Sit Down With Walter Isaacson and Ryan Holiday

In today's episode, Ryan Holiday sits down with legendary biographer Walter Isaacson for a wide-ranging, deeply thoughtful conversation recorded live at the Texas Tribune Festival. They talk about Walker Percy and The Moviegoer https://www.thepaintedporch.com/products/moviegoer?_pos=3&_sid=7b6c188b7&_ss=r, how Stoicism shows up in fiction, and why the ancient virtues still matter in the modern world. They talk through Marcus Aurelius, Seneca, Epictetus, Benjamin Franklin, George Washington, Viktor Frankl, and why history tends to outlast the noise of the present moment. 📚 Grab signed copies of Walter Isaacson's books https://www.thepaintedporch.com/search?type=product&q=walter+isaacson* at The Painted Porch: https://www.thepaintedporch.com/ https://www.thepaintedporch.com/search?type=product&q=walter+isaacson* Elon Musk by Walter Isaacson https://www.thepaintedporch.com/products/elon-musk?_pos=1&_sid=8ad4809fd&_ss=rSteve Jobs by Walter Isaacson https://www.thepaintedporch.com/products/biography20?_pos=7&_sid=8ad4809fd&_ss=rLeonardo Da Vinci by Walter Isaacson https://www.thepaintedporch.com/products/biography14?_pos=3&_sid=8ad4809fd&_ss=rBenjamin Franklin: An American Life by Walter Isaacson https://www.thepaintedporch.com/products/benjamin-franklin-an-american-life?_pos=5&_sid=8ad4809fd&_ss=rEinstein: His Life and Universe by Walter Isaacson https://www.thepaintedporch.com/products/einstein-his-life-and-universe?_pos=6&_sid=8ad4809fd&_ss=rThe Greatest Sentence Ever Written by Walter Isaacson https://www.thepaintedporch.com/products/the-greatest-sentence-ever-written?_pos=4&_sid=8ad4809fd&_ss=rWalter Isaacson: The Genius Biographies: Benjamin Franklin, Einstein, Steve Jobs, and Leonardo Da Vinci (Boxed Set) https://www.thepaintedporch.com/products/walter-isaacson-the-genius-biographies-benjamin-franklin-einstein-steve-jobs-and-leonardo-da-vinci-boxed-set?_pos=2&_sid=8ad4809fd&_ss=r 🎁 This holiday season, give the gift of Daily Stoic Premium | https://dailystoic.supercast.com/gifts/new 👉 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.

• 0:04Ryan Holiday?

  Welcome to the weekend edition of the Daily Stoic Podcast. On Sundays, we take a deeper dive into these ancient topics with excerpts from the Stoic texts, audiobooks that we like here or recommend here at Daily Stoic, and other long-form wisdom that you can chew on on this relaxing weekend. We hope this helps shape your understanding of this philosophy, and most importantly, that you're able to apply it to your actual life. Thank you for listening.

• 0:43Ryan Holiday?

  Hey, it's Ryan. Welcome to another episode of the Daily Stoic Podcast. It has been a bit nuts over here. I've been traveling a lot, trying to wrap things up for the end of the year. This is kind of the crazy time. There's last-minute stuff, like I'm doing a talk in a couple of days that they asked me to do like seven days before it was supposed to be. I just did the talk in Seattle. You know, it's Christmas time, the kids are about to get out of school, shopping. There's just like, you know, there's just a ton going on. And this is kind of the crazy time for Daily Stoic because signing lots of books, people ordering stuff in the bookstore, there's a lot going on. Then I was taking some clothes out of the washer last night, and I pulled a full chocolate croissant in the bag from Starbucks

• 1:27Ryan Holiday?

  out of a just-run load of laundry. So, you know, that was a wonderful surprise. Thankfully, it didn't ruin all the clothes. And how or why this ended up in my kids' pockets and then into the wash? There's a mystery of life. And amidst the craziness, I do try to go, hey, like, you're very lucky to get to do what you do. You're blessed. You're living your dream. And actually, something that was kind of a dream that just happened to me three weeks ago, two weeks ago, as I said all the time, sort of blurs to get there at this point. But Texas Triebfest is here in Austin. There's Texas Book Festival, then Texas Triebfest. They asked me if I would do a panel about bookstores. This is a couple of months ago. They asked me if I would do it. It was going to come up in November.

• 2:11Ryan Holiday?

  And I was like, I don't know, it's gonna be a crazy day that day. We already had like three birthday parties scheduled. As I said, this is the crazy time of year. They asked me if I'd do it and they said, look, how about if you do that? We'll do an interview with you and we'll pick someone cool to interview you on stage. And I said, oh, who were you thinking? And they said, what about Walter Isaacson? And I said, are you kidding? I mean, Walter Isaacson is one of the greatest writers of our time. I actually went and looked, because I had him sign all my books when I met him. I added up all the pages here. I have read 3,736 pages of Walter Isaacson's writing. And I guess that's just the first time.

• 2:53Ryan Holiday?

  I've also gone back and reread a bunch of the books because his books have shaped so many of my books. The Franklin Story and Ego is the Enemy is from his biography of Benjamin Franklin. There's a bunch of wisdom stories in Wisdom Takes Work that are from the Da Vinci book. Same with the Discipline book. There's even a chapter in Stillness is the Key that's got a Da Vinci story from one of his books. There's a bunch of Elon Musk anecdotes that led into that big part of part two of Wisdom Takes Work that I first learned about in Walter's books. I've read so many of his books, actually going even back, because I guess I use Steve Jobs in Obstacle is the Way. We carry a bunch of his books in the store.

• 3:36Ryan Holiday?

