The Habit That Changes EVERYTHING | Nick Thompson

Nick Thompson couldn’t change his father’s story, but he found a habit that helped him make sense of his own. In today’s episode, Ryan sits down with Nick, CEO of The Atlantic and author of The Running Ground. Ryan and Nick talk about why running is the ultimate teacher of focus and resilience, how to build discipline, and how running helped Nick process his complicated relationship with his father. Nick Thompson is the CEO of The Atlantic, an American magazine founded in 1857, which earned the top honor for magazines, General Excellence, at the National Magazine Awards in both 2022 and 2023. In his time as CEO, the company has seen record subscriber growth. Before joining The Atlantic, he was the editor-in-chief of Wired magazine. He is also a former contributor for CBS News and has previously served as editor. He has long been a competitive runner; in 2021, he set the American record for men 45+ in the 50K race. Check out Nick’s new book The Running Ground: A Father, a Son, and the Simplest of SportsFollow Nick on Instagram and X @NXThompson📖 Wisdom Takes Work by Ryan Holiday is out NOW! Grab a copy here: https://store.dailystoic.com/pages/wisdom-takes-work🎥 Watch the video episodes on The Daily Stoic YouTube channel: https://www.youtube.com/@DailyStoic/videos🎙️ Follow The Daily Stoic Podcast on Instagram: https://www.instagram.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, Twitter, YouTube, TikTok, and Facebook 📢 Share | ⚙️ Manage Subscription

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.

• 0:52Ryan Holiday?

  Hey, it's Ryan Holiday. Welcome to another episode of the Daily Stoic Podcast. I am recording this on a Sunday here in Bastrop, Texas. I'm not sure when you are listening to it, but I just woke up, went on a long walk with the dog, took the kids to Tracy's, the little grocery store we have in town, and then I drove over to Bastrop State Park, where I went for a long run. How long did I do? I did 7.26 miles, a little slower than I would have liked, but it's kind of a hilly park. It's one of my favorite parks here in Texas, one of my favorite places here in Texas. It's the Lost Pines Forest, this sort of freak of nature. The low-bowly pines are almost nowhere else this far west. You know,

• 1:35Ryan Holiday?

  you ever look at those Cold War maps of Germany, and you think Berlin was like on a border, but no, Berlin was just in the middle of East Germany, and was this sort of lost city, or this surrounded city. The filmmaker Richard Linklater has joked about the pine curtain, and Bastrop is Is the the sort of Berlin in that analogy. It's surreal, wonderful place. It's very hilly and sandy. It all tragically burned down in 2011, or a good chunk of it burned down in 2011. Then another chunk of it burned down in 2015. Then another chunk burned down because the county was doing a controlled burn that got out of control, even though there was a burn van at this time. None of this has anything to do with why I'm bringing this up. I have spent a lot of time in this park, running and walking.

• 2:19Ryan Holiday?

  In fact, I had the idea for the Stoic Virtue Series in this park six years ago. Stillness hadn't come out yet. I took the kids and Samantha out for a hike. I guess one would have been in the baby carrier, one was probably in the backpack. And we took a long hike. And by the time we got back from that hike, I had the idea for the series. And Samantha and I talked about it. And that's what I've been working on for the last six years. I guess what I'm saying is I love this park and I love the miles that I've put on in this park. And that would have been unfathomable to me, not just six years ago, that I'd be at the end of this series, which I am. But if you'd asked the high school version of me whether I would be logging miles voluntarily

• 3:01Ryan Holiday?

  20 plus years later, I would have said, what are you talking about? But here I am. I hated running in school and I can't live without it now. It's part of my stillness practice. It's part of my writing practice. It's part of my mental health practice. It's part of all of my practices. And that's why I was really excited to have today's guest on, because I think every runner has a unique relationship with the sport. You love it and you hate it, kind of like writers. You love it and you hate it. You like having done it probably more than you like doing it. But if you don't do it, you're miserable. Nick Thompson just released this fascinating book called The Running Ground: A Father,

• 3:42Ryan Holiday?

  A Son, and the Simplest of Sports, which is about his complicated relationship with his father and how running played a role in it. And in part one, we sort of nerd out about our running practices, how writing and running are both endurance activities, how life is an endurance activity and you got to figure it out, and how running is the sort of through line that connected him with his grandfather. Father and now his kids. I didn't know how this episode was gonna go. Nick is the CEO of The Atlantic. He's a great writer also, but but he's on the business side of The Atlantic, which is a publication I actually really like. I've had a number of their writers on over the years. I didn't know if this would be interesting from a stoic perspective, or I didn't know. But I was very excited. I thought it went great. We ended up splitting this into two parts because we went way over.

• 4:27Ryan Holiday?

  The Atlantic, if you've never heard of it, it actually goes way back even with Stoicism. Thomas Wentworth Higginson was one of the original translators of Apertitus, and he wrote for The Atlantic way back in the 1850s. It has won National Magazine Awards and every other award you can imagine. And while Nick has been the CEO, he has seen record subscriber growth. He was before that at Wired and many other places, and he is a very fast runner. He set the American record for the 50K, it's a very far distance, for men 45 and plus. You can check out his new book, The Running Ground of Father, a Son, and the Simplest of Sports.

• 5:10Ryan Holiday?

  You can follow him on Instagram and Twitter at NXThompson. I think you're really gonna like this interview. Let's get into it. I'll bring you part two later in the week.

• 5:24Speaker 01

  So I was looking, I have a funny detail about you and me. So I was looking at my email to like get the address or something. And I saw that you had written a story back, you were writing for BuzzFeed like back like 20 years ago.

• 5:35Ryan Holiday?

  Okay.

• 5:36Speaker 01

  And you wrote a story about Outbrain, or you had wrote a story that included something about Outbrain.

• 5:40Ryan Holiday?

  Yes.

• 5:40Speaker 01

  And this is gonna, this is gonna get interesting. And at the end of the story, Outbrain, you were like, Outbrain sucks, right?

• 5:47Ryan Holiday?

  Yes.

• 5:47Speaker 01

  And at the end of the story, Outbrain was like, well, we're on The New Yorker.

• 5:50Ryan Holiday?

  Yeah.

• 5:50Speaker 01

  And I was the, I ran The New Yorker's website then. And so that's email, I was sent that story and I was like, fuck, we have to get off Outbrain.

• 5:59Ryan Holiday?

  Yeah.

• 6:00Speaker 01

  But I couldn't get off them through Conde Nast. And so-

• 6:02Ryan Holiday?

  For people who don't know, Outbrain was, and maybe it still exists, but it's, it was like, when you get to the bottom of a story, it was this ad unit, but it didn't look like an ad unit. It looked like referring, like related articles.

• 6:15Speaker 01

  Yeah.

• 6:15Ryan Holiday?

  But they were all paid-

• 6:17Speaker 01

  Paid, and they were like the worst, right?

• 6:18Ryan Holiday?

  Yeah.

• 6:19Speaker 01

  And so- I had to get off Outbrain, right?

• 6:21Ryan Holiday?

  Yeah.

• 6:22Speaker 01

  And so, but we're part of Conde Nast and it's a big network deal. And so I then, we arranged a study where we analyzed subscription propensity if we had the Outbrain model on versus not. And we basically determined that it so alienated our readers that we were losing money by having it. And so I took that study and brought it to Conde Nast and we got rid of Outbrain.

• 6:41Ryan Holiday?

  Really?

• 6:42Speaker 01

  And it was actually like, it was kind of like an important moment in my career because it was like, oh, wait, you can actually like use the data to get to the outcome that is, you know, right for high quality journalism.

• 6:55Ryan Holiday?

  Yeah.

• 6:56Speaker 01

  And so I found like all the trail of all that in my like memory bank while like getting the address to the studios.

• 7:02Ryan Holiday?

  I was, I never wrote for BuzzFeed. I was do, I was writing for The Observer.

• 7:08Speaker 01

  Okay.

• 7:09Ryan Holiday?

  Which was a weird experience.

• 7:10Speaker 01

  So I mixed that detail up, but it was definitely you.

• 7:12Ryan Holiday?

  Yeah, yeah, yeah. No, I remember writing that piece because I hated those, I was like, I'll just write about stuff that interests me. And I hated those things. And yeah, it's this sort of blurring line where it's like, everyone knew the premise, the economics only worked because it was tricking people.

• 7:30Speaker 01

  Yeah.

• 7:31Ryan Holiday?

