Your New Stoic Role Models for a Stronger Life

Virtue is not a theory. It is something you practice. In the moments where you could overreact. In the moments where quitting would be easier. In the moments where doing the right thing costs you something. In this episode, Ryan explores the four Stoic virtues through conversations with people who actually live them. You’ll hear from a fighter pilot who shows courage under pressure, a marathon runner disciplined in daily practice, a historian who reframes justice as action, and Ryan himself on treating wisdom as a lifelong pursuit. 📚 Get a signed copy of each of the books in the Stoic Virtues Series:Courage is Calling https://store.dailystoic.com/products/courage-is-calling-signed-edition-pre-order,Discipline is Destiny https://store.dailystoic.com/products/discipline-is-destiny-the-power-of-self-control-signed?variant=43486120345798,Right Thing Right Now https://store.dailystoic.com/products/right-thing-right-now, andWisdom Takes Work https://store.dailystoic.com/pages/wisdom-takes-work 🎥 Watch the full episodes on The Daily Stoic YouTube Channel: https://www.youtube.com/@DailyStoic/videos Silence the 5 Inner Critics DESTROYING Your Confidence | Combat Fighter Pilot Michelle Curran https://www.youtube.com/watch?v=sN5FBB5Y8MsCEO of The Atlantic Nick Thompson on Stoic Lessons From Success https://www.youtube.com/watch?v=DNsHlF9_qiQWhy Do We Hate Our Jobs? The Truth About Success, Work, & Impact | Rutger Bregman https://www.youtube.com/watch?v=fqIqkv9m2JsHow To Avoid Destroying Your Mind | Billy Oppenheimer & Ryan Holiday https://www.youtube.com/watch?v=q5K7og1LNZM 👉 Michelle “MACE” Curran is a former United States Air Force fighter pilot with nearly 2,000 hours of F-16 flying time. She flew combat missions in Afghanistan and honed her skills across the globe, becoming the second woman in history to serve as the Lead Solo Pilot for the Thunderbirds, the Air Force’s elite demonstration team. 📚 Check out Michelle’s book The Flipside: How to Invert Your Perspective and Turn Fear into Your Superpower https://www.amazon.com/dp/1538768100/?bestFormat=true&k=the%20flipside%20michelle%20curran&ref_=nb_sb_ss_w_scx-ent-pd-bk-d_k0_1_14_de&crid=49ORZPBW0NKQ&sprefix=the%20flipside%20m Follow Michelle on Instagram @Mace_Curran https://www.instagram.com/mace_curran/?hl=en and learn more about her work at https://macecurran.com/ 👉 Nick Thompson is the CEO of The Atlantic, an American magazine founded in 1857. 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 Sports https://www.amazon.com/Running-Ground-Father-Simplest-Sports/dp/0593244125 Follow Nick on Instagram https://www.instagram.com/nxthompson/?hl=en and X https://x.com/nxthompson @NXThompson https://www.instagram.com/nxthompson/?hl=en 👉 Rutger Bregman https://rutgerbregman.com/ is a Dutch historian and author. In 2024, Rutger co-founded The School for Moral Ambition https://rutgerbregman.com/sma, a non-profit organization inspired by his latest book, Moral Ambition https://www.thepaintedporch.com/products/moral-ambition-stop-wasting-your-talent-and-start-making-a-difference. The initiative helps people to take the step toward an impactful career. 📚 Check out Rutger's book Moral Ambition https://www.thepaintedporch.com/products/moral-ambition-stop-wasting-your-talent-and-start-making-a-difference Follow Rutger on Instagram https://www.instagram.com/rutgerbregman/?hl=en and X https://x.com/rcbregman?lang=en | @RutgerBregman https://www.instagram.com/rutgerbregman/?hl=en 👉 Billy Oppenheimer is Ryan Holiday’s research assistant and the writer behind the newsletter,Six at 6 on Sunday https://billyoppenheimer.com/newsletter/. To read more of his work, check out his websitebillyoppenheimer.com http://billyoppenheimer.com/. 🎁 This holiday season, give the gift of Daily Stoic Premium | https://dailystoic.supercast.com/gifts/new No more waiting. Demand the best for yourself. The Daily Stoic New Year New You https://join.dailystoic.com/nyny26/ challenge begins January 1, 2026. Learn more and sign up today at dailystoic.com/challenge http://dailystoic.com/challenge 🎥 Watch the video episodes onThe Daily Stoic YouTube channel https://www.youtube.com/@DailyStoic/videos:https://www.youtube.com/@DailyStoic/videos 🎙️ Follow The Daily Stoic Podcast onInstagram https://www.instagram.com/dailystoicpodcast/?hl=en:https://www.instagram.com/dailystoicpodcast ✉️ Want Stoic wisdom delivered to your inbox daily? Sign up for the FREE Daily Stoic email athttps://dailystoic.com/dailyemail 🏛 Get Stoic inspired books, medallions, and prints to remember these lessons at the Daily Stoic Store:https://store.dailystoic.com/ 📱 Follow us: Instagram https://www.instagram.com/dailystoic/,Twitter https://twitter.com/dailystoic,YouTube https://www.youtube.com/@DailyStoic,TikTok https://www.tiktok.com/@daily_stoic?lang=en, andFacebook https://www.facebook.com/dailystoic See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

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

• 0:06Ryan Holiday?

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

• 0:52Ryan Holiday?

  Hey, it's Ryan. Welcome to another episode of the Daily Stoic Podcast. So I was walking my dog last night, walking down the dirt road we live on, and it's not exactly night, it's like dusk, it's starting to get dark. I have like a little flashing light I put on her collar, I have a flashlight, like a running flashlight that I have, it's actually this cool one, it's kind of like, it's like kind of like an L shape, you sort of hold it, it's almost like a, you grip it. Anyways, this has nothing to do with what I'm saying. I'm walking the dog, and I'm listening to music, and this car kind of comes up behind me, it's a pretty small, contained, little rural area we're in, so it's someone down towards the end of the road, and they're coming up behind me, and I can hear them,

• 1:34Ryan Holiday?

  and I get over to the side, and then they come like insanely close to me in their car. And I have the dog on the left side, and they're coming up behind me, so they're on my right side, and I'm like, whoa, what is this? I kind of like throw my hands up, you know, like in a, in a shrug, like, what the hell, man? And the car continues on, you know, maybe five yards, and then like I see the brake lights come on, and I go, oh, no. I'm saying, oh, no, not because like I'm afraid exactly, as I'm not, but it's more just like, they shouldn't have done this, I don't like that they did it, I'm fine, you know, but did I need to express my frustration with the situation and now have to have a confrontation with the person? I remember I was younger in New Orleans, and

• 2:19Ryan Holiday?

