How The Stoic Virtues Became Ryan’s Greatest Test | Billy Oppenheimer & Ryan Holiday

What does six years of studying and writing about the Stoic virtues really teach you? In today’s episode, Ryan sits down with longtime research assistant Billy Oppenheimer to look back on how the Stoic Virtues Series came together, from the first hike where the idea was born to the final chapter of Wisdom Takes Work. They talk about what it means to grow up alongside your own work, how each book became the lesson Ryan needed at that moment, and why wisdom can’t be outsourced. Billy Oppenheimer is Ryan Holiday’s research assistant and the writer behind the newsletter, Six at 6 on Sunday. To read more of his work, check out his website billyoppenheimer.com.📖 Wisdom Takes Work by Ryan Holiday is out NOW! Grab a copy here: https://store.dailystoic.com/pages/wisdom-takes-work🎥 Watch the video episodes on The Daily Stoic YouTube channel: https://www.youtube.com/@DailyStoic/videos🎙️ Follow The Daily Stoic Podcast on Instagram: https://www.instagram.com/dailystoicpodcast✉️ Want Stoic wisdom delivered to your inbox daily? Sign up for the FREE Daily Stoic email at https://dailystoic.com/dailyemail🏛 Get Stoic inspired books, medallions, and prints to remember these lessons at the Daily Stoic Store: https://store.dailystoic.com/📱 Follow us: Instagram, Twitter, YouTube, TikTok, and Facebook 📢 Share | ⚙️ Manage Subscription

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

• 0:06Ryan Holiday?

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

• 0:51Ryan Holiday?

  Hey, it's Ryan. Welcome to another episode of the Daily Stoic Podcast. I heard you guys. I have heard the overwhelming number one piece of feedback that you have given me on this podcast, at least on the interview episodes, which is that there's too much of the guests and not enough of me, right? I get it. I don't interrupt them enough. I don't answer my own questions enough. I don't give my point of view enough. I just ask really short, tight questions, and then I turn it over to the guest. And that's what I've been doing here on the Daily Stoic Podcast for years and years. And you want to hear more of me, right? I mean, look, obviously, I know that's not the feedback.

• 1:33Ryan Holiday?

  I do occasionally see the comments. They trickle back to me in some form or another that I'm not turning it over enough to the guest. I do say, as Tyler Cowen's great line is, that this podcast is the conversation I want to have, not necessarily the conversation you want to have. And that it's, I try to see it less as an interview and more of a discussion, but...

• 1:57Ryan Holiday?

  I am trying to get better. I have one of the, one, actually, one of the chapters in Wisdom Takes Work, which is out this week, is all about Xeno's famous dictum about having two ears and one mouth for a reason that we have to listen much more than we talk. I do try to practice that restraint. I think I'm getting better at it. So this really drives you nuts. This is probably not the episode for you, but I was excited to do this. And I'm actually excited for you to hear this one because it involves someone whose work I like, who I think is promising and sort of an up and comer. And I'm not talking about myself. I'm talking about the interviewer here because this is a turn the tables interview. Billy

• 2:39Ryan Holiday?

  Oppenheimer has been my research assistant for many years now. He has done all sorts of great work for The Daily Stoic. He helps me prep my articles. He helps me track down leads or ideas. I'm really bad at finding out how to get things that are behind various paywalls or out of print. He finds all sorts of obscure stuff for me. He was just helping me out this weekend. I'm going out of town first to Los Angeles to do a week of promo for the book and then to New York for a week of the promo of the book. And he is printing out my big collection of research for the book that I'm working on now. He's amazing at it. He's great. He also, I will say, has a great newsletter that you should subscribe

• 3:19Ryan Holiday?

  to called The Sunday at Six, which I have seen grow from a tiny little thing. I could take some credit. I was the one that sort of pushed him to start doing it. And now when podcast guests come into the studio, they go, is Billy here? Because they get his newsletter, which is always delightful to see. But my point is, Billy and I have worked together a long time. None of the books in the Virtue series would have been fully possible without him. Where they are good, in many cases, that was a direct contribution from him. Or they're bad, I'll take the hit for that. But Billy and I sat down and had a long conversation in early October before the media tour really started. So I could kind of work through what I was thinking on the book. He had some questions for me.

• 4:02Ryan Holiday?

  We talked about the process and, and this project we've been working on. Together. And I think it's a great interview. This question, is it getting harder for me to be lit up by stories? I have to get excited about stuff, to which my answer is unequivocally no. I fucking love doing this. I love doing this. And I am, as we talked about in the interview, like pumped about what I'm working on now. In fact, the only thing I don't like about tours is that it distracts me from getting to write the next thing. Hopefully you've picked up on this by now. You haven't been listening very closely if you haven't. But the new book Wisdom Takes Work, Learn, Apply, Repeat, the fourth and final book in the Stoic Virtue Series is out. We've got a bunch of awesome bonuses that we're continuing, dailystoic.com/wisdom.

• 4:45Ryan Holiday?

  You can get dinner with me to talk about the book. You can get pages from the manuscript, which have my notes on them. Sometimes they have Billy's notes on them and a bunch of other awesome stuff, including some chapters that I've been working on for a long time that I didn't get to put in the book. All of that, right now, dailystoic.com/wisdom. It would mean so much to me if you could preorder the book. And then I want to get into this episode right here, right now, and I hope you enjoy it. And as I said, sign up for Billy's newsletter. I get it every Sunday. I'm recording this on a Sunday. It will come two and a half hours from now, and it's always great. And it's always fun for us to talk about that email that he does. I reply most days. Anyways, let's get into it and I'll bring you part two later in the week.

• 5:32Ryan Holiday?

  Did you think we'd ever actually get here?

• 5:34Billy Oppenheimer?

  No.

• 5:35Ryan Holiday?

  Because you were at the beginning of the whole series, right? You started right as I was starting the research for Courage.

• 5:41Billy Oppenheimer?

  Yes, 2018. You had just finished Stillness.

• 5:46Ryan Holiday?

  No, 2019. Stillness finished. Oh, Stillness came out in 2019.

• 5:50Billy Oppenheimer?

  Yeah.

• 5:50Ryan Holiday?

  So wait, were you, so you were there before you even had the idea?

• 5:53Billy Oppenheimer?

  Yes. That's actually where I wanted to start.

• 5:56Ryan Holiday?

  Oh, did I have you fill in some stuff on the proposal?

• 5:59Billy Oppenheimer?

  Yes.

• 5:59Ryan Holiday?

  Really?

• 6:00Billy Oppenheimer?

  Yeah.

• 6:00Ryan Holiday?

  Okay. So that's the summer of 2019.

• 6:03Billy Oppenheimer?

  Yes. I remember one of the first articles I worked on when I started working for you was a piece you had, you were writing about having the idea for the series.

• 6:15Ryan Holiday?

  Oh.

• 6:15Billy Oppenheimer?

  After, sort of just of the articles, like you stepped away from working one day to go on a hike with your kids. And you had the idea on that hike.

• 6:23Ryan Holiday?

  Yes.

• 6:24Billy Oppenheimer?

  And then I remember a line in that, that piece, I was like, and just like that, my next four years had been laid out in front of me.