  But the law, it's interesting that you were able to verify, you were able to do some analysis of that because it's kind of a thing that's common in our society, right? Where it's like, okay, the short term profit is there.

• 7:42Speaker 01

  Yeah.

• 7:43Ryan Holiday?

  But it's hard to measure the long term decay of trust.

• 7:47Speaker 01

  Yep.

• 7:47Ryan Holiday?

  Or the opportunity cost of, of having that kind of exploitative relationship. And so a lot of that, that's why so much stuff sucks is people who are, now that everything is so highly measured, people are making a lot of decisions that are increasing the, you know, the per profit click, but not the long term health of the ecosystem.

• 8:08Speaker 01

  And so, you know, we sort of played the game. You fight, you fight fire with fire, right? We came with the data and we proved that it was better for our readers not to have, or better for economics not to have it.

• 8:16Ryan Holiday?

  I had a funny Conde Nast story. So I know Jonathan Newhouse a little bit. He's like a fan of Stoicism.

• 8:23Speaker 01

  Oh, he's totally a fan of Stoicism.

• 8:24Ryan Holiday?

  Yeah. And we had this, he invited me to some conference in Evian, France.

• 8:30Speaker 01

  Lucky you.

• 8:30Ryan Holiday?

  Yeah, it was, yeah, and it was like a panel. Like, I had to do like 30 minutes of work. But I remember we were having this dinner later and we're talking and we were talking about running and he asked me, because he was running, and he asked me if I stretch beforehand. And I was like, I never stretch. I hate stretching. And he was like, me neither. I never stretch. And my wife was like, I'm telling you, you have to start stretching. This is not healthy. And he goes, um, he's like, I've never seen my dog stretch. And I was like, oh, yeah, that makes sense, right? And then I got home, we picked up my dog from the dog sitter or whatever. And then I'm watching her for like five seconds and it's like, dogs stretch all the time.

• 9:08Speaker 01

  All the time.

• 9:08Ryan Holiday?

  They stretch before they get up. They stretch before they lay down. It was like, it was one of those perfect things where you hear something and you still want it to be true.

• 9:16Speaker 01

  Right.

• 9:17Ryan Holiday?

  That you're like, yes, the logic of that is flawless.

• 9:20Speaker 01

  Very funny.

• 9:20Ryan Holiday?

  And then is actually not only not flawless, it's just the opposite of the truth.

• 9:25Speaker 01

  Totally.

• 9:26Ryan Holiday?

  And I think about that all the time.

• 9:27Speaker 01

  Yeah, that's great. That's great.

• 9:28Ryan Holiday?

  Well, I'm glad you're here. I love, I love the book. I thought it was really interesting.

• 9:31Speaker 01

  Oh, awesome. So glad you did.

• 9:33Ryan Holiday?

  Yeah.

• 9:34Speaker 01

  If you had hated the book, this would be an awkward conversation.

• 9:36Ryan Holiday?

  No, no, no.

• 9:36Speaker 01

  But we still would have gotten through it.

• 9:38Ryan Holiday?

  Which leads me to my first question. Well, my first question is, why have I never been asked to write for The Atlantic? And then my second question is, did you run today? You can just answer the second one.

• 9:47Speaker 01

  I'll answer the first question. So I'm the CEO. I don't oversee editorial, but they should certainly talk to you. I did. I ran 13 miles around the lake with a guy in Austin named Brady Homer. We had a great time. It was lovely.

• 9:56Ryan Holiday?

  It's an amazing trail, isn't it?

• 9:57Speaker 01

  Amazing trail, flat, smooth. It's a little hot here, Ryan, I've noticed. But it was not as hot as it was yesterday afternoon when I tried to run around the lake and said, nope, gonna turn back home.

• 10:06Ryan Holiday?

  I was just running in New Orleans a couple of weeks ago and I was thinking like, where are the best places to run day to day in the United States? So not like, oh, there's this beautiful run in Yellowstone or something.

• 10:18Speaker 01

  Right.

• 10:18Ryan Holiday?

  But like where day to day are some of the best ones? I think the neutral ground in New Orleans is one. I think Town Lake in Austin is one. Probably up from Chelsea Pierce to the intrepid like that thing in Manhattan is pretty.

• 10:31Speaker 01

  It's a little loud.

• 10:32Ryan Holiday?

  It is a little loud, but it's, you know, you're not going to get that length with not having to stop. And New York City is.

• 10:37Speaker 01

  Yep.

• 10:38Ryan Holiday?

  And then I just did, you know, along like from Venice to Santa Monica, like that one, you know.

• 10:43Speaker 01

  I did that two days ago.

• 10:45Ryan Holiday?

  Oh.

• 10:46Speaker 01

  It's incredible.

• 10:46Ryan Holiday?

  Yeah, of course.

• 10:47Speaker 01

  Incredible.

• 10:48Ryan Holiday?

  Yeah, because you're like on the beach, but you're then when you get to Santa Monica, you're like up.

• 10:51Speaker 01

  You're up a little bit and there's nice little trails, but there's so much going on. It was so beautiful. I was doing it right at sunset.

• 10:57Ryan Holiday?

  Oh, amazing. I think the one around Austin is low key, one of the best ones in the United States. And I know you said it's hot, but it's so shaded most of the year that it's, and Austin isn't quite as humid as other places. I find I can do it at any time during the day.

• 11:11Speaker 01

  Yeah.

• 11:12Ryan Holiday?

  I did it yesterday. It's one of my favorites.

• 11:14Speaker 01

  No, it's a beautiful loop. I would add the Washington Mall is pretty cool too.

• 11:17Ryan Holiday?

  Yeah.

• 11:17Speaker 01

  Washington's just kind of underrated as a running city.

• 11:19Ryan Holiday?

  The problem with that Washington Mall loop is that you have to stop and cross those streets, like every quarter mile or mile or whatever. And it's not like, it's not quick and it's not like a New York City thing where you can, you know, you can just jaywalk.

• 11:35Speaker 01

  Yeah, but you also only a couple of miles from the Georgetown canals. There's like a lot to say for that.

• 11:39Ryan Holiday?

  Yeah, yeah, no, I love that run too.

• 11:41Speaker 01

  But I would take the lake over it, definitely. Austin Lake over the Washington Mall.

• 11:44Ryan Holiday?

  Yeah, it only recently like last like maybe six years, they put in this boardwalk for a part of it. So now you can do the whole thing. It's 10 miles and then there's just an infinite number of combinations you can do. It's one of my, my all time favorites.

• 11:58Speaker 01

  Yeah, so I did, I ran this morning.

• 12:00Ryan Holiday?

  But have you done Barton Springs before? Do you swim also?

• 12:02Speaker 01

  I've run up to Barton Springs. I've done.

• 12:04Ryan Holiday?

  You swim in Barton Springs?

• 12:05Speaker 01

  No.

• 12:05Ryan Holiday?

  Oh, it's one of the, the great public works achievements in the United States.

• 12:11Speaker 01

  That area, I've run by, there are like 12 million people swimming there. It looks very cool.

• 12:14Ryan Holiday?

  Yes, yes. And in the morning, there's no one there and you can do laps.

• 12:18Speaker 01

  Okay.

• 12:18Ryan Holiday?

  And I love that. Are you a morning person or a evening runner?

• 12:23Speaker 01

  I like both. I can kind of run anytime when there's time available. I tend to run to work and from work. So you're running the beginning of the day, you're running at the end of the day.

• 12:30Ryan Holiday?

  Yeah, that's interesting. Do you just, then you shower at the office?

• 12:33Speaker 01

  Shower at the office, shower at the gym nearby. Yeah, kind of work. Sometimes it doesn't work, like you forget to bring your belt or something. It's like, you're not always completely, and like when you're kind of the boss, you should really look the part, but sometimes I don't.

• 12:46Ryan Holiday?

  Yeah, although, do you find splitting it up, like it only starts working at a certain distance, not the exercise?

• 12:53Speaker 01

  Yeah.

• 12:54Ryan Holiday?

  I don't know about you, but like, if you told me, and people have told me, that like, the physical benefits of running are actually not that great. You know, like, there, there may even be some costs to it. I'm like, I don't give a shit at all. I'm not running for exercise.

• 13:07Speaker 01

  Right.

• 13:07Ryan Holiday?

  So, so for me, at a certain point, the distance, you have to do a certain amount of distance for the mental health benefits to start. Like, if I just run two miles, I might as well run zero miles.

• 13:18Speaker 01

  Right.

• 13:18Ryan Holiday?

  It doesn't, you gotta go longer than that.