  Something similar had happened, like a car whipped out and I was, you know, threw up my arm like this, the person got out and I don't remember the details exactly, but I was like physically menaced as a result. And then I was like, okay, like you're obviously in the right, the pedestrian is right here, but it's not something you need to die over. And so I generally try to, as exasperated and frustrated as I can get with people who are not endangering me or doing dumb things in their car, I generally try to be chill about it because, you know, it's not worth it. That's what I'm saying. So the car not only slows down, but then like I see like they come to a stop and then that like they reverse a little bit.

• 3:01Ryan Holiday?

  And so I'm like, ah, great. And then I remember, oh, I'm actually, I'm, because there's wild dogs in our neighborhood and sometimes hogs and stuff. I don't open carry. I guess I could, again, not a, not a big gun person if I don't have to be, but I do carry like a collapsible police baton. I've had to raise it over my head, let's just say. So I realized, oh, I've got this thing on me. So I'm like feeling a little more, not sure of myself, but I'm feeling a little like, all right, they don't know what's going on. And so as I sort of walk up to the car and half dreading, half just sort of going, I hope this goes good because it doesn't need to be bad. But I'm not as vulnerable as I initially thought, right?

• 3:46Ryan Holiday?

  I approached the car, they rolled down the window and it's, there's this sort of, a bunch of people live way down on the road and I know they don't speak English. And a guy rolls down the window, I don't think I've seen him before and he goes, "Sorry amigo." And then I go, "Oh, don't worry about it." And he rolls up the window. I, I was relieved, right? I was relieved in a couple of ways. It went from a negative situation. Then I was like, is this going to be the worst of people? To a thing where I'm like, this is the best of people, right? Like I was mad at myself for a little bit of lack of restraint that incited potentially a conflict. And then I was like impressed and pleased with this person who was in the wrong, by the way, like they almost clipped me with their car to de-escalate, like he de-escalated first,

• 4:30Ryan Holiday?

  even though he had no idea whether I was going to be upset or not, right? And what does this have to do with today's episode? Well, we're going to be talking about virtue in today's episode. And we tend to think of virtue as this big, high-minded thing. But I actually think these cardinal virtues, courage, discipline, justice, wisdom, they apply to situations like this, right? A lack of restraint, lack of discipline on my part. That was like a part of the inciting incident here. The willingness to make amends or admit error, right? That's what my neighbor illustrated there. But also the courage to not run away from a situation. Like just the, hey, I know how to handle myself in this situation.

• 5:14Ryan Holiday?

  I'm not going to needlessly back down from a situation. I'm gonna, I'm gonna go in and I'm confident in my ability to handle this. Like, I wasn't confident in my ability to have to do something. I was just confident in my ability that I didn't need to be afraid here. Because I knew I could handle myself, right? And then wisdom, when you're younger, you tend to fly off the handle. You tend to, you just don't know how bad things can get. And you don't always take things seriously that you should take seriously. Is this really the perfect illustration of courage, discipline, justice and wisdom? No, but it is just a little minor example that I was thinking about that tees up what we're going to talk about in today's little compilation episode.

• 5:56Ryan Holiday?

  Obviously, these are themes I talk to our various guests on the podcast about. And so I'm going to run you four sections on four of the different virtues. And I think there's going to be a lot to learn here. At the beginning, we're talking with someone who I'm incredibly impressed with. This is former Air Force fighter pilot, Michelle Mace Curran. She wrote a wonderful new book, The Flip Side: How to Invert Your Perspective and Turn Fear Into Your Superpower. She has nearly 2,000 hours of flight in an F-16. She flew combat missions in Afghanistan. She was also a lead solo pilot for the Thunderbirds. When it comes to courage, when it comes to sort of conquering fear, she knows what she's talking about.

• 6:45Ryan Holiday?

  You know Aristotle's concept of the golden mean?

• 6:47Speaker 01

  No.

• 6:47Ryan Holiday?

  So the golden mean is that all virtues sit between two vices. So like courage is not the opposite of cowardice. It's in the middle between recklessness and cowardice. And so I think there's something about confidence that sits between that sort of ego that we all recognize is the obvious ego, the sort of narcissistic, better than everyone ego, and then the sort of the quiet, well, I don't want to ask because I'll look stupid.

• 7:17Speaker 01

  Yep.

• 7:17Ryan Holiday?

  Or, you know, the game is rigged against me. Imposter syndrome ego, which we don't typically think of as ego, but I think those are the two vices. And then confidence is somewhere in the middle of those two extremes.

• 7:30Speaker 01

  A hundred percent. And I have a little story from in the jet that actually is how I got my call sign.

• 7:36Ryan Holiday?

  Oh.

• 7:37Speaker 01

  Which call signs come from a mistake you made.

• 7:39Ryan Holiday?

  Yeah.

• 7:39Speaker 01

  Everyone thinks you get to pick them like Maverick's like, that sounds cool. Let me be Maverick.

• 7:43Ryan Holiday?

  It's like soup because you ate a lot of soup one night.

• 7:45Speaker 01

  Yeah, sometimes they're as benign as that. Mine is like a kind of a cool flying story, but essentially second flight in Japan, mock dog fighting. So dog fighting, training, obviously safe guns. We're not actually shooting bullets at our instructors. So my instructor and I going up and I'm supposed to point at him, shoot him with the gun, call the kill, celebrate all the things, right? And I really want to do well because I'm so worried about what everyone thinks of me.

• 8:07Ryan Holiday?

  Yeah.

• 8:08Speaker 01

  So I light the afterburner, wait a few seconds, roll, pull back on the stick. The F-16 pulls nine Gs, no problem. So nine times the force of gravity.

• 8:18Ryan Holiday?

  Yeah.

• 8:18Speaker 01

  So I am experiencing that, which very easy to go unconscious from that. G induced loss of consciousness, blood gets forced out of your head. So I am doing that. I'm pulling, I'm just pulling and pulling and not able to point at him. And my experienced self later, or logically would be like, oh, so I need to change what I'm doing to adjust. Something's not right.

• 8:39Ryan Holiday?

  Yeah.

• 8:39Speaker 01

  I've done this like twice before in training. I'm just super young. But my ego is like, you must win, you must gun him. And I just keep pulling and I'm not giving up and I don't touch my throttle. So just max AB and I get to full light loss. So I am just blacked out as far as seeing nothing.

• 8:56Ryan Holiday?

  Yeah.

