Ezra Klein on Virtue, Self-Critique, and His Take on Stoicism

Ezra Klein is one of the sharpest voices in American politics, but this conversation is not about left versus right. It’s about virtue, responsibility, and character. Ryan and Ezra talk about why virtue matters in a democracy, what liberalism has lost by failing to speak clearly about responsibility, and why institutions alone can’t save a society if the people inside them abandon restraint, honesty, and self-critique. They also get into what Ezra thinks Stoicism gets right, where it falls short, and why Stoicism, or any philosophy, has to be tested in real life. Ezra Klein is a New York Times columnist and the host of The Ezra Klein Show https://podcasts.apple.com/us/podcast/the-ezra-klein-show/id1548604447. He is also the co-founder of Vox, where he served as editor-in-chief and later editor-at-large, and previously worked at The Washington Post, The American Prospect, Bloomberg, and MSNBC. 📚 Ezra Klein’s books: Why We’re Polarized https://www.amazon.com/Why-Were-Polarized-Ezra-Klein/dp/147670032XAbundance https://www.thepaintedporch.com/products/abundance?_pos=1&_sid=76c4ae81a&_ss=r 🎙️ Listen to The Ezra Klein Show https://podcasts.apple.com/us/podcast/the-ezra-klein-show/id1548604447 on Apple Podcasts https://podcasts.apple.com/us/podcast/the-ezra-klein-show/id1548604447, Spotify https://open.spotify.com/show/3oB5noYIwEB2dMAREj2F7S, or watch on YouTube https://www.youtube.com/@EzraKleinShow 👉 Follow Ezra Klein on Instagram | @ezraklein https://www.instagram.com/ezraklein/?hl=en 🎟️ DAILY STOIC LIVE https://www.dailystoiclive.com/| Ryan Holiday is coming to a city near you https://www.dailystoiclive.com/! Grab tickets here https://www.dailystoiclive.com/ | https://www.dailystoiclive.com/ 🎙️ AD-FREE https://dailystoic.supercast.com/| Support the podcast and go deeper into Stoicism by subscribing to The Daily Stoic Premium https://dailystoic.supercast.com/ - unlock ad-free listening, early access, and bonus content: https://dailystoic.supercast.com/ https://dailystoic.supercast.com/ 🎥 VIDEO EPISODES https://www.youtube.com/@DailyStoic/videos| Watch the video episodes on The Daily Stoic YouTube channel https://www.youtube.com/@DailyStoic/videos: https://www.youtube.com/@DailyStoic/videos https://www.youtube.com/@DailyStoic/videos ✉️ FREE STOIC WISDOM https://dailystoic.com/dailyemail | Want Stoic wisdom delivered to your inbox daily? Sign up for the FREE Daily Stoic email at https://dailystoic.com/dailyemail https://dailystoic.com/dailyemail See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

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

• 0:00Ryan Holiday?

  Welcome to the Daily Stoic Podcast, designed to help bring those four key Stoic virtues, courage, discipline, justice, and wisdom into the real world.

• 0:15Ryan Holiday?

  One of the things the Stoics understood is that a society doesn't fall apart all at once. It happens slowly. There's a good and a bad lesson in there, right? Like, it's that Julius Caesar doesn't magically overthrow the Roman Republic. There had been signs. There had been decay. There had been compromises, also a failure to compromise, of which I have not spared Cato some of the criticism, right? There's a great book, The Storm Before the Storm, that I've raved about. But each of these choices and decisions is bringing a society, a government, a civilization, closer to an inevitable collapse and failure.

• 0:58Ryan Holiday?

  And people's failure to step in and do something about it is sealing their fate. On the other hand, I sometimes point out to people when they're like, are we Rome? I go, Markius Aurelius is one of the last of the good Roman emperors, right? Sure, Pax Romana ends with Markius Aurelius, but the Visigoths don't sack the city of Rome until almost 250 years later. Like, the official fall of the Western Roman Empire is almost 300 years. The Byzantine Empire, which is like the remaining part of the Roman Empire, survives until the fall of Constantinople, like 1,000 years later.

• 1:42Ryan Holiday?

  So it can take longer than you think. It can take longer than many of our lifetimes stacked together. But when you live in a society where people aren't telling the truth, where leaders stop acting with courage, where institutions maybe keep some of their names and rituals and procedures, but only in name, only in theory. You get yourself on that path, or maybe even a downward spiral. And this is why virtue mattered so much to the Stoics. Not a word, not a slogan, not the thing you signal at, but actually trying to live it, to build it into the society, into the governance. It's got to be there in the character of the people. As John Adams famously said, like, doesn't matter how good the Constitution is.

• 2:25Ryan Holiday?

  And he said this 250 years ago, it doesn't matter how good the Constitution is. Without character in the people, you got big, big problems. And that's why I wanted to talk to today's guest Ezra Klein. Ezra is a journalist, a New York Times columnist. He's the host of the Ezra Klein Show. He's a co-founder of Vox. And he wrote two great books, Why We're Polarized and Abundance, which he co-wrote with Derek Thompson, whose work I also love. And in this episode, Ezra and I are talking about those themes that I was opening about. Virtue, responsibility, masculinity. What happens when our institutions begin to crumble? What happens when those institutions depend on qualities that really no law can legislate?

• 3:09Ryan Holiday?

  One of the questions I had for him that I remain fascinated with is why so many powerful people are afraid to use the power they have, are afraid to zealously enforce the prerogatives of their office, I'm looking at you, Congress? And why a healthy society requires both individual responsibility and collective responsibility? And then, of course, we get into Stoicism in this episode. Ezra was talking about why Marx, Schumpeter, and the Stoics haven't always landed for him. But I can feel, because I listen to his podcast, it's one of my favorites. I'm going to be listening to it on this long flight I got. I can tell he's coming around to some of the ideas, or at least he's turning back to some of these ancient ideas in a really interesting way, which is, by the way, what philosophy is supposed to help us do. It's not impractical and theoretical.

• 3:54Ryan Holiday?

  It was, for the founders themselves, kind of an operating system, not just for life, but for institutions and a culture. As I said, Ezra is one of the best journalists and political commentators and thinkers around today. You've probably seen his stuff in the New York Times.

• 4:11Speaker 01

  Times, if you don't listen to his podcast, you absolutely should. I was just listening to his episode with Helen Lewis, which I really liked. She's one of my favorite thinkers. She's been on the podcast. You've probably seen his stuff on Vox. He used to write for the Washington Post many, many years ago. I quote him in Conspiracy, in the preface of Conspiracy, actually disagreeing with him. But anyways, I've been reading his stuff and listening to his stuff for a very long time. You could follow him on Instagram at Ezra Klein. You could check out his podcast, The Ezra Klein Show, wherever you get your podcasts. And you can pick up a copy of Abundance at the Painted Porch, which you should absolutely do because it's a great book.

• 4:46Ryan Holiday?

  I was going to tell you, it was so funny that you called to prep before the episode. I've been doing this a long time and only one person has ever asked to prep for a podcast they were coming on before. And I don't think you would, you would ever guess who it was.

• 5:01Speaker 01

  Who was it?

• 5:02Ryan Holiday?

  It was General Dan Cain.

• 5:05Speaker 01

  Oh, interesting. There you go.

• 5:06Ryan Holiday?

  Yeah.

• 5:07Speaker 01

  You know, if you had put up a list, I would not have been shocked by that. I mean, the military men are very, are very methodical. I don't usually, but because I thought it would be good to see if we could direct to more interesting things, I thought it'd be good to connect.

• 5:22Ryan Holiday?

  I wasn't surprised, though. You do, you do seem, I was trying to think of the word. Is it thoughtful, conscientious? Like, I can tell when I listen to your podcast that you are very prepared.

• 5:35Speaker 01

  That is true.

• 5:36Ryan Holiday?

  You're not just like, hey, let's see where this goes.

• 5:38Speaker 01

  No, I go on podcasts for people to see where it goes and I find it shocking. It's also, it's two things, too. It's like, one, you got to know your strengths. I was just on Dax Shepard's show. I don't know if it's out yet. I don't think it is. And you know, it's like a real talent to just exist in the hang and to make the hang work, you know, with Dax and Rogan and some of the others have. But I think what I'm good at is actually like absorbing the other person's project and kind of coming out with like, like an interesting distillation of it. And then the other, which I've been trying to, I do a lot less now. I don't go on TV. I'm selective about what shows I go on. And one thing I want to try to do is then if I'm going to be selective, like be even more thoughtful about using those opportunities well,

• 6:22Speaker 01

  so that there's some reason to do it. And interesting things happen when I'm there that are creatively generative for me and good for the show I'm on. Be more narrow, but also more, put more into it.

• 6:33Ryan Holiday?

  It's interesting though, because I'm not sure from a listener's perspective, if they can always tell the difference. Like the external product can feel the same. Like I've been interested in the medium of podcasting, how, how often people sort of mistake it for something very deliberate and considerate, when it really is people sort of bullshitting. You know, like often the episode is, is people thinking out loud as opposed to having expressed something that they have put a lot of thinking into. And I'm not sure that the difference is always discernible to the listener. And so, you know, like people will be like, oh, sometimes I do audiobooks and sometimes I listen to podcasts. And I'm like, those are very different things.