• 13:21Speaker 01

  I don't know if that's true. Like, if you're in the middle of a really hard process, you can still get a mental benefit from a two-mile run.

• 13:27Ryan Holiday?

  Okay.

• 13:28Speaker 01

  So it actually depends on like, what is it breaking up? Like, if I'm on vacation.

• 13:32Ryan Holiday?

  Yeah.

• 13:33Speaker 01

  Right? I probably have to go run 10 miles to get anything. But if I'm in like, some hellacious week with like, board meetings, stress, like, all kinds of stuff going on, like, I can go run half a mile.

• 13:44Ryan Holiday?

  Interesting. Yeah, I find like, there's no, no walking distance so short that there's not some value. But I find like, to, to get what I need to get to even, to like, regulate.

• 13:54Speaker 01

  Yeah.

• 13:55Ryan Holiday?

  It's gotta be a certain distance. And I wonder if this, does the splitting give you twice, or is it actually like, half? You know?

• 14:03Speaker 01

  Yeah, so I, I don't know. Like, I would imagine that the mental health benefits of a 10-mile run are better than two 5-mile runs, right? Cause there's like, a little bit of a startup cost.

• 14:12Ryan Holiday?

  Yeah.

• 14:12Speaker 01

  On the other hand, the efficiency benefits of running to and from work and having like, some running break.

• 14:18Ryan Holiday?

  Yes.

• 14:18Speaker 01

  It's like a pretty good life hack.

• 14:19Ryan Holiday?

  Yes, of course. And then you're also just saving yourself whatever their commute time.

• 14:23Speaker 01

  Totally.

• 14:24Ryan Holiday?

  That time was already dead, and you turned it into productive time.

• 14:26Speaker 01

  Right. And you listen to a podcast, you run to work, it's the way to go.

• 14:29Ryan Holiday?

  Do you listen to podcasts when you run, or you listen to music?

• 14:31Speaker 01

  I never listen to music.

• 14:32Ryan Holiday?

  Oh, why?

• 14:33Speaker 01

  Well, so I believe that listening to music when you run kind of disrupts the training benefits. I mean, listening to podcasts might disrupt it a little bit, too.

• 14:42Ryan Holiday?

  Okay.

• 14:42Speaker 01

  Like, when I'm running a workout, I don't listen to anything. And so the physiological logic behind it is you're trying to like, understand your body, right? You're trying to understand your nervous system, you're trying to understand pain, you're trying to like, maximize like, coordination. If you're listening to music, A, you might go too fast, right? Like, you might be hyped up and you might not pace it perfectly, and then you haven't learned what you could learn about pacing. So if I'm running hard, I never listen to music.

• 15:08Ryan Holiday?

  Interesting. So in the Marikami book on running, he says that you run to acquire the void, right? I find music gets into the void faster, so I'm running for that. Like, I'm running to get to whatever that kind of-

• 15:20Speaker 01

  It's a different void, maybe?

• 15:22Ryan Holiday?

  But I find that there's something heightened about the music and the physical-

• 15:28Speaker 01

  I mean, it can definitely, it can definitely increase adrenaline, right? And it can definitely like, make you go when you sort of want to stop, right? But I feel like part of what you're trying to learn how to do is how to get your own mind to get you to go when you want to stop. And so music is, it's almost like putting on roller skates. And like, if somebody, if somebody can only run while listening to music-

• 15:48Ryan Holiday?

  Sure, sure.

• 15:48Speaker 01

  Like, go get them, right? If it's going to help you in a workout, go get them. But I also was like, I'm psychologically scarred from my college coach, who at one point was like, you know, "We're here to compete, we're here to win, you're ready to train hard, and if you don't want to do that, then go put on some music and run around campus drive," right? And so like, that moment stuck with me. So it's both these like, pure physiological, neurological things that I'm talking about, and it's also that like, young Nick was scarred at age 18.

• 16:14Ryan Holiday?

  No, no, I'm sure, I think we all pick up certain habits or values that were like, an offhanded comment from someone-

• 16:20Speaker 01

  Yeah.

• 16:20Ryan Holiday?

  That if you asked them about it in depth, they'd probably be like, "Oh, I didn't even mean that."

• 16:24Speaker 01

  I didn't mean that.

• 16:24Ryan Holiday?

  "It's not important."

• 16:25Speaker 01

  Yeah.

• 16:25Ryan Holiday?

  But I get your point. I'm like that when I see people swimming with fins.

• 16:28Speaker 01

  Mm-hmm.

• 16:29Ryan Holiday?

  Like, when they're doing, I'm like, "What are you doing? I don't get it."

• 16:31Speaker 01

  Right, right.

• 16:32Ryan Holiday?

  Like, you're cheating the whole thing that you're supposed to be doing. I don't, I don't get it. You're still swimming the same distance, or you're swimming a longer distance, why not just, what are you trying to be? Aerodynamic for it. I don't, it doesn't make any sense to me.

• 16:43Speaker 01

  So that's a little bit how I feel about it. Yeah. So I listen to podcasts, but not when I'm doing, if I'm doing a workout, I'm not listening to anything.

• 16:49Ryan Holiday?

  Yeah, I think this is all probably totally baffling to some people. Like, I was talking to my wife about this one and, and I was like trying to explain that like, this is what I have to do to get to even. Like, this is like, just like, that there's just a certain amount, physical activity. Like, if I don't do this, like, I'm just totally dysregulated.

• 17:11Speaker 01

  Yeah.

• 17:11Ryan Holiday?

  And that this is like, like, I think she was, she was, she was like resenting or somewhat peeved about how much time it was taking and, you know, or that this was like a hobby. This was a thing that I was enjoying. And I was like, I am enjoying it, but I don't think you understand.

• 17:27Speaker 01

  Right.

• 17:27Ryan Holiday?

  This is like table stakes for me being a functional member of society. Like, without, without this, it's not working. And you, and then for people who are not that way, who aren't broken in that way, or didn't get hooked on this coping mechanism in this way, they're just like, what are you talking about? This doesn't make any sense.

• 17:47Speaker 01

  You remind me of, I had this conversation before an ultra run and I was sitting with this guy. And he's like, I'm 75 years old. And I was like, what are you going to run tomorrow? He's like, I'm running the 100 mile, one of those races you get up there. And I was like, how long is it going to take you? He's like, well, I want to get it done in like, you know, 30 hours. And I was like, I don't know how it came up. I was like, and what does your wife think about this? And he's like, well, she doesn't like it, but I told her it was either this or a blonde in a Corvette.

• 18:09Ryan Holiday?

  It's his midlife crisis thing.

• 18:11Speaker 01

  Yeah.

• 18:11Ryan Holiday?

  Yeah.

• 18:11Speaker 01

  You know, in healthy marriages, everybody recognizes that there are things the other person does that are good for their mental health, but take time. And like, certainly I have that conversation with my wife.

• 18:31Ryan Holiday?

  I've found like, if I do other stuff, like, let's say I want to do CrossFit or I want to do. Jiu Jitsu or some other, there's no overlap. Like I'd still have to run. So like, like I can't trade one, like swimming a little bit, but not like if I swam for a week, I'd be like all fucked. You know, like, like I can substitute it maybe on one day, but like not three days in a row.

• 18:58Speaker 01

  Yeah.

• 18:59Ryan Holiday?

  Or the, the whole thing starts to get a little, a little wobbly. You could be like, hey, it's the same amount of time. You burned the same amount of calories, you know, or what, but it doesn't, it doesn't matter. It's just the kind of regular.

• 19:12Speaker 01

  The other argument to make to your wife, just to help you out here is that it's by far the most efficient way to do it because you don't like, you don't have to go to the pool. Right. You don't have to go to the Jiu Jitsu class. You don't have to schedule it, right? Like you don't have to worry about the time you're leaving. You just open the door and you go and you come back.

• 19:27Ryan Holiday?

  Yes. The only, the only time they've appreciated that efficiency is like when we travel.

• 19:33Speaker 01

  Yeah.

• 19:33Ryan Holiday?

  Then, you know, I get up early and I do that. And then the course of the rest of the day, I'm like showing them all, I'm like, I already know my way around.

• 19:41Speaker 01

  Right.

• 19:41Ryan Holiday?

  Here, I've already looked at the boring things that you don't care about. So we can cross those off the list.

• 19:47Speaker 01

  Yes.

• 19:47Ryan Holiday?

  And then, and then I'm like.

• 19:48Speaker 01

  Good life hack. This is good stuff.

• 19:50Ryan Holiday?