• 6:32Ryan Holiday?

  Wow.

• 6:33Billy Oppenheimer?

  And it turned out to be six years.

• 6:34Ryan Holiday?

  Yes. Well, and there was a pandemic in there and a lot of other stuff. That's really interesting. Well, it's funny because I was just, I just went for a run in that park over the weekend and there's like trees that weren't there before because the whole forest burned down in 2011 and then some other parts of it burned in 2015. So like, it was striking to me like how much it has changed. And then I made a joke in the talk that I did in Austin that like I can measure the whole series in inches because my, my youngest was like a baby when I had the idea. And so he's like this tall.

• 7:14Billy Oppenheimer?

  Yeah. He was like in a backpack on, on the hike.

• 7:17Ryan Holiday?

  Well, I was thinking about that because I was, I said that to Samantha and he, he would have been in a front carrier and the oldest would have been in a backpack because he would have been way, he was born in May. So he would have been too young to put in a backpack. But yeah, I thought that would be four years of work, but I ended up in the middle, right after Discipline, which Discipline came out of the gate much faster than anyone thought. Like it sold much better than even I thought. And so my publisher said, do you have any other ideas? And I told him I had these other two ideas, but part of the condition of that, those other two was that I would get an extra year off. So I took a year off between Discipline and Justice, which is actually more like 18 months, say, pushed. I slowed the whole thing down.

• 8:00Billy Oppenheimer?

  Yeah.

• 8:00Ryan Holiday?

  And so it took longer than.

• 8:02Billy Oppenheimer?

  Well, you put the Justice book in the metaphorical drawer for a little bit.

• 8:07Ryan Holiday?

  Which I had talked about in Discipline. Yeah. So I also kind of liked following my own advice a little bit.

• 8:11Billy Oppenheimer?

  It's crazy that you've been working on the series, Jones, his whole life, essentially.

• 8:16Ryan Holiday?

  Yes. That's what I'm saying. He's like this tall. I mean, he, he went from not being able to walk, to being able to walk, to not being able to talk, to being able to talk, to being able to like, read words in the final book.

• 8:27Billy Oppenheimer?

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

• 8:35Ryan Holiday?

  Uh huh.

• 8:35Billy Oppenheimer?

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

• 8:40Ryan Holiday?

  Education?

• 8:41Billy Oppenheimer?

  Yes.

• 8:42Ryan 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 book? I think it's a trilogy. Anyways, at 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

• 9:26Ryan 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 virtue 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 know, you're working from home, reimagining, it just like as it dragged on, and then justice in the middle

• 10:09Ryan Holiday?

  of a sort of social justice awakening, and then a political turbulence and turmoil, and then wisdom as my kids are, you know, sort of now fully in school, and the mainstream integration of artificial intelligence, and also, you know, a time of political misinformation and disinformation, and making sense, you know, Orwell talked about how to like, 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?

• 10:52Billy Oppenheimer?

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

• 10:57Ryan Holiday?

  Sure.

• 10:58Billy Oppenheimer?

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

• 11:02Ryan Holiday?

  Yep.

• 11:03Billy Oppenheimer?

  Which is just like, how ancient the-

• 11:07Ryan Holiday?

  Desire for shortcuts is?

• 11:08Billy Oppenheimer?

  Yes.

• 11:08Ryan Holiday?

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

• 11:16Billy Oppenheimer?

  Yeah.

• 11:16Ryan 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.

• 11:28Billy Oppenheimer?

  Yeah.

• 11:29Ryan Holiday?

  And

• 11:29Billy Oppenheimer?

  Slave is like an L L M for like,

• 11:31Ryan 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.

• 11:47Billy Oppenheimer?

  Mm hmm.

• 11:47Ryan Holiday?

  There was a different intro, which I don't remember what it was built around exactly, but that came later.

• 11:52Billy Oppenheimer?

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

• 11:55Ryan Holiday?

  Yeah.

• 11:56Billy Oppenheimer?

  And it made me think of the Seneca story.

• 11:58Ryan Holiday?

  Oh, is that what happened?

• 11:59Billy Oppenheimer?

  And I was like, probably a chapter on this.

• 12:01Ryan Holiday?

  Yes.

• 12:02Billy Oppenheimer?

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

• 12:06Ryan 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.

• 12:46Billy Oppenheimer?

  Yeah.

• 12:46Ryan 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,

• 13:28Ryan Holiday?

  if I'm remembering correctly. Courage is Churchill and justice is, who's the main person in justice? I don't remember. Florence Nightingale? No, no, in the intro. Oh. 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. Slammed on the phone.

• 13:54Ryan Holiday?

  What was it like to have it? I mean, you have an actual copy there. 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. Yes. 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. Right. Cause it leaves, it leaves, in my process, it leaves Google at some point and goes into Microsoft Word. Yes. 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 stuff. Yeah. 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.

• 14:39Ryan 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. Yeah. But even. I mean, I sat here in this room to do the audiobook and there was like still changes I was making.

• 15:22Billy Oppenheimer?

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

• 15:25Ryan Holiday?

  Yeah.

• 15:25Billy Oppenheimer?

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

• 15:37Ryan Holiday?

  Really?

• 15:38Billy Oppenheimer?

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

• 15:43Ryan Holiday?

  Yeah.

• 15:44Billy Oppenheimer?

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

• 15:49Ryan 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. 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. And I considered it and there just wasn't anything that like called to me that like really felt like that would be right.

• 16:34Ryan Holiday?

  And it wouldn't just be like sort of performative weirdness, you know? Like there, I had this fantasy, like, what if I just did like really short, you know?

• 16:41Billy Oppenheimer?

  Yeah.

• 16:42Ryan 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 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, it's just 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 things that I wanted to say.

• 17:25Ryan 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 it 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.

• 18:09Ryan 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 how do we sort of lionize one and then steer clear of the others? So it took a while. But it's funny that it came together on a bike ride.

• 18:30Billy Oppenheimer?

  Yeah.

• 18:30Ryan Holiday?

  I wonder when that was.

• 18:42Billy Oppenheimer?

  Part one opens with Montaigne.

• 18:45Ryan Holiday?

  Yeah.

• 18:45Billy Oppenheimer?

  A most unusual education.

• 18:47Ryan Holiday?

  Yeah.

• 18:49Billy Oppenheimer?

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

• 18:54Ryan Holiday?

  Like, sure.

• 18:56Billy Oppenheimer?

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

• 19:02Ryan 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,

• 19:44Ryan Holiday?

  is asking her 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.

• 20:21Billy Oppenheimer?

  Yeah.

• 20:21Ryan 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.

• 20:48Billy Oppenheimer?

  Yeah, there's a great chapter on finding your classroom, which seems related here, like, and it, the emphasis on like, your classroom.

• 20:56Ryan Holiday?

  Yeah.

• 20:56Billy Oppenheimer?

  You know, like, it's, it's relative, and it's specific to like, your interests and inclinations, and finding that place being crucial.

• 21:05Ryan Holiday?