• 8:57Speaker 01

  But I am not quite G-lock. I'm not quite unconscious because I can still hear. And my instructor ends up making a radio call to knock the fight off because he's like, something's not right.

• 9:06Ryan Holiday?

  Right.

• 9:07Speaker 01

  And so I was pushing that so far where I was like, the closest I've ever been to G-locking in my whole life.

• 9:13Ryan Holiday?

  Yeah.

• 9:14Speaker 01

  If you G-lock in a single-seat aircraft, people have hit the ground and died.

• 9:19Ryan Holiday?

  Right.

• 9:20Speaker 01

  Like, it is the highest repercussion.

• 9:22Ryan Holiday?

  Yes.

• 9:23Speaker 01

  This is a training flight, my second one ever in my new squadron. There was zero reason for me to push it that far.

• 9:30Ryan Holiday?

  Yes.

• 9:31Speaker 01

  But I was so worried about failing that that was more important to me than my physical safety.

• 9:36Ryan Holiday?

  Yes.

• 9:37Speaker 01

  Like, so illogical.

• 9:38Ryan Holiday?

  Yeah, it's insane. But that's, the appearance is mattering more than reality.

• 9:43Speaker 01

  Yep.

• 9:43Ryan Holiday?

  Yeah. And then the irony, of course, is that you did look really stupid, right?

• 9:48Speaker 01

  Yes.

• 9:49Ryan Holiday?

  Like, everyone is, you're afraid of being judged and you end up doing this thing that causes you to be judged so much more.

• 9:56Speaker 01

  Yes.

• 9:56Ryan Holiday?

  And that, yeah, your call sign, even that your call sign comes from it.

• 10:00Speaker 01

  Yeah. And so people ask otherwise. I accidentally went supersonic when I first lit the afterburner before I rolled and pulled, which is why I could pull so many Gs for so long and why I could never shoot my instructor because I couldn't turn tight enough.

• 10:12Ryan Holiday?

  Yeah.

• 10:13Speaker 01

  Imagine you're driving 60 miles an hour and you need to be driving 30 to make the turn.

• 10:16Ryan Holiday?

  Yeah.

• 10:17Speaker 01

  That was essentially me. And so they named me Mock at Circle Entry, which is just the turn circle entry for dogfight. It gets into pilot jargon, but people are always like, how'd you get your call sign? Did you pepper spray a guy in a bar?

• 10:28Ryan Holiday?

  Yeah.

• 10:28Speaker 01

  Like, not yet.

• 10:29Ryan Holiday?

  But, yeah, like, this thing is, this thing where you were like, well, I don't want to look bad in this one single encounter.

• 10:35Speaker 01

  Yeah.

• 10:35Ryan Holiday?

  Now follows you literally your entire career.

• 10:38Speaker 01

  And beyond.

• 10:39Ryan Holiday?

  And that's what we can't really think about in the moment.

• 10:42Speaker 01

  For sure.

• 10:42Ryan Holiday?

  It's funny, too, you talked about asking for help. There's something about that, too, where it's like, when other people ask us for help, we're like, oh, here, let me help you. We're not like, what a fucking moron, a loser.

• 10:52Speaker 01

  Right.

• 10:52Ryan Holiday?

  Right? Like, we're actually, like, excited, or it doesn't even register. And then the next day, we're like, well, if I ask for help. It's so cra- like, like, the thing, we get in our head about it, and then even though we have objective evidence that no one cares.

• 11:08Speaker 01

  Yeah.

• 11:08Ryan Holiday?

  There's actually a famous Marx realist quote where he says, "We're like soldiers storming a wall." He says, "You've fallen and you have to ask a comrade for help. So what?" And I love the "so what" of it, because it really does pierce this kind of insane chain of assumptions we make up in our head, where like, if you're all storming a wall and someone falls, you're not like, "I told you not to do..."

• 11:31Speaker 01

  Yeah, you idiot!

• 11:32Ryan Holiday?

  Yeah, that's not occurring to anyone. And in fact, they're like, there's something beautiful about being able to help that person. And yet, we're so reluctant to possibly ask for the help that we need to get better.

• 11:47Speaker 01

  When I was flying for the Thunderbirds, people would be like, "You're so brave. I could never do that." And I'd be like, I would be like, "What a weird thing to say to me. I'm not brave." Like, I've had so much self-doubt. I've had so many moments of fear. I just forge ahead anyway. And it was never about what they thought I was being brave for. The physical danger of the maneuvers was not the problem.

• 12:07Ryan Holiday?

  But it's interesting you said that, because that is the definition of bravery, though. Like, if you're not afraid...

• 12:11Speaker 01

  Then it's not brave.

• 12:12Ryan Holiday?

  Yeah. And like, if there was some pill you could give someone, and it just suppresses all fear and doubt. First off, you wouldn't do that. That'd become extremely dangerous, right? And, and that's why recklessness is, is the sort of vice that Aristotle holds up as the extreme end and that golden mean. But, but it's also like, it would make the thing less impressive in a way, just in the sense that, in the same way that steroids make the accomplishment less impressive.

• 12:38Speaker 01

  Right.

• 12:38Ryan Holiday?

  Because you're like, "Oh, it's not really you." I mean, there's part of you in there.

• 12:42Speaker 01

  Yeah.

• 12:42Ryan Holiday?

  But it changes how we understand what you really did.

• 12:48Speaker 01

  For sure. And that's what makes it impressive, right?

• 12:50Ryan Holiday?

  Yes.

• 12:50Speaker 01

  If we were just fearless and not in danger, and not afraid of that at all.

• 12:55Ryan Holiday?

  Yes.

• 12:56Speaker 01

  Like, anyone would do it.

• 12:58Ryan Holiday?

  Yeah, if you're not getting over something, it could still be impressive. It's just, we're just not talking about courage as the virtue that's there. Maybe it's discipline or some, some other thing. You're doing something that's hard, that's no question, but it's just... You're not being brave. It's only because it's scary to you and you don't know. Like, if someone could say, hey, the outcome is a foregone conclusion. You're definitely going to succeed. Well, like, obviously, a lot more people would do it. But then also doing it wouldn't be impressive in the same way. And it wouldn't require courage as we understand it.

• 13:36Speaker 01

  Yeah, if it was easy, everyone would do it.

• 13:38Ryan Holiday?

  And that's a hard thing to remember while you're doing it. Like, when it's really fucking hard.

• 13:42Speaker 01

  Yeah.

• 13:42Ryan Holiday?

