Pod Insights The Daily Stoic Premium (🔓) You Have to Fight for It | Is There A Dark Side To Stoicism? About this episode It would be wonderful if the world was naturally just, if people were automatically good, always doing the right thing. But of course, they don’t. 📕 Read more stories that will inspire you to live with justice in Right Thing, Right Now | https://store.dailystoic.com/🎥 Watch the video episodes on The Daily Stoic YouTube channel: https://www.youtube.com/@DailyStoic/videos🎙️ Follow The Daily Stoic Podcast on Instagram: https://www.instagram.com/dailystoicpodcast✉️ Want Stoic wisdom delivered to your inbox daily? Sign up for the FREE Daily Stoic email at https://dailystoic.com/dailyemail🏛 Get Stoic inspired books, medallions, and prints to remember these lessons at the Daily Stoic Store: https://store.dailystoic.com/📱 Follow us: Instagram, Twitter, YouTube, TikTok, and Facebook 📢 Share | ⚙️ Manage Subscription
Transcript Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.
0:00 Ryan 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.
0:14 Ryan Holiday? It would be wonderful if the world was naturally just, if people were automatically good, always doing the right thing. But of course, they don't. It's one of the most heartbreaking and frustrating things about life. Not only do people often not do the right thing, they will continue in error or evil even after they've been challenged, even after you've made every argument or followed all the procedures. Nothing illustrates this more than the fight to end segregation in America, which was more than just marches. It was a series of endless court cases, cases that took years to get picked up, years to get their day in court, years to get the right verdict. And ones passed were then often ignored by Southern politicians and law enforcement officers. But the reason the cause eventually prevailed
0:57 Ryan Holiday? was encapsulated by the legal philosophy of John Doerr, who served as Assistant Attorney General for Civil Rights during the 1960s. "You've just got to keep going back," he would explain. "The Southern strategy was one of holding out, of being so difficult, being so painful to deal with, the hope being that the North would do what they'd done during Reconstruction. They'd eventually be disheartened, and they would give up and leave." In the case of John Meredith, the black man who integrated the University of Mississippi, Doerr filed hundreds of motions, sat before multiple judges, appealed and appealed and appealed. He never lost heart, he never gave up. And neither did Meredith, it should be said, even after he was shot in the head. "You've just got to keep going back," he said.
1:42 Ryan Holiday? Justice, the most essential of the Stoic virtues, is not just about being right. It's not just having the moral high ground. You have to fight for it. You have to seize and command that high ground. Cato knew this. He was dogged in his determination to keep Rome a republic, and he wore himself down fighting over every example of corruption, every attempt to bend the rules, every effort by Caesar to take over. Cato didn't succeed, but his example inspired the founding fathers many centuries later, just as the words of those founders were taken up by people like John Doerr and Martin Luther King Jr. And Diane Nash and made real. Things weren't perfect. There was incredible resistance. It took longer than it should have, but it wouldn't have
2:22 Ryan Holiday? happened at all had they not kept going back, had they not made it happen.
2:39 Ryan Holiday? Hey, it's Ryan. Welcome to another episode of the Daily Stoic Podcast. Okay, so funny thing. I get these Google alerts on this, not my main email address. It's like an email address where all the spam goes. And that's where the Google alerts go. Because sometimes like I'll miss an article, or there'll be a video, or some cool person will say something they read in my books. Well, those Google alerts are basically worthless these days because last year, I gave a talk, I was telling you, at the 92nd Street Y. The event I did at the 92nd Street Y, I was interviewing Arnold Schwarzenegger. So right before the event, they had us post her some pictures, and then we sat in the chairs. Anyways, where does this lead to my Google result? This is kind of a funny thing. I'm sitting next to Arnold Schwarzenegger in this one picture, but I'm not in it. But
3:24 Ryan Holiday? the caption says Arnold Schwarzenegger interviewed by Ryan Holiday at the 92nd Street Y. So anytime anyone writes an article about Arnold Schwarzenegger these days, they, for some reason, use this photo, which then the caption then triggers my Google result. And so now just thousands of entries a day, just Arnold Schwarzenegger existing in the world, and my tangential connection to him. I don't know, I thought it was kind of a humbling little Stoic moment. Like, you think, oh, cool, I'm featured in X, Y, or Z. And it's like, oh, no, no, someone else is featured. And you were cut out of the photo that they were in. I, myself, went back to the 92nd Street Y to do this Q and A with Stephanie Rule. She was nice enough to interview me. It was a lovely conversation. I'm going
4:07 Ryan Holiday? to bring you some of that Q and A now. And here we are talking Stoicism and wisdom. Enjoy.
4:17 Speaker 01 Can you learn wisdom?
4:19 Ryan Holiday? Well, I see wisdom as a methodology as opposed to like a thing you have.
4:24 Speaker 01 Explain.
