Nick Thompson (8:23)

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.

Ryan Holiday (8:34)

Okay.

Nick Thompson (8:34)

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

Ryan Holiday (8:38)

Yes.

Nick Thompson (8:39)

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

Ryan Holiday (8:45)

Yes.

Nick Thompson (8:46)

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

Ryan Holiday (8:49)

Yeah.

Nick Thompson (8:49)

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

Ryan Holiday (8:58)

Yeah.

Nick Thompson (8:58)

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

Ryan Holiday (9:01)

And so for people who don't know, Outbrain was. Maybe it still exists. But 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, but they were all paid and they were the worst.

Nick Thompson (9:18)

And so I had to get off Outbreak.

Ryan Holiday (9:20)

Right.

Nick Thompson (9:21)

But we're part of Conde Nasten. 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.

Ryan Holiday (9:40)

Really?

Nick Thompson (9:40)

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 use the data to get to the outcome that is right for high quality journalism.

Ryan Holiday (9:54)

Yeah.

Nick Thompson (9:55)

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

Ryan Holiday (10:02)

I never wrote for buzzfeed. I was writing for the observer, which was a weird experience.

Nick Thompson (10:09)

I. Sorry to mix that detail up, but it was definitely you because it definitely.

Ryan Holiday (10:12)

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.

Nick Thompson (10:29)

Yeah.

Ryan Holiday (10:30)

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

Nick Thompson (11:07)

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

Ryan Holiday (11:15)

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

Nick Thompson (11:21)

Oh, he's totally a fan of stoicism.

Ryan Holiday (11:23)

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

Nick Thompson (11:28)

Lucky you.

Ryan Holiday (11:29)

Yeah. And it was like a panel. Like I had to do like 30 minutes of work. But I remember we 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, 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. All the time. They stretch before they get up. They stretch before they lay down. I was like, it was one of those perfect things where you hear something and you so want it to be true.

Nick Thompson (12:15)

Right.

Ryan Holiday (12:16)

That you're like, yes, the logic of that is flawless. And then is actually not only not flawless, it's just the opposite of the truth. And I think about that all the time.

Nick Thompson (12:26)

Yeah. That's great. That's great.

Ryan Holiday (12:27)

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

Nick Thompson (12:30)

Oh, awesome. I'm so glad you did.

Ryan Holiday (12:32)

Yeah.

Nick Thompson (12:33)

If you had hated the book, this would be an awkward conversation, but we still would have gotten through it.

Ryan Holiday (12:36)

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.

Nick Thompson (12:45)

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's lovely.

Ryan Holiday (12:55)

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

Nick Thompson (12:56)

Amazing trail. Flat, smooth. Good. 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.

Ryan Holiday (13:05)

I was just running in New Orleans a couple 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, you know, Yellowstone or something. You couldn't. But like, where day to day are some of the best ones. And I think the neutral ground in New Orleans is one. I think Town Lake in Austin is one, probably up, you know, from like Chelsea Pierce to the Intrepid. Like, that thing in Manhattan is pretty.

Nick Thompson (13:30)

It's a little loud.

Ryan Holiday (13:31)

It is a little loud. But it's, you know, you're not gonna get that length with not having to stop at New York City's brewery. And then I just did, you know, along, like from Venice to Santa Monica, like that one. You.

Nick Thompson (13:42)

I think that I did that two days ago.

Ryan Holiday (13:44)

Oh, it's incredible, of course.

Nick Thompson (13:46)

Incredible.

Ryan Holiday (13:46)

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

Nick Thompson (13:50)

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

Ryan Holiday (13:55)

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

Nick Thompson (14:13)

It's a beautiful loop. I would add the Washington Mall. It's pretty cool too.

Ryan Holiday (14:16)

Yeah, that's cool.

Nick Thompson (14:16)

Washington's kind of underrated as a running city.

Ryan Holiday (14:18)

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 quick. It's not quick and it's not like a New York City thing where you can, you know, you can just jaywalk.

Nick Thompson (14:34)

Yeah. But you're also only a couple miles from the Georgetown Canal, so there's like a lot to say for that.

Ryan Holiday (14:38)

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

Nick Thompson (14:40)

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

Ryan Holiday (14:43)

Yeah. It only recently, like the last, like maybe six years, they put in this boardwalk for 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 all time favorites.