  To go like, oh, this is keeping people out. But it is. Like, if, again, if there wasn't this sort of trough of despair in the middle, if there wasn't this valley that you had to go through, then everyone would do it because the rewards are obvious. Like, why people would want to be on the other side of it, very clear. It's just when you get in the shit of it that you can lose your bearings there. And so what those difficulties do is separate the people who really want it from the people who would just kind of think it would be nice to have.

• 14:18Speaker 01

  For sure. And I think it's one of those careers that people think is sexy. Again, not to reference Top Gun for the third time, but that is such a pop culture phenomenon that has like informed a lot of people's reality of the fighter pilot culture. So much of the job is so unsexy, right? It is stuck in a tiny cockpit for eight hours and going to the bathroom in there and sometimes messing that up. And like, where do I put my snacks to not have those two things overlap? And like, it's just that kind of stuff. And it's like sleep deprivation and sun's in your eye and trying to air refuel. And it's hard in the skill set, but it's also a grind just in like the work that has to happen. It's behind the scenes.

• 15:00Ryan Holiday?

  The bureaucratic shit and the fact that not everyone's nice and that you're not paid that much. Like, there's, if it was all green lights, everyone would do it. It's the, the point is there's a bunch of red lights and detours and obstacles. And that's, that's why not that many people make it all the way there.

• 15:19Speaker 01

  Yeah, I always laugh when people are like, what's like the behind the scenes of being a Thunderbird pilot? Because they see very tight flight suit aviators, you know, locked in, precision.

• 15:30Speaker 01

  And I'm like, the number of interviews I did for local media where you fly across country, so you fly four or five hour flight, you land from Las Vegas to Florida.

• 15:39Ryan Holiday?

  Yeah.

• 15:40Speaker 01

  You get out and there's like local ABC station there, whatever. It's like, tell us about the airshow. And I'm standing there talking on camera and I'm not going to turn around because I've had a piddle pack mishap halfway there. And I'm a 35 year old expert in my field on this pedestal that has pee pants.

• 15:55Ryan Holiday?

  Yes.

• 15:56Speaker 01

  I always think of like Adam Sandler, like all the cool kids pee their pants. It's like, if they only knew.

• 16:00Ryan Holiday?

  If it was glamour, if the practice was fun, more people would do it. Right? Like, like game day, you get the rush.

• 16:09Speaker 01

  For sure.

• 16:10Ryan Holiday?

  Why people want to be a professional athlete or whatever, but it's, it's, it's all the parts that are not fun, that you have to, in a way, learn to love and enjoy. Otherwise you just won't do it. Like the amount of shit you have to go through to be in the position to do the fun part. That's the, I think the ratio of it that people don't really understand. Like publishing a book is pretty fun.

• 16:36Speaker 01

  Yeah.

• 16:36Ryan Holiday?

  You know, but writing is not that fun. Having written is great.

• 16:40Speaker 01

  Yeah.

• 16:41Ryan Holiday?

  But it actually is fun to me. Like I, I've had to get to a place where that I understand that's, that's the part of it that I control. That's the part of it that's not going away. That's the part of it that, uh, you know, separates the amateurs from the, I have to go like, no, no, I like writing books, not having books. I like writing books. I don't like, like being an author is actually now like my least favorite part. I like doing the thing. And the more you like doing the thing, the more you're going to fucking do the thing.

• 17:11Speaker 01

  Yeah. I feel like that's why most authors don't have, I mean, 14, 50, how many books do you have this a lot?

• 17:16Ryan Holiday?

  I don't know.

• 17:17Speaker 01

  Cause you enjoy it.

• 17:17Ryan Holiday?

  Yeah. I just, I, I spend a lot of time doing the thing.

• 17:20Speaker 01

  Yeah.

• 17:21Ryan Holiday?

  And then like, when people ask you, they're like, when people ask for shortcuts, like there's this famous story, a samurai wants to attach himself to this sort of young master or to this famous master. And he says, um, you know, how long does it take? And he says it takes 10 years. And he goes, no, no, I'm gonna like work really hard. I want to do it like, I'm really excited about this.

• 17:42Speaker 01

  Yeah.

• 17:43Ryan Holiday?

  He goes, okay, 20 years. And he's what? You know, no, no, you don't understand. And he's like, I want to, I gotta get this done now. And he's like, okay, 30 years. And the point is like, if you're trying to rush through it, you're missing the whole point. Like whenever people are like, do you have any tips for speed reading? And it's like, no, the, the point is that it takes a long time and you do a lot of it.

• 18:04Speaker 01

  Yeah.

• 18:04Ryan Holiday?

  That you're trying, that you're looking for the shortcut is what is going to make it take a long time for you.

• 18:10Speaker 01

  Yeah. No, that some of it is just lived experience too.

• 18:13Ryan Holiday?

  Yeah.

• 18:13Speaker 01

  It's the reps.

• 18:26Ryan Holiday?

  And then next up, we have discipline. This is something I talked about with Nick Thompson, the CEO of The Atlantic. He's also an elite runner and marathoner. He talked a lot about his complicated past with his father and how that's helped him cultivate discipline in his own work and running life. Obviously, that's something I practice in my life. I'd run earlier yesterday morning. And then I was doing my sort of nightly dog walk in the afternoon. Nick also has an amazing book called The Running Ground. A Father, A Son, and The Simplest of Sports.

• 19:00Ryan Holiday?

  There's a famous quote about Tiger Boy is 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.

• 19:13Speaker 02

  Mm hmm. Yeah, it's true.

• 19:15Ryan Holiday?

  Yeah.

• 19:16Speaker 02

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

• 19:24Ryan Holiday?

  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 like gotten back, 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.

• 19:48Speaker 02

  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, after my first year, 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 believe discipline is cumulative. I think if you do a hard thing first thing in the morning, it's easier 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 gonna have a better time at your

• 20:33Speaker 02

  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.

• 20:48Ryan 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. And then at some point, you finish and you're like, oh, that was better than I thought.

• 21:08Speaker 02

  Right. 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.

• 21:19Ryan Holiday?

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

• 21:27Speaker 02

  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,

• 21:42Speaker 02

  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? See, I 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, 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?

• 22:14Ryan 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, 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?

• 22:53Speaker 02

  How did this happen?

• 22:54Ryan Holiday?

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

• 23:07Speaker 02

  Right.

• 23:08Ryan Holiday?

  I did it as each of its component parts.

• 23:10Speaker 02

  Yep.

• 23:11Ryan 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 I went, 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.

• 23:36Speaker 02

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

• 23:49Ryan Holiday?

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

• 23:56Ryan Holiday?