• 7:16Ryan Holiday?

  Like they're not even in the same ballpark as far as like what the finished product is, I guess, is what I'm saying.

• 7:23Speaker 01

  I think people can often tell the difference without knowing they're telling the difference. The way that when you see amazing athletes, their work looks effortless.

• 7:33Ryan Holiday?

  Yeah.

• 7:34Speaker 01

  I think the really, really, really good podcasters, in, in different ways. It's not always because he did so much preparation about the material. But the, the shows that are really good, people are seeing something that reflects an iceberg under the surface. A podcast, it seems strained. There are certain shows I have listened to where the amount of work going into the show is very, very present, and that's also not a good feeling.

• 7:59Ryan Holiday?

  Yes.

• 8:00Speaker 01

  You're trying to get to a point where it's a tremendous amount of work to make things feel effortless.

• 8:06Speaker 01

  Lot of effort to get there.

• 8:07Ryan Holiday?

  Yeah, it's a, it's an interesting medium because it, unlike I think a lot of journalism, it is not usually hostile. They're usually friendly conversations. And I think it's, that's sometimes conducive to giving people a pass. Like, you balance this in an interesting way, which is something I wanted to ask you about because it's always struck me as something that must take a lot of restraint for you, is you clearly have a lot of people on that you disagree with on a lot of issues, but the episodes are very rarely contentious. You disagree with a guest, but you don't call the guest out. You sort of, you often let them say something that I could tell you probably think is insufficient, but you sort of leave it there. How, how does that work for you?

• 8:49Speaker 01

  I am never trying to defeat my guests.

• 8:52Ryan Holiday?

  Yeah.

• 8:53Speaker 01

  That's just not what I do on my show. I am trying to understand them, and that means pushing to the point where I feel like I've come to the boundary of their response. So in a show where I really disagree with somebody, you'll often see me push harder than when what they're saying feels more intuitive to me. But once I feel like I have found what their response to that pressure is, I move on. I'm never, ever, ever, it has never happened on my show and it never will, but I'm trying to humiliate somebody before my audience. I never want to do that. People have ended up, a fairly small number of them, but people have ended up not loving how they performed on my show, but it's almost

• 9:34Speaker 01

  always because I ask them very straightforward questions and their answers just weren't very good. But I don't do debating tricks. I'm a, I think, a fairly good debater. I've been in that format a lot in my life and have had some experience with it. And one thing it has taught me is that debate is a skill. And so I don't mistake being good at that skill for being right about things. It's just, I don't know. I, it's never even occurred to me to, to make my, my show that way. I think that I learn a lot from the episodes where I disagree with people, but that's the intention, is to learn a lot, not to show that my views are better. I have home court advantage. I have control over the edit. It's my audience, listening to a show with my name, with album art, with

• 10:16Speaker 01

  my face. The idea that it is, I need to bring people on there to beat them, like, what kind of fair fight is that?

• 10:22Ryan Holiday?

  I bet I could guess what some of those episodes are. What I, what I found interesting about them is like, they were pretty straightforward questions you were asking, and it's clear that although this person is in many cases pretty experienced with being on shows, they've never actually been asked those questions or forced to, to answer them in a way that, uh, yeah, they, they haven't been forced to actually put it in black and white. They've, they've been able to dance around it a long time.

• 10:51Speaker 01

  Going back a very long time, I've had the view that softball questions are the true hardballs and hardballs are the true softballs. And what I mean by that is that if I had Donald Trump on my show and I were to ask him about the five most controversial, outrageous, malicious things he has said in the past year, I think he would know exactly how to handle that. And if I were to say, Mr. President, how do the dual eligibles in Medicaid work? I think it is very plausible. And I mean, this, if you know Medicaid issues is a huge issue. He would have no idea what I'm talking about. Now, I don't know if that's true, right? I've not asked Donald Trump that question, but I've seen this many, many

• 11:32Speaker 01

  times with politicians, with news, news figures and, and with people who are just experts in their field, that you ask people, and journalists do this all the time, this sort of pose of toughness. You ask them the question that's supposed to be most uncomfortable for them and they're fine with that. They knew exactly what that question was.

• 11:50Ryan Holiday?

  Someone prepped them for that very question.

• 11:52Speaker 01

  This thing you're saying, how does it work? How do you think about this obvious implication of it? And then you can really begin to see have they thought through it clearly. You know, when I, when I was at Vox, we always used to talk about this. There was actually, when you would do an explainer of a straightforward question, like, what is infrastructure spending?

• 12:16Speaker 01

  It would turn out that the amount of hiding in a term that we all thought we knew was tremendous. We actually just go through life pretending that there are, and I think convincing ourselves that there are far fewer holes in our knowledge than there really are. And, you know, part of, I think, the work of this stuff is actually understanding like the base layer of our intellectual pyramids, when it's very easy, if you know, you're reading the news and following controversies, to always be at like the peak, right? Always be at some narrow point everybody's debating, as opposed to like actually developing a foundational understanding.

• 12:57Ryan Holiday?

  Is this a transferable skill for you? I'm curious about this idea of like, you ask a question, you let the person explain up to their limits of understanding, and then you just go, okay, if that's your reality, that's your reality. Can you apply that in your personal life? That's something I struggle with, like.

• 13:13Speaker 01

  Tell me what you mean. Give me an example.

• 13:15Ryan Holiday?

  Well, like, let's say you're in an argument with your spouse, or you're just talking to someone on the street. Like, can you, can you exercise that level of restraint? Like, I would characterize part of what we're talking about here is not needing to get the last word, right? A very sort of human thing. Like, we want to, we want people to know how we feel, and sometimes we feel like it's mutually exclusive, like, rather than two people can have two different understandings of something. All right. Can you apply that outside the confines of your show?

• 13:47Speaker 01

  Not as well as I can on the show.

• 13:50Ryan Holiday?

  Yeah.

• 13:50Speaker 01

  So, I mean, depending on the situation. But, um, but the show is a very, I wouldn't even call the experience I have on the show as restraint. I really do want to learn from the people I have on the show, including the people I disagree with. So I do not have the experience in the room that many people emailing me seem to think I'm having of white-knuckling it through my own. Desperate desire to throttle the person in front of me. I am in a shared energy with them and am genuinely trying to understand their model of the world, even if it conflicts with mine. And yes, there are times people say things that I find distasteful or cruel, but I don't

• 14:35Speaker 01

  find it so impossible to be in a mode where I'm trying to inhabit their, their, their vision of the universe. I always think about this, I had a show back at Vox, same podcast, you know, but, but back when it was at Vox. And I remember having Rod Dreher on, who is a, you know, quite, I would say hard right Christian conservative. And I remember talking to him about his view of the world and finding it, and I remember trying to say this to my audience before the show started, because Rod and I were never going to agree. Like, we weren't, to him, biblical authority is a sufficient explanation for core questions about American and modern life. And to me, it just isn't.

• 15:20Speaker 01

  We are not sitting on ground that can be in any significant way, like empirically reconciled. So it was like very straightforward from there to say, okay, well, I want to understand how he thinks. I'm not trying to persuade him. He's not going to be persuaded of what I think, at least on some of these core issues. Whereas if I am talking to a family member or my partner, hopefully I am trying to understand the way they understand the world. But sometimes I have a, you know, more direct rooting interest in the outcome of that specific conversation. I can't hold myself quite as much at arm's length.

• 15:57Ryan Holiday?

  Yeah, I've been thinking about this with my kids, just trying to be more curious about things like, like, okay, but what did you think was nine and six? So just like, you know, wait, why did you think this was a good idea? Or like, wait, explain to me your understanding of what's happening here. And, you know, it can be difficult because it's easier to sort of tell or to explain, especially, you know, when you're dealing with things where, you know, safety is concerned or whatever. But the idea of like, actually trying to, as you said, sort of learn from the other person's point of view, again, maybe restraints the wrong word, but I think

• 16:38Ryan Holiday?

  it's not necessarily, our cognitive bias is not in that direction usually. It's usually the opposite direction.

• 16:46Speaker 01

  I think it's both. I think that if you look at the audiences and the nature of a lot of the big podcasts, not, I'm not talking about my own here, I think what you see is a audience that is more curious about many kinds of views than our politics. And in some cases, certainly our more elite cultures give them space to be. You know, I think if you listen to Theo Von or Rogan or some of these figures, and I do, one thing I often think is that the good of them and the bad of them are the

• 17:24Speaker 01

  same. There is a profound space of neutrality or even safety they create in their conversations, which allows really interesting and at times very emotionally intimate things to happen. And at the same time, there is a, or can be, I think, a absence of skepticism, an excess credulity. It kind of can lead you into conspiracy as it does for them sometimes. But it's not just a good thing or a bad thing. I've listened to podcasts like that where I'm really glad that they created the space for that conversation to exist because somebody who's more in the news media like I am, probably would not. There would have been too many things would have felt that we had to ask just to do our journalistic duty. And so

• 18:08Speaker 01

  there would have been no safety to get to the place of emotional intimacy and intellectual intimacy they found. And then there are times I listen, it's like, could you just ask the obvious question or appear to have done 17 minutes of research here?

• 18:21Ryan Holiday?

  Yeah.