Nick Thompson (14:57)

Yeah, so I did. I ran this morning.

Ryan Holiday (14:59)

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

Nick Thompson (15:01)

I've run up to Barton Springs.

Ryan Holiday (15:02)

I've done. Have you swum in Barton Springs? No. Oh, it's one of the great public works achievements in the United States.

Nick Thompson (15:10)

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

Ryan Holiday (15:13)

Yes. Yes. And in the morning there's no one there and you can do laps and I love that. Are you a morning person or an evening runner?

Nick Thompson (15:21)

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 run in the beginning of the day, you run at the end of the day.

Ryan Holiday (15:29)

Yeah. That's interesting. Then you shower at the office, shower.

Nick Thompson (15:32)

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.

Ryan Holiday (15:45)

Yeah. Although do you find splitting it up like it only starts working at a certain distance not the exercise. Like, 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 may even be some costs to it. I'm like, I don't give a shit at all. I'm not running for exercise. Like 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, right? It doesn't. You gotta go longer than that.

Nick Thompson (16:19)

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

Ryan Holiday (16:31)

Yeah.

Nick Thompson (16:31)

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.

Ryan Holiday (16:42)

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

Nick Thompson (17:02)

Yeah. So 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? Because there's like a little bit of a startup cost. On the other hand, the efficiency benefits of running to and from work and having like some running break, it's like a pretty good life hack.

Ryan Holiday (17:18)

Yes, of course. And then you're also just saving yourself whatever, the commute time, totally. That time was already dead and you turned it into productive time.

Nick Thompson (17:25)

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

Ryan Holiday (17:27)

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

Nick Thompson (17:30)

I never listen to music.

Ryan Holiday (17:31)

Oh, why?

Nick Thompson (17:32)

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. 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.

Ryan Holiday (18:06)

Interesting. So in the Murakami book on running, he says 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.

Nick Thompson (18:19)

It's a different void is maybe.

Ryan Holiday (18:21)

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

Nick Thompson (18:27)

I mean, it can definitely increase adrenaline. Right. And it can definitely 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 can only run while listening to music, go get them. If it's going to help you in workout, go get them. But I also was like, I'm psychologically scarred. From my college coach, who at one point was like, we're here to compete. We're here to win, here to train hard, and if you don't want to do that, then you'll put on some music and run around campus drive. And so that moment stuck with me. So it's both these pure physiological, neurological things that I'm talking about. And it's also that young Nick was scarred at age 18.

Ryan Holiday (19:12)

No, no. I think we all pick up certain habits or values that were like an offhanded comment from someone that if you ask them about it in depth, they'd probably be like, oh, I didn't even mean that. That's not that important. But I get your point. I'm like, that when I see people swimming with fins, like, when they're doing. I'm like, what do you do? I don't get it. Like, you're cheating the whole thing that you're supposed to be doing. I don't get it. You're still swimming the same distance or you're swimming longer distance. Why not?

Nick Thompson (19:38)

Just.

Ryan Holiday (19:39)

What are you trying to be aerodynamic for? I don't. Doesn't make any sense to me.

Nick Thompson (19:42)

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

Ryan Holiday (19:48)

Yeah, I think this is all probably totally baffling. To some people. Like, I was talking to my wife about this one 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 and that this is like. I think 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, right. 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.

Nick Thompson (20:46)

You remind me of. I had this conversation before in Ultra Run and I was sitting with this guy and he's like, I don't know, 75 years old. And I was like, what would you run tomorrow? He's like, I'm running the 100 mile. It's one of those races we get out there. And he 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, 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.

Ryan Holiday (21:08)

It's his midlife crisis thing. Yeah, yeah.

Nick Thompson (21:10)

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 certainly I have that conversation with my wife.