  Now, the next virtue is one that people tend to get confused about. This is justice. And as I was working on the virtue series, I was worried that this one wasn't going to resonate, right? That people think of justice as something you get from the law courts, or from a judge, or a juror, or from politics. But no, it's also how we treat our neighbors, right? It's apologizing when you get it wrong. It's being your own referee. It's the standard you hold yourself. It's how you treat people. Well, I spoke with Rutger Bregman over the summer. We had a really great conversation about justice as a virtue, not just how to embody it, but how to design our lives to bring more of it into the world. Rutger is a Dutch historian. He co-founded the School for Moral Ambition.

• 24:38Ryan Holiday?

  He has this great new book called Moral Ambition, which I've been raving about. You can grab that at The Painted Porch.

• 24:47Speaker 03

  In your justice book, you quote Aristotle, right? You don't become a harpist because you're born that way. You become a harpist by playing the harp, right? You become a builder by building.

• 24:56Ryan Holiday?

  Virtue is something you do.

• 24:57Speaker 03

  Exactly.

• 24:57Ryan Holiday?

  Yes.

• 24:58Speaker 03

  And that's, for me, such a fundamental insight. You're not born as a good person. You become a good person by doing good things. So just get started.

• 25:05Ryan Holiday?

  What I would add to that, then, because that's very groundbreaking to me, that it's about being asked. What great activists do is they don't write anyone or any segment of society off. They create inclusive movements. And like you look at Gandhi, you look at Martin Luther King, you look at Harvey Milk. What was almost frustrating about them to their followers was how uncynical they were in the sense that they were always trying to create alliances, collaboration. They didn't see anyone or anything as irredeemable, right? They were trying to bring people into the tent, which is kind of the opposite of how activism works today, right? Which is like, it's about purity, it's about exclusivity, it's about kicking people out

• 25:50Ryan Holiday?

  of the movement for not being totally on board with it. This is why the left has almost no political power, because they have, they not just kicked all the people out of the big tent, but they were so egregious in doing so that they went to the other. Other side. No one wants to exist in political no man's land. So when you decline an alliance with someone, you are often forcing them to ally with your opponents. Right. When you cancel someone from the left, it's not a coincidence. Most of them end up on the right. You know, and so the idea of, hey, everyone is capable of being good, of being on the right side of this. And we're not going to write you off for being currently on the wrong side of this. Like, I think, to go back to abolition, I'm forgetting the guy's name.

• 26:32Ryan Holiday?

  But the guy that writes Amazing Grace, obviously a song about grace and redeemability, is a former slave trader. They don't, they don't prevent him from joining because he did horrible things to other human beings. They actually see him as a potential ally for the movement because he knows how it works. And so the idea of like, who are you asking to join? And how are you bringing people along with you? That's what they say, leaders create leaders, right? Great activists help make people who are not currently politically engaged, decide that they should be engaged and capable of making a contribution.

• 27:07Speaker 03

  Every great movement throughout history, it was a coalition of people who very often didn't agree with one another. So my rule of thumb is always like, if, if someone agrees with you for like 70 to 80% of the time, that person is an ally, not your enemy.

• 27:19Ryan Holiday?

  Yes.

• 27:19Speaker 03

  And indeed, you see it when, again, the abolitionists, the Quakers initially didn't get much done. Yeah. Because they were this very weird Protestant radical sect who deeply believed in their own dogmas.

• 27:31Ryan Holiday?

  Yeah.

• 27:32Speaker 03

  It's only once they started working together with the evangelicals.

• 27:35Ryan Holiday?

  Yeah.

• 27:35Speaker 03

  That they, you know, started to galvanize a movement. And for us, it's, it's difficult to fully wrap our head around how difficult that was for them. Like, these were very, very religious people. And it's like, that's, that's pretty important that, that they were able to overcome those differences to build that coalition.

• 27:52Ryan Holiday?

  Well, I mean, even in the women's rights movement, right? There's all these debates about should we let Mormon women in, who were at that point polygamists, right? And so utterly foreign and objectionable to, you know, sort of conservative women in New York City or whatever. And then do we let black women in? Do we let, do we let poor women in, right? And The women's rights movement succeeds when it is this sort of big, broad tent that covers, you know, not just a good swath of American society, but British society as well, right? Like, the multiracial, multi-ethnic, multi-class, multi-viewpoint coalition is

• 28:33Ryan Holiday?

  ultimately like the one that succeeds. Insular movements tends, not only do they tend not to get a lot of support, but they tend to implode and take, you know, sort of silly and idiosyncratic stance. Like, they get themselves in trouble because there's not enough ideological diversity inside the movement.

• 28:53Speaker 03

  So that's one thing we need, the coalition building. The other thing that we can really learn here is the importance of perseverance.

• 28:59Ryan Holiday?

  Yes.

• 28:59Speaker 03

  So I already said that only one of the founders of the British Society for the abolition of the slave trade was still alive when they finally accomplished their goals. Well, take the women's rights movement. Of the 68 women who came together at Seneca Falls in 1848, you know, the first women's rights convention in the United States, only one was still alive in 1920, when finally, what is it, the 20th Amendment was passed? And, you know, the federal right to vote was there. And she was sick on the day of elections.

• 29:25Ryan Holiday?

  This is Carrie Chapman Cat, who wasn't even born until after Seneca Falls.

• 29:29Speaker 03

  I know which quote. Yeah, this is a very powerful.

• 29:31Ryan Holiday?

  To get the word "male" in effect out of the Constitution, it cost the women of the country 52 years of pauseless campaign. During that time, they were forced to conduct 56 campaigns of referenda to male voters, 480 campaigns to get legislatures to submit suffrage amendments, 47 campaigns to get state constitutional conventions to write women's suffrage into state constitutions, 277 campaigns to get state party conventions to include women's suffrage blanks, 30 campaigns to get presidential party conventions to adopt women's suffrage blanks, and 19 campaigns with 19 successive congresses.

• 30:04Speaker 03

  And this is, again, the thing. Like, we only, we study history and we know the end of the story. Like, we know, oh, all's well that ends well. You know, women got the right to vote.

• 30:13Ryan Holiday?

  Yes.

• 30:14Speaker 03

  But Susan B. Anthony, you know, she was dead before that amendment was passed. Elizabeth Cady Santon, she didn't get to see it. Like, so many of these, these great pioneers, they never saw what we know what happened in the end. And you had that realization that... That perseverance to be part of something that's much bigger than you, that just inspired in me an emotion that I like to describe as moral envy.

• 30:37Ryan Holiday?

  Yes.

• 30:37Speaker 03

  It's like I studied these great moral pioneers of the past. I'm like, this is what it means to live a great life. To be able to, how do you say that? Follow in the footsteps of those who came before you.