  I've been profoundly influenced by them. And, oh, you know what? This is great. This is what brings it all full circle. Okay, Walter Isaacson is himself mentioned in a chapter in Right Thing Right Now, where I talk about coaching trees, because he is part of the coaching tree of the great Walker Percy, who is himself part of the William Alexander Percy coaching tree. So being interviewed by Walter Isaacson, amazing. Well, Walter's people reached out and said, okay, but what would you want to talk about? And I said, well, we could talk about Stoicism, we could talk about Elon Musk. But what I'd really like to talk about is Walker Percy. And I'm looking here, I have a picture of Walker Percy on my wall. He's one of my favorite novelists. He wrote this book, Movie Girl, or one of my favorite novels, but then was very influenced by Stoic philosophy. And as I said, I-

• 4:21Ryan Holiday?

  I knew they were vaguely knew each other. I didn't know the full extent of the relationship, but that's what I wanted to talk about. So at the Texas Tribune Festival downtown in Austin, I think it was at the Omni, we sat down. He was interviewing me, but really I had more questions for him. We talked Walker Percy, we talked Stoicism, we talked Elon Musk and we talked everything that's happening in the world today. It's a great interview. I was very honored that he was even interested in chatting with me. And then I have a full note card here for the book that I'm working on now, where Walter gave me some advice on how to write a great biography. So this was honestly, like even if you hate this episode, which you won't because it's awesome, I got so much out of it. Like it was, it was the reason I do this podcast, right? Is like to learn and to be exposed to things.

• 5:06Ryan Holiday?

  And that very much happened here. Like I'm grateful to the folks at the Texas Tribune Festival for having me. It's a nonprofit politics and policy public news website headquartered in Austin, but their investigative reporting and stuff, it ripples through not just this state, which has millions and millions of residents, but you know, California and Texas, what happens here shapes in many ways the rest of the nation. So the Texas Tribune is a great news outlet. It's a great conference. I might bring you a chunk of that bookstore chat as well. But in the meantime, here is me talking with the great Walter Isaacson, who has a new book out called The Greatest Sentence Ever Written, which I bought on my way home from the Newark Airport two days ago at the Hudson Bookstore. And it's great.

• 5:51Ryan Holiday?

  It's about the first sentence of the Declaration of Independence. And just an absolute lovely book from a lovely writer. All of his stuff is amazing. We have some signed copies left. They'd make great gifts for the holidays. I'll link to that in today's show notes. But in the meantime, here's me and Walter Isaacson chatting away.

• 6:18Speaker 01

  I guess they feel you're a man who needs no introduction.

• 6:20Ryan Holiday?

  Likewise.

• 6:21Speaker 01

  We didn't even have a voice of God, but this is Ryan Holiday.

• 6:24Ryan Holiday?

  And this is the great Walter Isaacson.

• 6:28Speaker 01

  Big fan. We were talking backstage and I know we're gonna get to Stoicism. He said, but let's start with Walker Percy. Who in here, by the way, knows who Walker Percy is? All right, good. We both share a deep affection for Walker Percy.

• 6:43Ryan Holiday?

  Yes.

• 6:44Speaker 01

  And in particular, The Moviegoer.

• 6:46Ryan Holiday?

  Mm-hmm.

• 6:46Speaker 01

  And Aunt Emily in The Moviegoer, who in some ways is part of your path to the Stoicism idea, right?

• 6:53Ryan Holiday?

  Yeah, I bought it, I bought The Moviegoer at a used bookstore on Oak Street in New Orleans.

• 6:59Speaker 01

  I know that story.

• 7:00Ryan Holiday?

  And it was one of the first, I'd obviously known the Stoics and I'd read them, but it was the first time I, I saw them in fiction. And I think it's, obviously, the fictional take on the Stoics in Walker Percy is fascinating. It's one of my favorite novels. Then the, how Stoicism makes its way through that family, which is a multi-generational sort of path. He gets introduced to it by his uncle, William Alexander Percy. Has another amazing book, Lanterns of the Levee.

• 7:30Speaker 01

  Correct.

• 7:30Ryan Holiday?

  One of the great Southern memoirs.

• 7:32Speaker 01

  I didn't realize you were such a Southerner. I thought you were a Texan.

• 7:34Ryan Holiday?

  Adopted Southerner. I'm a Californian, like everyone that lives here now.

• 7:41Speaker 01

  All right, well, let's drill down on that, because I think you and I may have slightly different, we're trying to navigate that novel. William Alexander Percy, the uncle who raised Walker Percy, very much the Stoic and believes in the classical virtues of courage and, you know, honesty and whatever. And Aunt Emily in the book is the character there. Binks, the very beginning of the book, I think Binks's brother dies and Aunt Emily says, "You have to have courage. That's what you need." And Binks says, "Okay, that's easy. Is that really all I have to do?"

• 8:22Ryan Holiday?

  Yeah.

• 8:22Speaker 01

  And then he goes on the search, and in some ways, tell me what you think, I've always thought he said... I've gotta go further. I have to have the spiritual values, that leap of faith.

• 8:35Ryan Holiday?

  Yeah.

• 8:36Speaker 01

  How does that fit into Stoicism and then the question of something more spiritual?

• 8:43Ryan Holiday?

  Well, I do. I do think it's interesting in the novel, and we're really nerding out for people. This was one of the.

• 8:49Speaker 01

  All of you haven't read or know of Walker Percy, you can wait. We will spend about five minutes.

• 8:54Ryan Holiday?

  At one point, it was considered, I mean, it won the National Book Award when it came out. It was one of the great American novels. I think it's it's an incredible novel. But what I think is interesting, from what I know about Walker Percy, having read about him in the novel, is that the character finds both Stoicism and organized religion to be insufficient in the novel. But as the author, the person, he sort of relies on both of them. So I think it's interesting that the novel is sort of philosophically not critical, but exploring the inadequacies of those systems in the modern world. And then the the actual author himself is finds them perhaps more satisfying. So I think that's kind of an interesting thing. But yeah, you basically get the sense

• 9:37Ryan Holiday?

  that you have this young guy who's been through this horrible thing in Korea. And he's tempted by all the modern pleasures and ambitions. And then you have this old fashioned aunt talking to him about courage and justice and temperance and wisdom. And it's not work. It's not working. And I do think there's an analog a little bit to where we are now, where we sort of know this isn't working. And then when people try to talk to us about the old fashioned virtues, they just sound old fashioned.

