Kermit Roosevelt III on Theodore Roosevelt And Cultural Movements (PT 2)

On this episode of the Daily Stoic Podcast, Ryan talks with American author, lawyer, and legal scholar Kermit Roosevelt III on Honoring and doing what is right, Why peoples values and sense of honor are collapsing, How many people know who Marcus Aurelius is because of Gladiator, and his book The Nation That Never Was. Kermit is an American author, lawyer, and legal scholar. He is a law professor at the University of Pennsylvania. He is a great-great-grandson of United States President Theodore Roosevelt and a distant cousin of President Franklin D. Roosevelt. Roosevelt worked as a lawyer with Mayer Brown in Chicago from 2000 to 2002 before joining the Penn Law faculty in 2002. Roosevelt's areas of academic interest include conflicts of law and constitutional law. He has published in the Virginia Law Review, the Michigan Law Review, and the Columbia Law Review, among others, and his articles have been cited twice by the United States Supreme Court and numerous times by state and lower federal courts.✉️ Sign up for the Daily Stoic email: https://dailystoic.com/dailyemail🏛 Check out the Daily Stoic Store for Stoic inspired products, signed books, and more.📱 Follow us: Instagram, Twitter, YouTube, TikTok, FacebookSee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info. 📢 Share | ⚙️ Manage Subscription

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

• 0:03Ryan Holiday?

  Welcome to the weekend edition of The Daily Stoic. Each weekday, we bring you a meditation inspired by the ancient Stoics, something to help you live up to those four Stoic virtues of courage, justice, temperance, and wisdom. And then here on the weekend, we take a deeper dive into those same topics. We interview Stoic philosophers. We explore at length how these Stoic ideas can be applied to our actual lives and the challenging issues of our time. Here on the weekend, when you have a little bit more space, when things have slowed down, be sure to take some time to think, to go for a walk, to sit with your journal,

• 0:46Ryan Holiday?

  and most importantly, to prepare for what the week ahead may bring.

• 0:56Ryan Holiday?

  Hey, it's Ryan. Welcome to another episode of The Daily Stoic Podcast. I don't know when you'll be listening to this. I'm in a little bit of a limbo myself as I'm recording it. Found out my in-laws have COVID last night, so it's still there and out there, people. So I hope you're being careful as you're traveling for the holidays. But it's this opportunity to practice a little Stoic practice, which is you have the exposure. Our travel plans loom in the future, and it's out of my control whether it's going to affect things or not, whether the virus is in me right now or not. All I can do is, one, take precautions, not expose other people to it, and then not get in my own head about it, not drive myself nuts about it,

• 1:41Ryan Holiday?

  not let it cost me anything on top, right? Which is, can I be productive in this time? Can I be happy in this time, right? Can I just be present in this time and not ruminate or worry or bite my nails over something that's not in my control? And that's why I am recording this intro right now, which is part two of the episode I brought you earlier in the week, my interview with Kermit Roosevelt III. He has an awesome book that I will recommend, The Nation That Never Was. He's an expert on reconstruction. He's a legal scholar, and he is the great grandson. President Theodore Roosevelt, distant cousin of Franklin Roosevelt, comes from one of the great American dynasties. And he's a fascinating guy. We had a great conversation.

• 2:24Ryan Holiday?

  I'm really glad he came all out, all the way to the studio. And I think you're really gonna like this interview. We talk about one of my favorite heroes, a stoic hero of mine, Theodore Roosevelt. We talk about a bunch of different topics. I think you're really gonna like this interview. And you can follow him on Twitter, @Kroosevelt93. And you can check out The Nation That Never Was. And he's also got a number of, he's got two novels, In the Shadow of the Law, a novel, Allegiance, a novel. And he's also got a book on judicial activism. He's a legal and constitutional scholar, a fascinating guy. I hope you listen.

• 3:11Ryan Holiday?

  So what was growing up in that tradition like? Was it something talked about? Is it a set of values or stories that's passed down? Or is it just totally normal in the way that I don't really think of my great, great grandfather very much?

• 3:28Speaker 01

  I guess, on the whole, I would say it was pretty normal. We didn't talk about it in my family, really. We did have a bunch of books about Theodore Roosevelt lying around, probably more than the ordinary family did. And so I read those because I just read every book in the house when I was growing up.

• 3:45Ryan Holiday?

  That's kind of a Roosevelt tradition.

• 3:46Speaker 01

  Yeah, I guess so. And then, like, I don't know, my classmates teased me some. And when I was in fourth grade, they elected me president of the class because they were like, President Roosevelt, that makes sense. But then I like to think I did a good job, anyway.

• 4:03Ryan Holiday?

  Sure, sure. Yeah, I mean, One of my favorite quotes from Seneca, he says, "We can't choose our parents, but we can choose whose children we would like to be." And I like this idea that like the sort of family you're born into is not something you control. But you decide whether you follow the tradition or not, or whether you seek out a new... What parts of your family tree are you going to choose to come from? Like even the Roosevelt family, right? There's the good side, and then there's also, what, the alcoholism side, and the philandering side, and you know, like the racism side.

• 4:44Ryan Holiday?

  I mean, I guess there's a bunch of branches on that family tree, and you ultimately decide as an individual which ones you're gonna come from.

• 4:57Speaker 01

  Yeah. And, you know, I think you can find people that you like and want to emulate and want to learn from, and you can model yourself after them, even if they're not biologically connected to you.

• 5:11Ryan Holiday?

  Well, that was the Roman tradition that I didn't really understand much until later. But like, a family that didn't have a male son would often adopt

• 5:25Ryan Holiday?

  a prominent man, sometimes well into adulthood, to sort of carry on the family tradition. So Seneca's brother, for instance, the reason that most people wouldn't identify him as a Seneca is even though he's arguably more famous than Seneca, is because he, after he's adopted, he changes his name to Gaio, and he ends up in the Bible.

• 5:53Speaker 01

  Oh, I had no idea.

• 5:54Ryan Holiday?

  Yeah, so he's adopted, like that was a tradition, a famous tradition. You would adopt people, and so there was this idea that you would sort of identify with or be associated with different...

• 6:11Ryan Holiday?

  You know, groups or clans and sort of become part of it. And so I do like that idea that, you know, people go, this person was my mentor. And we assume that they mean, oh, they, you had a lot of direct conversations with that person. But I also feel like you can be mentored by or sort of in the tradition of someone that you've never met. You've just read them and studied them very deeply.

• 6:34Speaker 01

  Yeah, I think absolutely. I mean, I would say that people have had very strong influences on me without me ever meeting them.

• 6:40Ryan Holiday?

  Yes.

• 6:41Speaker 01

  Just reading them a lot.

• 6:42Ryan Holiday?

  Yeah. And the famous Stoic one similar to yours is Cato the Younger is actually the great, great grandson of Cato the Elder. So you think it's like a father and son situation, but they're separated by a very long period of history. So much so that when Stoicism comes to Rome from Greece, Cato the Elder is like, wants to ban the philosophers altogether. He thinks like, this philosophy is like rock music or some sort of like

• 7:19Speaker 01

  It's corrupting the youth.

• 7:20Ryan Holiday?

  Corrupting tradition. And then by the time his great, great grandson gets it, it's like the highest form of moral and civic excellence.

• 7:30Speaker 01

  Like Taylor Swift.

• 7:31Ryan Holiday?

  Yes, exactly. So, so it's funny how that works out. But there was, there's this tradition that they're following in, even though they would have disagreed severely on certain issues. He's still modeling himself after his great grandfather, great, great grandfather. And then the subsequent Stoics sort of choose Cato as their grandfather. You know, Seneca says, you have to choose yourself a Cato, like who's your ancestor that you're trying to continue their example? Or not let them down or follow in their footsteps.

• 8:11Ryan Holiday?

  I think we have to do that.

• 8:13Speaker 01

  Yeah. I think Theodore Roosevelt did that. I think that I felt that way, growing up to some extent. Because we did, like, we had a lot of old books lying around.

• 8:24Ryan Holiday?

  Yeah.

• 8:24Speaker 01

  So I read a fair amount of history and sort of classics.

• 8:30Speaker 01

  And yeah, I was kind of always looking for role models.

• 8:34Ryan Holiday?

  Was it, I mean, and then you kind of, the family kind of seemed like it would go to the same schools. I'm sure there are sort of traditions or like

• 8:44Ryan Holiday?

  things that felt like they tied you to that

• 8:51Ryan Holiday?

  that family lineage, right?

• 8:54Speaker 01

  Schools, yeah, like college, definitely.

• 8:57Ryan Holiday?

  Yeah, because you're like, he went here.

• 9:00Speaker 01

  Yeah.

• 9:04Speaker 01

  And there's a moose that he shot on the wall here.

• 9:07Ryan Holiday?

  Yes.

• 9:08Speaker 01

  At the freshman dining hall.

• 9:10Ryan Holiday?

  Yeah.

• 9:12Speaker 01

  Although, you know, I was also thinking it was very different back then. So he did go here, like, he walked along these streets, but it was a very different world also.

• 9:21Ryan Holiday?

  Yeah, well, I'm sure Harvard costs like $40.