Ryan Holiday (21:26)

This podcast is sponsored by Zbiotics and their game changing product, Pre Alcohol. By taking Zbiotics Pre Alcohol, drinking alcohol no longer means you have to make the choice between a great night or a great next day. You can enjoy a night out and still feel ready to have a productive day the next morning. ZBiotics Pre alcohol Probiotic drink is the world's first genetically engineered probiotic. It was invented by PhD scientists to tackle rough mornings after drinking. Because when you drink, alcohol gets converted into a toxic byproduct in the gut. And it's a buildup of this product, not dehydration. That's to blame for those rough days and rough mornings after drinking. And pre alcohol produces an enzyme to help break this byproduct down. You just take it before your first drink of the night. You drink responsibly and you'll feel your best tomorrow. Go to zbiotics.com stoic to learn more and get 15% off your first order when you use code STOIC at checkout zbiotics.com stoic thanks to Toyota Trucks for sponsoring this episode. When I bought my ranch in 2015 out here in Bastow County, I drove my car about halfway down the dirt road that we live on. Thought, this isn't going to work. Stopped, parked it, walked the rest of the way home, borrowed my wife's car, drove into Austin and bought a truck. What I bought was a Toyota Tacoma. And this truck wasn't just transportation getting me to and from my house. It unlocked a whole different style of living for us, not just on the ranch, but in our little Texas towns. There were places I could go now that I couldn't go before, especially out here in the piney forests, through the fields and on the unpaved roads like the one that I lived in. We got to go deep into the Hill Country's wild beauty. We've driven all the way out to East Texas. We've driven it across the country. And by we, I mean not just my wife, but both my kids, who I drove home from the hospital in that truck. Toyota trucks are built for those who understand that the best adventures happen when you're willing to veer off course, because you never know when you'll end up on a Toyota Adventure Detour. And of course, this is stoicism, too, because every detour, every obstacle is an opportunity. But it's helpful if you can handle the difficulty inherent in that, if you've got the resilience and the right companion to make it wherever the road takes you. Discover your uncharted territory. Learn more@toyota.com Trucks Adventure detours I 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 still have to run, so I can't trade swimming a little bit, but not like if I swam for a week, I'd be like, all fucked. You know, I can substitute it maybe on one day, but like not three days in a row or 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.

Nick Thompson (24:41)

And 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 jujitsu class in front of your house. Schedule it. Right. Like, you don't have to worry about the time you're living. You just open the door and you go and you come back.

Ryan Holiday (24:56)

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

Nick Thompson (25:02)

Yeah.

Ryan Holiday (25:02)

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

Nick Thompson (25:16)

Yes.

Ryan Holiday (25:16)

And then I'm like, this is a good life hack.

Nick Thompson (25:18)

This is good stuff.

Ryan Holiday (25:19)

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

Nick Thompson (25:26)

You can also, like. So the other hacks for helping your marriage, how old are your kids?

Ryan Holiday (25:33)

Nine and six.

Nick Thompson (25:34)

Okay, so you're of, 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? Okay. 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 gonna be for an hour and a half. You run for an hour and a half. You drive them home. You're in the plus, right, because you've done the errand.

Ryan Holiday (26:01)

No, no. I know this hack very well. Yes. This is mostly what I. What I do. Or 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 gonna run, or you're. You're. You're piggybacking it with the other thing.

Nick Thompson (26:18)

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 spend a ton of time with and a wife I'm devoted to is by like filling it into these cracks.

Ryan Holiday (26:35)

Yes.

Nick Thompson (26:35)

Right.

Ryan Holiday (26:36)

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

Nick Thompson (26:48)

Yeah.

Ryan Holiday (26:48)

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

Nick Thompson (26:53)

Yeah.

Ryan Holiday (26:53)

Doing this thing over the years.

Nick Thompson (26:55)

Yeah.

Ryan Holiday (26:55)

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.

Nick Thompson (27:04)

Yeah.

Ryan Holiday (27:04)

And then they, they were just there.

Nick Thompson (27:06)

Right.

Ryan Holiday (27:06)

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 funny. They're a little heavy to carry, you know, and I can't do both of them.

Nick Thompson (27:26)

Well, waited for a little bit longer. So now I, I train. I just turned 50 and I wanted to run a sub 5 minute mile on my 50th birthday and my 15 year old pays me to it right. Like this. So I now run with the kids. It's amazing.

Ryan Holiday (27:37)

So I'm thinking about trying to do this before my 40th birthday. So I ran a 502 mile my senior year of high school and I remember going, eh, that's good enough. My parents forced me to pick a sport, so I picked track and cross country. And I basically never really tried. Like 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 gonna regret calling it here.

Nick Thompson (28:12)

You've never gone under five?