• 18:22Speaker 01

  But it's a good and a bad, right? You know, you're not going to find a lot of Meet the Press is not a place in which people can really open up. They can't bare their soul. But on the other hand, they'll ask them the hard questions. And so I'd only say that I actually think that in politics, we and people who are very, very politically invested, understandably, and have very like deep, as I do, you know, feelings about what the right answers are, how things are going. I think there can be a sense that like, of course, hearing this kind of disagreement is raising everybody's blood pressure. But you look around, a lot of people don't experience the world the way we do. And they actually just want to hear people's ideas explored.

• 19:06Ryan Holiday?

  Yeah, there's an earnestness to it that I think is lacking in some parts of the culture. You and I were talking about this, like the sort of desire to improve, the desire to, you know, get in better shape, the desire to just sort of like optimize as a, as a person. I think that there are elements of what you call the manosphere or social media that have spoken to that really well. And somehow it's been politicized, but maybe in a way that we wouldn't have been expected. But like, it strikes me as something that needs to be spoken to because it is a, of part of modern life that people are struggling with.

• 19:47Speaker 01

  To go back to something you said earlier about podcasting in some ways being a nice medium.

• 19:53Ryan Holiday?

  Yeah.

• 19:54Speaker 01

  One of my jokes, but it is in no way a joke, is that X is where I go to dislike people I like. And podcasts are where I go to like people I dislike. Which is to say that over the course of a conversation with most people, I come to have some fundamental sympathy with them, or at least some fundamental understanding of them. Oftentimes, including people who have views that are irreconcilably different from mine. It doesn't mean I think they're right. And it doesn't mean I excuse morally what they do. But I can still feel a, a, a human connection, even with somebody I'm very far apart from. And that has to do, I think, with the way we are tuned towards each other in conversation.

• 20:39Speaker 01

  It's actually a common failure mode on my podcast that I'll have on somebody who disagrees with me or disagrees with my audience. And once in person, they will not be able to clearly articulate those disagreements because the the human tendency towards a relational closeness and tracking of the other person is so strong. Meanwhile, on X, where we are collapsed down to, you know, back in the day, at least 280 characters, but but still usually pretty small snippets, even people I like, even people I agree with,

• 21:14Speaker 01

  are expressing their opinions in such a sharp edged, tuned towards virality way that I don't like them. There's like no space. It's not how I it's not how even I understood that view, even if I hold it. And by the way, I think this is meaningful at the societal level. I think, you know, I'm not sure if this is still true, but it certainly has been true that X before that Twitter was the platform, maybe still is the platform of political elites. And I think they have become more like it, which has made our politics worse. And the platforms of communication and structures of communication that we use do change us.

• 21:58Speaker 01

  And so I've watched people I know over time have become more like their X personas. I've also seen people become more like their podcast personas. I've watched cable news folks become more cable newsy. It's like they can't turn it off. It's a it's an old insight from media theorists like Marshall McLuhan that you do not just use the medium and shape the medium. The medium uses and shapes you. And it's a thing that is worth, if you spend a lot of time in any form of media, algorithmic, television, anything, it's a thing worth being very careful about.

• 22:30Ryan Holiday?

  Yeah, just hearing you say that, it makes me think it's like, one is sort of fundamentally conciliatory and the other is fundamentally adversarial. And so one brings out sort of humanness and then the other brings out sort of anti-human traits, I guess you might say, like aggression, conflict, contradiction, you know, all these things.

• 22:50Speaker 01

  There's that dimension. There's also the reality that one is or was, I want to come back to this in a second, fundamentally contextual and the other is fundamentally decontextual and decontextualizing, which is to say that until fairly recently, what it meant to be on a podcast was to speak to somebody else for somewhere between 35 minutes and two to four hours. In, you know, maybe video, usually it was audio, and it only lived in that format. And whereas to be on X or Instagram or, you know, Facebook or any of these platforms was to crack yourself into shards. And then the only shards of

• 23:32Speaker 01

  you that anybody saw were the ones that elicited intense emotional reactions in other people, which is usually not a great way to communicate. You don't want to turn the emotional reactions of everybody up to 11 on everything you're saying. I worry a bit. I mean, you, you have a podcast and we're here in video and I've seen your Instagram page and we are now taking these shows that are tuned for a complex conversation. We just started this even before we officially started and now we're clearly in it and it's sort of evolving and there's an energy and the energy will keep shifting a little bit, but, uh, you know, what we're saying in 18 minutes will have something to do with what we are saying now, even if

• 24:13Speaker 01

  only energetically. And meanwhile, you're chopping this up, all of us, me included, into decontextualized.

• 24:22Speaker 01

  32nd to four minute bursts meant to elicit an immediate emotional reaction, even that reaction is, oh, that's interesting. Right. That's one. But obviously, the ones people see a lot of are things where somebody ends up humiliated, or they're really inspired, or they're really angry at what they said. I wonder, it does feel to me, as somebody who loves this medium, like we are entering into a period where we are doing violence to it because you're taking something that its fundamental quality was the richness of its context. And as we move into this clips economy, it doesn't mean that the rich context version doesn't also have a life.

• 25:02Speaker 01

  It does. But a lot of people are experiencing these things chopped up in ways that really betray how rich that initial piece of work was. And it's just, there's nothing I can do about it, but it makes me sad.

• 25:18Ryan Holiday?

  No, it's like we're doing to podcast what we did to media like 20, 30 years ago, where we took the newspaper, which was a package, or an hour long TV broadcast, and we broke it up into these pieces. And then those pieces competed with the pieces of other shows to see which one, you know, was the most clickable when it's sort of aggregated or algorithmized. And so, yeah, it's probably not good for the overall quality of the discourse.

• 25:48Speaker 01

  I think that's right.

• 25:50Ryan Holiday?

  Let's talk about virtue, because I think this is something I've heard you talk about on the show a bit, I think, is obviously something that sort of politically is out there. It's an interesting word. I think if you asked people what virtue meant, you know, they tend to think sort of self righteousness, or they think it has this religious context. And yet, we are. I think coming to terms with as a society with what happens when there is no virtue, right? Like, we're suddenly missing something that maybe we didn't value properly enough.

• 26:27Speaker 01

  I think that's right. I have been interested, maybe obsessively so, in what it would mean to have a liberalism that felt sufficient to this moment, this moment in which illiberalism is winning both here in America and in other countries, and a moment when liberalism itself feels quite exhausted. Its moral imagination feels thin, its political imagination feels thin, its leading politicians don't feel to me like they're the ones who are resonating. And I have a lot of views on what happened here, but but one is that if you go back into the old structures of liberalism, you see a lot of talk of virtue and virtues and self-mastery that be behind liberalism, before it was ever an ism, before it was ever a politics,

• 27:12Speaker 01

  is a virtue called liberality, which people talked about for 2,000 years before they ever talked about liberalism. And that virtue, liberality, is built on the word, it's a word that sort of means free and generous at the same time. It's a sort of an ethic of mutual generosity towards other citizens, which was associated with people in antiquity who are considered to be worthy of freedom or who are given freedom. And so there's something here about like the self-mastery and the behavior of a citizen expected of the aristocracy. Now, I don't want to see an aristocracy. I want to see a limited number of free people. But if you follow this thread, and through most of the history

• 27:56Speaker 01

  of being a liberal and then eventually liberalism, there is this idea that to live in a society, particularly one becoming more democratic together, requires the cultivation of the virtues of a citizen. And I think that over the past 30, 40 years, we've come to take all that for granted. We succeeded sufficiently in building the democracy we have now that the idea that we could lose it, the idea that we could lose this political system, that it could rupture into violence or into true dissolution seemed fantastical. A threat may be in other places, but not in our own. And I think we see now that that's not true, that this could break.

• 28:38Speaker 01

  We are already seeing shocking rises in political violence, rises in both successful and attempted political assassinations, January 6th, ICE agents in the streets in masks. And there's a lot that needs to be built, I think, to stabilize the system now and a lot of fundamental reform of how it works that needs to be done. But I think there's also a sense that, or needs to be a sense, that we actually need to rediscover an insistence upon democratic virtues, civic virtues, in our leaders and in ourselves. And one of the ironies of the moment is that, at the same time, the new right has discovered or rediscovered a language of virtue.

• 29:21Speaker 01

  It is led by the most virtuous person in modern American life, in Donald Trump. And I think that opens up both a sort of space in which to see how dangerous it is when this is missing, and also, if you're like me, a liberal in the American tradition, a political opportunity to actually take hold of that, of that energy, that yearning that will be there, to not mirror Donald Trump with a liberal version or a leftist version of him, but to actually recognize that there is power in rediscovering, I think, the way people want leaders and the way they want other people in politics to act.

• 30:00Ryan Holiday?

  Yeah, I think you get the sense that the founders built the system around some assumptions about human behavior, although they did have, at various times, an incredible amount of cynicism about human behavior and human drives. There was... Ultimately, this sense that you're sort of your public man and now public woman would comport themselves a certain way, that there'd be certain things that no honorable person would do, or that society would, would if told about, you know, sort of recoil in revulsion. And so a lot of these things weren't codified in law, they were just cultural assumptions.

• 30:45Ryan Holiday?

  And then when those cultural assumptions fall away, the inadequacy of the law to protect against them or enforce them suddenly becomes quite clear.