• 10:07Speaker 01

  Right. And at least for Percy, I don't know what his outcome is, but he calls it the search.

• 10:12Ryan Holiday?

  Yes.

• 10:12Speaker 01

  And you have to keep searching. So tell me how that fits in with your path to Stoicism.

• 10:18Ryan Holiday?

  So I was in college and I got passed a copy of Marcus Aurelius's Meditations. And that was the beginning of the search for me because I didn't know. I don't know what I thought philosophy was, but I didn't think it was the Emperor of Rome talking to himself about. Getting up early in the morning and not getting upset by things and, you know, trying to put up with how obnoxious people are. I thought philosophy was theoretical and abstract. And no, here it is, sort of urgently dealing with the questions of both practical, modern life, but then also, as I think the moviegoers about, this sort of quest and search for meaning. What is it for? What do you do with this brief amount

• 11:01Ryan Holiday?

  of time? There's a, my favorite passage in the, the book is, is on to Emily where she says basically like, "I don't know what we're doing here. We're insignificant cinders spinning around in the universe, but all I know is you gotta do your best and try to be a good person."

• 11:18Speaker 01

  And how does that tie in? Marcus Aurelius starts it, "epicitus," is that how you say it?

• 11:23Ryan Holiday?

  Epictetus.

• 11:24Speaker 01

  Epictetus, sorry. Tell me how they adopt the Stoic virtues and how you sort of discovered that was a good path for your search.

• 11:36Ryan Holiday?

  Yeah. So the Stoic virtues, as I said, the cardinal virtues, courage, discipline, justice, wisdom. You basically have for 500 or so years, these series of Stoic philosophers, some powerful, some powerless. You have Epictetus as a slave, Marcus Aurelius as an emperor, Seneca, a power broker, and Nero's court. So he might've had a sense of what's happening right now. But, but the idea that the Stoics are sort of wrestling with, you know, how do you stay good in a world gone bad? How do you stay focused in a world of endless distractions and temptations? And how do you, how do you deal with the fact that life

• 12:18Ryan Holiday?

  is unpredictable and capricious and often cruel?

• 12:22Speaker 01

  I've been looking through your books and your path started as sort of an advertising agency.

• 12:30Speaker 01

  Trying to trick people in a way. So tell me about your first book.

• 12:34Ryan Holiday?

  Well, as, as, as all marketers are, we're trying to get people to buy things. But yeah, I was, I was a marketer and I, my first book is this sort of expose of the media system. Actually, I was living in New Orleans. I, I was living in LA.

• 12:48Speaker 01

  On Bertanya Street between first and second. I say that for my wife. We live a block from there.

• 12:54Ryan Holiday?

  I was living in LA and I said, I don't want to do this anymore. This isn't what I want my life to be. And I found an apartment on Craigslist in New Orleans. I, I moved there. My, my future wife came with me. I will say she burst into tears when, when she saw it. I did not make a good pick.

• 13:09Speaker 01

  It's on the house.

• 13:11Ryan Holiday?

  The room in said house. But, but I, I wanted to write a book about what I'd seen and experienced. And I remember this is 2011. I was working on this book. I was basically working on a book about fake news in 2011. And I remember thinking, if I don't get this out right away, it's going to be irrelevant. I was probably a little bit ahead of the curve about sort of the flaws in the media system and how sort of bad actors or bad information can be sort of traded up that chain and sort of take hold in public consciousness. That's what that, that book is, is about.

• 13:45Speaker 01

  But in some ways, it seems your next, well, not your next book, but the two books, three books after that are a reaction to what you saw.

• 13:54Ryan Holiday?

  Yeah, I think that's right. There, there was a disgust and disillusionment. And there was, um, there was a difference between what I sort of personally believed and what I was philosophically interested in and then what I was doing in my day job, which is a little bit, you know, Binx's position in, in The Moviegoer. I think, well, of course, his most reactionary book, actually my favorite is Lancelot, which is much darker and it's a sort of a more disturbing book. But I was like, that's just not what I want to do.

• 14:26Speaker 01

  And so when you get exposed to Stoicism.

• 14:29Ryan Holiday?

  Yeah.

• 14:30Speaker 01

  Would you, how do you turn that into a book first? And then we'll get into the empire that comes from the book.

• 14:36Ryan Holiday?

  Well, as you can imagine, when I went to my publisher with the idea for an obscure school. A book about an obscure school of ancient philosophy. They they too saw an empire in the making. They had the option on my next book. They're a business imprint of Penguin Random, then Penguin, now Penguin Random House. And I I said, this is what I want to do. And and they said, are you sure? Could you maybe do something else, please? And they told me later, they they were just hoping to get it out of my system and and write more marketing books. But that that's really what I wanted to write about is I I wanted to write about ancient philosophy. I was a I was a research assistant for Robert Green. I don't know if you know who Robert Green is. He wrote The Forty Eight Laws of Power and Mastery, writes these sort of amazing nonfiction books.

• 15:18Ryan Holiday?

  So he sort of picks a theme and then illustrated with stories from antiquity. So that's how I got my start. That's what I wanted to do. I just had this sort of detour in the marketing world.

• 15:29Speaker 01

  And when did you figure out it was more than just a book? You could do the podcasts, there's meditations.

• 15:39Ryan Holiday?