Ryan Holiday (28:14)

No, no, no. I did it maybe in my mid-20s 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 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.

Nick Thompson (28:31)

Oh yeah. And I'd run fast in high school and then I'd Run some. But I hadn't run a sub 5 minute mile in a little. I mean I had run one straight down a mountain, but I hadn't run a five minute mile on 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 5 minute mile with his 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 and like what a cool fun thing to do for 50th birthday.

Ryan Holiday (29:03)

And you did it.

Nick Thompson (29:04)

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

Ryan Holiday (29:09)

He just lost count of the laps. We were, no, we were in the park.

Nick Thompson (29:12)

We just, 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. I was like, we were like way under. We were like five seconds under. And you only had 400 meters to go, dude.

Ryan Holiday (29:22)

Yeah.

Nick Thompson (29:23)

He's like, oops.

Ryan Holiday (29:24)

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

Nick Thompson (29:31)

Running a sub 5 minute mile at 50 did not make me feel like I was beating time. Running fast marathons and ultras. I feel like I'm countering the aging effects. I mean I got into the book not cause I wanted to write life lessons. I got into the book cause I thought there was an interesting story in my father's life. And then there was 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 two 40s in my 30s. So when I was in my physical prime, I was much slower so 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 there are 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 or one of the Points of the book is how to counter the effects of aging.

Ryan Holiday (30:18)

Yes, well, riding 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 musicians writing their best album at 23, or a Nobel scientist discovering something in their mid-20s. Or you're an old man in the NBA at like 32, right?

Nick Thompson (31:02)

Well, like, basically, you know, your reflexes decline pretty drastically. Like, you can't hit a baseball when you're 40, right? You're 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 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.

Ryan Holiday (31:38)

Yeah. And I feel like when I wrote when I was younger, I could just sort of like rip it out. And now I think I'm better, but it's harder. Do you know what I mean?

Nick Thompson (31:50)

That's interesting.

Ryan Holiday (31:50)

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 immediately now I'm noticing even I have to think more about those first couple miles. My body is literally warming up. And then there's just a tightness that wasn't there before, I'm sure.

Nick Thompson (32:15)

And you heal more slowly. 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 it'll be like a month. And I'm still like, off took the ibuprofen.

Ryan Holiday (32:28)

Like, if I sit down to write on an airplane, I'm immediately fall asleep, which, 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, 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.

Nick Thompson (33:04)

Is there any musician who's, like, struggled in their 20s and 30s and really crushed it in their 40s?

Ryan Holiday (33:09)

You know, every once in a while, but it's like. And every once in a while, like, a legacy act will have a new song that somewhat charts. But. 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.

Nick Thompson (33:50)

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

Ryan Holiday (33:54)

I think it's probably. It's probably the medium and then culture and. Yeah, 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.

Nick Thompson (34:16)

He has more knowledge.

Ryan Holiday (34:17)

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 the reflections of an older person on equal footing with.

Nick Thompson (34:53)

Well, you have fluid intelligence. You have crystallized intelligence. And I think as you get into your 50s, you have more wisdom, you know, more things. You're kind of less creative. And so it's a different kind of writing. Whereas in music, you really need, like, a huge percentage of the new song has to be creative.

Ryan Holiday (35:09)

Yeah.

Nick Thompson (35:09)

So maybe that's what it is.

Ryan Holiday (35:11)

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

Nick Thompson (35:17)

Yeah.

Ryan Holiday (35:18)

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 someone that, like, your favorite book that was only worked on for a year, you'd be like, what? 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 its highest form of what it's supposed to be. So I don't know exactly how this connects to running exactly.

Nick Thompson (36:04)

But, 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. I was like, well, mom, they are getting worse, but they don't have to get worse. 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 on the porch and have her reach out, working on her reflexes. I would have her stand on one leg and I would toss her a tennis ball.

Ryan Holiday (36:33)

Yeah.

Nick Thompson (36:33)

And she was like, wow, this is amazing.

Ryan Holiday (36:34)

Yeah.

Nick Thompson (36:35)

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

Ryan Holiday (36:39)

Yes.

Nick Thompson (36:40)

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.

Ryan Holiday (36:46)

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 are still doing it, and you wonder how much of it is that they never even despite the drugs and the drinking and the time on the road, they never, like, got out of shape. Like, 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.