• 30:57Speaker 01

  Let's give the founders a bit more credit, which is to say, they built structures meant to contain this kind of failure. And we are living in an era in which the structures have failed. And so we're here. And let me explain what I mean by that. So the founders feared a demagogue. They believed that the danger of democracy and the form of democracy they set up was very limited and attenuated. But they believed the danger of democracy was that the masses would choose a demagogue, a virtuous person good at appealing to the base passions of the population. How do you protect against that? Well, they had a couple of answers to that. One answer was to create certain checks on

• 31:40Speaker 01

  what kind of person could eventually inhabit the presidency. One of those checks is the electoral college, which was meant to be a check made of elites who would be appointed by the leaders in different states in order to act as a final go no-go on the person who won the election. So that if the masses chose a demagogue, the electoral college could reject them. That Donald Trump won his first election. After losing the popular vote but winning the Electoral College is a profound historical irony. Yeah. It is a profound perversion.

• 32:22Speaker 01

  The Electoral College was supposed to stop someone like him from becoming president and instead it made him president. So that's one dimension. But they understood that you could have a dangerous person become president even through that system. And so they created a presidency that was quite limited. And among the many ways in which it was limited was that you had this idea that there would be these three branches and ambition would check ambition. That the fundamental competition of American politics would be between the desire of Congress to arrogate power to itself. The desire of the president to wield power and the desire of the courts to do their role. The founders simply did not create a space and did not predict political parties.

• 33:09Speaker 01

  And that was fine earlier in the republic when our political parties were weak and fractured and fractious and internally divided. But, and this is a story I tell in my first book, Why We're Polarized, over time, we've developed highly ideologically unified parties that now compete across the branches. So instead of the branches competing with each other, Republicans cooperate. Republicans in Congress cooperate with a Republican in the presidency. And to a lesser but not absent degree, I mean, look at the Voting Rights decision that just came down, with Republicans in the courts, who they, of course, aggressively vet for ideological adherence before they nominate. And of course, Democrats also vet members of the court for ideological alignment before they nominate them.

• 33:53Speaker 01

  So it is impossible, it is just fundamentally impossible to argue that we have not broken the system of the founders. The Electoral College doesn't do what it was meant to do. The branches are not the site of competition and checks and balances. You have the fundamental institutions of political competition are political parties, which have no role, official role in the constitutional structure, and they compete and cooperate across branches, creating a situation where now where you can have a very, very dangerous president, who has a majority of his co-partisans in Congress, who he has quite a lot of control over those co-partisans. So they do not act as a check on him. Nobody believes it is possible Donald Trump could be impeached and removed, even for extraordinary levels of corruption and malbehavior.

• 34:38Speaker 01

  And so you have to, I think, confront. I mean, one, that your systems of checks and balances can always break down. So having decent leaders is not a, is not a small question. There is no political system good enough to deal with the wrong people over a long period of time. And two, I think we really do have to think institutionally about whether or not the system we have for a lot of reasons is operating as designed. I mean, we haven't even talked about money in politics, which I think if the founders could see the dark super PACs funding and dark money funding that we now have in unlimited amounts, they would be shocked that we think that is the constitutional way to set up a system

• 35:22Speaker 01

  as opposed to making sure that can't happen as being, you know, what would be required by their, by their fundamental principles. But we're just a long time from the founding and we have done less and less over time to overhaul or reform the system. And eventually even the best institutional structure will corrode and fall into disrepair. And as I often like to say in abundance, institutional renewal is a task that every generation faces anew and we don't get to escape it either.

• 35:50Ryan Holiday?

  Obviously, the sort of constitutional prerogatives is, is an important thing. The check of ambition against ambition. But I think about that, that moment, you know, when they, the repeal of the Affordable Care Act comes up, when McCain walks onto the Senate floor and almost certainly wants the ACA to be repealed, like ideologically, he has no problem with that happening. He just has a problem with the process, right? He feels like the process matters and he feels like he had criticized the other party when he, when they did something, he did not want to be a party to then going back on, you know, he didn't want to be a hypocrite, basically, right?

• 36:32Ryan Holiday?

  And so the sort of final check in the founder's system, I would think, or, and I think this is something you hear the Stoics talk about and it's sort of a philosophical concept. It's like the final check is ultimately the individual and their own conscience, right? The individual and what they're willing to be a party to where they draw the line, their own sense of. Honor or values. And I think to me, that's been the most interesting failure in the system over this period, right? It's like, yes, political parties have degraded it. Yes, money has been a part of it, but there is also just the it's been surprising the degree to which individuals are willing to debase, humiliate, contradict themselves.

• 37:15Ryan Holiday?

  In many cases, like powerful, important people who have some level of independence and self-respect, but sort of ultimately don't.

• 37:24Speaker 01

  But that should not surprise us. I forget the exact line, but there's a line in the Federalist Papers that if men were angels and no government would be necessary. And it was a American naivete, a pathologically self comforting exceptionalism that persuaded us that the vanality and corruption and cowardice and extremism that we had seen take hold of country after country after country after country over, you know, the nearly 250 years of our history to say then nothing of all the time that came before that.

• 38:05Ryan Holiday?

  Yeah.

• 38:05Speaker 01

  That somehow that something in our national character and fiber had made us immune

• 38:13Speaker 01

  to that same corrosion coming for us. Yes, one would think that rich and independently powerful people would have limits that they do not appear to have, that whatever Republicans might think of Donald Trump's policies, that the level of corruption that is swirling around him and his family would be understood as simply beyond the pale, the pulling in of investments in their crypto scams from Gulf states, the acceptance of a luxury jet from Qatar. I mean, the stories, if you were in politics and around this stuff, I'm not going

• 38:57Speaker 01

  to talk through things that I know to be true, but have not yet fully been reported. But it is even something Republicans talk about right now.

• 39:03Ryan Holiday?

  Yeah.

• 39:04Speaker 01

  That the level of corruption in Washington, the level of self dealing. Is cosmic in its scope. And yet, should it really be a surprise to us, given every other political system we have ever seen, that when a strongman gets in power and is there long enough to purge the people from his administration or from his regime who would oppose him, that the people left are the ones who are comfortable self-dealing and in fact will participate in it in many cases themselves? There's nothing new about that. We didn't invent that in the year of our Lord 2026. And so like, this is why we have laws and this is why we have independent investigations.

• 39:45Speaker 01

  You think of the small ball petty bullshit that led to special prosecutors in previous administrations, Hillary Clinton's previous trades in pig futures. I mean, that had an independent investigation into it. I mean, in, in New York City where I am, there was a investigation into Eric Adams for accepting gifts in the tens of thousands of dollars from Turkey and Turkish Airways. And of course, Donald Trump, who looked at that and said, who gives a shit? I'd prefer to have this guy in my pocket than in jail, then led, had his administration fire a series of Republican prosecutors, Republican prosecutors, who were going after Eric Adams, a Democrat.

• 40:28Speaker 01

  Because Trump saw there as being, one, I think saw nothing really wrong with Adams is doing because Trump is doing it on a scale like we can't even conceive of and certainly Eric Adams can conceive of. And two, to Trump, this is all transactionalism. It's all patrimonialism. Adams wasn't doing anything different than Trump is, so why was he getting prosecuted for it? And frankly, if people like Adams got prosecuted for something so small, then what did that mean for the possible future that Donald Trump might face? And so we have these laws and these rules and these structures for a reason, but when you have somebody with the power to destroy those rules, laws and structures, and you have a party not willing to enforce them, then of course the system will fail because the nature of a leader like Donald Trump is of course, he's not going to surround himself with the kind of people who will stop him.

• 41:12Speaker 01

  That's not what people like this do. I wrote about this, by the way, in the 2024 election before Trump won. They said perfectly clearly that they understood and they believe that the main problem of their first term is there were too many people that Donald Trump himself had appointed, who were insufficiently dependent and obsequious to Trump, and too often had acted as a restraint on his impulses. And that they were going to execute a vetting strategy, and this is part of what Project 2025 was, it was not just a bunch of policies, to make sure that there was nobody in this administration who would ever tell Donald Trump no. They have talked about there being a rule inside the building that if Donald Trump asks for something twice, you do it.

• 41:56Speaker 01

  You do not pocket veto him the way people did in his first administration, like when he said that the military should shoot protesters in the knees. And the acting secretary of defense just didn't. And so there is a dimension here where like, you know, they explained exactly what they wanted to do, they explained exactly what they thought the problem was in the first term, and they have gone about trying to correct it. And to a large extent, I think not one that is going to ultimately be good for the Republican Party or the country or for Donald Trump's legacy, but has at least given them more freedom of movement. That's what they've done.

• 42:29Ryan Holiday?

  So it's ironic then that we're having this sort of resurgent conversation about virtue, given that the people who in the previous administrations were particularly upset about the idea of virtue signaling, right? Like that virtue signaling was this super obnoxious thing. But now we have people who are talking about a need for the return to virtue while then sort of actively embracing not only not virtue, but open vice. But it does strike me that in both cases, that the virtue signaling is speaking to something very real that we understand as a culture, we have gotten away from and desperately need to return to.

• 43:09Speaker 01

  I think there's two really interesting things in there, and let me take them in turn. I always thought the discourse around virtue signaling was revealing in a way people didn't intend, because I think it is healthy for a society for the people in it to send signals of virtue.