• 9:24Speaker 01

  Yes.

• 9:26Ryan Holiday?

  And it was a very different institution also, right?

• 9:29Speaker 01

  Well, they really learned classics.

• 9:31Ryan Holiday?

  That's true.

• 9:32Speaker 01

  And they boxed. He did a lot more boxing than I did.

• 9:36Ryan Holiday?

  No boxing for you?

• 9:38Speaker 01

  No boxing. I did take some Krav Maga more recently with my son.

• 9:43Ryan Holiday?

  That's a tradition that's coming back. I feel like my six-year-old does Brazilian Jiu-Jitsu.

• 9:47Speaker 01

  Yeah. Krav Maga is probably the worst martial art to teach a young child.

• 9:52Ryan Holiday?

  Why is that?

• 9:52Speaker 01

  Though, well, because it's about inflicting maximum damage in minimum time. So it's the worst thing for them to like pull out in a playground scuffle. It's all like tiger claw, eye gouge. You know, bite.

• 10:07Ryan Holiday?

  My four year old jumped on me and did a jujitsu choke on me while I was in bed yesterday. And I was like, you don't even take jujitsu. You learn this from your brother and then you're like, which is a move he's not even supposed to be learning yet. And somehow I'm getting choked out in my bed while I'm sleeping. What's going on? But.

• 10:24Speaker 01

  Yeah. Well, yeah, so my son is 11 now and it was great up until like six because I let him attack me.

• 10:31Ryan Holiday?

  Yeah.

• 10:31Speaker 01

  And he couldn't hurt me and I felt like invulnerable. And then when he got to like eight, I was like, wait, that's starting to hurt. And now I have to be like, don't hit me, don't hit me.

• 10:42Ryan Holiday?

  Yeah, it's funny. It's but again, that's, I think, kind of an ancient tradition of like the sort of brood of feral children, all trained in martial arts of some kind. There's something lovely. I got this from what I've read about the Theodore branch of the Roosevelts, that it was a very loud house.

• 11:03Speaker 01

  Yeah, absolutely.

• 11:06Ryan Holiday?

  With a lot of mischief and a lot of animals and other forms of craziness.

• 11:12Speaker 01

  Animals in the White House.

• 11:13Ryan Holiday?

  Yes.

• 11:14Speaker 01

  Horses in the elevator.

• 11:15Ryan Holiday?

  Yeah.

• 11:17Ryan Holiday?

  And

• 11:20Ryan Holiday?

  how have you thought about that tradition with your own kids? Like I, I'm just like, I feel like, not that it matters, but most of us are just like regular people, right? There's not any like, there's not a particularly well-known lineage to explain or, you know, here's your grandpa, he worked at a factory, right? Like, you know, or grandma was a school teacher, right? There's not, there's not the more sort of historical story to go along with. How, how, how was that passed on to you? And then how have you thought about passing it on?

• 11:57Speaker 01

  Well, I just, again, like I mostly got it from books. You know, my, my parents didn't talk to me about it that much. But I did read about it and I was like, wow, that sounds cool. That sounds like a lot of fun, playing point to point.

• 12:10Ryan Holiday?

  Was it deliberate, you think, that they didn't talk to you about it? Or like a reaction to how it had been talked to them?

• 12:15Speaker 01

  Honestly, yeah, I don't know. And then like, I don't talk to my kids about it that much either. I mostly like let other people bring that up if they want to, don't you bring that up yourself?

• 12:27Ryan Holiday?

  Yeah.

• 12:30Speaker 01

  But it does seem like.

• 12:34Speaker 01

  I don't know, it would have been a lot of fun to be a kid in that house. And I sort of aspire to make my family life kind of like that.

• 12:41Ryan Holiday?

  Yeah.

• 12:41Speaker 01

  Fun, a little crazy.

• 12:43Ryan Holiday?

  Yeah, you would take him on these like walks, I read. So they'd go on these long walks and he would try to like walk them through a Russian river or over like a pile of rock. It was, it was about these, Dieter Roosevelt would do these kind of like nature walks slash, you know, American Ninja Warrior practice.

• 13:04Speaker 01

  Right.

• 13:05Ryan Holiday?

  To make like tough, resilient, active kids.

• 13:10Speaker 01

  Yeah, which I think is like the best way to do it. I mean, you can learn a lot of virtues, I think, through physical activity and physical challenge.

• 13:19Ryan Holiday?

  Yes. And, and certainly not learn some things by not doing like, like, or learn the wrong lessons by not experiencing challenges or shying away from challenges or having things come easily or without struggle.

• 13:38Speaker 01

  Yeah. I think that the experience of struggling and achieving something.

• 13:42Ryan Holiday?

  Yeah.

• 13:43Speaker 01

  Is really great and the experience of struggling and failing and realizing that that doesn't destroy you is equally important.

• 13:50Ryan Holiday?

  And I imagine in Dieter Roosevelt's time with his family, with his parents, they were probably quite concerned about raising indolent, spoiled, fragile children because didn't have to work, had immense resources. You know what I mean? Like, like I, I, I mean, there's the famous story, right? Like he has asthma and he's sort of weak.

• 14:15Speaker 01

  Yeah.

• 14:16Ryan Holiday?

  And his father says, you're smart, but like you have a weak body and you gotta make your body. And you can see the gym that at the, the house on, was it 21st Street, 19th Street?

• 14:25Speaker 01

  Yeah.

• 14:27Ryan Holiday?

  Like the, the strenuous life that Dieter Roosevelt sort of introduced to is a reaction deliberately so I think from his parents.

• 14:39Ryan Holiday?

  To the comfort and the potential entitlement that could come from that comfort.

• 14:45Speaker 01

  Yeah, which I think was exactly the right thing to do.

• 14:49Ryan Holiday?

  Yeah, so you you studied philosophy, right? You were gonna be a philosopher? Is that what you wanted to do?

• 14:55Speaker 01

  I well, I wanted to be a novelist. But I thought that teaching would be a good way to do that with a little bit more security.

• 15:02Ryan Holiday?

  Yeah.

• 15:02Speaker 01

  So I wanted to teach and I was trying to decide between law school and graduate school or philosophy. And my parents basically talked me into law school.

• 15:12Ryan Holiday?

  Because it's it's the it's more practical?

• 15:15Speaker 01

  Yeah, what they said was it's actually easier to get a law teaching job than a philosophy teaching job, which is true.

• 15:21Ryan Holiday?

  Sure.

• 15:22Speaker 01

  There's very few philosophy slots that open up. And if you do get a teaching job, you'll be working on things that matter to people, which at the time I didn't really care about as much. I was like, wow, but philosophy is so interesting.

• 15:34Ryan Holiday?

  Yeah.

• 15:36Speaker 01

  And philosophy can actually transform people's lives, of course. But professional philosophers tend to write on topics that are pretty narrow and inaccessible. So they were right about that.

• 15:50Speaker 01

  And then they also said, and if you don't get a teaching job, your law degree is worth something. Whereas your philosophy PhD is not going to do much for you.

• 15:56Ryan Holiday?

  Yes.

• 15:56Speaker 01

  If you're not teaching philosophy. So all of that made sense. And I went to law school. And I'm really happy with the way it worked out, actually, because now I do feel like I'm working on topics that matter. And I'm trying to say things that could have some impact.

• 16:12Ryan Holiday?

  It's kind of an indictment of what philosophy is, both academically and culturally, though. Like, the idea is like, you would study philosophy if you just want to live in a world of ideas. But you study the law if you want to participate in society, you want to make a difference, you want to help people.

• 16:32Ryan Holiday?

  The Greeks or the Romans would have found that to be a strange state of affairs, I feel like.

• 16:39Speaker 01

  Right. Well, so I think, you know, what people would say about that is philosophy doesn't touch people's everyday lives, but you're always being affected by the law. And then the answer to that is, well, philosophy is touching your life, you just don't realize it, because you haven't been sensitized to the role that philosophy plays. And I think, actually, Stanley Kavel, a Harvard philosopher, wrote something very much like that in The Claim of Reason. But I don't think that it went that far outside academic circles, is the thing. I mean, professional academic philosophy is kind of insular.

• 17:15Ryan Holiday?

  Yeah, I mean, in the ancient world, philosophy was about sort of practical questions and about how you lived. It was closer to a system of ethics and a kind of civic religion. And then, as it becomes more abstract, theoretical and academic, it becomes about these questions that feel like they don't pertain to everyday life. And it's true, a lot of them don't. But then it's sort of like, well, what is helping people answer those questions? Nothing. Do you know what I mean?

• 17:51Speaker 01

  Yeah.

• 17:52Ryan Holiday?

  Well, like, so I'm doing this series of books now on the cardinal virtues. So I did courage. Courage is kind of straight down the middle. Everyone knows why courage is important. I did discipline. Everyone wishes they had more discipline. They understand what discipline does. And then, as I've started to write about justice, you bump into this thing, which is, it's not just that justice to people feels like the legal system or politics, but it's almost like, like if you call someone a social justice warrior, that's like an insult. Like, what does that say about where we are as a society that we, that justice not only feels kind of like this one partial domain of life? Like, justice only comes into play when you commit a crime or break a law, or you

• 18:36Ryan Holiday?

  get, you get a letter from a lawyer, as opposed to justice, and I think by extension, philosophy as a whole, that it's this thing that pertains to all the decisions you make. What kind of car you drive, or how you treat people, or, you know, what business you enter, right? Like, actually, it's supposed to help us with all these questions. This is the, this is where it's supposed to help us derive not just knowledge, but also values.