Nick Thompson (37:15)

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

Ryan Holiday (37:22)

Yes.

Nick Thompson (37:23)

Like, if you stop Running, you'll put on weight, you'll get imbalanced, 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, it really will keep you a bit younger.

Ryan Holiday (37:42)

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.

Nick Thompson (37:50)

Oh, absolutely. Yeah. Definitely. Never stop.

Ryan Holiday (37:52)

Yes. Right.

Nick Thompson (37:52)

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

Ryan Holiday (38:00)

Yes.

Nick Thompson (38:00)

Yeah.

Ryan Holiday (38:01)

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

Nick Thompson (38:05)

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

Ryan Holiday (38:10)

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 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. And this sort of choice is. Is kind of everything.

Nick Thompson (38:49)

Yeah. 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 kind of. This funny moment in the book where I run a marathon and it's during COVID And so 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. 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. And then the next day, he saw.

Ryan Holiday (39:30)

What it did to you.

Nick Thompson (39:31)

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 has inspired one of you to, like, sneak out for a run? He's like 6 years old, and he's like, he ran.

Ryan Holiday (39:52)

If you're a kid in the park. That's hilarious.

Nick Thompson (39:54)

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

Ryan Holiday (40:01)

Sure.

Nick Thompson (40:01)

And then. So the book is partly it's about other people, but it's partly about my grandfather, who's great athlete, Golden Gloves champion, who intimidates my dad. My dad's not a natural athlete, hides from him behind the curtains, 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. And now, God willing, my running obsession will pass in a positive way that when my kids write their memoirs or think about things in their 30s, they're like, oh, so cool that my dad had this wonderful thing that he taught us and brought us into. Oh, my God. My stupid father, like, would always come home sweaty and smelly.

Ryan Holiday (40:47)

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?

Nick Thompson (40:57)

Yeah.

Ryan Holiday (40:58)

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

Nick Thompson (41:04)

Totally. Yeah, absolutely.

Ryan Holiday (41:07)

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

Nick Thompson (41:14)

And one of the other things that people often ask me is, my father led a very broken life, and by the end of his life, he's. I used to say, people are like, what do your parents do? I'd say, well, my mother's an art historian, and my dad runs a male 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 that's the baseline. And, like, if a father does that, then, you know, you owe them a lot.

Ryan Holiday (41:50)

Yeah, I guess.

Nick Thompson (41:52)

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

Ryan Holiday (42:00)

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

Nick Thompson (42:06)

I barely knew him.

Ryan Holiday (42:08)

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

Nick Thompson (42:12)

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. It's not really happy they live on. 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 gets himself a scholarship. He 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 a prominent east coast family. And my dad is on track. John F. Kennedy meets him, is like, this kid's going to be president before I am. And I found his Rhodes Scholarship recommendations. And the Dean of faculty is like, this is the best student we've had since Herbert Hoover. Right? This guy's, like, crushing it. But then he comes back and he's got his Rhodes Scholarship, he's got his DPhil from Oxford. And it doesn't really work. Life doesn't work the way he wanted it to, and he 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, whatever he thought he was gonna do. And then he realizes he's gay. And so obviously, after I'm born, which, thankfully, 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 this is part of it. Like, why did my dad end up the way he did? It's partly like, 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. 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. He was in a book called Remembering Denny, which is probably somewhere up here. It's a classic. And Roger Hansen 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 sleeping with everybody and bringing his totally inappropriate boyfriends into every conversation and every meeting and places. Like, just utter 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.

Ryan Holiday (44:42)

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

Nick Thompson (44:47)

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

Ryan Holiday (45:07)

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

Nick Thompson (45:12)

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 has an hour where he's in control. I remember I wrote a book with him when I was in my early 20s, 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. Just couldn't do it.

Ryan Holiday (45:38)

Wow.

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Ryan Holiday (46:38)

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Nick Thompson (46:44)

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Ryan Holiday (47:02)

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

Nick Thompson (47:07)

So he, 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, no, I can imagine. And he's in Dupont Circle. It's the AIDS crisis. Running 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 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 kept his demons partly at bay.

Ryan Holiday (47:38)

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.

Nick Thompson (47:52)

Right. And 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're on this podcast. It'd be super interesting. Like, the guy was so smart and, like, caring and interesting, and people loved him. He's just a maniac.