• 43:28Ryan Holiday?

  Yeah.

• 43:28Speaker 01

  Now, you can criticize people for sending false signals of virtue. That's a dangerous situation and a common problem. You can also worry about a situation where people are competing to be seen as decent without really thinking through what decency means, right? That's a kind of superficial virtue signaling. There's a lot of ways it can go wrong. But broadly speaking, trying to pulse virtue through the system is not something that should be looked down upon. And I think that the fact that people treated it as such a sin and were made so uncomfortable by it so often was telling about where some of them actually wanted to go.

• 44:11Ryan Holiday?

  Yeah.

• 44:12Speaker 01

  Which was not to a space of more modesty, or not just to a space where there was less performative actions of ethics or justice, but to a space where they were unrestrained by social norms and structures of acceptable behavior. So that's number one, and I think that is where many of them went, to vice signaling in many cases. Isn't it exciting? They can now say the word retard. Number two, there is an irony that there are many on the right, associated with like the new right, and maybe people around J.D. Vance, who did get into an interesting dialogue about virtues.

• 44:55Speaker 01

  But I think if you listened to them closely, they were not talking about virtues as a scaffolding of ethical behaviors and self cultivation meant to create a workable society, but they were actually using it as a way of talking about a past. Virtue was, in this telling, not a mode of action, but an older word that spoke to the ways people acted in more traditional classical societies and was part of a larger political vision that is fundamentally uncomfortable with the changes and dislocations of modernity.

• 45:41Speaker 01

  And there are even certain versions of this critique I'm myself sympathetic to. But I do think it was really important to tell the difference between people talking about virtue because they cared about acting virtuously and people talking about virtue because it was one of the set of aesthetic signals you could send about preferring a more masculine, traditionalist and hierarchical society to the one we now have. You know, when your name is a Bronze Age pervert and you're talking a lot about virtue, like you should possibly look more deeply into what is actually being said. And that, I think, was part of the tell, that there were a lot of people here who liked to talk about virtues because they liked to talk about the past.

• 46:25Speaker 01

  What they didn't want to talk about was the difficult things virtue might ask from them in the present.

• 46:30Ryan Holiday?

  Yeah, it's funny to be opposed to virtue signaling when literally the founding documents of American government are effectively virtue signals, right?

• 46:39Speaker 01

  Yes, they do not cohere to the actual society they're running, right? Which is why they ended up being so powerful. America founded on virtue signaling that is part of what has been the scaffolding of eventual movement towards virtue.

• 46:51Ryan Holiday?

  Martin Luther King understands this so brilliantly, you know, in the famous March on Washington speech, he's like, he said, "We're here to cash a check," right? Like Thomas Jefferson wrote a check and I'm here 100 years later, 150 years later, to cash that check. That's what virtue signaling does when it does best. Gandhi does the same thing. He says, you know, "Britain likes to see itself this way, and then here's what they're doing over here. Let me show you the contradiction, and then let's try to get these two things a little bit closer to each other." And I think you're right. Some of the political and cultural criticism about virtue signaling was really like, hey, even your pretense of caring about virtue is constraining to me and I don't like it.

• 47:35Ryan Holiday?

  Let's stop pretending. So I think there's that. And then you're right, there's something interesting. Doing this book, this series on the cardinal virtues, it's been really interesting to watch people read the books, to like the books, to get coverage for the books. And then some of those same people get really mad at me when I say, we should apply some of those ideas to the world that we are in right now, whether we're talking about corruption, or cruelty, or, you know, respecting other people's rights, or whatever we want to talk about. But there does seem to be this, you're right, this sort of idealization and lionization of the past, as if those people in the past weren't having to work

• 48:18Ryan Holiday?

  hard to live up to those virtues. Like, I think the most inspiring stories we hear from the past are people who really paid a price for those ideals, you know? And I think we just want to look at the statues and, and read the works, but not have to apply them to the modern dilemmas.

• 48:39Speaker 01

  In that vein, because I think, I should make sure we're living up to what we're talking about here. You have to be careful. We, on the broad left, have to be careful. And I think we're not, about being imbalanced in what these questions ask of us. And I think virtue signaling and the sort of politics that was around it at that time, the way in which it went wrong, as a, both a politics and a set of practices of how we relate to one another, is that there was a heavy weight placed on a form of in-group purity, on

• 49:22Speaker 01

  having the right opinions on all of the different things. And so a heavy weight placed on moral righteousness, which is important. I don't want to take anything away from that. I am somebody who does actually believe our society is systemically racist, and I believe in a lot of the things that now get called wokeness, and I have not changed in any of those beliefs. But there are also what I would call democratic civic virtues about how we deal with one another, and how we handle disagreement, and whether or not we listen. Like liberalism at its best is a way of Channeling the disagreement and division inherent in a complex society into a constructive

• 50:01Speaker 01

  politics. And I think social media really pushes people towards the prophetic voice, the unsparing moral condemnation of those who you and yours don't like, and away from the civic virtues that are often necessary to balance that of actually being in relationship with, of actually listening to, of actually exploring the textures of people who are unlike you, and people who believe differently than you, and not trying to cast them out of the civic commons. And this is a very, in my view, hard, hard, hard balance. You go too

• 50:46Speaker 01

  far to one side, and you become insensitive to injustice because you're trying so hard to allow disagreement to sit and flourish, and you don't want to be condemnatory of anybody. And so you lose the ability to take a moral stand, and you go too far to the other stand, the other side, and particularly when you've not done the political work to create a social consensus around it. And you create backlash, you push people away, you make it hard to correct your own errors in judgment, or see the own places where you are, or see the places where you are being intolerant. And so, one thing that I personally find inspiring in the history of liberalism, is that it is an ideology

• 51:30Speaker 01

  and a political practice built out of balancing acts. And if you, over and over and over again, if you fall too far to one side or another, you fall. And so it doesn't hold the view that there's simply one answer. It's not just, well, eventually the proletariat will rise up and win, or the true Americans will rise up and win, or my religious faith will rise up and win, and then we will have the society we imagine now without compromise, and then we will have hit our utopic end state. It's a constant balancing of the need for moral and social progress against the need for civic and small D democratic cohesion.

• 52:09Speaker 01

  And there is, I think, great virtue and moral ambition in doing that well. But it's hard. And I think it's made harder in the, in the, the current situation where, one, the right has abandoned many of the things and practices that kind of held us within a common set of political norms and practices and boundaries. And social media and algorithmic media and other things have created a communicative culture that is more hostile to the nuance and deliberation and balancing that I think has defined, you know, the best periods in our politics.

• 52:47Ryan Holiday?

  You know, it can be easy in this sort of thinking about virtue, thinking about justice, to get really concerned with, you know, what other people are doing, right? How other people are treating other people. And obviously, this does matter, but you can end up neglecting the things that are much more in your control or that you have much more sort of responsibility for, you're participating for. I thought this was an interesting sort of argument in, in, in abundance, right? You're like, hey, you put the sign in your front yard that says, hey, I'm a good person. I believe in all these things. And what you're not thinking about is the people that can't come into your neighborhood because of the, the restrictive, say, housing and zoning laws that you're, if not an active

• 53:32Ryan Holiday?

  participant in a beneficiary of, right? Like, like, it's so easy, I think, to think of the sort of very black and white examples of injustice or unfairness, corruption, as we're talking about. And ultimately, I think it, it behooves every person to condemn those things when they see them. But ultimately, the real work is not in condemning what other people are doing, but in thinking about what you're doing and where you can do better. And I think that, that is something that, that sort of has gotten lost.

• 54:02Speaker 01

  I think that is true. Look, self critique is always harder.

• 54:06Ryan Holiday?

  Yeah.

• 54:07Speaker 01

  If you listen to or read my work. The balance of critique is on the right because I think more of the problems are on the right. If you read my first book, Why We're Polarized, the balance of the critique is on the right because the right had polarized in a more aggressively anti-system way than than the left. And abundance was an act of self-critique. I'm a liberal Californian. Why isn't a Californian governed by liberals, leading to better outcomes for the working class people it claims to represent? I believe in green energy. Why aren't we building the green energy we've promised the country at the speed we've promised to do it? That we've said is important. I'm a person who believes deeply in public infrastructure and government action. Why is the government so often failing to build the public infrastructure it promises

• 54:49Speaker 01

  at a speed and a cost that is acceptable? And one of the places where, I mean, I think broadly speaking, people actually appreciated that quite a bit. But it was interesting that people saw anything I left out as a problem in the book, as me saying, or me and Derek saying, it wasn't a problem, right? The book is not particularly focused on corporate power, because in my view, the left understood the problems of corporate power and actually did quite a lot to try to think about them, even if it's a very hard problem and in cases like money and politics to solve, partly for constitutional reasons. But what it was not good at thinking about were the places where it was the problem, where the way it

• 55:30Speaker 01

  governed and where its ideals and even its own accomplishments were creating system-level dysfunction that was making it impossible for liberals, or for that matter, leftists or others, to achieve their goals. And I believe this is true for politicians, too, that self-critique is one way you show people you're serious about what you're trying to achieve. And there's actually a lot of good political science evidence on this, that, you know, when people hear a politician critique the other side, that doesn't register that much for them. They expected that. When they hear somebody critique themselves or their own side, that is a costlier signal for that person to send. And it gives them more credibility as, you know,

• 56:15Speaker 01

  somebody who's really committed to accomplishing the goals you're describing. Because the truth is, and I think correctly so, the public is very cynical. They know the system is broken. And what they believe is that the Republicans are only upset about the ways in which the Democrats are breaking it. And the Democrats are only upset about the ways in which the Republicans are breaking it. And neither side is willing to come in and make it work in a holistic way for a public that is, broadly speaking, not as much on one side or the other as all these political obsessives are. And what I'm describing there is not moderation, by the way. I don't think the public is all that moderate. What I'm describing there is a recognition that the public has,

• 56:58Speaker 01

  and that is true, that even if both sides are not equally at fault, there is a reality that both sides are somewhat at fault. And you're not going to fix this unless you're willing to acknowledge the entire array of faults.

