of doing this? Is this the worst idea ever?

• 10:23Speaker 01

  Mm-hmm.

• 10:24Ryan Holiday?

  You know, all that, that's the shitty part.

• 10:27Speaker 01

  Yeah.

• 10:27Ryan Holiday?

  There's another shitty part after you finish, but before it's out, where you're like, there is a conceivable chance that this could sell zero copies. Like, you know, they're like, we're talking to these media outlets.

• 10:39Speaker 01

  I'm there.

• 10:39Ryan Holiday?

  And like, none of them have committed yet, where you're just like, and then, did you do the audiobook?

• 10:44Speaker 01

  I did.

• 10:45Ryan Holiday?

  Yeah, then you have to go read it, like, I'm about to do my next book in here, I do them in here.

• 10:49Speaker 01

  Uh huh.

• 10:50Ryan Holiday?

  And like, I just want to kill myself after. I'm like, this is the worst fucking book.

• 10:54Speaker 01

  Thank God it's not just me.

• 10:55Ryan Holiday?

  No, because.

• 10:55Speaker 01

  There's certain points, you're like, 100 more pages, seriously?

• 10:58Ryan Holiday?

  Yeah.

• 10:58Speaker 01

  What more do you have to say?

• 10:59Ryan Holiday?

  You hate your, you hate the book just because it's taking, it's taking a lot out of you. And then you're only spending more time with it and getting no external validation whatsoever, right? So it's just your, it's you and your inner monologue, unless you're a delusional narcissist, that monologue is mostly about all the things that are wrong with it.

• 11:20Speaker 01

  Yeah. Yeah, it's absolutely true. And then there's the other part. Did you ever see Swingers?

• 11:26Ryan Holiday?

  No.

• 11:26Speaker 01

  Okay, so it's a funny movie.

• 11:28Ryan Holiday?

  Yeah.

• 11:28Speaker 01

  You have to be careful Googling it because like some other shit comes up. But you know, it's about young actors in Hollywood in the 1990s. It was like Jon Favreau's. So there's this part in it, you know, Jon Favreau is heartbroken the entire time and he's like having like this heart to heart with Ron Livingston. And Ron Livingston is talking about heartbreak and he's like, you know, it hurts all the time and then it hurts a little less. And then you kind of miss the pain. You know, and Favreau is like, you missed the pain? What the, like, what? And he goes, yeah, because you lived with it for so long. And then that, I feel like that's a part two.

• 12:03Ryan Holiday?

  Totally. No, I mean, I'm just finishing a four book series. So I've been with this series for seven years, six years. And so, and I've had these different periods. What the weird part about is it's like each book is a microcosm of the whole series, but there, but it's been this weird thing where it's like you work on one, is it good? And then it comes out, it does well. Then you have the elation, but then you go right in the shit of starting the next one. So this is like, this is the last part of it and then I'm, I'm done. And there's a quote I have, it's from Given, where he's talking about finishing the decline and fall of the Roman Empire. And he says, it's like taking leave of a, of, of an old friend or something like that.

• 12:41Ryan Holiday?

  And there's something to that where you're like, you're like, you miss it because you, you spent so much time with these people and these ideas and this thing. And then you're gonna go off and do what next? That's, it's a weird feeling.

• 13:05Ryan Holiday?

  I wanted to start with Andrew Luck.

• 13:08Speaker 01

  Sounds good.

• 13:08Ryan Holiday?

  Because as you say, it's like they're basically American gods. It's like the penultimate of American sports. You make ungodly amounts of money, famous, everyone wants you, all this stuff. And here you have a guy who walks away from it. Is he? The sane one, or is he the insane?

• 13:29Speaker 01

  Mm hmm. Andrew Luck is fascinating because he doesn't know.

• 13:33Ryan Holiday?

  Not supposed to do that.

• 13:34Speaker 01

  Yeah, well, he doesn't know the answer to that question.

• 13:36Ryan Holiday?

  Right.