Ryan Holiday (48:12)

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?

Nick Thompson (48:27)

No, it's very much. I watch it. I'm like, I'm not going to let this happen. And that's part of the. My running is a recognition. Like, I'm going to stay focused. I don't know exactly what the key is to not become him, but it's clear that I've spent a lot of my life trying to be like him. I go to the same schools. I do lots of the same things. 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 going to try something. And so he brings me over to the other table, and he's like, paul, this kid here, he's the son of one of our classmates. 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. So I'm quite similar in lots of ways. Right. 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.

Ryan Holiday (49:24)

Yeah. There's a famous quote about tiger boys, another Stanford person, and says 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.

Nick Thompson (49:38)

Yeah, it's true.

Ryan Holiday (49:39)

Yeah.

Nick Thompson (49:40)

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

Ryan Holiday (49:48)

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.

Nick Thompson (50:00)

Yeah.

Ryan Holiday (50:01)

He's just starting to feel and understand these kind of, like, forces, and, like, 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. Out.

Nick Thompson (50:20)

Yeah.

Ryan Holiday (50:20)

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.

Nick Thompson (50:29)

Right.

Ryan Holiday (50:29)

You know?

Nick Thompson (50:29)

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.

Ryan Holiday (50:34)

Yes, hopefully.

Nick Thompson (50:37)

And don't touch a stove that's too hot. Right. Keep him away from that stove.

Ryan Holiday (50:40)

Yes.

Nick Thompson (50:40)

That's the trick of parenting. Right. Like, you've gotta let them 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.

Ryan Holiday (50:57)

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.

Nick Thompson (51:06)

Yeah.

Ryan Holiday (51:07)

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 8, I'd be like, what?

Nick Thompson (51:15)

Yeah, right. What are you talking about?

Ryan Holiday (51:17)

Yeah, what are you talking about? 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. If you're an 8 year old and you're overstimulated in a school classroom, you can't like get up and leave and be like, I'm going to 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 much of being a kid is like the system, the world is designed for how most people are. 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. You think about this is true for adults too. If your dad was maybe straight and maybe had slightly less demons, maybe he does become a senator, or he had all the ingredients and had all the access to thrive in that sort of late 20th century political, intellectual, academic circles, but because just a couple 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.

Nick Thompson (52:36)

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 found all of his diaries. You know, crazily. He had like, gone to his house, which he had sort of was gonna be, you know, torn down while he was still alive. And there was like a filing cabinet out front. And I like, open up one drawer and there's a snake in it. And like, this is 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 him in the back of my car and I drive him back. And then after he dies, I'm like, I wonder what's in these filing cabinets. And it's like bank statements and crap. And then it's like his diaries.

Ryan Holiday (53:10)

Yeah.

Nick Thompson (53:11)

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.

Ryan Holiday (53:20)

Yeah. It's unusual. Usually it 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 with your dad where 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.

Nick Thompson (53:43)

Well, we would joke about that. He'd be like, we have a reverse father son relationship. Cause 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. 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.

Ryan Holiday (54:02)

Have you had to deal with some kind of codependency stuff from that? Like how? Like. Cause 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. He should be giving you hard won wisdom about how to be the age you are now.

Nick Thompson (54:24)

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 still very useful in that way.

Ryan Holiday (54:34)

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

Nick Thompson (54:43)

He could not do that. Yeah, yeah.

Ryan Holiday (54:45)

There's a eulogy that James Baldwin gives to his father who is 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 knew his sins, but we didn't know his wrestling. Like you tend to just think like, especially when you're a kid. Cause you're just entitled, I think, to get what you need from your parents. And when you don't, all that you feel is that you didn't get it. 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. All you see is the binary yes or no, not what went into falling short. All you feel is that it wasn't enough.

Nick Thompson (55:31)

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

Ryan Holiday (55:46)

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

Nick Thompson (56:09)

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 high school where I 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, help makes me cool at school as opposed to kind of a loser. So it plays that role in life. I then go to college, I'm not quite good enough. I leave the team after my first year. I take it back up in my 20s. And I definitely think that what you're talking about kind of the daily practice I've run, 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. I also believe that the focus required for running helps you with everything else. If you can go run two hours at a focused pace, you're 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 and I'm gonna do it again tomorrow. And I think it's gonna make everything else in my life work a little better.