• 19:04Speaker 01

  Right.

• 19:06Speaker 01

  But how can we get a broader engagement with that?

• 19:09Ryan Holiday?

  I'm trying, man, I'm trying.

• 19:10Speaker 01

  Right.

• 19:11Ryan Holiday?

  That's what I do.

• 19:11Speaker 01

  That is great. No, that's great.

• 19:13Ryan Holiday?

  Yeah, no, it's.

• 19:15Speaker 01

  Good. I love what you do. Actually, like, I hadn't known that much about it. But everyone I talked to was like, oh, my God, the Daily Stoic, that's amazing. And I was like, wow, really?

• 19:25Ryan Holiday?

  It's, it's funny because it's certainly not like what the reaction from my publisher was when I was like, I want to do this book on Stoicism.

• 19:35Speaker 01

  Yeah.

• 19:35Ryan Holiday?

  They were like, but you write marketing books. Wouldn't, isn't that what you should keep doing? And it turns out that I think people are well aware that this is a part of society and ourselves that is neglected. You know, like the sort of, the, this answers to the big questions as well as guidance in the practical matters, which I think is, that's the philosophy that I think people get excited about. I mean, like, there are interesting questions, the trolley problem and

• 20:09Speaker 01

  Right.

• 20:09Ryan Holiday?

  you know, how do we know we're not living in a computer simulation? But like,

• 20:15Ryan Holiday?

  philosophy also helps us with some slightly more practical matters as well as, as just things like, you're gonna die, what does that mean?

• 20:25Speaker 01

  Yeah. Yeah, the philosophy that I was studying in college was not that practical.

• 20:29Ryan Holiday?

  Yeah.

• 20:30Speaker 01

  I think it was like philosophy of language, philosophy of mind.

• 20:33Ryan Holiday?

  Yes. Lot of German names that are hard to pronounce.

• 20:36Speaker 01

  Wittgenstein.

• 20:37Ryan Holiday?

  Yes.

• 20:37Speaker 01

  Yeah, Fräger, yeah.

• 20:41Speaker 01

  And the are we brains in a vat? Which is basically the are we in a computer simulation? Yeah.

• 20:45Ryan Holiday?

  Yeah. And what am I supposed to, let's say you told me yes or no. What am I supposed to do with this information? Like, how, how does that help me with

• 20:55Ryan Holiday?

  anything?

• 20:56Speaker 01

  Right.

• 20:56Ryan Holiday?

  I'm not sure that it does. It's interesting, but it kind of, yeah, it's like, how many angels could fit on the head of a pin?

• 21:02Speaker 01

  Yeah.

• 21:04Ryan Holiday?

  And I think maybe part of it also is that religion answers those questions for a lot of people. And religion has, for the most part, done a pretty good job of selling itself as the answer to those questions.

• 21:16Speaker 01

  Yeah, religion's done a very good job of selling itself.

• 21:20Ryan Holiday?

  It stepped in and it filled the void.

• 21:22Speaker 01

  Well, also, religion, I think, to go back to something that I was saying earlier, religion fits into this agency detector slot that people have in their minds, where you're like, there are these patterns in the world, something's causing it.

• 21:37Ryan Holiday?

  Sure.

• 21:38Speaker 01

  It's a supernatural religious entity. So it's sort of, it naturally appeals to people.

• 21:44Ryan Holiday?

  How did we get here? Someone or something must have put us here.

• 21:47Speaker 01

  Right.

• 21:48Ryan Holiday?

  Yeah.

• 21:50Speaker 01

  Although there's something strange about how willing people are to accept that. They're like, I must have come from somewhere, the answer is God, but then like, where did God come from?

• 21:59Ryan Holiday?

  Right.

• 21:59Speaker 01

  Well, God is the first cause, right, the unmoved mover. But why does that seem like an answer? I don't know.

• 22:06Ryan Holiday?

  Yeah, Pete Holmes was a comedian, had this joke in his most recent special about how atheists and religious people essentially come to the same conclusion, which is the atheist is saying like, we come from nothing. And then a religious person is saying that God is everything and also nothing. And so, same thing.

• 22:26Speaker 01

  Right.

• 22:27Ryan Holiday?

  I thought that was interesting. But yeah, it is weird about philosophy. And it's just not, it's not, maybe, I think, I actually have this, I've been working on this idea that I think a big part of it is that people used to learn Greek and Latin, right? Which I, nobody taught me. And when they teach you Greek and Latin, one of the only ways to do that for most of human history was to have you read the people who wrote in Greek and Latin, which were the...

• 23:01Ryan Holiday?

  The philosophers, right? So, so you're, you're, like, when I learn Spanish, it's like, Paul goes to his house. Or, you know, like, I have pants. You know, it's like these not super interesting, basic rudimentary ways of stringing a question again together. But the way Latin and Greek were taught were like, memorize this passage from Cicero, or here's an epigram from Seneca, right? And so you're, you're being forcibly introduced to some actually pretty intriguing or interesting ideas that are loaded with a lot of the bedrock assumptions of Western civilization.

• 23:40Ryan Holiday?

  And that goes, when that slowly goes away, um, there's sort of a void left behind.

• 23:48Speaker 01

  Yeah. You know, I took, I only took two years of Latin.

• 23:52Ryan Holiday?

  Only two?

• 23:53Speaker 01

  My Latin teacher did, in fact, give me little epigrams to translate as like extra credit exercises sometimes. And I remember, like, carry on and be strong, this pain will be useful to you. I actually used to repeat that to myself.

• 24:06Ryan Holiday?

  And then that's how like Julius Caesar would have been taught Latin.

• 24:09Speaker 01

  Yeah.

• 24:10Ryan Holiday?

  You know, like, uh, that's a pretty ancient, not particularly innovative, but, uh, continuous tradition that went for on for like 2,000 plus years, that just kind of disappeared sometime in like, what, the mid 20th century permanently?

• 24:31Speaker 01

  Yeah. People still take Greek and Latin. They still have Latin Day at my kid's school.

• 24:37Ryan Holiday?

  But, but, but a very small minority.

• 24:40Speaker 01

  Yeah, it's definitely shrunk.

• 24:41Ryan Holiday?

  Like, I mean, when you see these, like, Latin expressions on the, the, you know, classical buildings and stuff, you're like, in America, they would have expected that people could read those or know what was happening. Or, like, even, even, I always think it's interesting, you know, reading some, like, Penguin Classics thing, and there would just be like, untranslated chunks of, you know, some poem in Greek or Latin.

• 25:05Speaker 01

  Right.

• 25:06Ryan Holiday?

  And, you know, Montaigne is assuming that you rec, not only that you can translate this, but that you recognize it's Virgil.

• 25:15Speaker 01

  Yeah.

• 25:15Ryan Holiday?

  Like, and not only do we not recognize the language, but we definitely don't recognize what work it's from, because we weren't taught it that same way.

• 25:24Speaker 01

  Yeah.

• 25:25Ryan Holiday?

  But if you quoted Scarface, maybe a teenager would recognize it.

• 25:28Speaker 01

  Well, maybe, but I mean, now, I think, less and less. Like, it used to be at least people would know Shakespeare.

• 25:34Ryan Holiday?

  Sure.

• 25:35Speaker 01

  And now, it's all STEM. You know, now we don't have English majors anymore.

• 25:39Ryan Holiday?

  Yeah.

• 25:39Speaker 01

  Which I think is a real loss.

• 25:50Ryan Holiday?

  I was talking to my wife about that. You know, like, Taylor Swift is the biggest thing in the world, right?

• 25:54Speaker 01

  Yeah.

• 25:54Ryan Holiday?

  But that that's how society is supposed to be. Like, in the sense that there's supposed to be forms of art, or artists, or plays, or works that everyone knows, right? And that that's where culture is derived from, is the ability to make the, like, Lincoln, he'd made quotes sometimes, but like, you look at his, his addresses, and huge chunks of them are allusions, riffing on the Bible, classical works. But these are unattributed allusions. You know, the mystic chords of memory, or better angels of our nature, judge not lest you be judged. People are no, people know what he's doing there, because they're all sharing this common

• 26:39Ryan Holiday?

  culture. It's not that we should have some sort of forced common culture, but it's the, I guess what I'm saying is, is that, this is not even an academic or a school criticism, it's that as culture has fragmented, because there's an unlimited amount of options, even the stuff that's really popular is capturing only a small percentage of the population at any given time. And so you don't have the ability to create reference points, or allude to ideas that everyone intuitively gets.

• 27:17Speaker 01

  Yeah, exactly. So I, I teach a creative writing seminar at the law school.

• 27:21Ryan Holiday?

  Yeah.

