3 Pieces of Advice Worth Keeping Close | Seth Wickersham

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1:09Ryan Holiday: If you're hiring now, then this is a job for Indeed sponsored jobs. Welcome to the Daily Stoic Podcast, designed to help bring those four key Stoic virtues, courage, discipline, justice, and wisdom into the real world. Hey, it's Ryan. Welcome to another episode of the Daily Stoic Podcast. I am recording this in my office, the painted porch, and it's kind of funny. I've got some stuff taped to my monitor, little notes. Got a quote from Marcus Rebellus off to the left of me. Waste no more time arguing what a good man should be like. Be one. Here to my right, I've got a quote from Martha Graham. Never be afraid of material.

1:54Ryan Holiday: The material knows when you are frightened and it will not help. I have a quote here from Hemingway. Do not worry. You have always written before and you will write now. All you have to do is write one true sentence, write the truest sentence that you know. I have a letter from Truman. I have a memo from Truman. I've got an email exchange with General Mattis and I that was a reminder. He just says, keep the faith, Ryan, hold the line. And then I even have some questions. Am I being a good steward of stoicism? I have a line from the novelist Winston Churchill, not the British statesman. He said, yet sidelights on the life of every great man are interesting.

2:38Ryan Holiday: Just something I've been thinking about as I'm working on this Stockdale book, that giving myself permission to go down the rabbit holes, that the lives that intersect him, the historical anecdotes, the things he witnessed, the things that happened during his lifetime. I want to give myself permission to explore those because they're what light me up in the books that I read. And I've noticed this is a habit a lot of people have. One, if you go into an NFL locker room or a baseball clubhouse, or even if you visit a CEO's office, this is something people do. Reminders that they want to keep in touch with, quotes they want to be inspired by.

3:19Ryan Holiday: And as it happens, my guest today, the great Seth Wickersham, one of our best long-form sports writers working today. He's the author of a bunch of New York Times who are selling books, including one on the New England Patriots, one on the American quarterback. He has a new book called Beyond That Hill, which is the best of his journalism over the year. That's won every award you can imagine, including making him a finalist for a National Magazine Award. He has three quotes on his desk. I asked him what those quotes were, why he keeps them where he can see them, and how they stuck with him and what they remind him about writing and life.

3:58Ryan Holiday: I've had Seth on the podcast a couple of times, one of my favorite writers and thinkers. And anyways, I wanted to explore this with him. Do check out his new book, Beyond That Hill, which is itself a quote from a Springsteen lyric that has been bouncing around his head pretty much his whole life. American Kings is great. And his book on the Patriots is great as well. You can follow him on Instagram and on Twitter, Seth.Wickersham. And you can see his excellent writing on ESPN as well. Let's get into it. So this idea of getting perspective on what you're doing, I think is interesting. And you have this line towards the end of the intro.

4:38Ryan Holiday: You mentioned three pieces of advice that you've pasted next to your laptop. One is from your dad. It says, worry is optional. The only thing that makes a difference is action. Michael Lewis, don't be deceived by life's outcome. and then Eric Neal, who's riffing on James Baldwin. Discipline, love, luck, but most of all, endurance. Tell me what each of those three mean to you and why you put them on your desk.

5:01Seth Wickersham: Well, I think my dad's was just like, you know, you've talked about it often where I think you talked about it the other day where you said, you know, what your anxieties have in common is you, right? And so, you know, that's a strategy for how to cope with that. Like, you know, you can study those things all you want or be anxious, but at the end of the day, you have to, you know, take action. And so that's a reminder to take action. Don't be deceived by life's outcomes. I mean, I hold that one near and dear to my heart. That was from Michael Lewis speech that he gave at Princeton. And it was about just the role of luck in people's lives.

5:36Seth Wickersham: And, you know, Michael loves talking about luck. And he often talks about himself as one of the luckiest people. And, you know, there's parts where maybe he moments where he takes it a little bit too far or self-deprecation too far. But this just rang so true to me because as soon as you accomplish something, you want to credit yourself. And I think that's important. And it's important to celebrate those things and, you know, justify why you did something. I did it because of X, Y, and Z. Going back to that Brady thing where I asked him about the randomness of being a great quarterback, he couldn't process that.

6:09Seth Wickersham: I'm great because I've done these things. And other people weren't. You know, but I think that, like, Like now, if you ask Brady, he would say a huge amount of my career had to do with luck and all of these things. And so don't be deceived by life's outcomes means just because you accomplish certain things like you kind of can't believe your own internal headlines.

6:31Ryan Holiday: Yeah, I mean, I found that, too. It's like whenever you're massive, like a friend of mine said once, you know, making a contrarian bet that turns out to be right can be a brain destroying experience. And his point is like, if you're Elon Musk and you have this idea for SpaceX and everyone tells you it's a terrible idea and then it turns out to be worth a trillion dollars, it's hard for you later on to be informed when you do in fact have a terrible idea, you know? And I think that's a good example of like, hey, just because it worked out doesn't mean you're right. and by the way, just because it didn't work out doesn't mean you weren't right.