  Yeah, you know, it was funny, I was actually just talking to this parent at my son's school, and he was thinking about writing a book. He's a very well-known athlete, and I was thinking about doing a book. And so I sent him the Chris Bosh book that I had worked on. And he said, your name's not in this, did you work on this? And I was like, yeah, I was the ghostwriter. And he was like, I don't want to like, hurt your feelings, but like, why would you ghostwrite a book? He's like, you could write whatever you want, why would you work on someone else's book? And I said, well, someone has to pay for my kids to go to this school, because it's not cheap. But I was saying that the reason I ghostwrote for a long time was that it was not just free reps, but it was like, getting paid. Paid to get reps, you know?

• 21:48Ryan Holiday?

  It was that I was learning the craft, even though obviously I was pretty good or I wouldn't have been being paid to work on someone else's book. But I've done all the books that I have done that people have seen, and I've also done, you know, a half dozen or more, and consulted and edited many, many others. Like, my breadth of experience is wider than just the things that have my name on them. And so my classroom was not just working for Robert Greene. And then, you know, I think I've gotten better at each one of my books. But my classroom was also, you could call this like a sort of publishing 101 education, where I'm learning the proposal process and I'm learning the writing process. And I'm dealing with difficult editors and great editors.

• 22:31Ryan Holiday?

  And what happens when you have too much, like, how do you solve? How do you, how do you work on a project where you have too much material? And how do you work on a project where you don't have enough material? And how do you work on a project where the person's super engaged? And then when they're not engaged? And, you know, how do you work on one for this kind of audience? And then an older audience, and then a younger audience? And, you know, just like, just doing it different ways.

• 22:55Billy Oppenheimer?

  Yeah.

• 22:55Ryan Holiday?

  My secret in life, I think, has been that I figured out how to get paid to learn a lot of things. And Robert Greene paid me to teach me how to be a researcher. And then I started getting paid to give talks from like the first talk that I ever gave. And so then I spent, you know, probably five or six years getting good at it. And then the last five or six years, you know, taking that education and, you know, like, whenever you can bite off more than you can chew and then have to scramble to learn on the job, that can be a stressful experience, but it's a pretty wonderful experience.

• 23:37Ryan Holiday?

  And it's like the ultimate sort of career slash life hack. Like, I think about it like, I was studying all these sort of military guys. And just like the idea of like the Navy or the Army or whatever, sending you back to get into it. It's like, you're getting paid to go to school, not like you're getting your school for free.

• 23:54Billy Oppenheimer?

  Yeah.

• 23:55Ryan Holiday?

  Like, they're getting paid to go to this university. That's like the dream, I think, right? Like, to, you know, and so I've always kind of sought those experiences out.

• 24:07Billy Oppenheimer?

  Yeah, there's, there's a, makes me think of a footnote, I think it's in the afterword. You also paid to leave school.

• 24:14Ryan Holiday?

  That is true, yes. When I dropped out of college, I went into the registrar's office to leave and I was like, you know, I'm here to drop out of college. And that's not really a thing, which I was surprised to find out. Like, I would have been nice to know before I told my parents that I was dropping out, you know, like, because then I could have said, oh, I'm taking a semester off. And that would have been a slightly lower stakes confrontation. But yes, I went through a bunch of papers that I had when we moved from my old office to this office. And I found the form and there was a receipt stapled on it. And it was like $40 to leave UC Riverside.

• 24:55Billy Oppenheimer?

  Yeah.

• 24:56Ryan Holiday?

  The other thing which I told at the Austin talk that I just gave, which is, you know, as you get older, just certain mortifying things that you did, just like going through your life, you're on a walk, you're falling asleep, you're talking to someone, and you just get like viciously attacked by the memory of something stupid that you did when you were younger. And you're just like, oh, no.

• 25:20Billy Oppenheimer?

  Yeah.

• 25:20Ryan Holiday?

  You know, and I don't remember exactly where I was, but it just, I just recalled one day that I had written my college admissions essays on the difference between schooling and education, which I thought was so clever. I remember thinking it was clever.

• 25:37Billy Oppenheimer?

  Yeah.

• 25:38Ryan Holiday?

  And then when this, I was like, oh, that, that's why I didn't get into the places that I wanted to.

• 25:43Billy Oppenheimer?

  You didn't know your audience.

• 25:44Ryan Holiday?

  Not only did I not even know my audience, it didn't even conceive to me that it hadn't been positively received. Like, I was just thinking like, oh, it must have been my grades or my SATs. And then in retrospect, it was like, probably all the essay as a disqualifying, like, just what a, what a presumptuous, petulant, like, like conceded, dumbass, 17-year-old thing to do.

• 26:12Billy Oppenheimer?

  Yeah.

• 26:14Ryan Holiday?

  And I don't think I thought there was anything trans. Maybe I thought there was something a little transgressive about it and I thought they would appreciate it, but like in retrospect, why would they appreciate? I was literally saying that I don't think school is important.

• 26:27Billy Oppenheimer?

  Yeah.

• 26:27Ryan Holiday?

  Please allow me to come to your school. But I ended up, I mean, I went to Usher Riverside on a scholarship and I met my wife there. So it worked out, but that was a dumb thing to do.

• 26:37Billy Oppenheimer?

  You tell the story of a conversation, I think it was when somebody in Hollywood of like, you can pay to stay in school and learn these things or go get like real world experience. And that was kind of the.

• 26:48Ryan Holiday?

  Well, what he said is he said, do you want to? So I was working at this talent agency, my, the summer of my sophomore year, I was about to go back. I put a deposit on the house that I was going to live in. I'd picked it, I'd gone back. Samantha still lived there, so I got back, I picked out an apartment. I was excited and I think I had enrolled in my classes. And he's like, so you're still thinking about going back? I was like, what do you mean still? Like, that's obviously what I'm doing. And he was like, what if you didn't? And what do you mean? And he said, well, you could work for me as my assistant. And I was like, you have an assistant, she's sitting right there. And he was like, yeah, she's not going to last very long. I would like you to be my assistant and not go back. And I thought about it and I think I decided not to do it.

• 27:31Ryan Holiday?

  And I remember this could have all been one conversation or a few, but I said, yeah, I think I'm going to go back. He's like, if you want to go back to school and read in the newspaper, and this is a example that I guess made more sense at the time, but he's like, do you want to read in the newspaper about stuff you could have been a part of? It's kind of like, you know, the Steve Jobs thing where it's like, you want to go sell sugar water for the rest of your life?

• 27:56Billy Oppenheimer?

  Yeah.

• 27:56Ryan Holiday?

  You know, he was like, look, do you want to go read about people doing stuff? Or do you want to do stuff? And I thought that was a pretty, I think it was right. And basically like a couple of days later, Robert Greene asked if I wanted to be his research assistant. And so my calculation was actually less thinking about the Hollywood thing and more thinking about like, if I wanted to be a writer and I was going to get a minor in creative writing, if the end of this.

• 28:25Ryan Holiday?