• 30:47Ryan Holiday?

  Yes.

• 30:47Speaker 03

  It's almost a form of transcendence. Like, I'm not a super religious guy myself. My, my father is a, is a Protestant minister, but I never caught the bug in that way. I don't go to church often. But for me, this is almost a kind of religion. This is how I believe in the afterlife, right? Is just this feeling that you can follow in those footsteps. And that, like I mentioned, factory farming. I, I don't think I'm gonna see the end of that. Like, or I think it's gonna take a lot, a lot of time, at least. But knowing that you're a part of, of something that's much bigger than you are, that gives me a lot of energy to work on that stuff.

• 31:20Ryan Holiday?

  There's a, a line from a Longfellow poem, which I'll probably butcher, but I think about it all the time. He says, "The lives of great men all remind us we can make our lives sublime and leave footprints behind us in the sands of time." He says, "Footprints that some other person, struggling difficulty, can take solace and inspiration from." That, that, that's the meaning of life, is, is that somebody did something that inspired you to do something. And you, in doing something, can leave something behind that inspires some other person. And that's, it's this idea of a procession of torches. We don't study the abolition movement enough, Thomas Clarkson. But Thomas Clarkson puts in motion this movement, which leads to the women's rights movement,

• 32:05Ryan Holiday?

  which leads to the civil rights movement, which leads to the gay rights movement, which leads to the environmental movement, which leads to everything that's happening right now. And that, that if you see it as this sort of one movement, learning and teaching and inspiring, and by the way, building up mailing lists and, you know, constituencies and experience and tactics and strategies that then the next group is inheriting and building on and adding on, that's really how you make a difference. It's like, how have you left? In that same Longfellow poem, he says, you know, like, "Tomorrow should find you further than today." It's weird to be talking about moral ambition,

• 32:50Ryan Holiday?

  but then also shrink it down to just that, which is like, how are you making progress on these things? That's the goal.

• 32:57Speaker 03

  This is for me, the form of immortality we can all believe in, no matter if you believe in God, yes or no. It's like building monuments in time. And no one can take that away from you, right? If you've done something, achieved something, created something that will inspire people who come after you. I mean, Thomas Clarkson is dead for two centuries now, and here we're fanboying about, you know, someone who's been so inspirational to us. And I read his memoirs, and it's speaking through me, you know, through the centuries. And I was like, indeed, this is what it means to live a great life. It's almost like as if he's reaching out through the pages and asking me that question, like, do you want to do this as well? I'm like, yeah. So yeah, it's been super influential to me. It's like, with this book, for example, I thought, you know, I spent a decade now in the quote unquote

• 33:42Speaker 03

  awareness industry, writing articles and books, which is powerful, which is important, sharing ideas. But learning more about these abolitionists really made me want to build something. So I became the co-founder of the School for Moral Ambition. We're helping as many people as possible to pivot their careers towards more socially meaningful jobs. And again, I never thought, if you would have asked me this a couple of years ago, I would have said, look, I'm just a writer, you know, I live in my little cave and I write books and that's what I do. I'm like, I'm not entrepreneurial at all. And reading about these people helped me to discover that, again, being entrepreneurial, this is not something you're born with. You can really get stuck in a kind of self-image, like, oh, that's not who I am. No, you become someone by just doing it. It's such a simple lesson, but very powerful.

• 34:25Ryan Holiday?

  Well, so the cardinal virtues of stoicism are courage. I think people know what that is. Discipline, people know what that is. Wisdom, they know what that is. And then justice is the one that we kind of skip over, or we think, we have a strange sense of, like, too many people think justice is a thing that you get, right? Like, you get justice from the legal system. You get justice from a judge or a juror. You get justice because the law says this is how things are supposed to be. What I've tried to do in my writings, and this is what I did in the Justice book, and what I tried to build this series around is the idea that, no, no, no, all the virtues, but justice, perhaps most of all, is a thing that you do. Like, justice is a thing that you give. Justice is not...

• 35:07Ryan Holiday?

  Like, hey, here's how I think society should be like in the like, I'd like people to treat other people well. No, justice is how you treat people. Justice is not, hey, what I want those politicians in Brussels or DC to be doing. Justice is like, you run a small business, right? Do you give your employees health insurance? Like, justice is not, hey, what should the minimum wage law be? It is, but justice is also like, what do you pay the person who cleans your house? Right? Like, justice is both smaller and bigger than I think we, we unfortunately.

• 35:42Speaker 03

  It's the most important one of all, right?

• 35:43Ryan Holiday?

  Of course.

• 35:44Speaker 03

  I read this piece the other day about, I think the author called it modern monks. You know, these men who spend a lot of time going to the gym, you know, getting the right vitamins, taking care of their body, I don't know, meditating a lot. And I think all of that is powerful, but the most important question is like, what for? Like, what's the purpose? If you're so healthy, if you're so powerful, like, what are you gonna do with all those talents? And the answer is, I would say, justice. Yeah. Right? So I think it's important.

• 36:13Ryan Holiday?

  All the other virtues are rendered meaningless, if not directed at justice. Right? So, so, yeah, you're like incredibly self-disciplined. You're working incredibly hard on your body and you're just getting really strong. That's just vanity. Have you created a strong body that can then work long hours in pursuit of something meaningful? If you are, there were a lot of brave soldiers in the Confederacy, right? There were, I'm sure, brave captains who led convoys of slave ships and challenged the elements. And, but if it's in pursuit of something morally bankrupt, it is itself morally bankrupt. None of these things exist in isolation, right? Like, the people who decided, I'm not gonna get a vaccine during the middle of a pandemic

• 36:57Ryan Holiday?

  and then like lost their jobs over, there's a certain amount of courage in that, I guess. It's just fucking stupid, though, right? Like, you've picked a dumb cause to go all in on, right? And so, yeah, justice has to be the thing that your life is.

• 37:11Speaker 03

  It's the most important question. What do you actually work on?

• 37:25Ryan Holiday?

  And then lastly, for the virtue of wisdom, that's the fourth and final book in the virtue series. That came out back in October. Thanks to everyone who helped make it a New York Times bestseller. I've been loving signing all your copies. I sat down and talked with my friend and research assistant Billy Oppenheimer for just sort of what I mean when I talk about wisdom, how I see it as not so much a destination, but as a byproduct of doing the right things the right way at the right time. And in this chunk, he's sort of turning the tables and asking me some questions. Billy has a great weekly newsletter that I get something out of each and every week. It's called The Six at Six on Sunday. You can grab that at BillyOppenheimer.com.