• 13:37Speaker 01

  Is he the one who got out at the right time? Or is he the one who turned away something that he'll never have again? And he knows that.

• 13:46Ryan Holiday?

  Yeah.

• 13:46Speaker 01

  I spent a lot of time with him in 2022 for an ESPN story. And it was the first time he'd spent anyone with a writer since he retired. And we first started meeting, I want to say, February. Story came out that December, so we met a lot.

• 14:02Ryan Holiday?

  Yeah.

• 14:03Speaker 01

  And part of hanging out with him was watching him replay this decision in his head.

• 14:08Ryan Holiday?

  Yeah.

• 14:08Speaker 01

  Knowing that in his heart, he made the right decision, but he was still uneasy with it. I think what led me to writing the book is like being a high school quarterback in Anchorage, Alaska, you know, in the 90s and losing out on the, on the starting job on varsity. You know, my entire identity was geared towards this thing. And you don't play quarterback, you are one.

• 14:33Ryan Holiday?

  Yeah.

• 14:34Speaker 01

  And he was one and his entire identity was wrapped up in this thing, but he knew he had to get away from it.

• 14:40Ryan Holiday?

  Why?

• 14:41Speaker 01

  I think that he didn't like who he was as a quarterback.

• 14:46Ryan Holiday?

  Huh. On the field or off the field?

• 14:49Speaker 01

  Oh, 100% off. On the field, I think he was very happy with who he was, but there's no roadmap. And that's one of the most interesting things I found about this, like spending time with current high school guys, you know, from Arch Manning to others, but like, there is no way to do this.

• 15:07Ryan Holiday?

  Yeah.

• 15:07Speaker 01

  Even though they've kind of tried to make there be a way to do this. And so there's no way to tell if what you're doing is the path to greatness. And he came to the Colts, Peyton Manning had been there, Peyton Manning ran the entire building.

• 15:22Ryan Holiday?

  Yeah.

• 15:22Speaker 01

  Andrew Luck was 22 years old and he thought, well, that's how you do this. And he basically tried to do his version of that with very little guidance. And when he realized that to get to game time, you cannot have any doubt.

• 15:39Ryan Holiday?

  Yeah.

• 15:40Speaker 01

  It's almost like you have to create like a fragile ecosystem around you where. You know, you're at the center of it. It's Andrew's world and everything kind of revolves around you. And that's the way he did it for a long time. And when he got hurt, he started to realize the fatal flaws in that mindset. In, in having like, almost kind of like reverse engineered his, his entire life to win football games. Once he was away from the game, he started to realize that there was limits to it. And he didn't know elements of himself at all.

• 16:14Ryan Holiday?

  Do you think that's a failure of like the system or culture? Or is it just inherently any elite performance is going to be inherently isolating? Because by definition of being the greatest or in this small minority, no one knows what it's like. And you're distant from everyone else.

• 16:33Speaker 01

  I, I don't have a great answer for that. You know, for ESPN, I spent a ton of time with Alex Honnold, you know, who obviously did Free Solo. And he reminded me a lot of a quarterback in the sense that like, people thought that he was this daredevil who was indifferent to death and didn't mind if he died. And when really it was the opposite. What was interesting about him was that he was so scared of dying that he memorized every single dimple and pebble and shift on El Capitan. And so that when he finally climbed it without any support system, he knew every single move that he was going to do. It took him years to do that.

• 17:15Ryan Holiday?

  Yeah.

• 17:15Speaker 01

  And that reminds me a lot of quarterbacking where you have to be obsessive on that level to be successful. And you have to tap into a part of your personality that either you need to get up to speed or pre-existed.

• 17:30Ryan Holiday?

  Well, I just mean, like, there's probably what? 10 sports writers, named sports writers? You know what I mean? Like there's, there, in any given field, there's only so many people doing it. So you must have some sense of what it's like. Like you, you have to turn yourself kind of, there's something fundamentally unbalanced about being one of the top people at the thing that you do. Probably you have to become unbalanced to get there. And then there's something unbalancing once you're there. Because you're like, There's no one who's like, let me show you how it goes because they want your spot or they know you, they, you want their spot.