  Education in politics and creative writing was that I could get a job for someone like Robert Greene. My parents would be like, good job. Like, that's why you went to school. And I would, I would think the same thing. So I'm gonna say no to that. Go back, finish the thing, and then hope that the offer's still here, or that lightning strikes twice, I get a similar offer. That seems crazy. So I, I dropped out. I remember being very, very stressed about the $900 deposit that I didn't get back, which in retrospect was just silly. Which is actually a great lesson, because I remember I was just talking to someone, you, you knew them, they worked for us for a brief time. They were like, making this major life decision about like, they were like, well, I have all my stuff, you

• 29:10Ryan Holiday?

  know, I can't do this, I have to put all my stuff. So, and I was like, a storage unit is $80. Like, you're gonna alter the course of your life because you don't wanna put boxes in storage to see where this goes? That seems dumb.

• 29:23Billy Oppenheimer?

  Yeah.

• 29:23Ryan Holiday?

  You know? And $900 is a lot of money to me in 2005, because I'm making like, nothing. But, but anyways, the funny thing is I, so I decided to drop out, and he was like, gonna let go of his assistant, and then tell everyone. And then I, so I went back to college, packed all my stuff to come, and blew up my life, basically. And then I came back, and that Monday, he wasn't there. And the assistant was there, and everyone was very confused as to why I was there. And he had checked into rehab over the weekend, and was totally unreachable. And

• 30:06Billy Oppenheimer?

  Did not inform that

• 30:07Ryan Holiday?

  Had not informed anyone, and no one knew what his future slash, you know, what had happened, why had happened, why it had happened, and why I was there. And obviously, this somewhat perceptive person picked up on the, you know, and it was, you know, it was like a rest of development. I may have made a huge mistake.

• 30:26Billy Oppenheimer?

  Yes. When did like, your sort of voracious reading, I, because there, you tell a story of, of a teacher catching you reading a Louis Lamour book, right?

• 30:35Ryan Holiday?

  Yeah.

• 30:36Billy Oppenheimer?

  And then I've heard you talk about like, later being introduced to like, Maybe higher.

• 30:40Ryan Holiday?

  Books?

• 30:40Billy Oppenheimer?

  Yeah.

• 30:41Ryan Holiday?

  I mean, not that he, and actually, his memoir, Education of a Wandering Man, is incredible.

• 30:45Billy Oppenheimer?

  Yeah.

• 30:45Ryan Holiday?

  It's totally a memoir about self-education and how you can get an untraditional and interesting education that fits you perfectly to do difficult, unusual, interesting, even lucrative thing. It's one of the great memoirs, actually. If we don't carry in the bookstore, we should.

• 31:03Billy Oppenheimer?

  What's it called? Education?

• 31:04Ryan Holiday?

  Education of a Wandering Man, I think. It's amazing. You're reading that Eric Hoffer book, right?

• 31:10Billy Oppenheimer?

  Yeah.

• 31:10Ryan Holiday?

  They're kind of similar.

• 31:11Billy Oppenheimer?

  Yeah.

• 31:11Ryan Holiday?

  Like, he is like, reading books like in these mining camps and, you know, like, working on dude ranches and stuff.

• 31:17Billy Oppenheimer?

  Yeah.

• 31:18Ryan Holiday?

  It's really good.

• 31:30Ryan Holiday?

  Yeah, in 4th grade, I was reading a Louis Lamour book, and my 4th grade teacher caught me reading it in class instead of paying attention. And instead of being upset, she was like, proud of me. I first didn't believe that I could possibly be reading this book. And that was like, the first time anyone sort of took any notice of me. And she put me in some special classes and stuff. But I mostly just read more books like that for like, the next 10 years. Because I don't think my parents had read, not that they're not smart, but I think like, if it wasn't like, at Costco.

• 32:04Billy Oppenheimer?

  Yeah.

• 32:05Ryan Holiday?

  It wasn't like, the kind of book they were reading.

• 32:07Billy Oppenheimer?

  Like, you're stealing your sister's books.

• 32:09Ryan Holiday?

  Oh, yeah. Like, yeah, I read all the Nancy Drew books and all the babysitters. I would just read whatever was there. The idea that there was like, this rabbit hole that you could go down, that you could follow different subjects. You just don't know what you don't know. And my parents didn't know stuff, and then I didn't know that. And I, I mean, I had the experience of going to the library, but they would be like, come over here to the kids' section, you know? And so I read a lot of young adult stuff, and some of it was informative, and I read a lot of Westerns. I do remember, so I loved Westerns, because I loved those Louis Lamour books. We would go to the grocery store, and there was always a little book section. And I remember, I'd read all the Louis Lamour books, so I grabbed this other one. It was this other series.

• 32:49Ryan Holiday?

  But it turned out to be like a, like a ladies' western, like it was like an erotic book. And that was pretty scarring and weird as I was like waiting for the gunfights. And then there was just like a lot of, just a lot of sex scenes, which was both eye opening and unnerving as like a fifth grader or whatever.

• 33:10Billy Oppenheimer?

  Waiting for the gun scene.

• 33:11Ryan Holiday?

  Yeah, yeah. When is it? It was just like, it was like the westerns, but instead of the gun scenes, there's just a lot of scenes in the bordello's and things. But, uh, so yeah, I read mostly, I wouldn't say trash as that seems to me. And reading is reading, but I read mostly a lot of those kind of books until, yeah, I just fell down or I started getting exposed to other, other books at some point.

• 33:33Billy Oppenheimer?

  Yeah. The reason I was bringing, like when you were talking about getting paid to learn through ghostwriting and real world, like, so I was thinking of the Da Vinci thing in the book of being a disciple of experience and a disciple of received wisdom. So at some point, like the combining the real world experience, but also all this reading you're doing.

• 33:54Ryan Holiday?

  Well, one of the things that working for Robert was amazing at is like, first off, he would be like, I need you to go read about this 16th century, you know, astronomer or this cleric from this or read about this. They were just assignments. So it was like being in college, but there was much more unusual. And then I'd be like, that was really interesting. Is there anything else like that? And he'd be like, well, have you ever read this? And the answer was like, almost always no.

• 34:20Billy Oppenheimer?

  Yeah.

• 34:21Ryan Holiday?

  And so, you know, there was that. And then obviously when I went to college and then, you know, I would obviously the Stoics, but you know, just reading these philosophers and then just being interested. Oh, I let me read the next thing and the next thing and the next thing. There's a scene, one of my favorite stories in the book, one of my favorite stories ever is this story about Harry Belafonte, where he's in the Navy and someone gives him a copy of W E B Du Bois's memoir. And he's reading it and he gets to the end and he's, he's like, I gotta read more stuff like this. And so it gets to the bibliography. It just says like, I bid, I bid, I bid, I bid, I bid a lot. And so he's like, well, I'll just read that, you know, who's that? And he goes to the librarian and he asks her, give me all the books you have by a bid.

• 35:06Ryan Holiday?

  And she goes, I'm sorry, there's no author like that. And he thinks he's being stonewalled by a racist librarian, which would have been a reasonable interpretation of the events in the 1940s. But and I'd never actually, I just, I knew what it was. No one, no one ever told me this either, that it stands for ibidis or ibetus. I don't know. I don't even know how to pronounce it. It's a word I've never heard a human being say. I've only seen in the back of books. But that just means like, like the book above, or you know.

• 35:36Billy Oppenheimer?