• 27:22Speaker 01

  And very often, I'm trying to talk about a particular technique, like, you know, where you build up this backstory, and then you reveal that this backstory was actually a lie, and there's this underlying world. And so I try to give an example of that, and it's so hard to find something that everyone in the class knows. Like, I can get, like, three people with Star Wars.

• 27:40Ryan Holiday?

  Yes.

• 27:41Speaker 01

  And I can get four other people with Twilight, or something like that. But there just isn't this common set of works.

• 27:49Ryan Holiday?

  Yes.

• 27:49Speaker 01

  That we can refer to and sort of build on in our discussions.

• 27:54Ryan Holiday?

  Right, yeah, like.

• 27:57Ryan Holiday?

  I was, I've been telling the story, but I, my, one of my sons got very into, he's gotten into Greek mythology. So he's like, uh, he was like, uh, the Odyssey. And there's something remarkable about the fact that I could tell him the story of the Odyssey, basically from memory, having learned it, but that that is, that is a very old, I mean, for thousands of years, that's true. But there, you could count on your hand, you know, the other works that you could do that for. Right, where, um, where everyone knows, right? And that everyone has been doing it generation after generation and it, it compounds and compounds and compounds.

• 28:34Ryan Holiday?

  The more people know and reference the same stuff, you know, like Harry Potter is maybe a, one of the recent additions to like the children's canon. And it's not the same, it's not the same level, right? But, but that the idea of like having these sort of cultural reference points that everyone knows. And like, I think about it, like, how many people know about the Stoics? Or when I talk about Marcus Verliss, they just know that because the movie Gladiator was famous 20 years ago. And then I remember I was talking to this, this, uh, guy's a football player and he goes, hey, like, I love this stuff in the Stoics. Like, are there any movies about the Stoics? And I go, well, there is this movie Gladiator.

• 29:18Ryan Holiday?

  And he was like, oh, I have to check that out. And I go, what? You know, what do you mean? And then I realized it came out when he was one years old.

• 29:26Speaker 01

  Right, yeah, no, with my students, part of it is that I'm just aging out of their demographics.

• 29:31Ryan Holiday?

  Yes.

• 29:33Speaker 01

  But also they don't seem to share it with each other. So it's not like there's something that they all know that I don't.

• 29:38Ryan Holiday?

  Yes.

• 29:38Speaker 01

  They just don't have anything in common.

• 29:40Ryan Holiday?

  Right, except Taylor Swift.

• 29:42Speaker 01

  Yes, well, I'm a Swiftie too, like everyone, yeah, everyone loves Taylor Swift.

• 29:45Ryan Holiday?

  But there's some, there's something magical about that. Like, there's something magical about 60,000 people attending the same thing, right? And the one tour being the thing that everyone's talking about and the, the, you know, like.

• 29:58Speaker 01

  And the movie that you can all see. Cause like, this is part of the problem that we have politically.

• 30:03Ryan Holiday?

  Yes.

• 30:03Speaker 01

  I think that everyone is getting different information from different information sources.

• 30:07Ryan Holiday?

  Well, one argument I heard that I thought was interesting is, is understanding Trump as a phenomenon like that. So there isn't, there aren't many mass cultural events anymore. Taylor Swift being a good example of a recent one. But like, or the Barbie movie being a recent one. But again, these are like exceptions that prove the rule, right? But like, Trump is a national slash international phenomenon that people are liking the community of. Like, put aside the repugnant political beliefs. Going to a rally with 50,000 people. What other rallies have 50,000 people? Like, it's not a, put aside politics. And there's not even like, big revival movements. Like, you think about the Great Awakening in the American issue.

• 30:51Ryan Holiday?

  There were these events where things like that happened, where people would go do these things. You know, you look at baseball stadiums when the games are televised. And there's like, 10,000 people in a 40,000-seat stadium, right? Like, even

• 31:06Speaker 01

  Oh, that's sad.

• 31:07Ryan Holiday?

  These pastimes are not what they were. So they're not shared, right? Like, you know, I read somewhere like, the single best time to have a heart attack in New York City was while the finale of Seinfeld was being aired.

• 31:21Speaker 01

  Because No traffic.

• 31:22Ryan Holiday?

  No traffic.

• 31:22Speaker 01

  Yeah.

• 31:23Ryan Holiday?

  But like, no other show since has wrapped up in such a big way.

• 31:29Ryan Holiday?

  Matthew Perry died. There's not actor, there's not gonna be actors like that anymore in the sense of a show where a regular episode is being watched by tens of millions of people. So you lack the ability to create or draw on shared frames of reference because you don't have a mass culture. So Trump is a form, is a, is one of the few mass cultural events. Like, that's why, I think that's why people have the flags. Even like, you think, like, I was talking to someone how

• 32:02Speaker 01

  Yeah.

• 32:02Ryan Holiday?

  When did flags become a form of political expression again? Right? Like, it's strange. But then you realize, oh, no, that's a way of saying like, I belong to this group. Even though that group is repugnant, in my view. People are saying like, I want to be a part of something. And they know that you know what the flag means.

• 32:22Speaker 01

  Well, yeah, do you mean the Trump flags or the American flags?

• 32:25Ryan Holiday?

  I mean, the Trump flag, but

• 32:26Speaker 01

  Yeah. The Trump flag is terrible. That's like the most un-American thing imaginable. It's like putting a person's name on the flag because we're not supposed to be loyal to people.

• 32:34Ryan Holiday?

  But have you also, have you also noticed that? As they made the Confederate flag more and more sort of politically incorrect, some of those same people just wave the regular flag now, the regular flag.

• 32:47Speaker 01

  Yeah.

• 32:48Ryan Holiday?

  But with the same kind of menacing intent, that's odd.

• 32:51Speaker 01

  Well, I mean, one of the things that saddens me so much is the changing meaning of the American flag. You know, and so to some extent, people were doing this with the Betsy Ross flag. And I'm like, you know, legitimately, I have some reservations about the Betsy Ross flag, right? 13 stars in a circle, every star represents a slave state.

• 33:10Ryan Holiday?

  Yeah.

• 33:11Speaker 01

  That's the first flag of the Confederacy too. It looks almost the same.

• 33:14Ryan Holiday?

  Yeah.

• 33:15Speaker 01

  But the idea that the American flag is like a divisive flag for Americans is very sad to me, but like, that's how it's being used. It's like this.

• 33:26Ryan Holiday?

  Like I live out in the country, my neighbor has this big ass truck and on the weekends, he puts an American flag in a special flag holder in the back, sometimes a Trump flag, and he just drives around with it. And you're like, what is, what is that, that, what is he trying to, what's going on there? Right? Like, what is that, what is it doing for him? And it's, it's belonging to something, but it's, it's about drawing on and expressing oneself through a symbol. And symbols are very, very powerful. And I think the quote unquote, good guys don't have that many symbols and aren't very adept at speaking through and creating symbols.

• 34:07Speaker 01

  Yeah, well, we need a better flag.

• 34:09Ryan Holiday?

  What, how so?

• 34:12Speaker 01

  Well,

• 34:14Speaker 01

  I'm trying to think of a flag that would be inclusive rather than divisive and threatening. Cause I think like a lot of people, I feel sort of like the really assertive American flag waving people, I find that kind of menacing. Cause it's aggressive.

• 34:31Ryan Holiday?

  Well, yeah, you know.

• 34:31Speaker 01

  It's like, we're the in group and you're the out group.

• 34:35Ryan Holiday?

  Right. Yeah.

• 34:36Speaker 01

  Yeah.

• 34:37Ryan Holiday?

  Yeah. And then people don't like the pride flag.

• 34:40Speaker 01

  Right. Exactly. So then like, there's the pride flag and then the pride flag gets you attacked.

• 34:45Ryan Holiday?

  Yeah. But I think symbols are, I think Theodore Roosevelt was good at understanding symbols, right? Or finding things that bind people together, national parks being a good example, right? Like, finding the ability to speak.

• 34:59Speaker 01

  Yeah, the national parks are the perfect example, because that's inclusive.

• 35:02Ryan Holiday?

  Yes.

• 35:03Speaker 01

  The whole idea there is this is something that is for everyone. This is something that we have in common.

• 35:07Ryan Holiday?

  Except for the Native Americans that it was stolen from, but...

• 35:10Speaker 01

  Yeah.

• 35:12Speaker 01

  No, a lot of times, like, I think I've come up with some great story about America, and then people are like, "And what about the Native Americans?" And I'm like, "Yeah, that was bad."

• 35:21Ryan Holiday?

  Yeah. Yeah. Well, like, I thought that a little bit during, um, during the Maui wildfires, you know?

• 35:31Speaker 01

  Yeah.

• 35:32Ryan Holiday?

  How people are, obviously, the Native people there are sort of upset with what's happening, and they're talking about, and then people here are sort of repeating what they're saying. And it's like, you know what happened there isn't that different than what happened here, too. It was just slightly more recent.

• 35:49Speaker 01

  Right.

• 35:50Ryan Holiday?

  Like, um, so it's, yeah, the more you dig into it, it's so, uh, you know that, you know this idea of negative capability? Keats talks about it, Fitzgerald talks about it. Basically, it's the ability to hold contradictory ideas in your head at the same time.