• 18:07Speaker 01

  Yeah.

• 18:07Ryan Holiday?

  Or they're dead.

• 18:08Speaker 01

  Yeah.

• 18:08Ryan Holiday?

  Like being like number one on the call sheet, as they say in Hollywood, the conductor stands alone. That's just how it goes.

• 18:15Speaker 01

  It is, and you have to be broken in the right places and healed in the right places. You know? Otherwise you end up like kind of flaming out. And I think that like, when it comes to Andrew especially, you know, he, he not only began when he was hurt and his shoulder was bothering him and, you know, he didn't know if he was going to return to be able to play. His wife was on the verge of, of leaving him. She was his girlfriend, you know, but like she was on the verge of leaving him because they had dated since Stanford. And he simply wasn't communicating anything with her. And here he was facing all this fear, identity crisis, pain. And he had to learn how to tap into that part of his personality.

• 18:57Ryan Holiday?

  Be a person.

• 18:57Speaker 01

  To be a person, to be a husband. And I think that like, once he did, he made it a point to see if he could make it. You know, he, he played that final season, the 2019 season, 18 season. And he won player, you know, comeback player of the year. And he had proved to himself that he could be someone that he liked being around.

• 19:18Ryan Holiday?

  And be good.

• 19:19Speaker 01

  And be good. And he wished he'd retired right then, but it's hard. It's a hard thing to walk away from.

• 19:25Ryan Holiday?

  Well, there's that line in Hamilton where King George, when he hears that George Washington is going to walk away. He goes, I didn't know that was a thing a person could do.

• 19:33Speaker 01

  Yeah, exactly.

• 19:34Ryan Holiday?

  Which is, which is, it's a great line. And then it is, I mean, the, the real line is, is crazy too, right? King George does hear that George Washington is going to return to his farm. He goes, what's George Washington going to do after the revolution? And, uh, you know, one of his men says, I think he's going to return to his farm in Mount Vernon. And he goes, if he does that, he'll be the greatest man in the world. Like you're not supposed to do it.

• 19:56Speaker 01

  It's not supposed to do it.

• 19:57Ryan Holiday?

  You can't walk away from the thing that everyone wants.

• 20:01Ryan Holiday?

  And so there's something truly majestic about it when people do it. And then there's the other part of us that's like, wait, you you walked away from being a professional football player to to preserve your marriage. You know, there's like some other part of us that finds it deeply shameful also. There's something beautiful about it. And then, like, we're mad that Obama is not more politically engaged.

• 20:27Speaker 01

  Well, you know, like, you're not supposed to walk away. Yeah, and that has to do with our like, American obsession and American ambition. You know, the first question I asked Andrew Luck when we started talking was I asked, you know, why did you become a quarterback? And his answer was, he laughed that that Andrew Luck laugh of his, but he and he said, well, I don't think I had a choice. And it was because, you know, once you're you've shown promise of being able to do this uniquely American thing that has this obsession around it. Like, you're on a track.

• 20:57Ryan Holiday?

  Yes.

• 20:58Speaker 01

  And you're going from high school, and he's a Texas quarterback. People forget that, like, all the phenomenal Texas quarterbacks over the years, he's one of them. And, you know, you're you're in that culture and it's like a tractor beam that takes you in. And I don't think he really stopped to think about what it had done to him and who it had kind of turned him into until he was injured.

• 21:21Ryan Holiday?

  Right. Yeah, you become a machine, you turn off some part of yourself to get that level. Or that's what we tell ourselves.

• 21:28Speaker 01

  Or refuse to acknowledge that it even exists.

• 21:30Ryan Holiday?

  Yeah.

• 21:31Speaker 01

  And, you know, I think that, like, quarterback has become so big that I think that to do it now, you know that the celebrity and the fame piece of it come with it.

• 21:42Ryan Holiday?

  Yeah.