  Yeah, my so I did The Obstacle is the Way. And then my agent said, you should do a page a day book of Stoic philosophy. He had been an editor at Harper's and he'd had the idea for this book called The Daily Drucker, which is one page a day from Peter Drucker that had been a monster hit. And I said, who reads these? You know, it wasn't a medium that I was familiar with at all. As it turns out, actually, now, one of my favorite books, Tolstoy, has a page a day book called The Calendar of Wisdom, which has a lot of the Stoics in it. So I didn't know that it was this sort of genre. But but he suggested it and he said, you know, you do a translation at the top and then you you riff on it each day. And I said, that sounds like an interesting idea, but you know, I don't, who's going to do the translations?

• 16:23Ryan Holiday?

  And he said, oh, I'll do them. And apparently, I was, you you speak Greek and Latin? You've been holding out on me. So I'm maybe one of the only people to ever write a book with their book agent. And it worked out.

• 16:36Speaker 01

  And you then turn it into?

• 16:39Ryan Holiday?

  So the Daily Stoic is a page a day. And then the idea is, well, what do you do on page 366? Well, actually, three is 67 because you have to do it for the leap you're in there. But the point is, what do you do up to the last page? And so I bought the DailyStoic.com and I just kept going. So I've done every day since mid 2015. I have done an entry first for the book. And now the email, it goes out to almost a million people every day.

• 17:10Ryan Holiday?

  And it's

• 17:11Speaker 01

  And what is motivating you to do this?

• 17:14Ryan Holiday?

  Well, that a million people are waiting on the other end of it is a decent motivation to write the Daily Stoic. But like Stoicism isn't this philosophy that you read. It's a philosophy I think you have to be reading. You're supposed to go over it over and over and over again, not unlike a recovery program or a prayer. It's this thing that you're kind of meditating on and reflecting on. And so for me, the writing is my philosophical practice. And then the reading is other people's philosophical practice. But I added it up at one point. It's millions of words that I've done, but it's kind of my penance. You know, it's my vocation. I sit down and I take a thing from the Stoics every day.

• 17:57Ryan Holiday?

  And I try to arrange it in a format that would make sense to me or someone that reminds me of something that either I need to know or I think people need to know. And that's what the practice of it has been. And it's consistent. Doesn't matter what's happening in the world. I got to get this thing out every day.

• 18:15Speaker 01

  And what has it changed you?

• 18:17Ryan Holiday?

  You know, I think when I came to Stoicism, as I think a lot of young men, it's particularly popular with young men. I was interested in the discipline, the virtue of the discipline or the courage, right? The how to be stronger, faster, more resilient, tougher, that element, the muscular part of Stoicism. But what's fascinating about it, and I think this is the Trojan horse of it, is it's also fundamentally, and I think you could argue primarily, an ethical philosophy. Justice is the central virtue of the philosophy. And over and over again, the Stoics are talking about the common good, our interrelationality between people. The opening passage of Meditations is an interesting one. Marxros opens and he goes, "Today, the people you'll meet will be annoying and obnoxious

• 19:01Ryan Holiday?

  and stupid and jealous." He lists all the things. And I think, for instance, when I first read it, I'm nodding my head. I'm attracted to the cynical side of it, right? That prepare for how people are going to be and don't let them get to you. But actually, as I think you spend more time with it, you realize the second part is actually the most important part where he goes, "Look, and you can't let them suck you down." But then he says, "Because we're made to work together." And they're like this because they don't know better, or they're struggling with things. And your job is to work with them and to do your job. And that the idea ultimately in Stoic philosophy that I think separated it from, say, the Epicureans

• 19:41Ryan Holiday?

  was that it was a philosophy for public life and public participation. And so it's centered around this idea of collaboration, connection, doing things for the common good. The Stoics talk, Marxros specifically talks about the idea of the common good 80 times in Meditations, which is probably not a concern of Nero or Caligula. So the idea for the Stoics was this sort of public-mindedness. And so I think it's changed. The ethical side of it took longer for me to catch on to, but ultimately, that's where it's probably impacted me the most.

• 20:18Speaker 01

  We've gone this far in the conversation, and probably half the people here don't exactly know what Stoicism is. Or they were like me before I started reading you, and they think, "Well, it just means not being emotional and containing your emotions." And then when I read your stuff, it's definitely being emotional.

• 20:48Speaker 01

  Give us a definition and also the sort of the whole surrounding ecosystem of Stoicism.

• 20:55Ryan Holiday?

  So Stoicism is founded in the 4th century B.C. by this guy, Zeno. Zeno suffers a shipwreck, washes up in Athens penniless. He's introduced to philosophy, builds it up. I think it's fitting that it comes out of a disaster. It's got a disaster at the origin story. And then the philosophy is built around the idea that disasters are inevitable, but how you respond to those disasters is what it's about. That it's a philosophy about the response. I sort of summarize Stoicism often to people as we don't control what happens. We control how we respond to what happens. And the idea is that you have to respond with these virtues or with virtue. And so whether we're talking about a shipwreck or a jerk in traffic

• 21:38Ryan Holiday?

  or an economic downturn, the idea for the Stoics is what virtue is this presenting you an opportunity to practice? That's the philosophy. So when we think about it as being emotionlessness, what the Stoics are really saying is, you know, have the emotion, just probably don't let the emotion color your response. So you can get angry and then you go, okay, but why is this person acting this way? Is me responding angrily who I want to be? Is it the right thing to do? So it's this kind of framework for stopping, pausing, reflecting, and then being as rational and self governed as possible in how you respond.

• 22:17Speaker 01

  And we think of it as a classical philosophy.

• 22:20Ryan Holiday?

  Yeah.

• 22:21Speaker 01

  Greeks, the Romans. How does it get carried forward after that?

• 22:26Ryan Holiday?

  Yes, so it starts in Greece, goes to Rome, sort of disappears during the Dark Ages. It is absorbed.