• 36:07Speaker 01

  Yeah.

• 36:08Ryan Holiday?

  You can't understand, you can't survive slash understand slash be good in American life without the ability to hold these wildly contradictory notions in your head. Like, you're talking about stories in your book. You really have to be able to understand multiple simultaneous stories, because different people were having very different experiences, and different things meant different things to different people.

• 36:35Speaker 01

  Yeah. Well, and I think it's easier, a lot of times, just to forget.

• 36:38Ryan Holiday?

  Yeah.

• 36:39Speaker 01

  Some of them.

• 36:39Ryan Holiday?

  Sure.

• 36:40Speaker 01

  And we just, we suppress them.

• 36:41Ryan Holiday?

  Well, and then, certain people's thought, certain people's viewpoint is...

• 36:50Ryan Holiday?

  We can't talk about these things. And by you repeatedly bringing them up, you're making things hard on me or them or whatever. So stop. Like, let's just all agree on a simple, unpleasant version of the story and then ignore the other stuff.

• 37:08Speaker 01

  Right, well, it is hard on them. I mean, I think it's it's hard to try to hold these contradictory ideas in your mind because there is a sort of natural tendency to try to make things coherent.

• 37:19Ryan Holiday?

  Yeah.

• 37:20Speaker 01

  And have a worldview that makes sense. And so you kind of squeeze out the inconvenient splinter, even if it's a splinter of truth.

• 37:29Ryan Holiday?

  Yeah, cognitive dissonance is is the thing we're always fighting, always.

• 37:33Speaker 01

  Yeah.

• 37:34Ryan Holiday?

  And, yeah, it's tough. It's really tough. But you have to sort of swim against that tide. Like, I heard someone say once, like, if it's pleasant, it's probably not history. Like, if the narrative is reassuring or clarifying to you, you're probably not anywhere near history. You're somewhere in the realm of propaganda or fiction or story.

• 38:06Speaker 01

  Yeah, I think that's true. I mean, on the other hand, I think that stories are very valuable and helpful. You know, even though they're not completely true and they do have an ideological angle.

• 38:20Ryan Holiday?

  Well, because if you don't have them, what do you have?

• 38:22Speaker 01

  Right, this is what brings us together.

• 38:24Ryan Holiday?

  Yeah.

• 38:25Speaker 01

  And the stories teach you virtue. You know, we have these ideas about what it means to be a good American.

• 38:32Ryan Holiday?

  Or a good person.

• 38:34Speaker 01

  Or a good person.

• 38:35Ryan Holiday?

  Yeah, there's the the line from one of Roosevelt's early biographers. He said, he grew up reading about great men.

• 38:45Ryan Holiday?

  And decided to be just like them. And a child needs that. I mean, people need that. A country needs that. A team needs that. Like, if you don't have the sense of what you're aspiring to be, what do you have? You have sort of cynicism and nihilism. You have nothing. And so you need these stories to inspire you, to show you what's possible, to measure yourself against. The problem is, if you're intellectually honest or have any kind of self-awareness, the closer you get to the story, the more you explore them, they crumble a little better. They show themselves to be more complicated, right? Theodore Roosevelt himself being a great example. If you just look at him as the strenuous life,

• 39:27Ryan Holiday?

  great American president, you know, it's, there's a lot to like. But then you kind of dig in more, and there's a lot not to like. And then you dig in more, and then you find other stuff you like that you didn't know you would like.

• 39:40Speaker 01

  Yeah, I mean, there are, there are different angles. Theodore Roosevelt contained multitudes, and I think, you know, we can learn from his mistakes, too. We can learn from his weaknesses. Because it shows us that no one's perfect. And that people have particular kinds of blind spots, and sometimes their strengths turn into weaknesses in some ways. And all of that, I think, is good perspective. I mean, it does complicate it. You don't necessarily want that all at once. I think maybe your first exposure to Theodore Roosevelt when you're a child could be like the teddy bear story.

• 40:13Ryan Holiday?

  Yes.

• 40:14Speaker 01

  That's a good one.

• 40:15Ryan Holiday?

  Yeah, I mean, even, you know, he's, he's hunting with Leroy Percy, who's, you know, in a bound segregationist. And also, yeah, they're just hunting a bear, you know?

• 40:31Speaker 01

  Yeah.

• 40:32Ryan Holiday?

  Which was quickly thereafter hunted, nearly to extinction. You know, so even just like you're poking around in that story, it's a little strange.

• 40:39Speaker 01

  Oh, yeah, no. So if you poke around in that story, it turns out to be not very accurate, the way that it's traditionally told. Because he did refuse to shoot the bear, but then they killed the bear anyway, and they ate it.

• 40:51Ryan Holiday?

  Somebody else just shot it. Yeah, it's just the kind of like, I'm not personally going to do it.

• 40:56Speaker 01

  Yeah.

• 40:58Ryan Holiday?

  I won't get my hands dirty, but I will eat it.

• 41:01Speaker 01

  You know, I'm not the kind of person who would do that then.

• 41:03Ryan Holiday?

  Yes.

• 41:04Speaker 01

  But someone else can.

• 41:05Ryan Holiday?

  Yes.

• 41:06Speaker 01

  I do parkour with my kids.

• 41:08Ryan Holiday?

  Really?

• 41:08Speaker 01

  Yes. My coach, Patrick, is a fan of this podcast.

• 41:10Ryan Holiday?

  That's so cool.

• 41:12Speaker 01

  Yeah. And we started out and we were at this gym and they're like, the first thing we teach you is how to fail. And I was like, that's really good. Learn how to fail safely, right? And then you fail safely, you build on that.

• 41:23Ryan Holiday?

  Like how to not hurt yourself falling?

• 41:25Speaker 01

  Yeah. Like the first thing you do before you try to actually land the move.

• 41:29Ryan Holiday?

  Sure.

• 41:29Speaker 01

  Is you think about, I'm gonna do this, I'm not gonna make it, what happens next? And then how can I do that safely? And parkour, I mean, the thing that impresses me the most about it is it always shows me that I'm capable of more than I thought. So usually like each class, there's some thing that we're building up to. And, you know, you practice the different components and then you try to put them all together. And it's a lot harder to put it all together than do them individually. But I almost always end up doing things where at the beginning of the class, I was like, there's no way I can do that.

• 42:00Ryan Holiday?

  It's also an interesting hobby or sport, I guess, in the sense that, I mean, it's you against yourself. Or it's you against your physical limitations, but primarily you against your sense of what you're, against you against your fears.

• 42:17Speaker 01

  It's primarily mental.

• 42:18Ryan Holiday?

  Yeah.

• 42:18Speaker 01

  Yeah. So I'm more scared than I need to be, is the thing that I learned from a lot of it.

• 42:25Ryan Holiday?

  And the muscle.

• 42:26Speaker 01

  Occasionally, I've hurt myself, but never that badly.

• 42:29Ryan Holiday?

  But building the muscle of being able to do something that you're afraid to do is pretty great.

• 42:35Speaker 01

  Yeah. I think it's really useful. And also, it feels incredible. You're like, wow, I didn't believe I could do that, but then I did.

• 42:43Ryan Holiday?

  Well, that's the letter I was telling you about. When I was so struck by it, I wrote about it in my courage book. Is basically, he thinks he's gonna, he wants to meet Booker T. Washington. Deere Rose wants to meet Booker T. Washington. And he's like, I'll invite him to the White House. And, and for this split second, he thinks about what a shitstorm is going to result from, from doing that. And. And then he decides to do it because of that feeling. And that can't be the first time that he did that. Right? That's a muscle. Like, the first time you do that is not when you are president, touching the third rail of American politics at that time, which is race. Right? You, that is the hunting trips and the boxing

• 43:27Ryan Holiday?

  and the explorations and the mountain climbing and the publishing. You know, it's, his whole life was leading up to doing, as Emerson said, do the thing you're afraid to do.

• 43:38Speaker 01

  Yeah.

• 43:39Ryan Holiday?

  You have to build, that's a muscle.

• 43:42Speaker 01

  Yeah, totally.

• 43:44Ryan Holiday?

  And cultivating it, doing parkour, helps you when you're gonna write a novel, which could feel like, I don't know about you, but when you put like some artistic thing out in the world, there's that, is this cringe? Is this weird?

• 43:58Speaker 01

  Yeah, it's scary. Oh, definitely.

• 44:00Ryan Holiday?

  You know, are people gonna laugh at me?

• 44:02Speaker 01

  Yeah, and like when you're writing, there are different choices you can make. And there's like the riskier one and the safer one.

• 44:07Ryan Holiday?

  Yeah.

• 44:07Speaker 01

  And the one that sounds like everything else.

• 44:09Ryan Holiday?

  Yeah.

• 44:09Speaker 01

  Yeah. And sometimes you do wonder if your vampire novel is gonna make you look ridiculous.

• 44:14Ryan Holiday?

  Yes.

• 44:14Speaker 01

  And I tell people about it and they sort of laugh, but I'm really gonna do it.

• 44:18Ryan Holiday?