• 21:43Speaker 01

  And so I think to do it now, you have to have that whole.

• 21:47Ryan Holiday?

  You have to want that from the beginning. It's not a like, I just want to be a quarterback and I don't like the fame part. Like, you were you knew that was the bargain from the beginning.

• 21:55Speaker 01

  Like, Steve Young and I at one point, like, talked about all the hats you have to wear as a quarterback. And I think we stopped at like, 24. You know, from matinee idol to field general to, you know, astonishing asshole to amateur psychologist to, you know, spokesperson of a multi-billion dollar organization, all these things. And oh, by the way, you also have to be able to throw the ball through windows that nobody else can see, much less take advantage of. But I think that like to do it now, you not only have to be able to have the ability to throw, but you have to have that hole in your personality that requires constant adulation and reassurance and love.

• 22:32Ryan Holiday?

  Yeah.

• 22:32Speaker 01

  That's very similar to a politician or a lead singer, something like that where it's like that just kind of has to be part of the equation at this point. And what is that doing to people? What does that do to teenagers? When we're so obsessed with spotting genius early without really understanding what makes the genius in the first place? That is going to be really interesting to see.

• 22:55Ryan Holiday?

  When it's not like you're given time to develop a fully rounded out personality with diverse interests and connections because you have, you have been specialized since you were 10 or earlier.

• 23:09Speaker 01

  Absolutely.

• 23:10Ryan Holiday?

  And like. So you don't have the things that would actually help you manage that thing. Like, like in music, they call it LSD, like lead singer disease.

• 23:18Speaker 01

  Yeah.

• 23:18Ryan Holiday?

  Like you're catching this quarterback disease at like 10.

• 23:32Speaker 01

  One of the characters in my book is a kid who's at LSU now named Colin Hurley. And he was on the fast track and he wanted to be the youngest person, really to do just about everything.

• 23:46Ryan Holiday?

  Yeah.

• 23:47Speaker 01

  In the, in the space of quarterbacks, like he didn't play middle school football. He went straight from like sixth grade to starting on varsity. And he graduated high school and started at Louisiana State when he was 16 years old. When he started, not started, but he started attending. And when he got to campus, until he turned 17 years old, there had to be a football staffer on him at parties because legal age of consent is 17 in Louisiana. And I mean, this is, you're talking about like a college freshman.

• 24:18Ryan Holiday?

  Yes.

• 24:19Speaker 01

  Who, you know, barely has his driver's license.

• 24:22Ryan Holiday?

  And you think about even the parents that would subject their kid to said situation.

• 24:26Speaker 01

  And his dad is an interesting guy. He's, he's a loving, hard ass. His name is, is Charlie. And he was, he was a former cop and homicide detective in Miami. And so he's seen everything.

• 24:38Ryan Holiday?

  Yeah.

• 24:38Speaker 01

  And he was, he had a premonition for so long that this might not end well, just because of how young his son was in this dangerous world that he was entering. And, you know, last Christmas, Colin returned to campus with a car and his dad didn't want him to have a car, but he's getting NIL money.

• 25:00Ryan Holiday?

  Yeah.

• 25:00Speaker 01

  Yeah, you're going to LSU, you know, if you want to get a car, you, what are you, what are you supposed to do? And he wrote a note to his son, or he wrote a note in the, and he put it in the glove box. And it was like, in case of emergency, please call me. And it was Charlie Hurley, and he gave his phone number. Cause he knew from life that that's where cops look.

• 25:20Ryan Holiday?

  Yeah.

• 25:21Speaker 01

  And two weeks later, you know, Colin was in a near fatal accident at three o'clock in the morning when he ran his car into a tree right on the edge of the LSU campus.

• 25:32Ryan Holiday?

  Jesus Christ. The inability to turn stuff down when everyone is throwing it. I think that's what you think about the Washington thing. It's like, what do you mean? You're resigning your commission and going home? What do you mean you don't want to stay president for like, we, we're, we're just not good at walking away. I think about this, do you listen to Marc Maron's podcast? Oh, he's like, basically he started the podcast.