• 22:33Speaker 01

  So does everything. That's why they're called dark.

• 22:35Ryan Holiday?

  Yes, I mean, but one of the reasons is it's absorbed into Christianity, right? They share the cardinal virtues.

• 22:43Speaker 01

  Well, wait, let me pause there. The teachings of Jesus and the teachings of Marcus Aurelius do not seem the same to me. But am I wrong?

• 22:51Ryan Holiday?

  I would say, an interesting aside is Seneca, the other famous Stoic, is born the same year as Jesus. They both exist in the same Roman Empire at the same time as these wildly popular philosophies. Seneca's brother is in the Bible.

• 23:05Speaker 01

  Really?

• 23:06Ryan Holiday?

  Yeah, he lets Saint Paul go. So, interesting little aside, Marx's realist philosopher, Rosticus, kills Justin Martyr. So, not all, they cancel each other out.

• 23:18Speaker 01

  And Marcus Aurelius's kid doesn't turn out to be-

• 23:20Ryan Holiday?

  Commodus, not so good. Not so, not so good. That's the question I get the most, like, what happened with Commodus?

• 23:27Speaker 01

  Oh, yeah.

• 23:28Ryan Holiday?

  And I go, well, you know, Marcus was 40 when he became emperor. Commodus was 16. How would you have done at 16? Probably not great, but I wouldn't say exactly that Stoic philosophy is- the Stoicism of Marx's realist is what we see in the Bible. But I would say that the virtues of Stoicism get absorbed into Christianity and this sort of Western thought. And then ultimately, we see, you know, right around the time of Montaigne, it starts to bubble back up, Stoicism. The Victorians really rediscover it, bring it back. This is where it enters the Percy family to bring this full circle.

• 24:04Speaker 01

  But it's interesting, because the Victorians rediscover it, but most of classical thinking gets rediscovered in the beginning of the Renaissance-

• 24:13Ryan Holiday?

  Yes.

• 24:13Speaker 01

  And Lucretius and others.

• 24:15Ryan Holiday?

  Yes.

• 24:16Speaker 01

  Why don't the Renaissance people rediscover the Stoics?

• 24:19Ryan Holiday?

  They do to a degree, but not to the same degree as like Lucretius. I think you tend to see the Stoics come up a bit later. You know, Montaigne, for instance, has a line from Epictetus carved in the beam of his ceilings. I don't know exactly, that is kind of an interesting question. It just comes, it comes a little bit later, comes a little bit later. The Enlightenment thinkers, though, love the Stoics. Jefferson dies with Seneca on his nightstand. John Adams is a big fan of the Stoics. George Washington, you know, is probably the only one of the founders who doesn't read the Stoics in Greek or Latin, only in English.

• 25:02Speaker 01

  Right.

• 25:02Ryan Holiday?

  And-

• 25:02Speaker 01

  Although he epitomizes the virtues the best.

• 25:05Ryan Holiday?

  He is probably the ultimate model of them as far as the American tradition goes. Two other little quick things. Cato, there's a play by Joseph Addison called Cato. Which I like to joke was the Hamilton of its day.

• 25:18Speaker 01

  Right.

• 25:19Ryan Holiday?

  But that's all Stoicism right there and is like so familiar to the founders that they're quoting it all the time, like in the way we might go immigrants, we get the job done. Lines like, I regret I have but one life to, you know, these are all lines from that play. And then, interestingly enough, Thomas Wentworth Higginson is the first American translator of Epictetus, and he leads a black regiment of troops in the Civil War. He's a friend of F. Emerson and stuff. So it just, it happens a little bit later and now they bring it up.

• 25:50Speaker 01

  The reason I was asking is it happens when the Enlightenment, the Age of Reason, and the scientific revolutions are happening. I was wondering if you thought those were connected?

• 26:00Ryan Holiday?

  Yeah, you're right. It's, it is a reason. It's a reason-based philosophy, and that's probably why it's so appealing there. And I mean, as a, I grew up Catholic, I'd probably classify myself as agnostic now. What I liked about Stoicism is I felt like it was making arguments that I was familiar with, having grown up in the church. But instead of saying, God wants you to do this, or if you don't do this, you're gonna go to hell, it's more saying like, you'll live an unhappy shitty life if you don't do that. Like, it's, it's an argument about your purpose and your meaning, but it's, it's less metaphysical than the religious argument. So I wonder if it has to do with the idea of the reason and logic is, that's the resurgent in that.

• 26:44Speaker 01

  Is Stoicism supposed to be just a path to virtue? Or is it a path to fulfillment?

• 26:49Ryan Holiday?

  I think both. It is not designed for a life of ease. It is.

• 26:54Speaker 01

  It's not the Epicurean.

• 26:56Ryan Holiday?

  Yes.

• 26:56Speaker 01

  It's rival philosophy.

• 26:58Ryan Holiday?

  Yeah. The distinction in the ancient world between the Epicureans and the Stoics, as Seneca says, is that an Epicurean will get involved in politics only if they have to, and a Stoic will get involved in politics, and by this they mean public life, unless something prevents them. So they're involved in the world. Instead of philosophy being the sole pursuit, I think the Stoics saw philosophy as a pursuit in whatever calling or domain you happen to be operating in. So there's the Stoicism of the soldier, there's the Stoicism of the statesman, the Stoicism of the blacksmith, the Stoicism of the slave, the Stoicism of the senator. It's how are, how is this philosophy helping you in whatever your unique circumstances are?

• 27:41Speaker 01

  Well, let me get back to Binks's dilemma at the end of the movie Golar, when he talks about, is that all there is? Is there a leap of faith? Is Stoicism in some ways divided from religion and spirituality?

• 27:55Ryan Holiday?