  Well, one of the things I do is I don't tell people about creative things I'm considering because like, when I, when I tell you about the book idea that I have, it's obviously not the best explanation of that idea because I haven't done it yet, right? Like, at the end, I can tell you exactly what the book is. But as it's, you know, still a thing I'm figuring out, by definition, I'm not gonna give a great explanation, right? It's like, you can give the elevator pitch for Google after it's Google easier than you can when you're thinking about what Google is gonna be. And so I, I would find that as I would tell people, hey, I'm thinking about quitting my job to write a book. Oh, really? What's the book about? There's no explanation I can give you of the book

• 45:01Ryan Holiday?

  that's gonna make you tell me that it sounds like I should definitely do that. Right?

• 45:06Speaker 01

  Yeah.

• 45:06Ryan Holiday?

  You're gonna be like, oh, good for you. I hope it works out. And I'm gonna pick up on your skepticism and it's gonna make me self-conscious. So I basically don't tell people about stuff I'm working on until I'm basically done.

• 45:17Speaker 01

  Yeah, I think that's a good idea. And actually, like, that's usually what I do.

• 45:22Ryan Holiday?

  Yeah.

• 45:23Speaker 01

  It's been so long with the vampire novel. I kind of plotted it out mostly that I was telling people about it. But usually, yeah. I find that like the feedback I get when I'm in the early stages of a product, a project tends to make me less confident.

• 45:36Ryan Holiday?

  Yes.

• 45:36Speaker 01

  About it.

• 45:37Ryan Holiday?

  So I might kind of float the, I might float it around but not tell you or, you know, like I might talk about the ideas but not be like, I think I'm gonna write a book about it.

• 45:46Speaker 01

  Yeah.

• 45:46Ryan Holiday?

  But the awkwardness of the half-baked idea, a lot of things can get killed there. And you've got to have good people around you who are not that. Spouses can be great at this, right?

• 45:59Speaker 01

  Yeah.

• 46:00Ryan Holiday?

  Like, oh, it sounds amazing. You know, it didn't, but they told you that because you needed to hear that. You know what I mean?

• 46:08Ryan Holiday?

  I guess that's another tradition you've continued, the sort of writer, scholar, lawyer.

• 46:13Speaker 01

  Yeah, well, I always wanted to write fiction. And then I got, I got sort of more interested in nonfiction and, and politics and social issues, just sort of through the practice of teaching constitutional law, I guess, because it made me pay more attention to what was going on.

• 46:30Ryan Holiday?

  Sure.

• 46:31Speaker 01

  And then I thought, in order to understand what's going on now, I need to understand where it came from. So I started trying to learn more history.

• 46:40Speaker 01

  But I love writing. I mean, I, I love pretty much every aspect of my job.

• 46:44Ryan Holiday?

  Yeah.

• 46:45Speaker 01

  I sort of go back and forth between whether the writing is my favorite or the teaching is my favorite. It's really sort of whatever I'm doing at the time.

• 46:55Ryan Holiday?

  And, and you've done, what, three books? You've done two novels, one nonfiction?

• 47:00Speaker 01

  And also, there's a book called The Myth of Judicial Activism, which is about Supreme Court decisions, sort of trying to decide whether the Supreme Court is abusing its power. So I wrote that in like 2005, back when the criticisms of the court were coming from the right. And people were like, this liberal activist court is doing these terrible things. And so I tried to come up with a perspective that would let you Say something about whether the court was behaving appropriately. Sort of what we want a Supreme Court in a constitutional democracy to do.

• 47:33Ryan Holiday?

  Yeah.

• 47:35Speaker 01

  And so then like the test for that is now that the criticisms of the court are coming more from the left, does what I said still make sense? And I think it does. I mean, I think it works out pretty well. Because my basic idea there was the court is one actor in our system of constitutional democracy and other people are supposed to interpret the Constitution too. And sometimes maybe what they think is worthy of respect from the court. So other institutional actors like Congress can decide whether what they're doing is necessary to protect interstate commerce better than the court can.

• 48:11Ryan Holiday?

  Sure.

• 48:12Speaker 01

  Probably. And often they can decide whether some group of people is being treated appropriately or not better than the court can. Because it's just nine people in Washington who are often out of touch. So there are some constitutional issues where it makes sense to defer to representative legislatures and so on. And then there's some where it doesn't. And you can sort of look at what's been going on historically and how good different institutional actors are at making certain kinds of decisions. And whether there are like defects in the political process that would make you not trust what's going on, depending on, you know, who wins and who loses with a particular law or something. And it all kind of works pretty well, I think, to figure out like when the court should be asserting itself and stepping up and saying, we're going to decide this.

• 48:56Speaker 01

  And when they should be holding back and saying, we're going to leave this to ordinary politics.

• 49:08Ryan Holiday?

  We were talking earlier about this idea of duty, like this is my role, this is my job, I'm going to do that job come hell and high water. I think one of the things we're missing, there's a great Pericles quote where he goes like, a person can't abdicate their responsibility or their engagement without forcing the engagement upon someone else, right? And I feel like a good chunk of the American problem, but maybe you could argue this sort of globally, is that When people who are in positions of leadership or something falls in their realm of responsibility, when they don't step up and do that job, it just defers it on to someone else.

• 49:50Ryan Holiday?

  So the court has been forced to adjudicate a whole bunch of issues. And also, not adjudicate, because that is their job. The court has been forced to decide a bunch of major political questions in the absence of a functioning Congress, right?

• 50:14Speaker 01

  Yeah.

• 50:15Ryan Holiday?

  Or a functioning legislative branch. And because people aren't, in the same way that the president is getting stuck with the responsibility for what's happening at the border, as although that's not a legislative issue, right? So, or the border agencies are being forced to deal with what's happening on the border because they're not giving good instructions from both the court and the president and Congress. So when one society or one institution doesn't do their job, it forces, that pressure finds a different way to go. And that pressure is often not, that pressure breaks the institution that it's being redirected towards

• 50:59Ryan Holiday?

  because it's not made for that pressure either.

• 51:01Speaker 01

  Yeah, the institution's not made to do.

• 51:03Ryan Holiday?

  Yes.

• 51:03Speaker 01

  Right, so the president's not supposed to be making laws.

• 51:06Ryan Holiday?

  Yes.

• 51:06Speaker 01

  But when Congress doesn't act, the president does what he can through executive orders.

• 51:11Ryan Holiday?

  Yes.

• 51:12Speaker 01

  And yeah, like same thing with the Supreme Court, I think. One of the things that people have complained about with some Supreme Court decisions is, oh, it looks like legislation. Because you're setting out this detailed code. That was one of the things that people objected to with Roe v. Wade. And it's true. You know, if Congress did more or if the political branches resolved conflict better, maybe we wouldn't be punting so many things to the court.

• 51:37Ryan Holiday?

  Yeah, like I think it's funny you have these certain congressmen and senators who are mad about woke businesses. Like, why are these businesses getting political? And it's like, to me, it's very obvious. It's because those businesses, which are made up of people, feel like the government is not being responsive to the problems that they have brought to their attention. That actually, there's a broad consensus around a number of pressing issues, right? But Because of our sort of janky system, you don't actually get any satisfying legislative or governmental solutions to those problems. So people go, if I can't get my congressperson, like, this is one of the most gerrymandered districts in the entire country right here, right?

• 52:21Ryan Holiday?

  And so because I have no hope of reaching my congressman about anything, I might talk to my book publisher about something, or my boss about something, right? I might, where I have leverage as a person, I'm gonna try to use that leverage, because everyone wants the world to be the way that they think it should be, or, let's just be more generous. Everyone wants the world to be better. If they don't, if, if they cannot bring about political change through the system as it's intended to do, to go, they go, I'm an employee at Facebook, Mark Zuckerberg, you're my boss, I'm gonna quit if you don't do something about it. Right?

• 53:02Speaker 01

  Yeah.

• 53:03Ryan Holiday?

  And so it creates, it, it's directing that pressure into institutions that are not designed for that pressure and are not particularly able to express political viewpoints very effectively. And so it's, by someone not doing their job, which is politicians, other people are doing double or triple duty, or stepping into things that are like, because we had such a woeful pandemic response, social networking companies found themselves having to make public health decisions. And now we're mad at them for making these public health decisions. It's like, they were under a lot of pressure from customers, from employees, you know? And ironically, from government,

• 53:47Ryan Holiday?

  as if government didn't have their own solutions to this problem.

• 53:51Speaker 01

  Yeah, I mean, sometimes I think it's not so bad. You see this with climate change, where, you know, if you can't get the action that you want from the government, maybe you can pressure businesses

• 54:01Ryan Holiday?

  Right.

• 54:02Speaker 01

  into doing the right thing. So sometimes it works.

• 54:06Ryan Holiday?

  But when people are like, why are these companies being so political? It's because politics isn't working.

• 54:11Speaker 01

  Yeah. Yeah, well, I do think our political system, Congress in particular, is broken.

• 54:17Ryan Holiday?

  Yes. Well, why do we have the same number of representatives that we've had for so long?

• 54:22Speaker 01

  Oh, we should definitely have more representatives.

• 54:24Ryan Holiday?

  Yeah.