  Yeah, it's like we, we've already used the title. It's a shorthand for like same book, different page.

• 35:41Ryan Holiday?

  Same title, yeah, same title, different, different footnote.

• 35:44Billy Oppenheimer?

  Yeah.

• 35:45Ryan Holiday?

  Connected. And so he just didn't, he didn't know that. And he stormed, he stormed out of the library in anger. And he later tells W. E. B. Du Bois's story. And he said his dying regret was that he never got to meet the librarian again to apologize. But I, I had that experience of just like, reading a book and then being like, I love this scene. And I learned this to do this with Robert too, where you're like, you read something and it's just that this section is really interesting to you. And you go like, well, where do they get this section? And then you go to the, like, for many years, I would almost always find my next book from the bibliography of the book that I just finished. And not always the bibliography, sometimes it's just mentioned in the text itself. And

• 36:27Ryan Holiday?

  I would circle it and go back to it. But yeah, once you get connected to a couple good books, you almost don't need anyone else.

• 36:35Billy Oppenheimer?

  Yeah.

• 36:36Ryan Holiday?

  Because you can follow that chain for the rest of your life.

• 36:39Billy Oppenheimer?

  Yeah. Well, that made me think of the, the John Wheeler thing of like, as your shore of knowledge grows, so does, or island of knowledge.

• 36:48Ryan Holiday?

  Island of knowledge grows, so does the shoreline of ignorance. As the island gets bigger.

• 36:53Billy Oppenheimer?

  Yeah.

• 36:53Ryan Holiday?

  It touches more shit that you don't know.

• 36:55Billy Oppenheimer?

  Yeah.

• 36:56Ryan Holiday?

  Which is kind of an interesting way. It's an interesting, I think I put this in the, with the bibliography of ego. Do you know where I heard that, that quote?

• 37:03Billy Oppenheimer?

  No.

• 37:04Ryan Holiday?

  So again, this is the idea of traces. Okay. I was on a Southwest flight and I was reading the Southwest magazine. Again, this is a long time ago, apparently, because they don't even do that anymore. But I'm reading the Southwest magazine and there is a interview with Neil deGrasse Tyson.

• 37:20Ryan Holiday?

  He says, he's like, it's like that famous quote, you know, he mentions it in some way, not directly, but he alludes to it or he riffs on it. And I was like, I've never heard that before. What is that? And I went and I found like the original source for it. So many of my books come from random, one-off.

• 37:38Billy Oppenheimer?

  Yeah. Well, another good example of that is the Izzy Rabbi story.

• 37:43Ryan Holiday?

  Oh, yeah. That was a weird one.

• 37:45Billy Oppenheimer?

  Where you first came across it, it was told as if it happened to someone else.

• 37:51Ryan Holiday?

  Yes.

• 37:51Billy Oppenheimer?

  And then you track it down.

• 37:53Ryan Holiday?

  Yeah, that is true. Yeah, I read it in the Patrick Raden Cleef, oh, Patrick, whatever, Empire of Pain.

• 37:59Billy Oppenheimer?

  Yeah.

• 37:59Ryan Holiday?

  About the Sackler family. And what, yeah, what was really interesting about that story is he tells it as if it happened to him in that book. Arthur Sackler tells that story as if it happens to him. But we traced it, I think Kristo did that research on that, right? That's my other research assistant, my first research assistant. And I was, usually what you'll do is you'll find an anecdote or an idea. And it's not like the primary source. You gotta go back and find more about it. And so we went back and it turns out he first told the story like in the 60s or something. But it had been about his friend growing up, a different scientist.

• 38:39Billy Oppenheimer?

  Yeah.

• 38:40Ryan Holiday?

  And then over time, and this is something that keeps me up at night. Over time, he told the story so many times that he just made himself the center of it.

• 38:47Billy Oppenheimer?

  Yeah.

• 38:48Ryan Holiday?

  And he cut out his friend. And at the book I'm doing now, I'm like, it was interesting. We just found like, in his oral history, he tells this story about being on the block where this famous person lived. But then we found a letter that he wrote in 1952 where he vividly describes to his parents, meeting the person and shaking his hand. So which one do you trust? Yeah. Do you trust the memory of the person in their eighties? Even though in their eighties, they're telling the less interesting version of it? Or do you trust the younger version, the contemporaneous version, which is more interesting? And then you go, well, which one would they be like?

• 39:31Ryan Holiday?

  Like you would, you'd probably normally defer, you'd play it on the safe side. But then you're like, is that actually the safe side? Like, because like, this is a pretty detailed lie, if it's a lie. Yeah. So anyways, this is all inside baseball of whatever. But that one was interesting where it's like, that story was really good. But the problem with that story is that the Sackler family sucks. Like they're directly responsible for the opioid crisis. Yeah. And although Arthur Sackler dies before. Right. What's it called? Oxycontin is invented. It's his nephew that does it and his brothers.

• 40:12Ryan Holiday?

  But I had a way, if it was him, I was going to circle back to him as an example, as a cautionary example also. So I was going to do positive and negative. But then to find out that actually it's about a different Nobel Prize winning physicist. It was him asking Isidore, why did you become scientists? Yes. And not a lawyer or? Yeah. And he says, well, my mother, every day when I would get home from school would say, you know, did you ace your test? Or how are your grades? She would say, did you ask a good question today? And I love that story. It's an amazing little anecdote. And then, yeah, all of this, you know, when Hemingway talks about the iceberg, this is all the iceberg part. Yeah. Like the underwater part, this is all there that the reader doesn't see. But you have the checking and cross checking, whatever. I think I've gotten better at that.

• 40:55Ryan Holiday?

  I would say my books are, there's more submerged than was on the earlier ones. What do you mean more submerged? Like I found when I went back to do The Obstacle is the Way, there were some things in there that I would, I wouldn't have let myself. That like, maybe I was right, but I was, I didn't actually have the facts at hand to be that right. To be that certain then, or I wouldn't have written that sentence. I would have needed more information. Or evidence to support that assertion. So when I went back and did it, there was just changes that I made that like, yeah, just my, I would just say like, I think one of the things that I don't like about this space

• 41:39Ryan Holiday?

  that I'm in is that a lot of the people who write business books don't hold themselves to any academic or intellectual standards whatsoever. Like if it sounds good, they'll go with it.

• 41:55Billy Oppenheimer?

  Yeah.

• 41:55Ryan Holiday?

  If they heard it somewhere, they'll go like, I was just reading a book the other day and he was like quoting a Twitter account.

• 42:01Billy Oppenheimer?

  Yeah.

• 42:01Ryan Holiday?

  And I was like, I would never do that. But maybe I would have thought about it a while, you know? I tried to get more stringent.

• 42:08Billy Oppenheimer?

  Yeah.

• 42:09Ryan Holiday?

  With my standards as I've gone on.

• 42:12Billy Oppenheimer?

  Yeah, well, it's one of my big lessons from your process is just like the rigor of like, you see a story in one book and you're like, let's find everywhere this is told.

• 42:23Ryan Holiday?

  Yes.

• 42:24Billy Oppenheimer?

  Not only to confirm, but like, maybe there's a detail that's left out in this book and it's over here.