• 57:15Ryan Holiday?

  I was listening to your episode where you were talking about sort of the history of liberalism. And you had a good line that is making me think about it in my own writing. You said something like liberalism, and here you don't mean like the Democrats, you mean sort of people believe in sort of liberal society, don't have a good way of talking about responsibility, which is to say obligations. We have a lot of language for freedom, opportunity, toleration, all of these things. But we struggle with the flip side of that coin, which I think the founders, again, sort of took for granted that people would feel obligated to do or understand is part of your ethical and philosophical obligation

• 57:59Ryan Holiday?

  or your religious obligations. But this idea of like what we owe each other or what we owe society, that this society we've been lucky enough to be born into, that side of the coin does feel like something we're having trouble talking about.

• 58:17Speaker 01

  I agree with that.

• 58:20Speaker 01

  I think a way to think about this is that traditionally, the left struggles to recognize the reality of individual responsibility, and the right struggles to recognize the reality of collective responsibility. So the right is often unwilling to say, if you fall through the cracks of society and you need help, it is on us to help you because this world, this society, this country is not fair. And the people who made it had a lot of luck and the people who failed had a lot of bad luck. Everything from being born with predilections to intense mental illness, to being born into an abusive family, to losing a job during recession that was not their fault and took them off the path, to being in a place where the housing prices spiked up

• 59:04Speaker 01

  and they couldn't afford their home and they were evicted. There is a lot that happens to people that is not their fault. The left, in part because of that, has been increasingly more tentative about recognizing the dimension of our lives that are under our control. And this has been a tension that different politicians, I think, have managed with different levels of success. Bill Clinton, very famously, was one way that he really tried to reform the Democratic Party, was to put questions of individual responsibility more at its center, both in his rhetoric and in policies like welfare reform. Now, I am actually not somebody who believes welfare reform was done well. I'm not against the underlying concept they were trying to do. I think they did it very, very badly. And so I think that that policy was actually a failure.

• 59:47Speaker 01

  But the politics Bill Clinton was trying to achieve, and remember, he's running at a time when Republicans have won the last three presidential elections in a row, in part because the public doesn't trust Democrats to demand enough of the people that Democrats are trying to help, is quite successful. Obama also has more of this dimension to his politics. And there's a backlash to this with Obama, a feeling that he's practicing responsibility politics, a sense that he is too bought in on a sort of an ethic of individual responsibility and he's telling, you know, young black men to pull up their pants and father their children. And this creates a kind of backlash. And then comes Trump.

• 1:00:28Speaker 01

  And one, I think, under-recognized effect Trump had on the Democratic Party, it led to a lot of people on the left saying, well, they don't have to compromise on anything, nor do we. And this isn't quite right as a read of Trump on policy because he throws overboard the Republican Party's opposition or support for Medicare privatization and support for social security cuts. He does moderate on certain issues, and that helps him trade, at least in the way the public thinks of it. But in terms of the way he talks and in terms of what he is willing to embrace, he's completely no holds barred. And he shows that you can do things in politics that people that you couldn't and still win. And so there's a sense that that needs to be mirrored and that lesson needs to be

• 1:01:10Speaker 01

  absorbed. And the ways in which Democrats were trying to balance the contrasting impulses and values of the society they thought they sought to lead were concessions to another side that is making no concessions to us. And I think as a matter of politics that has proven to be unsuccessful, that if you want to build a majority big enough, a tent big enough, to keep the illiberal right a lot more at bay than it has been, you have to absorb some of the values of people more to your right, who just look at the state of the country around them. And, you know, if you're in, say, California or San Francisco

• 1:01:52Speaker 01

  or Los Angeles, where all of a sudden Spencer Pratt, of all people, has a real chance at the mayorship. And the reason he does is that people look around in Los Angeles and they see, you know, tents on their streets and people, you know, shitting in their front yards. And they say, I'm being asked to pay high taxes and this is what I'm getting for it? I'm being asked to be a normal, like, contributing member of society, and I'm being told that nothing can be done about these trailers lined up with trash all around them on my street? And you can hold, as I do, a view that you want to treat people who are homeless with compassion, and also recognize that there is a responsibility

• 1:02:34Speaker 01

  to maintain order in a society. And there are places like San Francisco, although not so much now under Daniel Lurie, and Los Angeles, where the feeling was that the order was allowed to crack. That was also true at the border with a number of migrants coming in under Biden. And so, good politicians balance the things that they and their side believe and also some amount, some tincture. Of the contrasting impulses because this is a complicated society where people believe many things and they need to know that you at least see their perspective and are able to hold it somewhat in your own views. And Bill Clinton was a masterful balancer. Barack Obama was a masterful balancer and the leaders who have come after them have

• 1:03:16Speaker 01

  not been. And that is part of what allowed Trump to come back into power.

• 1:03:20Ryan Holiday?

  That's such a revealing phrase too. Oh, you're just practicing responsibility politics as though that would be a thing that like most people when they hear that phrase wouldn't be like, that sounds like a good thing. You know, it's like one of those sort of shibboleths that kind of reveals an assumption that although probably comes from a good place and if you actually sort of broke it down and saw what they meant, you'd largely agree. But it's like, it sounds like a good thing to your average person. It sounds like a very good thing.

• 1:03:48Speaker 01

  So, you know, the debate on around this like has to do with the ways in which arguments about cultural breakdown were weaponized against black communities that had been the subjects of enormous amounts of predatory American policy, which kind of pushed them into more breakdown. And it's interesting because now over time, you've seen those same things happening in white communities and JD Vance and others respond with tremendously more compassion.

• 1:04:17Ryan Holiday?

  Yeah, a lot of empathy and a lot of explanation.

• 1:04:22Speaker 01

  So there was a feeling that, you know, these questions of, you know, kids sagging their pants was a distraction from the need to have jobs programs and healthcare and so on. But for Obama, who believed in the jobs programs and the healthcare to also maintain in his politics, a recognition that how we act individually matters and how the leaders and icons in our society expect us to act also matters. That's not just good politics. That's just, I think, being a human being. I mean, my, my view basically is that I want the government to treat people like. Luck really matters and I want people to treat themselves like individual responsibility really matters.

• 1:05:00Ryan Holiday?

  Yes.

• 1:05:00Speaker 01

  And leaders have to do two things at once. They have to create the policy that is the structure of society, the physical, material structure, and they have to speak to the values that undergird that structure in society. And so a good politician has to be able to bring those two things into alignment.

• 1:05:17Ryan Holiday?

  Yeah, and then you have to understand that how sort of normal people see things and experience things and what they what they expect, right? And how oftentimes you think, you know, you're expressing something and it's going to come off one way and it actually comes off as the exact opposite way. And that that that level of savvy is really important.

• 1:05:40Speaker 01

  I think that's right. And that's why good politicians have a touch for politics and why politicians who spend too much time on social media lose that touch. Because they cease to represent the way most people think and act and become brain poisoned by these really warped and perverted engagement caves that they and all their friends are locked into together and some of us are locked into. And it's not that these things, when people say Twitter acts, it's not through a world, it's not the world, it affects the real world, though, because it reshapes the people in it and those people affect the real world.

• 1:06:21Speaker 01

  And they begin to see the world through those enmities and through those collisions.

• 1:06:26Ryan Holiday?

  Well, that goes to where we're talking about with self-improvement, which is like, look, most people are not thinking about politics, they're not thinking about world events, they're thinking about how they can lose 10 pounds, or they're thinking about how they can, you know, get through to their kids, or they're thinking about, you know, just sort of basic human day-to-day stuff. And, you know, they're going to go to the people that that make it clear that they understand what that is. And if those people happen to be actually, you know, sort of sliding a political agenda into that messaging, that's where they're going to sort of imbibe a lot of their political views.

• 1:07:09Speaker 01

  You do not want to abandon not just the language, but the belief in personal aspiration to the right.

• 1:07:18Ryan Holiday?

  Yeah.

• 1:07:19Speaker 01

  Because aspiration is a very powerful human force. Most of us want to be better tomorrow than we are today. And we might fail, but we try again and again and again and again. And if you treat that as politically suspect or immature, you're going to sever your connection to a fundamental human drive. I want to be better tomorrow than I am today. You know, I work out and I eat protein in the morning and the whole fucking thing. And those are just, it's just really potent. I think that it's interesting. The right, I think, was more comfortable with the discourse of personal improvement.