Ryan Holiday (57:09)

Yeah. Like when you're two thirds of the way into a manuscript and you're like, is this a fucking book? This is taking longer than I thought. It's not coming together. I don't wanna do it. I hate this. You're like, oh, I know this feeling. You just keep going.

Nick Thompson (57:23)

You just keep going.

Ryan Holiday (57:24)

You keep going. And then at some point you finish and you're like, oh, that was better than I thought. Right?

Nick Thompson (57:30)

And the thing you learn about running, 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.

Ryan Holiday (57:38)

And it always happens, but imperceptibly so. There's not some magic day where you're like, oh, so it's just this cumulative gain that you're getting block by block.

Nick Thompson (57:48)

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 going to take. It takes a little time to recover. Like, it's hard to recover from a race. It takes a while. But I guarantee you, like, I'm just going to run every day for the next six weeks. I'm going to run a bunch of workouts, and six weeks from now, I'm going to 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? So you go to 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 do it a little bit here, you do it a little bit there, and, like, it gets done right. Eventually it's done right.

Ryan Holiday (58:33)

Well, at some point, you have the capacity to do a thing that seems unimaginably difficult. So, like, 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 heart, whether it's a marathon or an ultra marathon, and you go, where did my ability to do that thing came from? It came from these little things. And writing is similar in the sense of, like, you've worked on it for 20 minutes. You worked on it for. You thought about it. You read these books. It's just all this stuff is going in. And then at some point you have a editable manuscript. Where did all this go?

Nick Thompson (59:11)

How did this happen?

Ryan Holiday (59:12)

I was just sitting in here yesterday, and I finished the audiobook for the. The book that I just did. This thing was almost unrecognizable to me because I didn't ever do it as a thing, right? I did it as each of its component parts. 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 at. 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'm starting here and I'm ending here. It's this cumulative project, this chipping away. And eventually, cumulatively, you have a thing, right?

Nick Thompson (59:52)

And then when you have the thing, the other hard question is, okay, when do you stop? Right? Because if I made it better yesterday, that means I might be able to make it better tomorrow. So when do you call it off?

Ryan Holiday (60:04)

Yeah, when is it done? And shipping, that is very difficult.

Nick Thompson (60:08)

There's a really big moment in my career that gets to this lesson. It was one of the most important moments of my career. And I was a young editor at the New Yorker, and I guess this would have been 2013, and I was just running the New Yorker's website, and I didn't have any confidence in my writing, right? And I hadn't written at the level of the. I could. I was a great editor, but I wasn't great writer. And the Boston Marathon bombs happen, 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. I was like, no, I've got to manage this. I've got, like, three other freelancers we're working with. We're 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. I was like. 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. And so I'm like, okay. And so I wrote the story, and it was done in an hour. It was pretty good, 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.

Ryan Holiday (61:28)

Why do you think he thought you were ready at that moment?

Nick Thompson (61:32)

It was so clearly, I knew so much about marathoning. I had grown up in Boston. If there was ever a story that was the right story for Nick Thompson to do, it was this story. And I don't think he knew my insecurities about writing. He maybe knew it a little bit, maybe intuited a little bit, but he was just like, do it well.

Ryan Holiday (61:52)

What an incredible gift to give someone.

Nick Thompson (61:53)

Absolutely.

Ryan Holiday (61:54)

To sort of 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.

Nick Thompson (62:05)

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?

Ryan Holiday (62:09)

Well, yeah. Like, there's actually this really great passage. It's from BH Liddell Hart, the British historian. He's talking about William Tecumseh Sherman, and he's saying, look, there's a sort of pantheon of military heroes, right?

Nick Thompson (62:22)

Yeah.

Ryan Holiday (62:23)

And he's like, some of them, you're 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. But every step of the way, they're accumulating a certain amount of confidence. They're doing the thing. And he says that success is much sweeter for them because they earned it. 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. And so you go, okay, this guy thinks he was entitled to do it and is disappointed that he hasn't done it. Then when he does do it, yeah, there's probably a certain amount of letdown even then because, like, you believed you deserved it. And the external accomplishments never give you what they think they're gonna give you. 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.