7:13Ryan Holiday: Because like life is so much about probability. So like, let's say something was a good call 80 % of the time and you make that call and then it doesn't work out. It still could have been absolutely the right thing to do. You know, honesty is generally the best policy, right? So you tell the truth, it blows up in your face. Do you take from that? Like, oh, I should be a dissembling liar. Like, no, that's the wrong lesson. And so that, yeah, I think that idea that outcomes can be deceiving or maybe even like distortive is really what they are. That's a great piece of advice.

7:46Seth Wickersham: And outcomes aren't within your control. You know, and like there's two stories in the book that kind of deal with those moments. One smaller, one very famous in the sports world. The smaller one is from the AFC championship game this past year where Sean Payton goes for it on fourth and one. And they don't get it. And that ends up being kind of the difference in the game. And he's just beating himself up over it. And then the other one famously is, you know, when the Seahawks decide to throw the ball at the goal line against the Patriots in the Super Bowl and Malcolm Butler, you know, makes this phenomenal play.

8:18Seth Wickersham: And everyone's like, oh, why didn't you just hand the ball to Marshawn? But that story is a classic case about how you manage through catastrophic outcomes, how you manage it, how you cope with it, how you try to figure out a way to persevere through it and Pete Carroll and Russell Wilson and Richard Sherman all had very different ways of going through it. But that's really what that story is about. And it speaks to exactly what you're talking about. I'd be curious for you, like, I mean, whenever I go into the office of a coach, your books are in their office. Like, what is it like being the guy that everyone turns to for wisdom?

8:57Ryan Holiday: It's very, it's very weird. I mean, look, the popularity of those books is a good example of what we're talking about. Right. So like I get credited for sort of like predicting this trend. Right. It's like, oh, you were so smart. It's like, look, I know what I accepted for that book deal about, you know, stoic philosophy. Like neither me nor the publisher had any inkling that this is where we would be 10, 12 years later. Right. Like, I mean, I thought it could work. Right. Like it's not like I didn't think it could work and it worked. it was more like I thought it could do okay and then I'd write about something else and then I'd write about something else and I thought about or write about something else like some musician once or music producer once talked about the difference between a hit and a freak you know and like sometimes you you get a freak you know and so I try to really consciously remember like I was just interested in this idea and I thought it was a good I I thought it wasn't a waste of time, right?

9:57Ryan Holiday: Like I, I've, I did the math and I was like, okay, this will pay my expenses for a year or two. I'm intellectually interested in this thing. Let's do it and we'll see what happens. Right. And then it takes your life in this whole other direction. And the idea that like, it would work in professional sports is like ridiculous. Like it's, it's ridiculous. Like Not at all what I predicted. I will say I had something to do with it. I remember I sent an article. Like, Michelle Tafoya had talked about it on a podcast. This is like some inside baseball, literally, I guess. Michelle Tafoya talked about it on a podcast, and I sent that link to Greg Bishop at Sports Illustrated, and he turned it into a piece.

10:44Ryan Holiday: Like, the books were working in sports, But as you know, there's nothing quite like a trend piece to make a trend real. And so that piece about it sort of made it more real than it was at the time. But I guess the point is, it can be very easy to be deceived by the outcome there, which is like, oh, you can decide consciously to take an ancient school of philosophy and make it popular again. Like, that's not what happened at all. Like, I was interested in writing a book about an ancient philosophy and one thing led to another. And so, yeah, like, it's weird when like people that you admire are asking you for advice.

11:31Ryan Holiday: You're like, this doesn't, I don't, I don't, I don't have anything to tell you. You know, like I try to remember that, like what I'm good at is writing books about this thing. And like, like I had Dan Coyle in here recently and I don't know who he is, but he like works for he works with teams. And I saw Michael Gervais the other day. He works. I've tried to be, you know, maybe it's a little imposter syndrome, but I've tried to be very honest with myself that that is not what I know how to do. and it's not what I'm qualified to do and also not what I like doing.

12:08Seth Wickersham: Well, and I think that like that word again, it's wisdom. You know, when people look at you for a certain thing and I think that like what balances, what probably makes it work for you is that you're great at explaining wisdom. Yeah. And giving examples of the things that probably have the best chance to prove wise. You know?

12:26Ryan Holiday: Well, I think I'm good at writing. I'm good at putting it in writing, which is like the thing I actually like doing, right? if you told me I had to show up for work every day at, you know, a locker room for a sports team, like that might seem cool, but I would actually hate it. I would hate it so much, like because I would not be in charge of my schedule. I would be in meetings all day and I would be not operating in the medium that I am most comfortable in, which is the written word. So like it is really important. I think that's, we can deceive ourselves with our own outcomes. Like I've actually talked about this in the ego book.

13:05Ryan Holiday: Like it's very common, for instance, like someone makes a great general and then somebody says you should run for office. And like very few military figures have ever actually been successful politicians because they're totally different forms of leadership, right? One, you have authority and the other you have to basically use the bully pulpit of persuasion and public opinion. And they're just different skills. Like it's been done, but the chances of one success in one outcome convincing you that you'll be good at the other is like, those are some rocks that a lot of people have crashed on.