• 1:07:59Ryan Holiday?

  Yeah.

• 1:07:59Speaker 01

  And the left more comfortable with the discourse of healing. And so if you think about what left self-help looked like, you know, in the kind of past decade or two, it's much more therapeutic. It's not that it doesn't have a language of aspiration, becoming better, but it's more about healing from the way you've been wounded.

• 1:08:17Ryan Holiday?

  Yeah.

• 1:08:17Speaker 01

  And it's, you know, and at times like moving into the space of psychedelics and other things, but more often, you know, you hear a lot about boundaries. And I'm not against any of that, right? I have a therapist, but I do believe you ended up with a kind of feminine and masculine like split in what kinds of self-help and approach were considered okay. And the right to its discredit also was dismissive of that. And same way, the left was often dismissive of the more kind of self-improvement approach. And again, I don't mean to keep coming back to this, but I do believe that one of the things that you need to do, and maybe this goes back to what we're saying about the way I approached my show at the beginning, is you are trying to absorb enough of lots of perspectives of society that they all make at least a bit of sense to you.

• 1:09:02Ryan Holiday?

  Yeah.

• 1:09:02Speaker 01

  So you can begin to balance them in your own worldview. And that's why maybe when I'm in a conversation where I really disagree with somebody, I don't find it, not do I not find it difficult. I mean, I can find it difficult. I want to say it never happens, but there is something of the gift in it to me because I'm trying to have this worldview where the way they feel makes sense to me. So I can pull 15% of that worldview into my own model of the world. And it doesn't mean I have to agree with them, but I don't want to be insensitive. To how the world feels to them, because probably at least some part of how it feels to them makes sense and comes from somewhere. And I need to be able to, I need to find

• 1:09:47Speaker 01

  that motivation and that path legible, even if I don't find the place it brought them agreeable.

• 1:09:55Ryan Holiday?

  So I got to ask you about this then, and we'll play the clip. But I thought it was so interesting when you had Gavin Newsom on your podcast, the governor of California. You famously, at the end of the episodes, you talk about some books the guest would recommend to the audience. And he brings up Marcus Aurelius's Meditations.

• 1:10:10Speaker 02

  I hate to bring this book up because it's such a universal, obvious book. I had never read it. I've had 10 copies. I finally picked it up off the shelf. I'm like, what the heck? Meditations from Marcus Aurelius. And I'm like, where the hell have I been? Or where's that book been?

• 1:10:26Speaker 01

  See, when you get into podcasting and immediately the Stoics.

• 1:10:28Speaker 02

  I'm telling you.

• 1:10:29Speaker 01

  Can't be, can't be a podcast or not get into the Stoics.

• 1:10:32Speaker 02

  How could you not? I don't think there's, perhaps there's never been more important and impactful words ever written. And they were written by the most powerful leaders in the world, thousands of years ago.

• 1:10:43Speaker 01

  Doesn't do it for me. I've read it. I've read it.

• 1:10:46Speaker 02

  You didn't.

• 1:10:47Speaker 01

  It's not a, I, I have a feeling about it. And I think this because I get more to meditation.

• 1:10:52Speaker 02

  It was never a book for publication, as you know, so it was not intended to inspire.

• 1:10:56Speaker 01

  The thing I don't always get with it is that, yes, if I could just not worry about all this, I wouldn't. If I could just look at all the problems in my life, think, yeah, you know, can't change what I can't change. I wouldn't, I wouldn't.

• 1:11:07Speaker 02

  I read something very different. It's not, it's not about denying the existence of things.

• 1:11:12Speaker 01

  I don't think it's about denying.

• 1:11:13Speaker 02

  It's about understanding what you can influence. But no, the opposite. I see. That's so interesting. I think it expresses the practice. And that is, you can control what you can control. You can't control the third thing. And that's powerful. And this notion of accountability, responsibility, agency, and taking accountability for what happened, you can't. And I just think that's powerful. But it's the core of minor psychology as well, in terms of just this notion that we have agency and that we can shape things and change the future.

• 1:11:46Speaker 01

  My inbox after admitting that.

• 1:11:48Speaker 02

  Yeah, you're in trouble, buddy.

• 1:11:49Speaker 01

  I'm in bad shape.

• 1:11:50Speaker 02

  Unbelievable. All those Stoics out there listening.

• 1:11:53Ryan Holiday?

  And I think you said something like, I've read it, it just didn't do it for me. So walk me through why it didn't do it for you. I'm fascinated to hear.

• 1:12:02Speaker 01

  I will, I will say, I was a little bit just teasing Governor Newsom. Then he got into podcasting and immediately is like, well, I'm into the Stoics now.

• 1:12:11Ryan Holiday?

  Of course.

• 1:12:11Speaker 01

  Which is good for him, right? It's actually good, I think, good politics. And one thing I respect about the governor is that he is actually, it's what that whole episode that I did with him is about. It's like, what are you learning from all these conversations you're having with people on the right and Gen Z, you know, video game streamers? And like, how are you absorbing that into your own politics? In one way, I think, is he's reading Marcus Aurelius. It has been a little while since I read Aurelius, I should say. But I often find the Stoics, and I'm here with Mr. Stoicism himself, to be a little bit too declarative about how you should approach life, as opposed to practice

• 1:12:51Speaker 01

  oriented about what it would require to develop that capacity to approach life that way. And I'm not saying that there are no exercises anywhere in Stoicism, or even that Marcus Aurelius, who I believe would start every day by repeating to himself a little mantra about all the people who are going to act ungenerously and uncharitably and insensitively to him and how he wanted to treat them, that there's nothing to the way he approaches life. But sometimes I find Aurelius to be aspirational for people to read because they would like to act that way. I think I found this way myself, without actually being all that helpful to read, because in fact, they do, they have not built the, or I have not

• 1:13:30Speaker 01

  built, the emotional and perceptual musculature to actually respond that way. That's what I would say, but it is a soft feeling, as opposed to coming mostly from a joke, rather than a, I'm not anti-Aurelius.

• 1:13:46Ryan Holiday?

  No, no, I think, I think it's really interesting. I think it's a fair critique. I suspect, the irony of you picking up on that is like, I think the declarative sentence or the view is, in a way, the practice, right? We tend, because we have Meditations, this one book, we think, oh, this is him writing down what Stoicism is, as opposed to capturing a brief period in his life. We don't know when he started, we don't know when he finished. Him reminding himself of what Stoicism is. Like, the, the book is the byproduct of the practice, which was the journaling.

• 1:14:25Speaker 01

  Yeah.

• 1:14:26Ryan Holiday?

  And so there's something interesting about it where, as a reader 2,000 years later, you're like, well, that's easy for you to say. And it's like, what actually wasn't easy for him to say. He was saying it to himself again and again and again, because it's so fucking hard.

• 1:14:40Speaker 01

  I think that's a good read of that book, which I, I would expect from you. I also think it's funny, it's called Meditations. It's not funny, but, but I always think about how, you know, meditation has these two very different meanings.

• 1:14:51Ryan Holiday?

  Yes.

• 1:14:51Speaker 01

  And, you know, one way meditation's like, I'm offering you a meditation on something is used, is I'm telling you what I think about the thing. And obviously, the other use of the term meditation more as a verb and a practice, is I am trying to sit without being so reactive and caught up in what I think about something. And for me, who can become very caught up in what I think about things and telling, telling stories that I believe first.

• 1:15:21Ryan Holiday?

  Yeah.

• 1:15:22Speaker 01

  The practice that has been more transformative for me is of the second sort. I am, I've meditated for a long time and I put a lot of day-to-day work not into, into actually trying to unconvince myself of my view of events.

• 1:15:44Ryan Holiday?

  Yeah.

• 1:15:45Speaker 01

  And that's not to say one is better than the other. It is actually more to say that different people need different things. And, and that's been more the path that has been resonant for me.

• 1:15:53Ryan Holiday?

  Also, though, like, that practice doesn't leave much in the way of a historical record. Right? So like, there's an interesting line in Meditations where he's like, dude, you gotta put down the books and the journals and go do this stuff. Right? And so you could imagine that he does that. And then there's a six-month period where he doesn't write anything down because he's doing it. But that, obviously, that gets fast-forwarded over as blank space. Right? And so I do wonder, I, I think about this too. Like, if I'm, if I'm sitting, and I do all the ridiculous sort of wellness. Things too, if I'm in a sauna or a cold plunge, I'm not thinking about philosophy. I'm trying to not think about stuff like the, the practice of sort of getting all this stuff out of my head and just being present for a moment.

• 1:16:39Ryan Holiday?

  In, in a way, that's the real work, but that doesn't create the stuff that's shareable or talk aboutable, or that doesn't get translated and retranslated for 2000 years.

• 1:16:49Speaker 01

  Let, let me ask you something, and this is coming from a place of genuine ignorance. I've read a little bit of Stoicism, but, but not enough to feel confident that I understand it. My pop sense of Stoicism, and certainly the way it is brought forward in the culture, is that what it is describing is a way of being buffeted by life without feeling buffeted by life, without getting so entangled in these waves of pain and sentiment and glory and, and, and collapse. That there's supposed to be a kind of steadiness at the center of it. Is that fair?

• 1:17:32Ryan Holiday?