  Well, the Stoics certainly believed in the gods. And so there was, there was this, certainly this recognition of, of the higher powers, or that you are not in charge. I think fundamentally, the Stoics are saying, you're not God, or if there is a God, it is fundamentally indifferent to you. And so we have to figure out how to adapt ourselves and respond to whatever God's nature, fate, fortune sends our way.

• 28:26Speaker 01

  It sort of ties into deism then.

• 28:27Ryan Holiday?

  Yes. And again, this is, I think, why it makes so much sense to the founders. There's not the vengeful, omnipotent, all-controlling God, but there is, you know, when Washington says, "The event is in the hand of God", he just means, "We don't know how it's gonna go. Circumstances are gonna happen, but let's do our best." Actually, there's, there's a great line in that Cato play that I think encapsulates Stoicism, where they say, "We can't guarantee success, but we can do something better. We can deserve it."

• 28:57Speaker 01

  Yeah.

• 28:57Ryan Holiday?

  That's Stoicism. It's you do everything you can, and then you understand the outcome is ultimately not up to you.

• 29:04Speaker 01

  Let's get into some of the sayings, which you have at least 365 in any year. But the obstacle is the way, is the way you start it.

• 29:14Ryan Holiday?

  Yeah.

• 29:14Speaker 01

  Explain those type, they're not zen-like, they are, but they make you work.

• 29:20Ryan Holiday?

  That, that is what is so unique about Marx's Realist's Meditations. I think it's unprecedented in the philosophical canon, in that it was not intended for publication. It is not a philosophical argument. It is not an encapsulation of a school. It is a singular person riffing, reminding themselves of what they believe and what's important. And the reason there's so much repetition in it is that he needed that repetition. And actually, it's not in the Steve Book, I think it's in the beginning of your Da Vinci book. You talk about Da Vinci's journals and you you you mention that Steve Jobs, when you were working on the jobs book, he was trying to show you some journals he'd written

• 30:05Ryan Holiday?

  on a computer and even Steve Jobs couldn't get access to it.

• 30:08Speaker 01

  Right, right.

• 30:09Ryan Holiday?

  Because it was on a computer.

• 30:10Speaker 01

  It was on the next, you remember when he was in the wilderness, he had next computer.

• 30:14Ryan Holiday?

  Yes.

• 30:15Speaker 01

  And he was dying at this point and he still has an old next computer and he can't boot it up. And it did make me think there's really something beautiful about paper.

• 30:25Ryan Holiday?

  Yes.

• 30:25Speaker 01

  Which Leonardo used. It has an infinite battery life. It's operating system never goes out. And Steve could never get those memos and letters from the 90s.

• 30:36Ryan Holiday?

  Yeah.

• 30:37Speaker 01

  So.

• 30:37Ryan Holiday?

  And and I think Mark Schurros's meditations alongside Da Vinci's journals are the sort of ultimate testament of that because they're they're not for us and yet in spending time with them, we're able that that from the incredible specificness of them, there's a universality. And so here you have this this guy writing to himself. And and when he says you, he doesn't mean me, but he means him. And yet somehow centuries collapse and power dynamics collapse and cultures collapse. And you're like, oh, he's also talking to me. He's talking to all of us. But in in this famous passage, and he's he's almost certainly talking about somebody who was causing trouble for him. You know, he says, when people get in our way and obstruct us.

• 31:22Ryan Holiday?

  And then the passage continues, you know, this is nothing. He says, that can't actually happen. He says, because nothing can impede our intention or disposition because we can always change it. And he says, the impediment to action advances action, stands and the way becomes the way. The the Buddhists do have a saying, the obstacle is the path. So both east and west saying some version of the same idea that whatever this problem is, is actually not an obstacle, but an opportunity for you.

• 31:48Speaker 01

  So the impediment to the act, the impediment to the action is actually.

• 31:53Ryan Holiday?

  Where it's at. Yeah.

• 31:54Speaker 01

  Yes.

• 31:54Ryan Holiday?

  Where it's at. Where to go, what to struggle with. And that's not to say you hurl yourself at it endlessly. It might be the action is in going around, the action is in the patience for waiting it for it to go away, learning humility. What do you, it's basically, what are you learning? And what are you doing differently because of this thing that happened?

• 32:12Speaker 01

  Give us a couple more that are your favorites of the Stoic, or the either Marcus Aurelius's meditations or your own.

• 32:20Ryan Holiday?

  I can give you an unlimited amount. That's the one thing I'm good at.

• 32:22Speaker 01

  Three hundred and sixty-five.

• 32:23Ryan Holiday?

  I'll give you, I'll give you one from Epictetus. He says, "It's not things that upset us. It's our opinion about things."

• 32:29Speaker 01

  Interesting.

• 32:30Ryan Holiday?

  So, you know, the event is objective. What the person said to you is not rude. It is random sounds coming out of their mouth. And then you have told yourself that it's rude, or you've told yourself that you've been harmed by it, or humiliated by it, or insulted by it. So that the things are, and then we make opinions about them. And realizing that, oh yeah, like when I'm offended, that's because I have chosen to take that offense. That doesn't mean you should go around and say whatever you want to people and not care. But it's saying that, that we are, our sense of what these things mean and the interpretation we give of them determines how they affect us.

• 33:09Speaker 01

  So, and understanding that leads you to a more Stoic approach?

• 33:12Ryan Holiday?

  Yes, yes. Another one from, from Seneca, which I love, which I think is the, a life-changing one for me. He says, "It's wrong to think of death as something that's happening in the future once, that we're moving towards it." He says, "Death is now. Death is happening." He says, "The time that passes now belongs to death." And, and so to think of your life not as, you know, how many years do you have left? But how many years have you died? The Stoics are trying to get you to understand that, as Seneca says, you know, we're, we're protective of property, and we're protective of money, and then frivolous with time. And the Stoics want you to understand that your life is what's happening now, not this thing that might end in the future. It's ending now.