• 54:25Speaker 01

  Uh, we should have more states.

• 54:27Ryan Holiday?

  Of course.

• 54:27Speaker 01

  We should have small blue states so that Senate malapportionment doesn't have a partisan tilt. Because it really shouldn't have a partisan tilt. That's the problem.

• 54:35Ryan Holiday?

  Mm-hmm.

• 54:37Speaker 01

  We should have ranked choice voting. Final five voting would be a great idea. So this idea is you have an open primary and then the top five vote-getters go on to the general election and you have ranked choice voting with instant runoffs.

• 54:50Ryan Holiday?

  Yeah.

• 54:50Speaker 01

  Because one of the reasons, I think maybe like the main reason that the political system works so badly is it's basically primary voters who determine the outcome. Because you've got all of these safe districts. And the people who vote in the primary are the most intense partisans and very often they're motivated by negative partisanship.

• 55:08Ryan Holiday?

  Right.

• 55:08Speaker 01

  Which is they just think the other side is the enemy and wants to destroy me. So they elect this person and then if that person's like, "I'm gonna reach across the aisle and work with the other party," they're like, "You're a traitor."

• 55:18Ryan Holiday?

  Yeah.

• 55:18Speaker 01

  And they get rid of them.

• 55:19Ryan Holiday?

  Sure.

• 55:20Speaker 01

  So obviously, like, you're electing people and then you're punishing them for actually doing something.

• 55:26Ryan Holiday?

  Right.

• 55:26Speaker 01

  So you end up with this negative polarization in the government too, where people are really afraid to work with the other side.

• 55:35Ryan Holiday?

  Well, I think if you ask someone like Theodore Roosevelt, obviously he had his imperial streak, so he would have thought this for slightly different reasons, but I bet he would have been surprised at how little growth there has been in some of these institutions, in the sense that there are only marginally more states than when he was president, right? That, uh, there haven't been some of those changes or... I think the, the idea was never that you get to a point and then you cease to grow and then everyone just fights over the same number of seats or, like, a dynamic system is growing and expanding and changing and so...

• 56:20Speaker 01

  And improving.

• 56:21Ryan Holiday?

  Yeah, right. Otherwise, you get bogged down in some form of kind of trench warfare where it's only with really big mistakes or really big buildups that you get kind of a breakthrough. But yeah, if Puerto Rico was a state, it would force both conservatives and Democrats... To adjust.

• 56:41Speaker 01

  Right. Puerto Rico, Puerto Rico would be an interesting state.

• 56:44Ryan Holiday?

  Of course.

• 56:44Speaker 01

  Because it would be kind of up in the air.

• 56:46Ryan Holiday?

  Yes.

• 56:46Speaker 01

  District Columbia.

• 56:47Ryan Holiday?

  Mm hmm.

• 56:47Speaker 01

  That would also be a good state.

• 56:49Ryan Holiday?

  Yes.

• 56:49Speaker 01

  I think. I mean, that's like.

• 56:50Ryan Holiday?

  That would force a dynamism.

• 56:51Speaker 01

  Taxation without representation.

• 56:53Ryan Holiday?

  Of course. And it would, but it would cha, you would, instead of everything, all the lines being very established and only something like COVID shaking things a little bit.

• 57:04Speaker 01

  Right.

• 57:05Ryan Holiday?

  You would be having new changes that are happening all the time. I'm not saying you should be capturing Pacific Islands and making them into states, right? But, but like if, yeah, if California was suddenly four states.

• 57:15Speaker 01

  Yes. If we've got two Dakotas, we should have four Californias.

• 57:18Ryan Holiday?

  Yes.

• 57:19Speaker 01

  I usually say three, but I'd go for four, too.

• 57:21Ryan Holiday?

  Yeah.

• 57:21Speaker 01

  And we should have a national popular vote because that makes California matter.

• 57:26Ryan Holiday?

  Mm hmm.

• 57:26Speaker 01

  Right? There's three million Republican votes in California and they count for nothing with the Electoral College and the winner take all system. And no one cares about California. You know, it's all about Pennsylvania, Ohio, Wisconsin, North Carolina.

• 57:44Speaker 01

  But if you have a national popular vote system, then every vote actually matters.

• 57:48Ryan Holiday?

  Sure.

• 57:49Speaker 01

  And if you change someone's mind, that helps you, even if it's in New York or Texas or California.

• 57:54Ryan Holiday?

  Right.

• 57:55Speaker 01

  Right? And you don't get the obsessive focus on changing people's minds in Pennsylvania.

• 57:58Ryan Holiday?

  Yeah, it's like, I grew up in California. I live in Texas. In both states, my vote doesn't matter.

• 58:05Speaker 01

  Yeah.

• 58:06Ryan Holiday?

  Because they're just, it's already decided.

• 58:09Speaker 01

  Right.

• 58:09Ryan Holiday?

  It's effectively already decided.

• 58:12Speaker 01

  Yeah. And the vote of someone in Wyoming counts like three times as much as yours.

• 58:18Ryan Holiday?

  Yeah.

• 58:18Speaker 01

  Which is an offense against our basic principle of political equality. I mean, if there is a founding American principle, I mean, there are a couple probably. One, I said before, is loyalty not to a person, but to an idea, loyalty to the Constitution, which is why the Trump flag is so bad. But political equality of citizens.

• 58:36Ryan Holiday?

  Yeah.

• 58:37Speaker 01

  So at the founding, they're very big on this idea. There's no kings, there's no aristocracy. There are no superior insiders. They're okay with the inferior outsiders, which is the enslaved people.

• 58:48Ryan Holiday?

  Yeah.

• 58:49Speaker 01

  But there is this idea that Americans, no American is better than any other American.

• 58:53Ryan Holiday?

  Sure.

• 58:53Speaker 01

  And it's just wrong for some Americans' votes to count more because that's basically an aristocracy. So right now, we've got like this rural, low population aristocracy. And you get minority rule from that.

• 59:06Ryan Holiday?

  But don't you think also the meta sort of lesson of America or meta story of America is also

• 59:13Ryan Holiday?

  that change is possible? So, America founded by change, right? It's like

• 59:18Speaker 01

  Yeah.

• 59:19Ryan Holiday?

  Break off and then you have this revolution, you have this new system of government that's never existed. And then you have the Articles of Confederation, which are a disaster and they go, this is a disaster. Let's change it. They change it and they go, oh shit, we missed a bunch of important things. We're going to amend it with 10 amendments, the Bill of Rights. And then, by the way, we're going to continue to add to the Bill of Rights. We're gonna, we're gonna make alcohol illegal. And then we're gonna realize that was a huge mistake and just a couple amendments later, change it. And then at some point, like what, like 1970, we were like, no more. Everything is, nothing changes, same number of representatives effectively.

• 1:00:00Speaker 01

  Right.

• 1:00:00Ryan Holiday?

  Same, like, no, it's impossible to add to the Constitution. And now everything's the same. So you get bogged down. And so I, I think there is this sense for now, more than a generation, where we don't have agency over the governmental system, that it simply is what it is. You can't change it.

• 1:00:23Ryan Holiday?

  It, it, it, it won't be radically different in your children's lifetime than it was in your lifetime. And there's something very sad about that.

• 1:00:30Speaker 01

  Yeah. And the end of the amendments is just about the rise of originalism. It's like the same time period. And we were talking about this before, and I think there's actually something to that. Because it's the rise of originalism that makes us think of the founding moment as a concrete moment when everything is fixed.

• 1:00:49Ryan Holiday?

  Yes.

• 1:00:49Speaker 01

  And all of the answers are there. And then we're sort of building out and trying to live up to the ideals and more fully realize them and so on. But it's all there at the founding.

• 1:00:58Ryan Holiday?

  Right.

• 1:00:59Speaker 01

  And in fact, the historical understanding of the time was, it was fluid.

• 1:01:02Ryan Holiday?

  Yeah.

• 1:01:02Speaker 01

  Things were changing. And maybe the biggest lie that we tell ourselves about the American story, I think, is that it's this sort of steady progress of fuller realization of founding ideals. That the essence of America is there in 1776. Whereas really, like, the story that you were telling is it's failure and reinvention.

• 1:01:23Ryan Holiday?

  Yeah.

• 1:01:24Speaker 01

  And we work within the system that we have for as long as we can, as long as we think it's going to get us where we need to go. And then at a certain point, again and again, we realize this isn't going to take us where we need to go. We have to break it and start something new. And that's like the story of the revolution, and it's the story of the failure of the Articles of Confederation, and it's the story of the Civil War and Reconstruction, too. I mean, first, the South is like, the system's not working anymore, we're leaving.

• 1:01:50Ryan Holiday?

  Yeah.

• 1:01:50Speaker 01

  And then the rest of the country's like, no, you're not.

• 1:01:52Ryan Holiday?

  Yeah, we paid for all that stuff.

• 1:01:53Speaker 01

  Yeah, right, give us back our forts.

• 1:01:55Ryan Holiday?

  Yeah.

• 1:01:56Speaker 01

  But then, like Reconstruction, they're trying to work within the system, and the 13th Amendment is enacted through the normal process, and then they can't get the 14th Amendment ratified.