13:42Seth Wickersham: And no more so than in sports, I think, because you see it all the time where you have a good assistant coach who becomes a head coach. Yeah. And they had an expertise for calling plays or coaching pitchers or whatever it might be. But like to be a good head coach, you need to have a completely different skill set, a completely different ego and gall and, you know, fragile self-belief to stand in front of people and get them to follow you, not get them to run a certain play that you're calling. Like, I think that it's so interesting. You look at the Bulls in the 90s and you would Phil Jackson and Tex Winter.

14:23Seth Wickersham: And those two were the perfect mix of that, where you had one person who knew his expertise. And that was designing offenses and communicating how to make this offense that ends up revolutionizing basketball and the career of Michael Jordan work. Yeah.

15:09Seth Wickersham: To me, it's just like that dynamic and those two personalities are fascinating. And you see why, one, the fact that they both knew their lanes, I think, is what made it work.

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17:48Ryan Holiday: And basically what they're trying to do is help people have not just meaningful careers, but impactful careers. how to have positive impact on the world. And you can find all episodes of the 80 ,000 Hours podcast over at 80 ,000hours.org slash stoic. That's 8-0-0-0-0-hours.org slash stoic. That awareness, both of like what you're good at and not good at, and also what actually the role entails and doesn't entail. Like there's an anecdote in the Sean Payton story you did recently where it's like he has to step out of a meeting to talk to someone in travel logistics about like how many tickets the family will get to the Super Bowl or whatever.

18:38Ryan Holiday: And you go, oh, the head coach is doing a whole bunch of things that the fans and probably even the players have no idea exists. I was thinking about that when I was talking to Michael Gervais. he was showing me his Super Bowl ring. And we were talking about like the list that gets made over who gets the ring or not in the organization, right? And who doesn't and, you know, how they thank the people. And anyways, it was like, oh yeah, like the head coach is either hired someone who's good at that or is themselves good at it. And having to think about the politics of ranking everyone's contributions and deciding who's in the circle and not in the circle And like, oftentimes people think they know what a job entails and they think they're going to be good at it.

19:29Ryan Holiday: And that's actually precisely where they end up, you know, failing because they just didn't actually understand this really key leverage point and they took it for granted. And then that's the weakness.

19:45Seth Wickersham: Yeah, I mean, you referenced that Sean Payton story. So, you know, I spent the two-week playoff run with, you know, complete access to Sean. I was there for 14 - and 16-hour days. That story's in the collection. I think it's the best story I've ever written. Just to see, just to be that close to the flame. And to see what it takes to win at the highest level of the NFL. But I spent days with him where, you know, if you're in the playoffs, especially in the championship game, you have to, the league makes you prepare for the Super Bowl. So, you don't want to. but you have to and so he would have these moments where he's yeah he's arguing with management over how many seats the coaches get to have extra on the team plane yeah he's figuring out what suits they're going to wear if they get when they're getting off the plane he's figuring out what the green room is going to look like at the team hotel at the super bowl he's figuring out the practice schedule because he wants to be practicing on the sunday before the game when the other team arrives Like he wanted the split shot of his team practicing and the other team getting off the airplane in pads, practicing in pads, by the way.

20:48Seth Wickersham: He was coming up with all these crazy ideas, like getting little canisters, little oxygen tanks made for the players with labels on them. So that because he was going to use a lot of no huddle offense and use the mile high air against as a weapon. And so he wanted to use that and make it memorable and then come up with a video, a scene from Everest, where he tried to make it funny and communicate that point. All of these things have to do with being a head coach and none of them have to do with what you decide to do on Fourth and One. And that, to me, the different drawers that you have to kind of pull out and the different pieces of your brain that you have to be able to access at a moment's notice, I thought was one of the most fascinating aspects of it.

21:35Ryan Holiday: So the last quote was discipline, love, luck, but most of all endurance.

21:40Seth Wickersham: That's be on that hill. You got to have the endurance to be on that hill and then to be on the hill the next day. And I think that we were in journalism school at a particular time. And, you know, I look back at the people who are still practicing and still doing it, you know, because not a lot are. Most people aren't. But, you know, people consider Missouri like, you know, one of the world's best journalism schools. And yet, I'd guess that 20 % of our graduating classes are active practicing journalists. And I think that, like, when I look at who is doing it, you know, I think passion's part of it.

22:12Seth Wickersham: Like, you know, some people lose their passion. They want to do something else. That's fine. But I think that like the endurance to just pick yourself up, make the phone call, spend the extra day on the road if need be, do all of those little extra things. You know, that's what being on that hill means. And, you know, I'm not saying that I'm on that hill. I'm saying that like, you know, I try my best to be on that hill. Sure. And, you know, those are the stories that came out.

22:38Ryan Holiday: I love all the advice. I think it's great.

23:13Seth Wickersham: Transcription by CastingWords stories worth talking about. Get AI tools for work. Upgrade to Google Workspace with Gemini at goo.gle slash workspace with Gemini. That's goo.gle slash workspace with Gemini.