• 33:54Speaker 01

  All right, one more.

• 33:55Ryan Holiday?

  One more. Okay, what's a good one? Uh, Marcus Aurelius says, and this is one I think about these days. Maybe this, this ties to your, to your Elon Musk book. Here we have the most powerful man in the world. In some ways, an exception to the rule that absolute power corrupts absolutely. And there's a passage in Meditations where he talks about, he says, "Be careful not to be imperialized or stained purple." And so he's, he's wrestling with how How success, fame, an audience, all these things can change us. And, and so I think you, he says, you have to fight to remain the person that philosophy tried to make you.

• 34:34Speaker 01

  Wow.

• 34:34Ryan Holiday?

  And so, again, if we think of the philosophy as this aspirational thing, this standard that we'll probably never meet, not unlike the, the, the opening of the Declaration of Independence, that we're trying to live up to, that's probably closer to what the philosophy is, is supposed to be.

• 34:51Speaker 01

  Well, you raised your very wealthy neighbor from Bastrop, Texas, on the outskirts of Austin, and you've written about Musk in ways that allow you to reflect on Stoicism and him. Tell us that.

• 35:05Ryan Holiday?

  And we- Well, I was very influenced by your book, and I, and obviously I've read quite a, quite a bit about him. I just finished this series on the cardinal virtues. So, the courage, discipline, justice, the last one is wisdom. And I presented him as a, as a character, because I think he's someone sort of straight out of the pages of Plutarch, both incredibly gifted and incredibly flawed at the same time. And I, I tried to make the, first, the positive case for him being one of the smartest people on, I, I think I say at the beginning, to say that Elon Musk isn't smart, as some critics now try to do, is like saying he's not rich.

• 35:42Speaker 01

  Yeah, right.

• 35:43Ryan Holiday?

  It's hard to argue. He's done incredible things, and that's what makes the turn, or some of the other things that have, have been said or believed so, I think, both alarming, but also fascinating. How does someone become stained purple or Caesarified, changed by power, wealth, isolation, the algorithm?

• 36:07Speaker 01

  Mm-hmm.

• 36:08Ryan Holiday?

  I think, to me, one of the things I, it's like, if it can happen to him-

• 36:11Speaker 01

  Right.

• 36:12Ryan Holiday?

  What chance do the rest of us have to resist?

• 36:14Speaker 01

  And he sometimes fancies himself an adherent of Stoicism.

• 36:19Ryan Holiday?

  Yeah, I think he follows The Daily Stoic on, on Twitter.

• 36:23Speaker 01

  He's a fan of yours, even if it's not fully mutual.

• 36:26Ryan Holiday?

  Well, I'll say, I, I like to write about dead people. It's easier.

• 36:29Speaker 01

  I know. Trust me, I learned that. Yeah.

• 36:33Ryan Holiday?

  Also, you know, I wrote a book a few years ago about Peter Thiel. And actually, the epigraph is a line from Mark R. Percy. But I will say that was hovering in the back of my mind. It's you don't want to write about an angry vindictive billionaire. It's a scary thing, but I'm a fan in many ways. I just, I find, I find it emblematic of our times that here you have this person who in many cases should know better, not able to pull himself out of the either doom loop that he's in. Or, you know, I think.

• 37:07Speaker 01

  The demon loop.

• 37:08Ryan Holiday?

  The demon loop. Yeah, yeah. Well, I found that so fascinating in your book. I'd be curious to hear about it, but it's like so much of the mythology of the working endlessly in the factory and pulling it back from the brink. How often that was the same. It's like that famous meme of the guy in the hot dog suit where he's like, we're trying to find out who did this. Like you put yourself in the situation and then you're heroically going into demon mode to save it. The point is to not have to go into demon mode.

• 37:38Speaker 01

  But that's what he thinks, which is I can save it. I'm going to be the gladiator.

• 37:43Ryan Holiday?

  Yeah.

• 37:44Speaker 01

  I've got to put on the cape and do it. And he kind of pulls that up from classical philosophy, he thinks.

• 37:50Ryan Holiday?

  Really? But isn't, isn't an ounce of prevention worth a pound of cure?

• 38:07Speaker 01

  So tell me about The Cardinal Virtues was a great book. I read it on the way down, which is how that would apply to, you know, somebody trying to make their way in the world, all the tech bros here in Austin.

• 38:20Ryan Holiday?

  Yeah.

• 38:21Speaker 01

  How can you say, all right, here's the virtues you got to live by?

• 38:25Ryan Holiday?

  Yeah, I mean, I think courage, discipline, justice, wisdom. These are, these are timeless virtues for a reason. And they sort of pop up in almost all the different spiritual and religious traditions. Maybe sometimes they're rendered as five or seven or 10 or whatever. But they're all, we're all kind of dancing around the same human traits that we hold up. But I think, you know, wisdom is, I think, in many ways, the more relevant one in this moment right now, in this world of AI, where, where like people are convinced that all of a sudden you can have a computer do your thinking for you. And in fact, what, what AI presents to me is a. If you want to get, if you want to get a lot out of it, or you want to be prevented from being eaten alive by it, what you need is a, a strong liberal arts education.

• 39:10Ryan Holiday?

  So you know how to ask it the right things, how to parse the information and how to spot when it's obviously, and as they say, sort of hallucinatingly incorrect as it, as it often is. And so I, wisdom is, is the, the virtue I waited to the end of the series about, because I think it's sort of the one that unlocks all the others.

• 39:31Speaker 01

  And it is so much more important now.

• 39:34Ryan Holiday?

  Yeah.

• 39:34Speaker 01

  The wisdom, because as you say, many other things you can outsource. But that seems to be a fundamental human trait, right?

• 39:42Ryan Holiday?