• 42:30Ryan Holiday?

  Yeah.

• 42:30Billy Oppenheimer?

  And so now my bias as like a reader is to like, go find where the story is told. And often it's like, you can't find it anywhere else.

• 42:39Ryan Holiday?

  Yeah, sometimes it doesn't exist.

• 42:40Billy Oppenheimer?

  Yeah.

• 42:40Ryan Holiday?

  Yeah. And you go, oh, this person just, you just like, we talk about AI hallucinating stuff.

• 42:45Billy Oppenheimer?

  Yeah.

• 42:45Ryan Holiday?

  You go, oh, this was hallucinated or this was deliberately manufactured to make a point. And I don't get it always right. I mean, we're just going through the bibliography now and we found out that there's a quote that's like, not as firm as I thought it was.

• 43:02Billy Oppenheimer?

  Yeah.

• 43:03Ryan Holiday?

  So I'll have to change that in the future editions or whatever. But yeah, Robert was like that. Robert, I do this whole thing and be like, ah, no, not enough, not enough, not good enough.

• 43:11Billy Oppenheimer?

  Yeah. I've heard you talk about like, being surprised by like, he just paid me to do all this work and he's not going to use it.

• 43:17Ryan Holiday?

  Yeah.

• 43:17Billy Oppenheimer?

  But like, that's the.

• 43:19Ryan Holiday?

  Yes.

• 43:19Billy Oppenheimer?

  It's not just because you put in a lot of work that like warrants using it.

• 43:22Ryan Holiday?

  No, you gotta have really high standards. Yeah. And I, I, I think a lot of people are writing books because they want it to be a business card or they wanted to get speaking gigs. They don't actually care. And so they're just, they're just producing slop before AI slop exists. And that I like books, you know? I like, I, I respect the medium.

• 43:43Billy Oppenheimer?

  I was thinking of the story of like, another example of triangulating, like the story you tell in the. Marathon video and article.

• 43:53Ryan Holiday?

  Yeah.

• 43:53Billy Oppenheimer?

  Of first coming across like that run.

• 43:55Ryan Holiday?

  Yeah.

• 43:56Billy Oppenheimer?

  In Robert's book.

• 43:58Ryan Holiday?

  Yeah.

• 43:58Billy Oppenheimer?

  Thirty, thirty-three strategies of war.

• 44:00Ryan Holiday?

  Yeah.

• 44:01Billy Oppenheimer?

  Finding it in like John Green, some other Green.

• 44:04Ryan Holiday?

  Peter Green. Yeah, I forget who it was. Yeah.

• 44:06Billy Oppenheimer?

  And it being like a big moment for you as a writer.

• 44:09Ryan Holiday?

  I mean, that was like the lightbulb moment for me. That's when I, I think that was the first time that I understood how it worked, like how the pieces came together. Cause yeah, I remember I was in a pizza restaurant in Santa Monica. No, no, a pizza restaurant in, on La Cienega in Beverly Hills.

• 44:24Billy Oppenheimer?

  Philly's.

• 44:25Ryan Holiday?

  What?

• 44:25Billy Oppenheimer?

  Philly's Pizza.

• 44:26Ryan Holiday?

  Yes, Philly's Pizza, because that's what Philadelphia is known for. This is when I was the research assistant and an assistant at that agency. And I, yeah, I read this story about the Battle of Marathon, which of course I'd never heard of and I had not learned about in any class, college or high school. And Robert Green vividly tells the story of the Battle of Marathon. And I just emailed him and I said like, hey, um, what should I read about this? Like, where did you get this? And that's actually been one of my favorite questions to Robert. It's like, what books did you read when you were working on this? And whenever I go to his house, his books are organized largely by books he wrote.

• 45:10Ryan Holiday?

  So it'd be like, as he's writing Thirty-three Strategies of War, he would get a bookshelf and then they would all go there.

• 45:17Billy Oppenheimer?

  Oh, wow.

• 45:17Ryan Holiday?

  So like, you know, obviously he has all his books from his whole life, but like, you end up reading so many books when you're working on a book that it kind of messes up your whole system. So he would just be like, this is mostly the stuff from the war book. This is mostly the stuff from the seduction book. And so I would kind of be like, oh, I'd never heard of that, you know? And I would read them, but I, and I found so many of my favorite books that way. But yeah, I asked him what book he'd read and he recommended this book by this academic about both the Persian invasions of Greece. And I read it and then that was the first time that I was able, because the Forty Days of Power had been out for a long time by the time I read it, 10 years.

• 45:57Ryan Holiday?

  Yeah, about 10 years. And which is crazy, by the way, that would be like, if obstacle is 10 years old, that would be like you starting working for me now. That's where Robert was in his. Oh, wow. Because it came out in 98 and this was in 2007, 2008. But yeah, I, I read that book, which is obviously about, you know, Robert's, Robert's section on the Battle of Marathon is like two pages, three pages. And I'm reading a 300 page book about it. And, and then I go, oh, this is like, as I'm reading the whole thing, I'm seeing the little pieces that informed that condensed, you know, synthesized version.

• 46:42Ryan Holiday?

  And there was one sentence I remember jumping out at me that like Peter Green or whoever the guy's name is, wrote it, did it pretty well. And then Robert, you're like, oh, this is why this book sold 800 copies. And this book sold 800,000 copies. Like, that's why. Yeah. Because you did it better. Yeah. And you took not just that, and then I went and read Faradid. There's obviously other tellings of it, but I was like, oh, this is how the source material gets compressed down to this. Yeah. Like, have you seen that video where Dave Grohl is explaining the drum sound on Smells Like Teen Spirit? Yes.

• 47:26Ryan Holiday?

  And then Pharrell like immediately knows what he's talking about. And you're like, fuck, oh, like you just realize there's like, oh, there's a lot. You think it was this Sue Generous thing. And then when you're able to see the combined influences, the equation suddenly makes sense. It doesn't make it less impressive. It makes it more impressive in some ways. Yeah. Because you realize, oh, this person is like.

• 47:54Ryan Holiday?

  A genuine connoisseur of music and they just happen to be expressing it in this style.

• 48:01Billy Oppenheimer?

  Yeah. So it demystified.

• 48:04Ryan Holiday?

  Totally.

• 48:05Billy Oppenheimer?

  For you.

• 48:05Ryan Holiday?

  Yeah, I mean, that's, I think, working for Robert, what it really showed me is how it worked as a craft. Like, if you are working, like, like, when I walk by a house that's under construction, that's as mystical to me as, and as much a form of art as writing or music or whatever. But if I, I'm sure if I shadowed a contractor, you'd be like, oh, this is how they start this phase. And this is, you know, you just, you, I just watched it happen and then you realized it's a, it's a series of discrete tasks and a set of skills.

• 48:47Ryan Holiday?

  And there's a map, you know, and then there's somebody making the creative decision. And like, that's, that's not to say that it's any easier once you know it. Like, it's still a shit ton of work, but it is suddenly not magic.

• 49:02Billy Oppenheimer?

  Yeah.

• 49:02Ryan Holiday?

  You know?

• 49:03Billy Oppenheimer?

  Yeah.