  Is like, it's like a golfer walks the golf course before, you know, the, they play. And it's your, you're sort of getting your sense of the city.

• 19:57Speaker 01

  You can also like, so the other hacks for helping your marriage, like I'm, I'm not, how old are your kids?

• 20:03Ryan Holiday?

  Uh, nine and six.

• 20:04Speaker 01

  Okay. So you're, you're like the same, mine are 17, 15 and 11, but like obviously the running stroller is a huge hack. And then running to errands, that's super useful. Right?

• 20:14Ryan Holiday?

  Okay.

• 20:14Speaker 01

  Like, and then dropping your kids, running while they're doing their thing and then bringing them back. Then your spouse, A, doesn't know you've run and B, you've got in your workout, right? Like you drop them at like the camp where they're going to be for an hour and a half. You run for an hour and a half, you drive them home. You're in the, you're in the plus, right? Because you've done the errand.

• 20:32Ryan Holiday?

  No, no, I know this hack very well. Yes. This is mostly, mostly what I, what I do, where I drop them off at school, I run and then I come to the office. But I've, you're, you're sort of, you're not running, you're not driving to the place that you're going to run or you're, you're, you're, you're piggybacking it with the other thing.

• 20:49Speaker 01

  I say it kind of as a joke, but like part of, part of the, I mean, I've run. Pretty aggressively now for whatever 30 years. And part of the way I've made it work with a busy job with three kids who I spent a ton of time with and a wife I'm devoted to is by like filling it into these cracks.

• 21:06Ryan Holiday?

  Yes.

• 21:06Speaker 01

  Right?

• 21:07Ryan Holiday?

  Mm hmm. And then also you think about this, they're just now two, like one of them I can kind of convinced to get in the bike stroller, even though he's like technically over the weight limit.

• 21:19Speaker 01

  Yeah.

• 21:19Ryan Holiday?

  But it's you just realize like, oh, we spent like hundreds of hours together doing this.

• 21:24Speaker 01

  Yeah.

• 21:24Ryan Holiday?

  Doing this thing over the years.

• 21:26Speaker 01

  Yeah.

• 21:26Ryan Holiday?

  Now it's like, I used to be able to justify the walks because it's like, not justify, they didn't have to consent to the walk. Because I could just strap them in.

• 21:35Speaker 01

  Yeah.

• 21:35Ryan Holiday?

  And then they, they were just there.

• 21:36Speaker 01

  Right.

• 21:37Ryan Holiday?

  And now, now it's this awkward phase between, well, first off, I have to like bully or bribe them to come. They want to stop like, you know, 60 seconds in, like, what are we turning around? It's like, we're not even at the end of the driveway yet. And then, and then they're just, they're a little heavy to carry, you know? And I can't do both of them.

• 21:57Speaker 01

  Well, wait for a little bit longer. So now I, I train, I just turned 50 and I wanted to run a sub five minute mile on my 50th birthday and my 15 year old paced me to it.

• 22:05Ryan Holiday?

  Wow.

• 22:05Speaker 01

  Like this, so I now run with the kids. It's amazing.

• 22:08Ryan Holiday?

  So I'm thinking about trying to do this before my 40th birthday. Cause I, so I ran a 502 mile my senior year of high school. And I remember going, eh, that's good enough. Like my parents forced me to pick a sport, so I picked track and cross country. And I basically never really tried. Like I, I was in that teenager rebellious thing where it's like, you try kind of, but not enough that if you don't succeed, you would have to look in the mirror and feel bad. And I remember even looking at the clock and going, oh, that's close. I wonder if I'm going to regret like calling it here.

• 22:43Speaker 01

  So you've never gone under five?

• 22:45Ryan Holiday?

  No, no, no. I did, I did it maybe in my mid twenties once. But it's been a long time. So I was thinking I would try to do it again at some point, you know, before I turn, I've got, I've got two years or a year and a half. So I was thinking about doing it again. You've done it before, I'm guessing, right? Many times?

• 23:02Speaker 01

  Oh, yeah. And I'd run fast in high school and then I'd run some, but I hadn't run a sub five minute mile and little, I mean, I had run one straight down a mountain, but I hadn't run a sub five minute mile on the flat course. And I was training for an ultra and I was like, you know what? I'm also going to try to do it on my birthday. And my 15 year old son, who's like, he had run a sub five minute mile with his, you know, track team. He was like, yeah, let's do it. And so we trained, we did like 400 meter workouts on the track together. I'd lead one, he'd lead one, I'd lead one, he'd lead one. It was awesome. It's just like great parenting.

• 23:30Ryan Holiday?

  Sure.

• 23:30Speaker 01

  And like, what a cool, fun thing to do for 50th birthday.

• 23:33Ryan Holiday?

  And you did it?

• 23:34Speaker 01

  I did it. He dropped out at 1200 meters because he wasn't quite sure how much the time there was to go. He thought we were only halfway through.

• 23:40Ryan Holiday?

  You just lost count of the laps?

• 23:42Speaker 01

  We were, no, we were in the park. We just like, we were like, went into Prospect Park. We're like, we're gonna go run a mile. And like, he didn't quite know. He's like, oh, Dad, I thought we were way off pace. And I was like, we were like way under, we were like five seconds under and you only had 400 meters to go, dude?

• 23:53Ryan Holiday?

  Yeah.

• 23:54Speaker 01

  He's like, oops.

• 23:55Ryan Holiday?

  And how did it feel? Is there some part of you that feels like you're beating time? Like, or defying something?

• 24:01Speaker 01

  I don't, running a sub five minute mile at 50 did not make me feel like I was beating time. Running like, fast marathons and ultras, I feel like I'm countering the aging effects. I mean, like, I got into the book, not because I wanted to like, write life lessons. I got into the book because I thought there was an interesting story in my father's life. And then, there's a very interesting question of why I had been able to run a 229 marathon, which is very fast, at age 44, when I'd only been able to run like, two 40s in my 30s. So when I was in my physical prime, I was much slower than was in my 40s. So why did that happen? Right? And that was like, that led me down an interesting psychological explanation that I thought made a good story. And then, my father's life's a good story and their other stories. So that's why I wrote the book. So I do feel a little bit like, the point of the book is how to

• 24:46Speaker 01

  Well, one of the points of the book is how to counter the effects of aging.

• 24:48Ryan Holiday?

  Yes. Well, writing and running are two of the only kind of like elite or difficult things, right? Like you have the arts and then you have athletics where it is you don't fall off a cliff. Like, a lot of writers do their best writing very late in life, or very, very good writing late in life. And then runners, especially it seems like in the very high endurance level running, not sprinters, but tend to do it later and later than you would have guessed. And this is all compared to, you know, like musicians writing their best album at 23.

• 25:24Speaker 01

  Right.

• 25:24Ryan Holiday?

  Or a Nobel scientist discovering something in their mid 20s, or you're an old man in the NBA at like 32.

• 25:32Speaker 01

  Right. Well, like, basically, you know, your reflexes decline pretty drastically. Like, you can't hit a baseball when you're 40, right? Like, that's all reflexes. But your, like, lean muscle mass doesn't change that much, right? So, your top end speed changes a whole bunch. You essentially, as you age, certain things get worse and certain things get better, right? Like, you get the benefit of age, you get the benefits of wisdom. There are some, like, internal physiological changes that happen that help you. There's some, in general, like, the metaphor, like, is that you're on a moving sidewalk and it's going slowly backwards, right? But you can use some of what you're learning to kind of go faster than the moving sidewalk is going backwards. So you can still go forwards.

• 26:08Ryan Holiday?

  Yeah. And I feel like, when I wrote when I was younger, I could just sort of, like, rip it out.

• 26:15Speaker 01

  Yeah.

• 26:16Ryan Holiday?

  And now, I think I'm better, but it's harder.

• 26:19Speaker 01

  Mm-hmm.

• 26:20Ryan Holiday?

  Do you know what I mean? Like,

• 26:21Speaker 01

  That's interesting.

• 26:21Ryan Holiday?

  So, and it's kind of true with running, too. Like, I could eat anything I wanted, I could get any amount of sleep, I could just get up and leave and immediate. Now, like, I'm noticing even, like, I have to think more about, like, those first couple miles. Like, my body is literally warming up.

• 26:41Speaker 01

  Yeah.

• 26:42Ryan Holiday?

  And then I'm just, there's just a tightness that wasn't there before.

• 26:45Speaker 01

  And you heal more slowly.

• 26:47Ryan Holiday?