• 38:13Billy Oppenheimer?

  You say in the Afterword to Justice that that book was a kind of ethical will to your kids.

• 38:20Ryan Holiday?

  Yes.

• 38:21Billy Oppenheimer?

  And I wondered if wisdom is sort of like the way you were thinking about.

• 38:26Ryan Holiday?

  Education?

• 38:27Billy Oppenheimer?

  Yes.

• 38:27Ryan Holiday?

  A little bit, although, you know, it's funny in the Taylor Branch series on Martin Luther King, at the end of the last one, and these are like, that's like, if you want to talk about a trilogy, that's like an epic trilogy. Is it four books? I think it's a trilogy. Anyways, in the acknowledgements at the end of the Taylor Branch book, he talks about how his son, who was born as he was starting the first one, helped with the research of the final book, like his senior year of college or something. And you're like, so you're like, that's like an adult life, like from infant to functioning member of society, like the arc of it. So I remember being struck by that. So this is just a much smaller version of that. But yeah, well, one of the reasons I wanted to save the wisdom book for last

• 39:11Ryan Holiday?

  in the series is that I just thought. Who I would be for five years later, I would have more to say about it. And then I also knew my kids were little. And so some of the thoughts on education and setting up an education would be more relevant to me. Weirdly, it's turned out every book in the Virgic series has been exactly the book that I needed to be thinking about in that moment. So courage during the depths of the pandemic, discipline during the other depths of the pandemic, the sort of where you're working from home, reimagining it, just like as it had dragged on.

• 39:53Ryan Holiday?

  And then justice in the middle of a sort of social justice awakening and then a political turbulence and turmoil, and then wisdom as my kids are now fully in school. And the mainstream integration of artificial intelligence and also a time of political misinformation and disinformation and making sense. Orwell talked about how to see what's right in front of your nose is the hardest thing to do in the world. That's the wisdom that I was interested in when I was writing the book, not just like knowledge for knowledge sake, but like, how do you make sense of the moment that you were in, which is a timely and a timeless moment?

• 40:38Billy Oppenheimer?

  Yeah, if you had started with wisdom, like AI wasn't yet in the conversation.

• 40:43Ryan Holiday?

  Sure.

• 40:43Billy Oppenheimer?

  The way, and now this book opens with that great story of Seneca.

• 40:48Ryan Holiday?

  Yep.

• 40:49Billy Oppenheimer?

  Which is just like how ancient the.

• 40:52Ryan Holiday?

  Desire for shortcuts is?

• 40:54Billy Oppenheimer?

  Yes.

• 40:54Ryan Holiday?

  Yeah. Yeah, he's talking about this guy who hires these slaves to basically be his chat GPT.

• 41:01Billy Oppenheimer?

  Yeah.

• 41:01Ryan Holiday?

  Like to just be the repository of knowledge that he could have at any moment. And then he could, he could be smart without having to do the work. To earn the knowledge that he was throwing around.

• 41:14Billy Oppenheimer?

  Yeah. Each slave is like an LLM for like.

• 41:17Ryan Holiday?

  Yes, totally. Yes. And, and you know, Seneca is laughing about how, you know, it's not something anyone can do for you and there's no shortcuts. And he says, you know, no one was ever wise by chance, like no one's beaten the system, basically. Yeah, that came very late in the book, I think. There was a different intro, which I don't remember what it was built around exactly, but that came later.

• 41:38Billy Oppenheimer?

  I remember forwarding you an email. Somebody had sent me.

• 41:41Ryan Holiday?

  Yeah.

• 41:41Billy Oppenheimer?

  And it made me think of the Seneca story.

• 41:43Ryan Holiday?

  Oh, is that what happened?

• 41:44Billy Oppenheimer?

  And I was like, probably a chapter on this.

• 41:47Ryan Holiday?

  Yes.

• 41:47Billy Oppenheimer?

  And then when I saw the first galleys, it was in the intro.

• 41:51Ryan Holiday?

  Well, well, credit where credit is due, that was a great find. And there's something, my relationship with the Stoics, having read them many times, is that you, it's all kind of there. And why you have to reread the Stoics is that the, the thing you're looking for, or that would explain the moment you're in, it kind of pops out at you, right? Like, and so, so that's why you have to have this kind of ongoing relationship with the text. Because when I first heard that story, however many years ago it was, I didn't go, oh, this will perfectly explain modern America's relationship with technology and wisdom in the year 2025. Obviously, that's insane.

• 42:32Billy Oppenheimer?

  Yeah.

• 42:32Ryan Holiday?

  So, but it makes an impression and then you comes back to you and you're like, oh, this would work perfectly here. I used to write very intentional intros for my books. Robert Greene is the opposite. Robert Greene, if I remember correctly, does the intro last? And I'm now kind of split the difference. Like I do kind of a light intro or a basic, it's like a warm up, like the intro is really just warming up the vibe and the tone that I want. And then I understand that almost certainly the ideas that it's going to be built around are going to come later. So that was like, oh yeah, because I do like, I do like it when the intros have a story. Like Discipline, I think, is mostly built around Eisenhower, if I remember correctly.

• 43:16Ryan Holiday?

  Courage is Churchill and Justice is, who's the main person in Justice? I don't remember.

• 43:23Billy Oppenheimer?

  Florence Nightingale?

• 43:24Ryan Holiday?

  No, no, in the intro.

• 43:26Billy Oppenheimer?

  Oh.

• 43:26Ryan Holiday?

  There's, there's usually a story in the intros. Let me see for, this is more than you can have in your head. Oh, Hyman Rickover, do what you think is right. Slam down the phone. What was it like to have it? I mean, you have an actual copy there.

• 43:43Billy Oppenheimer?

  Yeah, so this is my experience on all of the books, which is that, you know, I see them in Google Docs as you're working on them.

• 43:50Ryan Holiday?

  Yes.

• 43:50Billy Oppenheimer?

  And then my sort of role, I sort of off-ramp and you have a lot more work to do. And then I see the galleys and it's like.

• 43:58Ryan Holiday?

  Right, because it leaves, it leaves, in my process, it leaves Google at some point and goes into Microsoft Word.

• 44:05Billy Oppenheimer?

  Yes.

• 44:05Ryan Holiday?

  And then, then there's really no sort of research assistant tasks pertaining to the more or less complete manuscript and then, and then all the edits and the stuff. Yeah.

• 44:17Billy Oppenheimer?

  And so when I see, when I get the physical book, like, I don't recognize, I don't recognize, it's like a new book to me.

• 44:25Ryan Holiday?