• 49:03Ryan Holiday?

  The output's still magic, but you realize, oh, this is a thing that you do.

• 49:08Billy Oppenheimer?

  Yeah. I've heard Greta Gerwig tell a similar story of like, that moment in her life. And it was, she, she used the metaphor of just like, it put a mountain in front of me. It didn't make it easy to climb the mountain, but it was there. Whereas before that, it was like, she didn't even know where she was going.

• 49:25Ryan Holiday?

  Brian Koppelman's podcast, I don't know if he still does it. I think he does it sporadically because he doesn't need to, but it's called The Moment, and it's like about those moments.

• 49:32Billy Oppenheimer?

  Yeah.

• 49:33Ryan Holiday?

  And I remember there's one, he was interviewing Bill Hader, and Bill Hader was like obsessed with movies and he's watching some movie and he, for the first time, understands the shot the director is doing. It's like, oh, the camera is here and it's moving on a track this way while the person, and he was like, oh, a movie is just, is that. 900 times, or however many shots are in a movie.

• 49:59Billy Oppenheimer?

  Yeah.

• 49:59Ryan Holiday?

  And there, yeah, that moment where it gets demystified, that's pretty magical. And that, I'm not sure if that's wisdom. I was gonna think about that as an element of wisdom. And I think I'm gonna save it for, I think what that is, is excellence. There's this idea of phronesis, like practical knowledge. But the ability to sort of technically understand how a thing works and the component parts and how they come together. That's a component of wisdom. That's not, I wouldn't exactly call that wisdom, the moment like it snaps in where you get it. But like, someone's ability to conceive of a path forward

• 50:40Ryan Holiday?

  or a way to do something where everyone else is either hopeless or can't see it or missed. That's like, that's, I think, what you're working towards.

• 50:51Billy Oppenheimer?

  Yeah, it's the more specific knowledge, which, I mean, Elon Musk is a cautionary tale in this book.

• 50:59Ryan Holiday?

  We should talk about that in a second, but I do, we talked about that, the Pharrell.

• 51:03Billy Oppenheimer?

  Yeah.

• 51:04Ryan Holiday?

  Video. I watched another one, I love those videos where it's like shots of musicians in the studio. And it was Billy Joe from Green Day. And he's just fucking around on the guitar as the early chords of Boulevard of Broken Dreams come in. He's fucking around. And then you just watch him figure out the guitar riff. He's obviously done it so many times that at some level, you notice that he recognizes it, but it's not like a, fuck, that's it. It's like messing around and then not messing around anymore. And then the riff that you've heard on the radio a bunch of times exists. Those moments are real, like you kind of figure it out. Those are great. That's why I love cracking the structure on a book where you're like, this is gonna be the main character.

• 51:49Ryan Holiday?

  This is gonna be the main character. This is gonna be the main character. And then you don't, you haven't figured it all out, but you've solved suddenly in a moment. It's like you're doing a puzzle and you're like.

• 52:00Ryan Holiday?

  And like it now is a rectangle.

• 52:02Billy Oppenheimer?

  Yeah.

• 52:03Ryan Holiday?

  Or whatever. And you're like, okay, I now I just got to connect these two, these two. It's that a bunch of times that still a lot of work and it might take you.

• 52:10Billy Oppenheimer?

  Yeah.

• 52:11Ryan Holiday?

  Six months, but like you are now at least heading in the right direction.

• 52:16Billy Oppenheimer?

  Yeah. That example, Billy Joe, is that his name? Makes me think of discernment, like.

• 52:22Ryan Holiday?

  Yes.

• 52:22Billy Oppenheimer?

  Him messing around, but then having the ear to decide this is, let's grab onto this and move more in this direction.

• 52:30Ryan Holiday?

  Yeah, these two things go together.

• 52:32Billy Oppenheimer?

  Yeah.

• 52:32Ryan Holiday?

  It usually like on my books, like I, for a while, I'm just generally writing a lot of stuff down on no cards. Or I'm just reading and thinking. And then there's some moment, usually it's forced where you're like, okay, today I'm going to sit down and think about it. And I'm going to start and then you're like, oh, I started going through the cards and I'm like, these two connect, these two connect and these five connect. Oh, this is obviously a chapter and you don't get it all at once, but you might get set like on Monday, you just had, you know, 2,000 no cards. And then on Tuesday, you still have 2,000 no cards, but 300 of them or 200 of them.

• 53:08Billy Oppenheimer?

  Yeah.

• 53:09Ryan Holiday?

  Are in chapters.

• 53:10Billy Oppenheimer?

  Yeah.

• 53:11Ryan Holiday?

  And now you have 10 of the 30 chapters you're doing. And now it's exists. There's, it's like you're walking by a construction site and one day it's, you know, flat. And then you see them pouring the foundation, dig it, they're putting in the pipes and then you see the foundation. And then you see like a bunch of wood arrive and then you drive by like two days later and the whole thing is scat, like a three story house is suddenly scaffolded up. Or framed up and you're like, oh, wow, that, that went fast.

• 53:40Billy Oppenheimer?

  Yeah.

• 53:40Ryan Holiday?

  That's usually what happens.

• 53:41Billy Oppenheimer?

  Is it getting harder to, cause you've, you've read so much, harder to have the experience of being like lit up by a story?

• 53:49Ryan Holiday?

  I mean, I'm in the middle of it right now. I'm fucking loving this book I'm doing.

• 53:51Billy Oppenheimer?

  Yeah.

• 53:52Ryan Holiday?

  No, I don't think so.

• 53:53Billy Oppenheimer?

  I was talking to Rick once about how this happens to musicians, whereas they get more and more technically proficient.

• 54:00Ryan Holiday?

  Yeah.

• 54:00Billy Oppenheimer?

  To stimulate themselves gets harder and harder.

• 54:03Ryan Holiday?

  Oh, sure.

• 54:03Billy Oppenheimer?

  They kind of like. Make stuff that's way above the heads of audiences.

• 54:08Ryan Holiday?

  Rush did that.

• 54:09Billy Oppenheimer?

  Yeah.

• 54:10Ryan Holiday?

  There's a documentary about Rush where at one point they were, they, they, they all got together and they're like, we took this as far as it's technically possible to go. This can't, this is no longer the, like, they're like, the music can't get weirder and harder. It's gotta get, it still has to be challenging and interesting, but we're, this is a dead end. You know, like, we're in a cul-de-sac, like, this is, we're either gonna kill ourselves or it's just gonna stop being interesting. It's just turning into like, you know, theoretical physics or something.

• 54:40Billy Oppenheimer?

  Yeah.

• 54:41Ryan Holiday?

  And so like, the music went in a different route. Who is it servicing to make it harder and harder? Harder to play?

• 54:48Billy Oppenheimer?

  Yeah.

• 54:48Ryan Holiday?

  What you're doing is you're thinking about yourself and not the idea that this is to be consumed by anyone.

• 54:54Billy Oppenheimer?

  Yeah.

• 54:55Ryan Holiday?

  Like, you might as well be doing like cryptography or something.

• 54:57Billy Oppenheimer?

  Yeah.

• 54:58Ryan Holiday?