• 25:52Speaker 01

  Yeah.

• 25:53Ryan Holiday?

  He's like the biggest one, was the biggest one. And he's walking away after like 16, and people are like, what are you doing? You know, like you're not supposed to stop. Like, and part of what he's talking about is like, nobody ever quits. And there, that, that would, you're not supposed to turn down millions of dollars on your kid's behalf because they might get in a car accident. You know, like even though at some level, we know it's not healthy or good, but you just don't.

• 26:21Speaker 01

  Everybody gets swept up in it.

• 26:22Ryan Holiday?

  Yeah.

• 26:22Speaker 01

  And even being around, you know, it.

• 26:24Ryan Holiday?

  Yeah.

• 26:25Speaker 01

  I got swept up in it a little bit, you know what I mean? Cause like, I'm trying to learn in this book, I'm trying to give readers like the clearest eye possible of, you know, what it means to be a quarterback.

• 26:37Ryan Holiday?

  Yeah.

• 26:37Speaker 01

  And what it has meant and. In all the great ways and all the cruel ones. And, you know, even when, you know, red carpets and VIP treatment and all of those things, you know, witnessing it up close, it's easy to get.

• 26:53Ryan Holiday?

  There's an energy to it.

• 26:54Speaker 01

  There's an energy to it and there's a seductiveness to it. And then when you're not a quarterback, even if you retire on your own terms, you still live with that. And the hardwiring that you had to create within yourself to survive, I think is uniquely ill-suited with A, being content away from the game and B, a lot of everyday interactions. Like John Elway, one of my main characters, he was my, my guy growing up. He was the first quarterback who was number one out of high school.

• 27:27Ryan Holiday?

  Yeah.

• 27:27Speaker 01

  First pick in the draft, first ballot Hall of Famer. And so I knew that he had to create something within himself to withstand that.

• 27:36Ryan Holiday?

  Yeah, to say, I deserve this.

• 27:38Speaker 01

  And to survive it, you know? Yeah. And, and, and we were talking at one point and he was just talking about how warped you get.

• 27:46Ryan Holiday?

  Yeah.

• 27:46Speaker 01

  And how because of the things you go through, you're almost like incapable of feeling empathy. Like his son, Jack, was a quarterback in high school. And you think about the pressure of being a quarterback in Denver with your last name Elway. And his dad was the offensive coordinator, his dad was retired. And Jack was feeling the pressure very understandably. He was a good quarterback. He got a scholarship to LSU or to Arizona State and he walked away after a year. He was just kind of burned out. But when he was in high school, he was feeling that stress. And, you know, his dad, of all people, you'd think would be the one who would know what it's like to go through that and could empathize. And he couldn't do it. And he told me.

• 28:29Ryan Holiday?

  He had to turn off that part of himself to be able to do it. So the idea that some, that someone else would struggle with it. It's like, wait, I, I had that option? I think about this, like, there's a strain analogy to be sure. But like, there's an argument that people who think that being gay is a choice.

• 28:49Ryan Holiday?

  Think that in part because it's a choice for them. You know what I mean?

• 28:53Speaker 01

  Totally.

• 28:53Ryan Holiday?

  Like you've turned the like, what do you mean? I'm turning off weird things that I feel inside. Why aren't you doing it? So to see someone who's just like themselves or struggling with themselves. It's like, what do you mean? So there's this kind of for, for people who've gone through some form of adversity or harrowing experience or struggle with something. You'd think it would turn on empathy, but it turns off empathy because they had to turn it off to be whatever weird thing they are themselves.

• 29:19Speaker 01

  Yeah, I mean, to survive that winnowing where you go from one of 16,000 starting quarterbacks in high school across the country to, you know, one of the top 10 in the NFL to one of the three who make it to the Hall of Fame. And, you know, those are some vaguely sociopathic tendencies.

• 29:33Ryan Holiday?

  Yeah.