  Yeah. Yeah, I did, I did find that on Robert Greene's books. It was hard because I, yeah, I would see all these different things or I'd read it as a galley, but then I would never actually sit down and read it as a finished, physical book. And there was something sad about that to me that I didn't, like, I love the access and the appreciation, but the cost was that I didn't get to experience it like everyone else. Like you, like, if you work on a movie, you don't get to watch it for the first time in the theater with everyone. That's never going to be your experience. And so there's a little bit of that with seeing a book get made.

• 45:01Billy Oppenheimer?

  Yeah.

• 45:02Ryan Holiday?

  But even, I mean, I sat here in this room to do the audiobook and there was like, still changes I was making.

• 45:07Billy Oppenheimer?

  Yeah, I also was going through the box of note cards.

• 45:11Ryan Holiday?

  Yeah.

• 45:11Billy Oppenheimer?

  The section of where you're kind of kicking around different structure ideas.

• 45:14Ryan Holiday?

  Mm-hmm.

• 45:14Billy Oppenheimer?

  And what ultimately became the structure of this book, there was like a note card and it was like on bike ride in like 2020 or something.

• 45:23Ryan Holiday?

  Really?

• 45:23Billy Oppenheimer?

  Yeah, I forget the date, but it was like, and there was, you know, you had one that was like internal and external.

• 45:29Ryan Holiday?

  Yeah.

• 45:29Billy Oppenheimer?

  So do you remember like nailing down, because I know the importance for you of like cracking the structure.

• 45:35Ryan Holiday?

  Yeah, we should find that note card. That's cool. I forgot about that. Yeah. And I'm trying to do better at saying when I found stuff because like it's cool to me going back to it. There's a lot of it you just forget, but no, I do remember that for the three other books, the three-part structure was obvious and pretty clear.

• 45:56Ryan Holiday?

  And for this one, it was not. And actually, when I talked to Rick Rubin, I was talking about doing the fourth book. And he was like, have you thought about for the fourth one, just like doing something totally different? Which I liked the idea. That's a very Rick Rubin thing.

• 46:11Billy Oppenheimer?

  Yeah.

• 46:12Ryan Holiday?

  And I considered it and there just wasn't anything that like called to me that like really felt like that would be right. And it wouldn't just be like sort of performative weirdness, you know? Like there was, I had this fantasy, like, what if I just did like really short? You know?

• 46:27Billy Oppenheimer?

  Yeah.

• 46:27Ryan Holiday?

  And then that was like one of the lessons, you know? And then I wouldn't have to do a long book like, and, and so I thought about a bunch of different ways and there was, it just didn't feel like it would come together. But the idea of like, quite like, and that is an idea in the book, which is like, you respect precedence and, and tradition, but you question convention. And so I had done the same style in the same structure for the first three. And then you go to first principles, you go, what is actually the best way to organize this book? Putting aside what has been done before, what is the best way to do it? And I think doing it as a three-part structure, I eventually found the, the things that I wanted to say.

• 47:10Ryan Holiday?

  And I knew from the outset that I wanted Lincoln to be a main character. Lincoln was originally going to be at the beginning as the self-education person, because that's what he's so famous for. And then I found that actually I wanted to talk about him more in moral terms. So he became at the end. So then it was who's going to be at the beginning? And that's where Montaigne came in. And then it was sort of who's going to be in the middle. I guess all of which is to say, the structure took a lot longer on this book and was a harder puzzle to crack. But the idea of sort of, here's how you inform yourself. Basically, it's like that thing from The Office where Dwight says like, what I figured out is I asked myself, what would a stupid person do? And I don't do that.

• 47:55Billy Oppenheimer?

  Mm-hmm.

• 47:55Ryan Holiday?

  I wanted to spend a lot of time, not just sort of talking about what wisdom is, but as I did in the ego book, like what is anti-wisdom? Like what is the opposite of wisdom? And, and how do we sort of lionize one and then steer clear of the others? So it took a while.

• 48:12Billy Oppenheimer?

  Yeah.

• 48:12Ryan Holiday?

  But it's funny that it came together on a, on a bike ride.

• 48:15Billy Oppenheimer?

  Yeah.

• 48:16Ryan Holiday?

  I wonder when that was.

• 48:16Billy Oppenheimer?

  Part one opens with Montaigne.

• 48:19Ryan Holiday?

  Yeah.

• 48:19Billy Oppenheimer?

  A most unusual education.

• 48:21Ryan Holiday?

  Yeah.

• 48:21Billy Oppenheimer?

  And in some ways, it's very relevant to.

• 48:26Billy Oppenheimer?

  Education today, like

• 48:27Ryan Holiday?

  Sure.

• 48:28Billy Oppenheimer?

  His upbringing, his dad instilled was like a love of learning that almost gets snuffed out in the schooling system.

• 48:35Ryan Holiday?

  Well, you know, what's funny is his dad like travels, he was like a soldier or something. His dad had traveled around Europe and was like fascinated by like these breakthroughs that were happening in education. Like he talked to all these educate, in the 1500s, he talked to these experts on education and then brought home these like cutting edge strategies. So there's something like kind of timeless and timely about like, well, what the old way is obviously not working. What's the new way? And it's like, this new way is 500 years old. But it also, when you're reading it, it feels radical. And this was actually something that my editor, Adrian, he was asking, my wife Samantha, he's asking her

• 49:18Ryan Holiday?

  about what we were doing for education for our kids. And she was like, well, you know, we've tried this, we're wondering about this, we don't know about this, you know, do you do private, do you do public, do you do tutors, what do you do? And he was like, the one thing I know is that there's not anyone of any socioeconomic status, high or low, you know, that is like, things that they're like crushing. Like, no one's like, we figured it out. It's perfect. We are totally happy with the option. So I guess the idea is that people have been struggling since there have been people to try to figure out the best way to teach their kids.

• 49:54Billy Oppenheimer?

  Yeah.

• 49:54Ryan Holiday?

  I did, the hard part about writing part one of the book is like, I didn't just want it to be about your kids. And I didn't just want it to be about how your education should have been. I wanted to think about the principles of learning generally, because like, the epigraph of the book is like, if you think it's too late, you don't understand what wisdom is. Like, it's an ongoing pursuit, and it has to be seen as an ongoing pursuit. But like with learning languages, like younger is better.

• 50:24Ryan Holiday?

  Obviously, these four virtues are the subject of the Four Virtues series, right? Courage is calling, discipline is destiny, right thing right now, and wisdom takes work. You can buy all four books as a set, or you can grab a signed copy of any of them. I'll link to that in today's show notes. And I hope you are having a great holiday break. 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.