  I think so. It's steadiness at the center, and maybe my critique of some of the eastern stuff is like, look, it's easy to be centered in a 10 day silent meditation retreat. Like, not, not easy, not easy because that's a lot of work. I'm just saying like, by removing the stimuli, it's easy to be less stimulated. And I think what I take from the Stoics as being important and relevant, particularly in today's world, is like, Marcus Aurelius is trying to keep an even keel in the most stressful job in the world, right? Epictetus is trying to think about inner freedom when he is literally enslaved. Seneca has the worst boss in the world in Nero. And so these are people in the center of busy, noisy lives. They have ambitions.

• 1:18:17Ryan Holiday?

  They have relationships. They have a lot going on. When they're talking about, you know, focusing on what you control, when they're talking about not getting too high and low, they obviously mean this inside the context of a full and busy and active life as opposed to none of this matters, detached from everything.

• 1:18:38Speaker 01

  So the place I would go with some of that, and this again is, it's where my head, we're talking the day after. I just got to have one of my favorite interviews I've ever done with the Buddhist nun Pema Chodron. And which was such a pleasure for me. But one thing that I sometimes worry about, and I don't really want to be in the anti-Stoicism, but I want to come on the podcast and play with it, is I think, and I think this actually particularly afflicts men, there can be too much of a desire to either not feel what we're really feeling or not act like we're really feeling it. And I have certainly struggled with that.

• 1:19:21Speaker 01

  And one thing, and this is sort of different from the question of silent meditation retreats, but one thing that I have been working much, much more with, as simple as this sounds, but I don't really think it is that simple to do, is to really feel what I'm feeling and to really be with it. And that's not to say to act from it. Maybe in terms of where Stoicism goes and where these, you know, practices go are not that dissimilar. In fact, I think a lot of paths end up taking you to a similar point. But one, I think, space where I have at least sometimes not connected

• 1:20:04Speaker 01

  to what I have read of Stoicism or the way it is often presented to me, is for me, actually, the impulse to be stoic can be self-destructive. And if anything, is overdeveloped. Whereas I have really had to get to a point where I am willing to feel the full range of what I'm really feeling, willing to be less afraid of the things I'm really feeling in order to go into places that I otherwise could not go. Because I, because it actually would break my stoicism. And, you know, look, I'm in my 40s now and I'm still learning this shit. And so I don't want to frame that necessarily as a critique of stoicism because I'm sure

• 1:20:48Speaker 01

  there's a lot, I mean, it's a lot of different people doing a lot of different things. But I do think, because we've also been talking about self-improvement and some other dimensions of this, that one thing I think people in our society struggle with a lot is just I think they're insufficiently embodied. And the ability to distract ourselves from how we're feeling by looking at a screen or by taking a drug or by, you know, absorbing some other kind of stimuli is too high. And we actually do disconnect much more than we even realize we have with how we are feeling. And being willing to actually feel it and just like sit with it and let it be there and not run from it, not because you're, and not in a sense where you don't get high or low, like you can get high or low, but for it to be okay to be high and low, has

• 1:21:31Speaker 01

  at least for me been a really significant dimension of my work as a, as a person and frankly, as a, you know, political figure.

• 1:21:39Ryan Holiday?

  I think, I think that's totally right. And the Stoics do have sort of a wide-ranging view of emotions. It's certainly not all like stuff it down and pretend you don't feel it. I think in my life, it's like getting more in my body about, yeah, like love or, I don't want to say the emotions that matter, but, but like there are a bunch of emotions I need to get more in touch with. And part of the way to do that is to, is to see how much energy and time is going into emotions like anxiety or jealousy or desire, you know, these other things that we have that sort of take up a lot of space in our lives and are often, when you sort of really put them up for review, based on very little and certainly have very little constructive value.

• 1:22:25Ryan Holiday?

  I know we got to wrap up because I got to go pick up my kids for school.

• 1:22:28Speaker 01

  The true virtues.

• 1:22:29Ryan Holiday?

  Yes, I have three books I want to recommend to you very quickly.

• 1:22:32Speaker 01

  Oh, wonderful.

• 1:22:33Ryan Holiday?

  I'd be very curious if you've read any of these. Okay, so you mentioned Pema Chodron. Have you read Karen Armstrong's biography of Buddha?

• 1:22:40Speaker 01

  Long time ago, probably did not read it fully then either.

• 1:22:43Ryan Holiday?

  I think this book is incredible for similar reasons, as you were just saying about Pema Chodron, where the perspective of a person earnestly in one spiritual tradition, writing very openly and curiously about another spiritual tradition, that, that combination is very, very powerful.

• 1:23:00Speaker 01

  Yeah, I went through a big Karen Armstrong phase in college. Her stuff is amazing.

• 1:23:05Ryan Holiday?

  Okay. All right. Well, so the first one you already read.

• 1:23:08Speaker 01

  No, I'm not sure if I fully. So.

• 1:23:10Ryan Holiday?

  Okay.

• 1:23:11Speaker 01

  Oh, this book is great.

• 1:23:12Ryan Holiday?

  Have you read this?

• 1:23:14Speaker 01

  Yeah.

• 1:23:15Ryan Holiday?

  Okay.

• 1:23:15Speaker 01

  This book is cool.

• 1:23:16Ryan Holiday?

  Incredible. So good. So good. All right. Well, then if you've read this one, then the other one I would give you is Papyrus by Irene Vallejo, which is basically about the notebook. Basically, this book starts in the 1400s about sort of Renaissance.

• 1:23:32Speaker 01

  Didn't you find this book, though, made you feel bad?

• 1:23:35Ryan Holiday?

  In what way?

• 1:23:36Speaker 01

  Because look at the way all these people kept their notebooks. Look at their beautiful sketches in them. I mean, I keep a notebook and it's actually really important to me to keep things on paper. It's part of why I was interested in that book. And then I opened it and I felt like so small and my handwriting is so bad. And I'm not doing diagrammatic sketching of anything and I almost never see a leaf and put up a perfectly done botanical. It made me feel so bad about my penmanship.

• 1:24:07Ryan Holiday?

  My handwriting gets worse by the day. It is quite terrible. I don't do any drawings or sketches, though. I guess I didn't think about that. Journaling is one of those habits that I wish I'd started earlier, you know? And I don't think there's anyone that journals that's like, oh, I wish I'd started this later.

• 1:24:24Ryan Holiday?

  Okay, so let's see if you can go three for three. Have you read this? This is a very old one.

• 1:24:28Speaker 01

  No, I've not read this.

• 1:24:29Ryan Holiday?

  This is The Lion and the Fox, the first political biography of Franklin Delano Roosevelt.

• 1:24:35Speaker 01

  That sounds great.

• 1:24:36Ryan Holiday?

  Yeah, I think, you know, we tend to think of presidents as these sort of great men of history. And we often, so we're interested in what was their mother like? How were they? When were they born? You know, the sort of moving up the ladder to greatness. But we often underplay their political acumen, which it strikes me as something you talk a lot about. A companion book I would give you is President Lincoln by William Lee Miller, which is a political biography of Lincoln as a politician.

• 1:25:05Speaker 01

  When is that FDR one published? Because I think it's a really, really underrated thing that people should read older books than they do.

• 1:25:11Ryan Holiday?

  When I am researching, I almost always try to find old, out of print books on Amazon. Those are my favorites because.

• 1:25:18Speaker 01

  I agree. And it's so easy now with Amazon and A-Books. You can get such treasures.

• 1:25:23Ryan Holiday?

  This is 1956.

• 1:25:25Speaker 01

  Yeah, so it's nearer to him, right?

• 1:25:27Ryan Holiday?

  Yes.

• 1:25:27Speaker 01

  I mean, now we have more documentary evidence, but I do think there's something about being nearer to these figures. I would love to read that. I will. I will go find that one.

• 1:25:35Ryan Holiday?

  I think you'll like it because again, we think of so often, we think of him as this moral figure, or we think of him as the voice on the radio. And obviously, Caro does this well in his Lyndon Johnson biography, but we don't think about them as a guy whipping votes, right? We don't think about this as a guy getting political leverage. I think Doris Kearns Goodwin's The Bully Pulpit is another good example of this. The contrast between Taft and Roosevelt, their understanding of the media. I think the left particularly seems to have just taken this idea that being morally correct about the issue is sufficient to win, as opposed to being good at not just communicating it, but then realizing that vision on a policy and public level.

• 1:26:20Ryan Holiday?

  That's what great politicians do.

• 1:26:22Speaker 01

  Yeah, I think there's a lot of truth to that.

• 1:26:24Ryan Holiday?

  All right. I think you'll like this one. I'm glad I went one for three, but.

• 1:26:27Speaker 01

  I'm not sure if I read the Karen Armstrong one. I was like, when you put it up, I was like trying to remember if that's one of the ones of hers. I read her biography of Jesus, and I think I've read her one on, she has one on Muhammad, doesn't she?

• 1:26:38Ryan Holiday?

  Yeah, yeah, yeah.

• 1:26:39Speaker 01

  Yeah, I think I've read that, but I'm not. I'm not sure if I've read her Buddha one. So you might be two for three. I'm just trying to literally remember what I've got of hers. This was super fun, man. I really appreciated it.

• 1:26:48Ryan Holiday?

  Yeah, thanks for taking the time.