  It does. And, and, you know, I think Elon Musk is a fascinating example of like, what happens when your information diet is corrupted?

• 39:49Speaker 01

  Correct.

• 39:50Ryan Holiday?

  When, when, when bad info gets in and then how it compounds.

• 39:54Speaker 01

  When you're training on a bad data set.

• 39:56Ryan Holiday?

  Yeah.

• 39:57Speaker 01

  Garbage in, garbage out.

• 39:58Ryan Holiday?

  Yeah, that's what's fascinating to me about his, his AI company. That, that seems like a flawed premise. Twitter, I can't imagine a worse data set for, if you're trying to deduce human wisdom out of something than, than, than scraping lots of tweets.

• 40:12Speaker 01

  Yeah, it's a good line. And thought, yeah.

• 40:14Ryan Holiday?

  Yeah, that's a scary thought. But, but I think, obviously, we're both biased as writers and authors. But I think people consume way too much real time information, way too much news. And actually, you'd be better off studying the life of Leonardo da Vinci or Benjamin Franklin. And that would tell you a lot about what's happening now and help you understand the world as it is now. And, and part of that is because not only have we had time to actually think and reflect on what this stuff means, but you're, you're less likely to project your biases or your partisanship on it. You, you want to go back and, and, you know, read about Truman or in the middle of COVID, read about the Spanish flu.

• 40:56Ryan Holiday?

  Or, um, you know, you want to, you want to study historical figures. I think it was Truman said, the only thing new in the world is the history you don't know.

• 41:05Speaker 01

  Right.

• 41:06Ryan Holiday?

  And, and so how do you root yourself in information with a long? Half-life, that to me is one of the the main arguments of the wisdom book. The thing and cardinal virtues being something that's had a pretty good half-life. Ideas that are still going to be here and still going to be true a long time from now. As opposed to the latest speculation about X, Y, or Z.

• 41:26Speaker 01

  Yeah, it's an anecdote to our information overload. But often, when you go back to the founders, as you've been talking about, they each exhibit the cardinal virtues, but in different proportions.

• 41:39Ryan Holiday?

  Yes.

• 41:40Speaker 01

  Washington of great rectitude, the passion of a John Adams or Samuel Adams. But it did seem to me, and I'm biased, that it took the Franklin, who was the wisdom person, the older person, twice as old as the rest of them. That was what held them all together.

• 41:58Ryan Holiday?

  I think so. And and I talk about this a little bit in the wisdom book. What I think is fascinating about Franklin is here you have the the smartest and and one of the most successful people on the planet. And he didn't have any enemies. People liked him, even even the British liked him.

• 42:15Speaker 01

  Right.

• 42:15Ryan Holiday?

  And he added on top of all of the virtues, a a friendliness and a savvy and an understanding of human interaction that that I think we don't celebrate enough. Like oftentimes, people use being smart and successful as as a way to disconnect from people, or it makes them like people less. But he.

• 42:39Speaker 01

  And that's Elon's case, which is that empathy is not your friend.

• 42:42Ryan Holiday?

  Yes.

• 42:43Speaker 01

  You don't want people to like you because that's a vanity.

• 42:46Ryan Holiday?

  Yeah.

• 42:46Speaker 01

  Whereas Franklin, to the extent he had a flaws, what you consider to be his virtue is he was so eager to make everybody like him.

• 42:55Ryan Holiday?

  Yeah.

• 42:56Speaker 01

  He did not exhibit the courage virtue in your book.

• 42:59Ryan Holiday?

  I think he did in some ways, but sure.

• 43:01Speaker 01

  Signing the declaration was an act of courage.

• 43:03Ryan Holiday?

  Yes. But but yeah, he he was, he had the.

• 43:07Speaker 01

  Well, I guess what I'm asking is, can you go too far to wanting people to like you?

• 43:12Ryan Holiday?

  Well, Aristotle said, you know, all the virtues sit as a midpoint between two vices.

• 43:17Speaker 01

  Right.

• 43:17Ryan Holiday?

  And I think some of some of us are more of one than the other. I think we're all kind of. And what what is so interesting about the cardinal virtues and why it's such a, I think, a genius formation is is that they all moderate each other. So.

• 43:35Ryan Holiday?

  Courage, not just is moderated by, at a certain point, it becomes recklessness, but courage, if not in pursuit of justice, becomes an empty and a valueless virtue. Wisdom tells us not just what causes are sort of good or bad, but also how one might bring them into the world, right? Like, what the competence needed to bring about a political revolution or outflank a bureaucracy. I mean, I think Elon deserves a lot of credit for not just that he had these brilliant scientific ideas, Steve Jobs as well, but their ability to organizationally and logistically

• 44:18Ryan Holiday?

  bring them into the world, that's also, I guess, probably discipline, the sort of the work ethic. But so all the virtues balance each other. At Zeno, 2,500 years ago, is basically saying they are separate but inseparable from each other.

• 44:34Speaker 01

  And that's something we've lost today is the notion that balance is the key to things, that going way out with any particular virtue can be a flaw.

• 44:44Ryan Holiday?

  Yes, yes, that you can have too much of a good thing or not enough of a good thing. And that's, I think, discipline is sometimes rendered as temperance.

• 44:53Speaker 01

  Yeah.

• 44:54Ryan Holiday?

  And that's not a very sexy word in, you know, in especially in America.

• 44:58Speaker 01

  Although, in the virtues of Ben Franklin, he has 12, and then adds humility. Temperance is number five.

• 45:04Ryan Holiday?

  Yes.

• 45:04Speaker 01

  Now, I did not listen. We were in the green room talking, and we're having such a good time. And I think you came in and told us all the logistics, like exactly how long we're supposed to go. Ryan Holiday, an amazing dude.

• 45:18Ryan Holiday?

  Thank you so much.

• 45:24Ryan Holiday?

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