  So, yeah, I, I mean, what I'm excited about in the book that I'm doing now is that it's just, it's a different, it's not a different medium, it's just a different style of writing.

• 55:05Billy Oppenheimer?

  Yeah.

• 55:05Ryan Holiday?

  And so that's challenging and it's all sort of one person. But I guess maybe the fact that I am as surprised at how lit up I am is maybe a sign that I was less lit up the last couple of years, but I'm like really liking it. So I, it hasn't gone away yet.

• 55:22Billy Oppenheimer?

  Yeah. Well, I also mean, just like as a reader, and I guess an example of like how this doesn't happen is we've been working on the bibliography of like, just how many Lincoln books you have read.

• 55:34Ryan Holiday?

  And like, that was a total surprise.

• 55:36Billy Oppenheimer?

  Yes.

• 55:37Ryan Holiday?

  Well, especially because I just, I just redone Obstacle and Lincoln is the main character in the third chapter of part three of Obstacle. I think I told myself, and this is when you're running, like, the last, uh, last two miles downhill will be easy. But actually, like, chances, you don't know that, you're just lying to yourself to like, keep, keep you going. So I think I told myself that last part would be pretty easy. Cause I'd already written about, a bunch about Lincoln. And then, like, I maybe made it like two sentences and I was like, I don't, I don't have it.

• 56:09Billy Oppenheimer?

  Yeah.

• 56:10Ryan Holiday?

  Like, I don't have it in a way that's interesting to me. Like, I probably could have done it, but I just didn't, I didn't have what I needed.

• 56:17Billy Oppenheimer?

  Was it a, a block, a writing block and then?

• 56:20Ryan Holiday?

  No, I don't believe in writer's block really.

• 56:23Billy Oppenheimer?

  Yeah.

• 56:23Ryan Holiday?

  But I definitely know the feeling of not having the material.

• 56:27Billy Oppenheimer?

  Yeah.

• 56:27Ryan Holiday?

  Like, writer's block doesn't exist. You just don't fucking have the material. And when you have the material, the writing comes together. That's not to say it's always easy and fun, but if you have the material. And so like I found this on part two of, of Discipline. I was gonna write about Queen Elizabeth and I'd read one book and I'd read another book. And I started to write. I was like, how, 900 pages on the Queen seems like enough.

• 56:51Billy Oppenheimer?

  Yeah, yeah, to write like 20 pages.

• 56:54Ryan Holiday?

  Yeah.

• 56:54Billy Oppenheimer?

  Yeah.

• 56:55Ryan Holiday?

  And I think I read like 4,500 pages on Queen Elizabeth or something. There wasn't one, I emailed Andrew Roberts. I was like, who, the biography, I was like, what is the best book on the Queen? And he referred me to one. And then that guy had another book coming out, so I had to wait for a book to be published.

• 57:14Billy Oppenheimer?

  Also on the Queen.

• 57:15Ryan Holiday?

  Also on the Queen, that guy had his, so I think I read two books from him that were like eight or 900 pages. And then I read, read a lot. And then I'm also reading articles and watching things and, but yeah, I think, I think I tallied it all up in there about Lincoln. But it's like several thousand pages. They stacked up all the books in the bookstore. We did an Instagram post of like all the books that I've read about Lincoln. And it's like this tall.

• 57:39Billy Oppenheimer?

  Yeah, you had something in one of the reading list emails about like, every time I think I've read enough on Lincoln.

• 57:45Ryan Holiday?

  Yeah.

• 57:45Billy Oppenheimer?

  You find something, you are continually fascinated.

• 57:48Ryan Holiday?

  Well, if you go to the, the museum at Ford's Theater, they have, it's like three stories or something. And they have this spiral tower made up only of books about Lincoln.

• 58:00Billy Oppenheimer?

  Wow.

• 58:01Ryan Holiday?

  And that's where the ideas for this and for the tower in the bookstore came from. Yeah, it's pretty crazy.

• 58:06Billy Oppenheimer?

  Yeah. It's crazy that like every writer that comes along is like, there's not, there's still something to be written about Lincoln.

• 58:13Ryan Holiday?

  Yeah, I think he's the, other than the Bible, he's maybe, this was a long time ago. Oh, yeah. Look at this.

• 58:20Billy Oppenheimer?

  All Lincoln.

• 58:21Ryan Holiday?

  Those are all, if you scroll a couple ways, those are all books about Lincoln. So what's the date on the photo? Can you see the top?

• 58:27Billy Oppenheimer?

  April 4th, 2017.

• 58:28Ryan Holiday?

  So that's where the idea for the book tower came from. That's insane. Um, but someone told me once that every sentence or phrase in the Gettysburg Address, and maybe the second inaugural, are book titles. Like, "These honor dead, full measure of devotion of the people for the people," but like that every phrase has been turned into a book by someone. Whoa. And I mean, just to think about how, what that says about the caliber of writing, that like, multiple sentences could be, or phrases could be broken down to be their own book titles. So, obviously, a lot of people write about Lincoln.

• 59:11Ryan Holiday?

  But yeah, I think every time I read about him, I, I take something else out. Yeah. So yeah, it's been a lot. It was a lot. And, but I definitely got lit up. I mean, it wasn't a slog. Yeah. You know, like I, I had fun. Yeah. And I think it's some of the best writing that I've done, that chapter, like, I'm pretty proud of it. Yeah. That Tolstoy story is fucking incredible, though. Which? Well, Tolstoy is like, visiting these, this tribe in the Caucasus Mountains, and they're asking him to tell him, them stories about like, the great conquerors from history. And then, he finishes, and the chief goes, "But you haven't told us of the greatest of them all." And he goes, "Who are you talking about?" And this is like, 1905 or something, the end of Tolstoy's life.

• 59:55Ryan Holiday?

  And he's, "Who's the greatest hero of all?" And he says, you know, "The man with a, a voice like thunder and deeds as strong as the rock." And Tolstoy says, "Who are you talking about?" And he says, "Abraham Lincoln." And he just goes, the idea that Abraham, they would even know Abraham Lincoln's name. Yeah. Um, and Tolstoy sort of concludes that, that what, what separates Lincoln from all the other people that he'd been talking about is that Lincoln, unlike Napoleon, didn't like, I mean, Napoleon is a great man of history, and Alexander the Great is a great man of history, and, but, most of their accomplishments were fundamentally selfish. Like, they, they're impressive. Julius Caesar, who he was and what he did is impressive.

• 1:00:37Ryan Holiday?

  But the more you look at it, the more you're like, oh, he's also a war criminal. You know, like, all those characters share this ambition. And Lincoln has this great quote about, he says, "Every man has his peculiar ambition." But he says, "Mine is to leave the world better than I found it." Actually, Lincoln has a speech where he talks about these great men of history, like the man on horseback, basically. And he says, "Some men's ambition will lead them to make slaves of other men, and other men's ambition is to free the slaves." Or something like that. But you go, oh, Lincoln is great not because of who he conquered,

• 1:01:17Ryan Holiday?

  but is one of the first great heroes of history to become great because of who he freed.

• 1:01:23Billy Oppenheimer?

  Yeah, wow.

• 1:01:27Ryan 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.