• 29:33Speaker 01

  That you have to turn on and nurture. And like, there's not a lot of outlets and support system to help you regulate that.

• 29:42Ryan Holiday?

  No.

• 29:43Speaker 01

  And it was, so it was interesting because he, you know, he, he told me flat out, I didn't care what my son was going through. He was like, I figure just compete on the field and let the chips fall where they may. His son goes off to Arizona State, decides it's not for him after a year. And at Elway's 50th birthday party, his son comes up to him and he says, you know, I feel like I've let you, I let you down. And, you know, John said, no, you didn't. And then Jack said something really interesting, which was, um, you know, that he missed it, that he missed being a quarterback. Cause like, you can't, you can't not. Once you, once you kind of get a, it's just unlike any other job in sports. And it's like that for, for a lot of different reasons, but like, again, it's something that like, once you've done it, that piece of you is always alive.

• 30:28Ryan Holiday?

  Yeah. I was thinking about, when I was thinking about like, what, how do you prepare someone to be a quarterback? Not how do you make them be able to do it on the field? Which is, I think your point is that that in some way, that's the, the one thing they all can do. You get to a level and then that's actually not that important anymore. It's this other stuff that you can either do or not do.

• 30:47Speaker 01

  Well, yeah, I mean, when I was playing, you know, I was just fascinated like, how do they fit the ball into that window?

• 30:53Ryan Holiday?

  Yeah.

• 30:54Speaker 01

  And then at the end of the book, you know, that's what made me want to be a quarterback and studied, made me want to study that. And then, you know, at the end of this process, I kind of realized that's the thing they they have to be able to not think about.

• 31:05Ryan Holiday?

  But also, it's like you go to the comment, they can all put the ball through the window. Yeah. So like, there's something else that either makes you, it's like, yeah, I was actually thinking of Tom Wolf's The Right Stuff, and I was reading your book, like, you either have the other right stuff, or you don't. Yeah. But I was thinking about like, how do you prepare someone for something so inherently alienating and strange and isolating? And the precedent, and what I write about is, there's this, so Hadrian is the emperor of Rome, and he doesn't have a son. So he has to, there's this period in Roman history where the emperor picks his heir. Yeah. And so he sees something in this kid that he thinks, he thinks the kid has it, but the kid's too young. So he adopts an older Roman senator named Antoninus,

• 31:47Ryan Holiday?

  on the condition that Antoninus in turn adopts this boy Marcus Aurelius. So he sets in motion this succession plan, that, you know, he probably thinks it's going to be like a couple year, you know, process. Instead, Antoninus lives for 20 years. But it's, so Marcus Aurelius has 20 years of on the job training. You know, you think about the jockeying back and forth between, you know, the first and the second string quarterback, and how much they hate each other. Now imagine, like, you're the future emperor, and there's this other dude in front of you who's emperor, who's not your dad. You have no, like, like, you should, you're both gonna hate each other. But how does this sort of partnership, it's remarkable historically in that it's totally unprecedented before and since. Like, they

• 32:29Ryan Holiday?

  not only don't kill each other, but they work together, and then they both do a good job. But there's this interesting passage in Meditations where Marcus Aurelius, he's writing to himself, obviously, he's now the emperor, and he says, "You have to take care not to become Caesarified." He says, "You be careful that you are not stained purple," because the emperor wears a purple cape. And so he's talking about this thing that we know, the way that power corrupts. And he seems to do a pretty good job. But but it is, it's just fascinating to me that there doesn't seem to be any process by which you can prepare someone to have a job. Like, in the case, I think there'd been like 15 emperors before him. How many, you know, like, multi-season NFL quarterbacks have there

• 33:14Ryan Holiday?

  even been? What, 100 maybe, 200? Like, not that many. Not that many. And so you're like, you're being groomed at eight or 10 for the potentiality of doing a thing that, as a rule, almost everyone fails at. And it ends, although it could end financially lucratively, it ends badly for everyone involved. It's just, it's crazy.

• 33:40Ryan Holiday?

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