  Yeah.

• 26:47Speaker 01

  You get it, like, you turn your ankle and it takes forever. Like, my son and I will both turn our ankle the same day, exact same extremeness, and he'll be like, the next day he'll be back and he'll be Like a month and I'm still like, oh, took the, took the ibuprofen.

• 26:59Ryan Holiday?

  Like if I sit down to write on an airplane, I'm immediately fall asleep. You know, I might have like an amazing session when I'm 22 on an airplane because you're just physiologically different. And so, but I'm sure that's also true for Tom Brady or LeBron James, but there's only so much they can transcend that. There's still this hard limitation that, you know, right? Like, nobody cares what a musician in their 50s is writing as far as their new stuff. They just want to see them perform the old stuff.

• 27:35Speaker 01

  Any musician who's like struggled in their twenties and thirties and like really like crushed it in their 40s?

• 27:39Ryan Holiday?

  You know, every once in a while, but, but it's like, and every once in a while, like a legacy act will have a new song that somewhat charts. But like, we basically go like, no, after this age, you have transitioned from, you know, like sort of one phase in your career to another. Writing and then also comics. I think we let comics bloom slightly later than, like, what's the difference between being a comedian and an actor? Not that much, but we would allow a comedian to hit their stride in their 40s or 50s and be at the top of their game in a way that maybe we wouldn't with, you know.

• 28:21Speaker 01

  And is that cultural allowance or is it just like where creativity comes from?

• 28:25Ryan Holiday?

  I think it's probably, it's probably the medium and then culture. And yeah, I think, I think it has a lot to do with what will, what our preconceived notions are because arguably the musicians are much better. Like they're experiencing Bruce Springsteen as a songwriter now is obviously better than he was when he was 20. I just mean like, he has.

• 28:46Speaker 01

  He has more knowledge.

• 28:47Ryan Holiday?

  Yeah. And some of the songs I think are really good. And if he had written them in 1983, might we accept them differently? But culturally, we go, no, no, no, we don't want to hear new singles from you. I think that's partly it. And then there must also be something about the energy of, that we expect from. Some forms of art or athletic. Like, the vibe is different. Whereas maybe with writing, because writing is much more about perspective and wisdom and less about energy, we're willing to hear, you know, the reflections of an older person.

• 29:22Speaker 01

  Right.

• 29:22Ryan Holiday?

  On equal footing with.

• 29:24Speaker 01

  Well, you, you know, you have like fluid intelligence, you have crystallized intelligence. And I think as you get into your 50s, like you have more wisdom, you know more things, you're kind of less creative. And so it's a different kind of writing.

• 29:34Ryan Holiday?

  Yeah.

• 29:35Speaker 01

  Whereas in music, you really need, like, a huge percentage of the new song has to be creative.

• 29:39Ryan Holiday?

  Yeah.

• 29:40Speaker 01

  So maybe that's what it is.

• 29:41Ryan Holiday?

  Yeah. And maybe with writing, you know, you're getting better at figuring out how to do this thing.

• 29:48Speaker 01

  Yeah.

• 29:49Ryan Holiday?

  And there's something kind of otherworldly about the music. It is less technique and more something, I don't know, it's more lightning in a bottle than I think writing is because, you know, you even read about some of the greatest albums of all time. They're like, we worked on this in the studio for a year. And then if you told, if you told someone that, like, your favorite book, that was only worked on for a year, you'd be like, what?

• 30:12Speaker 01

  Yeah.

• 30:13Ryan Holiday?

  Like, there's something about writing, and maybe this is also true for comedy, where it's like, the genesis of the thing that's doing most of the lifting, that's part of it. But then it's the going over it and over and over until it becomes.

• 30:27Speaker 01

  Yeah.

• 30:28Ryan Holiday?

  Its highest form of what it's supposed to be. So I don't know exactly how this connects to running, exactly, but.

• 30:35Speaker 01

  Well, I do, I mean, one of the things that I'm really interested in is, I had this conversation with my mom, where my mom was like, well, my reflexes are just getting worse. I'm 77 years old. And I was like, well, Mom, they are getting worse, but they don't have to get worse. Like, and then I kind of convinced her that they didn't have to get worse. And so we went out every day when we were together this summer, and I would toss her tennis balls, like, on the porch and like, have her like, reach out, like, like, you know, working on her reflexes. I would have her like, stand on one leg and I would like, toss her a tennis ball.

• 31:03Ryan Holiday?

  Yeah.

• 31:04Speaker 01

  And she was like, wow, this is amazing.

• 31:05Ryan Holiday?

  Yeah.

• 31:06Speaker 01

  And I said, yeah, your reflexes are, there's definitely be pressure making your reflexes worse.

• 31:10Ryan Holiday?

  Yes.

• 31:11Speaker 01

  But if you're out there with the tennis ball and you're trading your reflexes, you're going to improve them faster than you're declining. And your reflexes will get better.

• 31:17Ryan Holiday?

  Yes, that is also interesting. When you look at the, some of it's probably survivorship bias. But when you look at these like musicians or golfers or athletes that that are like still doing it. And and you wonder how much of it is that they never, even despite the drugs and drinking and the time on the road, they never like got out of shape like they never, they never accepted that they were old. They've just been doing some version of this youthful activity nonstop for this whole period of time. And there's something about that that I think keeps you.

• 31:48Speaker 01

  Totally. So one of the things that I, one of the things that I believe you don't stop running because you get old. You get old because you stop running, right?

• 31:53Ryan Holiday?

  Yes.

• 31:54Speaker 01

  Like if you stop running, like you're, you'll put on weight, you'll get imbalanced, like things will go wrong. If you keep going, actually like you'll be able to hold off a lot of the effects of aging. Yes, we all will get older, we all will die. Yes, like that does happen. We all do slow down. But really, if you keep at it and you have a daily habit of running every day, really will keep you a bit younger.

• 32:13Ryan Holiday?

  And this is true inside an individual run also, like you would think stopping and resting would be helpful. And it's like the worst thing you can do.

• 32:21Speaker 01

  Oh, absolutely. Yeah, definitely. Never stop.

• 32:22Ryan Holiday?

  Yes.

• 32:23Speaker 01

  I mean, in a long ultra, you can like stop to digest like for a couple of minutes that you're at an aid station. But no, never stop on a run.

• 32:30Ryan Holiday?

  Yes.

• 32:31Speaker 01

  Yeah.

• 32:31Ryan Holiday?

  So running is this thing that kind of runs through your family. It must be cool to see your kids picking it up.

• 32:36Speaker 01

  Yeah, it's wonderful to see them doing it. Yeah. And they're like, they clearly have wonderful talent at it. It's great.

• 32:41Ryan Holiday?

  Well, speaking of Bruce Springsteen, I was thinking about this thing I heard him say when I was reading your book. He talked about how we can choose to be an ancestor or a ghost in our kids' lives, you know? And and that sort of.

• 32:54Speaker 01

  That's interesting.

• 32:54Ryan Holiday?

  His father was this kind of ghostly or ghastly presence in his life because his dad's haunted by all these demons. And he's sort of abusive and it's just there and it's this thing that haunts him. And that's very different than someone who has, you know, like a loving parent or grandparent, or, you know, there's some kind of like guiding force in their life from another generation. This sort of choice is is kind of everything.

• 33:20Speaker 01

  Yeah, it's very, and it's very hard to, as a parent, it's very hard to know what you're giving your children. I write about this, this kind of this funny moment in the book where I, I run a marathon and it's during COVID. And so I run like, I run with one other person. I run 26 miles on this little loop in Prospect Park, right? And. I finish it and I've just completely destroyed myself. I come back to the house and I like, I lie under a blanket and I'm like shivering and kind of convulsing for a couple hours. I remember watching a movie with my oldest son, who was probably like 11 or 12 then. And afterwards, he's like, you know what, Dad? I'm never gonna run again.

• 34:00Ryan Holiday?

  Because he saw what it did to you?

• 34:02Speaker 01

  He saw what he did to me, right? And then the next day, I go out in Prospect Park and I'm going for a walk. And what do I see? But I see my youngest son like running around the park. I'm like, what are you doing here? He's like, I wanted to run around the park. I was like, wait a second. So this very same thing that I just did has inspired one of you to like sneak out for a run?

• 34:20Ryan Holiday?

  Yeah.

• 34:21Speaker 01

  He's like six years old and he's like-

• 34:22Ryan Holiday?

  You ran at your kid in the park. That's hilarious. Yes.