• 1:02:07Ryan Holiday?

  Right.

• 1:02:08Speaker 01

  And that's when the Reconstruction Congress is like, okay, we're destroying the original states. We're going to break this and move forward. So, we get these moments of radical reinvention, and those are really often the moments of progress. So like, one of the lessons that I think we should take from American history that we downplay is that very often it's conflict

• 1:02:28Ryan Holiday?

  Yeah.

• 1:02:28Speaker 01

  that leads to progress.

• 1:02:30Ryan Holiday?

  And maybe one thing I would add to that, that I think is both hopeful, and then maybe something that's missed, is that that work was primarily done by young people. The founders are remarkably young.

• 1:02:42Speaker 01

  Yeah.

• 1:02:43Ryan Holiday?

  You know, they're all kind of under 40 for the most part. Benjamin Franklin's like the lone old guy. Obviously, the Civil Rights Movement, we tend to, we see it as Martin Luther King and Rosa Parks, both of whom were essential, but we forget that it's really the students in Nashville and the sit-in movement, the kids who are putting their bodies on the line, that actually transform it into this, you know, it's the freedom riders that make it from an issue that's affecting the people in Montgomery to a federal issue that draws the North in and really brings about the chain. And so, you know, the idea that This isn't like old people kind of fiddling around with things at the margins,

• 1:03:26Ryan Holiday?

  but it's also young generations going, hey, you guys have screwed it up in some cases, or you guys have taken this as far as you're willing to take it, and we're gonna pick up the torch now. I'm writing about this, and I think this is historically true. I write about Thomas Clarkson, the British abolitionist. He writes a college essay about this question of whether it's wrong or right to own a human being. And he wins this prize, and he's walking, riding his horse away from Oxford. And he's won the essay, but he was just writing what he thought they wanted to hear to win. Like, he was just writing, he wrote not even what they wanted to hear. He tried to write what he didn't think anyone else would write, and that's what wins.

• 1:04:11Ryan Holiday?

  He writes that, no, you can't own a human being. And as he's riding away, Adam Hochchild writes about this in Bury the Chains, but he has this sort of road to Damascus moment. He's on the road, and he goes, if I'm right, someone should do something about this. And then he goes, that person could be me.

• 1:04:32Speaker 01

  Yeah.

• 1:04:32Ryan Holiday?

  And one man eliminates essentially the oldest institution in human history, you know, from a college essay. And that is a remarkable, but then timeless thing right there. That's what those college students, those vets who came home from World War II were like, I don't want to ride on the back of the bus. I don't want to be pushed around. Like, I want to go eat a sandwich with my friends, and I'm gonna do something about it. You know? The idea that that young people can demand that the system change and then remake the system in their image kind of stopped with the baby boomers.

• 1:05:10Speaker 01

  Yeah, I mean, you do see young people doing that now, like organizing around climate change, organizing around gun violence.

• 1:05:21Speaker 01

  I hope it's gonna work.

• 1:05:22Ryan Holiday?

  I hope so. I hope it's not too late. Yeah.

• 1:05:25Speaker 01

  Yeah.

• 1:05:28Ryan Holiday?

  Yeah. Yeah, it's, but this generation is up against so much entrenched sort of, there's not room because a lot of the offices haven't been vacated.

• 1:05:42Speaker 01

  Yeah.

• 1:05:43Ryan Holiday?

  I think that's a big part of it.

• 1:05:47Ryan Holiday?

  I don't think the lifetime appointments idea ever anticipated people living to be 100 years old.

• 1:05:54Speaker 01

  No, it also didn't anticipate the party system. So if we're talking about lifetime appointments for federal judges and the Supreme Court in particular, that's terrible. That's completely broken. It's completely messing up our system of governance now. Because the way things are now, justices retire strategically so that the president who appoints their successors is going to appoint someone like them. They're sort of replacing themselves. And what that means is the current composition of the Supreme Court can persist pretty much indefinitely.

• 1:06:28Ryan Holiday?

  Or in a random accident.

• 1:06:30Speaker 01

  Yeah, as long as the Republicans win one out of three or one out of four elections. Because you know, you wait 12 years, then four justices retire, you replace them with young people, you keep that majority forever. And that's not the way it was supposed to work.

• 1:06:44Ryan Holiday?

  Yeah, stasis is not natural. It's supposed to be change and dynamism.

• 1:06:48Speaker 01

  Yeah. I mean, more generally, I think we're seeing some problems with how old some of our political leaders are. And it would be better if we had younger political leaders.

• 1:06:59Ryan Holiday?

  Yeah.

• 1:07:00Speaker 01

  But life tenure on the Supreme Court is like a particular structural problem. It could be fixed. The proposals are out there, like 18-year term limits. Let each president appoint two justices per four-year term. We could really do that.

• 1:07:15Ryan Holiday?

  We could do that.

• 1:07:17Speaker 01

  We could do that, yes. I'd like to see more action on it.

• 1:07:20Ryan Holiday?

  I don't even think there's the belief that we could do that.

• 1:07:22Speaker 01

  Well, it's weird. It's weird, because it seems like political actors don't think that we can, even though there's broad bipartisan popular support for it. And yet, people are acting like, no, it's not possible. We can't do that.

• 1:07:37Ryan Holiday?

  Yeah.

• 1:07:38Speaker 01

  I don't know why not.

• 1:07:39Ryan Holiday?

  Yeah, it's...

• 1:07:42Ryan Holiday?

  Yeah, as if it was supposed to stay the same forever.

• 1:07:46Speaker 01

  Yeah, well, so there's this idea that changing the Constitution is like unwise or unpatriotic or something like that, which is crazy because, one, like, the Constitution provides for a method of amendment, and then, two, like, the things that we like the best about the Constitution are basically the amendments, right? No one's like, "I feel a swell of American pride when I recall that the president has to be a natural-born citizen."

• 1:08:09Ryan Holiday?

  Right.

• 1:08:10Speaker 01

  They're like, "I feel a swell of pride when I think about life, liberty, and property being protected by the due process clause."

• 1:08:16Ryan Holiday?

  Yeah.

• 1:08:16Speaker 01

  Which is the Fifth Amendment or the Fourteenth Amendment. You know, I think that our protection of free speech is so great, which maybe it is, maybe it isn't, like, it's kind of been applied in a funny way sometimes, but that's an amendment. Like, we love the amendments.

• 1:08:31Ryan Holiday?

  Well, last question, actually, because you, which you would be, as a constitutional scholar, you'd be the expert. There was this sense, right, Franklin Roosevelt tries to propose his packing the court, and there's this sort of rebellion against it, right? Like, the story we tell ourselves is like, "The people and Congress were horrified, and he backs off." As I understand it, it's like his vice president was very opposed, a southerner. How much of it was actually an understanding by, in the Democratic coalition, which at

• 1:09:11Ryan Holiday?

  that point included all the Southern Democrats, that if he fucks with the composition of the court, our tenuous hold on the levers of power, that's like, that, like, FDR's mistake was thinking, "Hey, I'm gonna pack the court so I can get some of these social safety net programs through." And the actual reaction was, "You're threatening this whole segregation thing."

• 1:09:44Speaker 01

  I don't know, actually. I haven't really heard that.

• 1:09:47Ryan Holiday?

  I just made it up.

• 1:09:49Speaker 01

  It's possible.

• 1:09:50Ryan Holiday?

  But do you know what I was thinking?

• 1:09:51Speaker 01

  The other thing about the court packing plan is, no, he didn't end up packing the court, but also the court kind of changed its tack.

• 1:09:59Ryan Holiday?

  Yes.

• 1:10:00Speaker 01

  So, you know, it's not entirely clear that he didn't get most of what he wanted.

• 1:10:05Ryan Holiday?

  Right. But there was this kind of arrangement in the Democratic Party that like, I mean, Kennedy ironically puts in a bunch of the justices, not justices, judges who are most resistant to his civil rights program because he's rewarding, it's political patronage. He's like, I'll give you the judges you want. So there was this kind of schizophrenic, you know, division in the party where, yeah, sure, we all agree we should have these social safety net things. But if you put a bunch of northerners on the Supreme Court, or a

• 1:10:45Ryan Holiday?

  bunch of more modern liberals on the Supreme Court, how long is our ability to continue to interpret the 13th, 14th, 15th Amendment the way we are? How long is that going to last? And does suddenly the whole legal edifice of the South become vulnerable?

• 1:11:05Speaker 01

  Maybe, yeah. I don't know. I mean, the thing that did happen was you got the social programs and the social safety nets, and then they were applied in a racially discriminatory way.

• 1:11:16Ryan Holiday?

  A compromise.

• 1:11:17Speaker 01

  Kind of. It is a compromise, yeah. Like, people are against redistribution, but it's okay if it ends up really only going to white people.

• 1:11:26Ryan Holiday?

  Sure.

• 1:11:26Speaker 01

  It's like redistribution that increases racial equality. That's like the third rail.

• 1:11:34Ryan Holiday?

  Well, this was awesome. Thank you.

• 1:11:35Speaker 01

  Yeah, thank you. Really interesting.

• 1:11:44Ryan 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.