• 34:25Speaker 01

  Literally six years old, right? He's like running around Prospect Park, not the whole thing, but running this inner loop. And so I was like, oh, the very same act.

• 34:31Ryan Holiday?

  Sure.

• 34:32Speaker 01

  And then, so the book is partly, it's about other people, but it's partly about my grandfather, who's a great athlete, Golden Gloves champion, who intimidates my dad. My dad's not a natural athlete, hides from him behind the curtains, you know, very academic, doesn't want anything to do with him, and feels just this constant pressure to be a different person than he was. My father then takes up running and has the exact opposite effect on me, where my father's a cool runner and I'm like, I want to run with this guy, right? And so I'm five or six years old and I'm running with my dad.

• 35:01Ryan Holiday?

  Yeah.

• 35:01Speaker 01

  And now, like, God willing, like, my running obsession will, you know, pass in a positive way, that when my kids write their memoirs or think about things in their 30s, they're like, ah, so cool that like my dad had this wonderful thing that he taught us and brought us into, not, oh my God, a stupid father, like would always come home sweaty and smelly.

• 35:18Ryan Holiday?

  Yeah, it's like that story about the two brothers and one is asked, like, why are you an alcoholic? And he says, because my dad was an alcoholic. And then the other is asked, why don't you drink?

• 35:28Speaker 01

  Yeah.

• 35:29Ryan Holiday?

  And he says, because my dad was an alcoholic. And so the same event can send people down very different paths.

• 35:35Speaker 01

  Totally. Yeah, absolutely.

• 35:38Ryan Holiday?

  Yeah, you don't know if you're breaking the cycle or perpetuating the cycle in just some new way.

• 35:44Speaker 01

  Right. And so, and like, one of the other things that people often ask me is like, my father, you know, led a very broken life and by the end of his life, he's, I used to say, and people are like, what do your parents do? I'd say, well, my mother's an artist or anything. My dad runs a mail brothel in Bali. And- He's like bankrupt, I'm supporting him and he's blackmailing me, saying he's basically like begging for money to pay his prostitutes and like, why did I put up with this? And part of the answer is, he always loved me and he always supported me, right? And like, that's like, that's the baseline. And like, if a father does that, then you know, you owe them a lot.

• 36:21Ryan Holiday?

  Yeah, I guess.

• 36:23Speaker 01

  I mean, like, I could easily have broken with him and said, you know, dad, like, enough of this, like, we're done, I'm not gonna talk to you anymore. Like, now you've crossed one too many lines.

• 36:31Ryan Holiday?

  How long did it take you to understand that he's this way because of this other person? Like, did you meet your grandfather?

• 36:37Speaker 01

  I barely knew him.

• 36:38Ryan Holiday?

  But how long did it take you to understand, oh, this guy is this way because of this other guy?

• 36:43Speaker 01

  Well, I don't know if he was that way because of the other guy. Like, so, my father has this really interesting life, where he grows up in Oklahoma, and he's got this intimidating father, he's not really happy, they live on, um, his father is the president of Bacon Indian University, and so they're like, living in Bacon. And my father wants to get out. And he hears about this school called Andover, up in New England, he applies, he like, gets himself a scholarship, he like, delivers newspapers by horseback to pay for the rest of it, then gets himself a scholarship to Stanford, then wins a Rhodes Scholarship, and then marries in my mother's family, which is like, a prominent East Coast family. And my dad is on track, right? John F. Kennedy meets him and is like, this kid's gonna be president before I am, right? And I found his like, Rhodes Scholarship recommendations, and the dean of faculty is

• 37:28Speaker 01

  like, this is the best student we've had since Herbert Hoover, right? This guy's like, crushing it.

• 37:32Ryan Holiday?

  Yeah.

• 37:32Speaker 01

  But then he comes back, and he's got his Rhodes Scholarship, he's got his D Phil from Oxford, and it doesn't really work, right? Like, life doesn't work the way he wanted it to, and he like, can't really control his drinking, he's not really getting the jobs he wants, he's not really on track to become a senator, or whatever he thought he was gonna do. And then he realizes he's gay, right? And so, obviously, after I'm born, right? Which, thankfully, you know, that's the one argument that forcing people into the closet in the 1970s was good, because otherwise it wouldn't be here. And so, he realizes he's gay, he comes out of the closet. And so, that, this is part of it. Like, why did my dad end up the way he did? It's partly like, you know, he whom the gods wish to destroy, they first make promising. It's partly like, not living up to his youthful promise. It's partly like, trying to deal with the chaos of coming out.

• 38:17Speaker 01

  He's the first openly gay presidential appointee, working for Ronald Reagan, in the 80s. I'm very proud of that. Not being able to manage money and eventually heading towards bankruptcy. And then there's another really important moment in my dad's life, which is there's another guy who we thought of as his twin, this guy Roger Hanson, who's in a book called Remembering Denny, which is probably somewhere up here, it's a classic. And Roger Hanson is also a Rhodes Scholar, also destined for greatness, also doesn't achieve it, also gay. And Roger Hanson commits suicide, and he commits suicide in my father's garage. And when that happens, my father is like, I am going to be the most flamboyantly open person ever. And so then he just starts like sleeping with everybody and like bringing his like totally inappropriate boyfriends into like every conversation and every meeting and places like just utter

• 39:02Speaker 01

  madness. Like his love life, it's not even his love life, his sex life becomes utterly out of control. And so that is a lot of what leads him into this place he ended up in.

• 39:13Ryan Holiday?

  The sex life thing is probably connected to the sort of drinking life addict thing.

• 39:17Speaker 01

  It's the same sort of thing. Like he never figures out how to deal with his addictions. He never, he never gets the like stoicism, right? He never like figures out like, okay, this is how every day I'm going to do this and not this, and I'm going to like work through. And he never figures out how to build positive habits, like how to not drink, how to like get control of himself. He's never able to get control of himself.

• 39:38Ryan Holiday?

  Yeah, the things are in control of him rather than he, is he in control of them.

• 39:43Speaker 01

  He never figures out how to manage a day, right? He has lots of dreams, he's amazing to talk to, he has all these big plans, but he never like, he never has like an hour where he's like in control. I remember, you know, I wrote a book with him when I was in my early twenties, not a very good book. And, you know, we'd be writing it and I'd like, I'd be like, Dad, how's it coming? He'd be like, it's going well. And I'd like look and he'd be like surfing porn, right? Like he just couldn't, he just couldn't do it.

• 40:08Ryan Holiday?

  Wow.

• 40:21Ryan Holiday?

  Yeah, and so running was the one sort of positive habit that he had?

• 40:26Speaker 01

  He was able to like, at the moment, his worst moments, which is when he's like turning 40, you know, it's time of the divorce, he's coming out of the closet, and it's not easy to come out of the closet in 1982, and he's like-

• 40:35Ryan Holiday?

  No, I can imagine.

• 40:36Speaker 01

  And he's in Dupont Circle, it's the AIDS crisis, he, running like helps him keep it together, right? And so he runs marathons, he runs with me, he does really well, I watch him, it's wonderful. And I, you know, running is a great force for good. And then, as he got older, we would still run, and he would still run. And it was a way that he like kept his demons partly at bay.

• 40:56Ryan Holiday?

  Yeah. It's not as simple as going, oh, he had this sort of abusive, intimidating father, and that's why he was. It's that, and then a series of kind of shattering events and a certain amount of pressure that ultimately he just can't handle.

• 41:11Speaker 01

  Right. And what, like, why he was never, why he couldn't end up handling pressure, why he couldn't, you know, why he couldn't focus that much? On the other hand, the guy is like, he's an amazing guy. Like, if you were talking with him, he'd be loads of fun. If you were on this podcast, it'd be super interesting. Like, the guy was so smart and like caring and interesting, and, you know, people loved him. He's just a maniac.

• 41:29Ryan Holiday?

  Yeah. And what's your reaction to all this? Do you kind of go in the opposite? Because again, you could go in one direction or the other. Do you see this, and you sort of understand this as a cautionary tale, and you want to button it up and go in a very different direction? Or does that reaction evolve over time?

• 41:46Speaker 01

  No, it's very much, it's, I watch it, I'm like, I'm not gonna let this happen.

• 41:50Ryan Holiday?

  Yeah.

• 41:50Speaker 01

  And that's part of the, my running is a recognition, like, I'm gonna stay focused. Like, I don't know exactly what the key is to not become him.

• 41:57Ryan Holiday?

  Yeah.

• 41:57Speaker 01

  Right? But it's clear that I've spent like a lot of my life trying to be like him. I go to the same schools, I do lots of the same things. I'm like, I was at lunch in San Francisco not long ago with one of his friends, so one of my father's contemporaries, who's now in his 80s. And another one of their Stanford classmates walks in and sits at a different table. And the guy I'm having lunch with is like, yeah, I'm gonna try something. And so he brings me over to their table, and he's like, Paul, this kid here, he's the son of one of our classmates. You know, you've never met him, who is he? And he looks at me and he goes, that's Scotty's son. I was like, oh my god, right? Like, so I'm quite similar-

• 42:31Ryan Holiday?

  Yeah.

• 42:32Speaker 01

  -in lots of ways, right? You know, not in all ways. And so I know that I don't want to be like that, so it's unquestionably a force for focus in my life.

• 42:42Ryan Holiday?

  Yeah, there's a famous quote about Tiger Woods, another Stanford person, and says, uh, one of the, after all the stuff had happened, someone who knew him and his father, he said, "Mirror, mirror on the wall, we become like daddy after all."

• 42:56Speaker 01

  Mm-hmm. Yeah, it's true.

• 42:58Ryan Holiday?

  Yeah.

• 42:59Speaker 01

  And I try, like, so I try very hard not to let my discipline drop, in part because I don't want to be that.

• 43:07Ryan Holiday?

  Yeah. I think about this with my oldest, who's very similar to me, and I try to remind myself, like, I've had 30 more years than him to figure out how to deal with this stuff.

• 43:19Speaker 01

  Yeah.

• 43:20Ryan Holiday?

  He's just starting to feel and understand these kind of like forces and like he's, he has all the same ingredients, but none of the coping strategies, none of the experiences. He hasn't touched this stove and been burned in this way. He's on this path to kind of figuring it out.

• 43:38Speaker 01

  Yeah.

• 43:39Ryan Holiday?

  And that, like, part of what's driving me nuts about it is like he's doing stuff that I don't let myself do.

• 43:47Speaker 01

  Right.

• 43:48Ryan Holiday?

  You know?

• 43:48Speaker 01

  Right. And you have to let him do it. And like, he's gonna touch the stove and he'll learn from touching the stove.

• 43:53Ryan Holiday?

  Yes, hopefully.

• 43:54Speaker 01

  Yeah. And don't touch a stove that's too hot, right? Keep him away from that stove.

• 43:58Ryan Holiday?

  Yes.

• 43:59Speaker 01

  That's the trick of parenting, right? Like, you've gotta let them, like, take risks and be on their own. And you have to also protect them without, like, them knowing that you're like, you know, you have to create boundaries and safety that they're not quite aware of. So they feel they have total freedom, but they're not really at risk.

• 44:16Ryan Holiday?

  Yeah. And then you go, okay, it took me relatively recently to understand, hey, if I don't do X, Y, and Z, I'm not regulated and these things are harder for me.

• 44:25Speaker 01

  Yeah.

• 44:25Ryan Holiday?

  And it's like, again, I was like a grown ass person when I figured this out. Like, if you had tried to explain this to me when I was eight, I'd be like, what?

• 44:34Speaker 01

  Yeah, right.

• 44:35Ryan Holiday?

  You're like, what are you talking about?

• 44:36Speaker 01

  Yeah, what are you talking, that doesn't make any sense. And then even if I was like, okay, I get it. I not only couldn't actually do it, but I wouldn't have literally had the freedom to do it. Like, you don't control your environment or your life or to sit, if you're, if you're an eight-year-old and you're overstimulated in a school classroom, you

• 44:52Ryan Holiday?

  can't like- Get up and leave and be like, I'm gonna go to a different. You can't design, you have no ability to design your environment or make choices that are better for you or do things in the order that you would like to do them. And so, so much of being a kid is, is like, the system, the world is designed for how most people are. You know, and if you're one of those people, you fit really nicely into this thing. And if you're not, you're gonna have a rough go of it. And you think about, this is true for adults too, you know? If your dad was maybe straight and maybe had slightly less demons, maybe he does become a senator. Or like, he's gonna, he had all the ingredients and had all the access to thrive

• 45:35Ryan Holiday?

  in that sort of late 20th century political, intellectual, academic circles. But because just a couple of switches aren't the way that everyone else's were, he probably feels totally alienated, like an imposter. Or, you know, he's having these feelings that ultimately kind of make him blow it all up.

• 45:54Speaker 01

  And if he had been able to deal with disappointment and like not living up to expectations. And there's still some things, like I had, I found all of his diaries. You know, crazily, he had like gone to his house, which he had sort of, it was gonna be, you know, torn down while he was still alive. And there was like a filing cabinet out front and I like opened up one drawer and there's a snake in it and like, um, this is, he moved to Asia, live snake, he moved to Asia. Like, everything was just madness in his life. And I'm like, I'll take these filing cabinets. And I like put them in the back of my car and I drive them back. And then after he dies, I'm like, I'm gonna wonder what's in these filing cabinets. And it's like bank statements and crap. And then it's like his diaries.

• 46:29Ryan Holiday?

  Yeah.

• 46:30Speaker 01

  So I had a lot of insight into his life. But there's still things I don't understand, like I don't really understand, like when it, when he kind of started to lose control.

• 46:38Ryan Holiday?

  Yeah, it's unusual, it usually goes in the other direction. Right? The story is like, my parent didn't have it together. And then they got it together and as a, when we were both older, we reconnected and figured it out. You had kind of like a Benjamin Button situation. He's like, as you're getting older and responsible and mature and thriving and functioning in the world. It's like you have a teenage son.

• 47:02Speaker 01

  Well, we would joke about that. He'd be like, we have a reverse father-son relationship. Because I was like, Dad, you've got to like, you cannot go out tonight, right? Like enough of this, right? Like you have a husband, like no more carousing, right? Like, and you have stuff to do. You have to get your column for the Jakarta Post and you have to file it tomorrow. Like, get that done, Dad. And he's like, no, I'm going out. And you're like, oh, God.

• 47:21Ryan Holiday?

  Have you had to deal with some kind of codependency stuff from that? Like, how, like, because these are conversations you shouldn't have to have. It's not just you. Yes, you had this reverse relationship, but it's probably not good for you to have this relationship with your dad. You should be able to go to your dad and ask for advice about stuff, right? He should, he should be giving you a hard-won wisdom about how to be the age you are now.

• 47:42Speaker 01

  And he did do that, right? And he would help me through any hard dilemma. And if I had, like, he would read my essays, like, give me smart commentary on them, right? So he was, he was still very useful in that way.

• 47:53Ryan Holiday?

  But he can't give you the experience of being a well-adjusted, functioning 80-year-old, because he's not a well-adjusted, functioning 80-year-old. He can't give you that perspective.

• 48:02Speaker 01

  He could not do that.

• 48:03Ryan Holiday?

  Yeah.

• 48:03Speaker 01

  Yeah.

• 48:04Ryan Holiday?

  There's a eulogy that James Baldwin gives to his father, who was like, this not a guy that he super loved. And he said something about, it's like, it's kind of a ballsy thing to say at someone's funeral, I guess. But he said, you know, like, we, we knew his sins, but we didn't know his wrestling. Like, so you tend to just think, like, especially when you're a kid, because you're just in, you're in, entitled, I think, to like, get what you need from your parents.

• 48:28Speaker 01

  Yeah.

• 48:28Ryan Holiday?

  And when you don't, all that you feel is that you didn't get it.

• 48:32Speaker 01

  Yeah.

• 48:32Ryan Holiday?

  But you don't know how hard they were working to give it to you, or how hard they were trying to be different, or the shame they felt about, like, you don't, all you see is the binary, like, yes or no.

• 48:44Speaker 01

  Yeah.

• 48:45Ryan Holiday?

  Not what went into falling short. All you feel is that it wasn't enough.

• 48:50Speaker 01

  Right. And I was, I was blessed where I had this, you know, crazy dad. And I had a, like, infinitely loving mother, like, infinitely patient, raising these three kids on her own. Like, you know, who did an amazing job, like, you know, just creating shelter with the chaos of my father's life around us.

• 49:05Ryan Holiday?

  Yeah. Do you feel like running was maybe for you an outlet? Like, like, running is a place where you're in control. It's simple. It's, I always say, like, I've never left for a run and not, you know what? Like, like, I've walked back, but like, every time I've left my house, I've come back. So it's like, it's this win baked it, baked into your. Into your life, into your day.

• 49:28Speaker 01

  It's definitely that. So I get, you know, I run a little bit when I was like five or six years old with my dad. And then I get back into into high school where I, you know, get cut from the basketball team, join the track team, and then like suddenly I'm very good, right? And that creates this like self-confidence cycle that then helps me do better work, helps makes me cool at school as opposed to kind of a loser. So it plays that role in life. I then, you know, go to college, I'm not quite good enough. I leave the team after the, um, after my first year, and I take it back up in my twenties. And I definitely think that what you're talking about, kind of the daily practice, like I've run, I, I believe discipline is cumulative. I think if you do a hard thing first thing in the morning, it's easy to do the next hard thing, right? I also believe that the focus required for running helps you with everything else. Like if you can go run two hours at a focused pace, you're

• 50:12Speaker 01

  gonna have a better time at your hard meeting at work, right? Like, I absolutely believe that it creates these habits. And so part of why I do it is this like daily practice of, I'm gonna do this hard thing, I'm gonna do it again tomorrow, and I think it's gonna make everything else in my life work a little better.

• 50:27Ryan Holiday?

  Yeah, like when you're two thirds of the way into a manuscript, and you're like, is this a fucking book? Like, this is taking longer than I thought. It's not coming together. I don't want to do it. I hate this. You know, you're like, oh, I know this feeling. You just keep going. You keep going. You keep going. And then at some point, you finish and you're like, oh, that was better than I thought.

• 50:48Speaker 01

  Right. And, and the thing you learn about running, like, it's one of the best lessons is that if you run every day, and if you run hard from time to time, you get faster. Like, it just happens, and it always happens.

• 50:58Ryan Holiday?

  But imperceptibly so. Like, you know, there's not some magic day where you're like, oh, it's just this cumulative game that you're getting.

• 51:06Speaker 01

  Block by block. I had that feeling this morning, right? So I ran this race two and a half weeks ago, 100K. I haven't really run much since. I went out and ran 13 miles this morning. I was just like, God, I am so slow. I'm like, look at my heart rate, look at my pace. Like, what is going on? I'm like, Every single time, right? Like, it's gonna take, it takes a little time to recover. Like, it's hard to recover from a race. Takes a while. But I guarantee you, like, I'm just gonna run every day for the next six weeks. I'm gonna run a bunch of workouts, and six weeks from now, I'm gonna be back in great shape, right? And it just happens. And so that was a lesson, like, when I was writing this book, which took me, like, I have a hard day job, right? CEO of the Atlantic, I gotta work all the time at the Atlantic, right? So I'm working on the book, like, 20 minutes this morning, or like, you know, like, 30 minutes that night. But part of it was the self-confidence from running, that you just, you just do it a little bit here, you do it a little bit there, and like, it gets done, right?

• 51:50Speaker 01

  Eventually, it's done, right?

• 51:52Ryan Holiday?

  Well, at some point, you have the capacity to do a thing that seems unimaginably difficult. So, like, you're running, you run 10 miles, and you run 20 miles, and then you run 8 miles, and you just do this day in and day out. And then, when you go do a hard, whether it's a marathon or an ultra marathon, and you go, how, where did my ability to do that thing came from? It came from these little things. And, and writing is, is similar in the sense of, like, you worked on it for 20 minutes, you worked on it for, you thought about it, you read these book. It's just, all this stuff is going in, and then at some point, you have, like, an editable manuscript. Where did all this come from?

• 52:30Speaker 01

  How did this happen?

• 52:31Ryan Holiday?

  I was just sitting in here yesterday, and I finished the audiobook for the book that I just did. This thing was almost unrecognizable to me, because I didn't, I didn't ever do it as a thing.

• 52:41Speaker 01

  Right.

• 52:42Ryan Holiday?

  I did it as each of its component parts.

• 52:44Speaker 01

  Yep.

• 52:45Ryan Holiday?

  Like, one day, I showed up, and I wrote this paragraph. And then another day, I wrote these seven paragraphs. And then at some point, I stuck them together, and moved them around, and edited them. But like, I never, there was never at any point, and maybe there are some writers this way, where I had the whole thing in my head, and then I, I'm starting here, and I'm ending here. It was, it's this cumulative project, this chipping away, and eventually, cumulatively, you have a thing.

• 53:10Speaker 01

  Right. And then, when you have the thing, the other hard question is, okay, when do you stop, right?

• 53:17Speaker 01

  Like, if I made it better yesterday, that means I might be able to make it better tomorrow. So when do you call it off? And when is it done and shipping? That is very difficult. There's a really big moment in my career that gets to this lesson. It was one of the most important moments in my career. And I was, I was a young editor at The New Yorker and I was, I just put it in 2013. And I was just running The New Yorker's website and I didn't have any confidence in my writing. Yeah. Right? And I hadn't written at the level, I could, I was a great editor, but I wasn't a great writer. And the Boston Marathon bombs happened, right? And I'm following it and David Remnick, one of the greatest journalists in the world, one of my idols, boss of The New Yorker, comes into my office and he's like, Nick, you're going to write about the Boston Marathon bombing.

• 54:01Speaker 01

  I was like, no, I've got to, I've got to manage this. I've got like three other freelancers we're working with already. I'm trying to call this guy. And I was like, I really, I don't think I should do it. And David's like, no, you're going to write about it. And I was like, what? And then he's like, stop. He's like, this is what's going to happen. You're going to put your phone down right now and then you're going to close the door. And in one hour, I'm going to open the door and you're going to hand me your story. And that's what we're going to do. And so he closes the door and goes away.

• 54:28Speaker 01

  And so I'm like, okay. And so I wrote the story and it was done in an hour. It's pretty good. Yeah. You know, but it was like a really good lesson. It was like, just, he would just do that, right? He would be like, I'm going to write this piece. I'm going to close my door and I'm going to open it in a few hours and I won't have done anything else in those few hours and I'll have the story for you. Why do you think he thought you were ready at that moment? It was like, it was so clearly, I knew so much about marathoning. Like I had grown up in Boston. Like if there was ever a story that was like the right story for Nick Thompson to do, like it was this story. And, you know, I don't think he knew my insecurities about writing. He maybe knew it a little bit, maybe intuited a little bit, but he just like, do it.

• 55:10Ryan Holiday?

  Well, what an incredible gift to give someone.

• 55:12Speaker 01

  Absolutely.

• 55:12Ryan Holiday?

  To sort of like override their self-consciousness, imposter syndrome, whatever, and just force them to do a thing. And then you come out of the other side, having done it, and you go, oh, I can do that.

• 55:23Speaker 01

  I can do that. And I like, you know, I ended up writing like lots of good things that I'm proud about for The New Yorker, right?

• 55:28Ryan Holiday?

  Well, yeah, like, there's actually this really great passage. It's from, it's from B. H. Liddell Hart, The British History, and he's talking about William Tecumseh Sherman. And he's saying, look, there's a sort of pantheon of military heroes, right?

• 55:41Speaker 01

  Yeah.

• 55:42Ryan Holiday?

  And he's like, some of them, your Napoleons, are born just like thinking that they're Napoleon, and they deserve to be Napoleon, and they can conquer the world. And then there's these other ones, and it's interesting because both Grant and Sherman are very similar in this way, have this kind of unglamorous, slow-plodding rise that in many ways is a surprise to themselves.

• 56:03Speaker 01

  Yeah.

• 56:04Ryan Holiday?

  But every step of the way, they're accumulating a certain amount of confidence. They're doing the thing. And he says that, you know, like, success is much sweeter for them because they earned it.

• 56:15Speaker 01

  Yep.

• 56:15Ryan Holiday?

  And in some ways, you almost imagine, like, you think about Julius Caesar famously stands in front of this statue of Alexander the Great in his 30s, and he starts weeping because he hasn't accomplished everything that Alexander had by that age.

• 56:30Speaker 01

  Yeah.

• 56:31Ryan Holiday?

  And so you go, okay, this guy thinks he was entitled to do it.

• 56:34Speaker 01

  Yeah.

• 56:35Ryan Holiday?

  And is disappointed that he hasn't done it. Then when he does do it.

• 56:39Speaker 01

  Yeah.

• 56:39Ryan Holiday?

  There's probably a certain amount of letdown even then, because like, you believed you deserved it, and that external accomplishments never give you what they think they're going to give you.

• 56:49Speaker 01

  Totally.

• 56:50Ryan Holiday?

  But if your expectations are lower, that letdown is probably less a little bit. Because when you exceed even your own expectations, you're like, oh, this is nice. 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.