4:25 Ryan Holiday? You know, wisdom is the byproduct of reading. It's the byproduct of coming to lectures and talks. It's a byproduct of having good teachers. It's a byproduct of asking the right questions. It's a byproduct of experiences and travel and so many other things. It is not the end, but it is a byproduct of heading in the right direction and doing the right things.
4:47 Speaker 01 How concerned are you about people not reading? David Rubenstein says aliteracy is one of his biggest concerns. The antithesis of Stoicism is those who are not reading, who are not participating.
4:59 Ryan Holiday? So the founding of Stoicism goes back to Zeno. As I said, Zeno is traveling the Mediterranean as his merchant and he stops at the Temple of Apollo where the Oracle of Delphi sits. And he asks the oracle for basically the secret to the good life. And the oracle tells him, "You will begin to become wise when you start to have conversations with the dead." And he has no idea what this means.
5:22 Speaker 01 I don't either.
5:24 Ryan Holiday? The oracle was obviously, was historically vague and confusing. It may have been because beneath the Temple of Apollo, there was these noxious fumes that would come up and they think that she would go and huff them and get high and then just say these silly riddles that people then take to mean something. But the oracle tells him that talking to the dead is the secret to the good life. And it's not until he suffers that shipwreck and he ends up in Athens and he's walking through the agora, the busiest part of the marketplace of Athens, and he hears a bookseller reading, you know, from a scroll from a book. And he realizes in this moment, because he's reading something from Socrates. That that's what talking with the dead is.
6:08 Ryan Holiday? It's reading. Reading is a way to talk to people who are no longer alive. And so if you think about reading as this like superpower, this way of, I mean, I'm talking to you about Zeno and Marcus Aurelius and Seneca as if they're real and here. And they are to me because my relationship with them goes way back. And that's a lovely, magical thing. And it is crazy that some people don't do it. General Mattis has said, you know, if you haven't read hundreds of books, you're functionally illiterate. And his point is that just being able to read is not really the skill. The skill is the desire and the hunger and the lifelong commitment to reading.
6:50 Ryan Holiday? And so I think it's deeply alarming that we're living in a society where reading rates are declining. If that was in isolation, it would be less scary than the intersection of this aliteracy with AI.
7:04 Speaker 01 I was just, I'm like, please say, AI is basically saying to us, don't pause what you're doing. Don't even pause the TV. I'm going to summarize it for you. So how panicked, I shouldn't say panicked. How concerned are you that the summarization of everything is what AI is?
7:23 Ryan Holiday? I am not a Luddite. I have spent hours and hours reading about AI, messing with the different platforms. I have tried to find ways to help it make me be better at what I do, to learn things I wouldn't otherwise know about. All of my experiences with AI have had this interesting effect of convincing me that the thing most needed in a world dominated by artificial intelligence is a strong background in the humanities. Like, if you have a good liberal arts education, you will be able to take advantage of AI. And if you don't, it's going to eat you alive.
7:58 Speaker 01 Okay, that's what's amazing because conventional wisdom is telling young people the opposite right now.
8:06 Ryan Holiday? AI hallucinates 10 to 20% of the time, right? Like, so if you don't have a good sense of what's bullshit and what's not, like, if you don't have a vague sense, if you're asking it questions that you don't even know what the wrong answer is, how are you going to know if it's giving you the right answer? You're going to need to cultivate. The ability not just to know how to ask good questions, have a broad base of knowledge you can input into it to find the things you want to take out of it. But I'm also finding, I don't know if you see this, but like I get pitches and emails. I see comments and I'm having to have a good eye for what's human and not human.
8:42 Speaker 01 Yes.
8:43 Ryan Holiday? Right? And so again, if you're not, if you are already falling from bullshit from humans, imagine you now live in a world where AI slop can produce an infinite amount of it. You're going to be in trouble. Like if you're not good at separating things that are convenient or impossible or unrealistically simplified. If you don't know what, like the ballpark of what the right answer is, or you don't have it, like AI can help you find something that's in a book, probably. But if you haven't read the book and if you don't know what's in the book, like you're going to have trouble getting it to access that.
9:18 Speaker 01 But doesn't AI undermine, right, right? So to me, I believe the three things that we don't have control of are time, health and the weather, which is why I think those three things should be honored no matter what.
9:33 Ryan Holiday? Yes.
9:33 Speaker 01 But what AI has told us is time is irrelevant. I'm going to cut time. You don't need to worry about time. I'm going to give you everything fast and it disrespects the honor of effort.
9:43 Ryan Holiday? Well, not just disrespects the effort, but it's actually depriving you of the real benefit of doing the effort. Like the, the reading a book and writing an essay about it in school. The benefit is not that you wrote the essay and got a grade. It's that you spent the time reading about the thing and then were forced to think very hard about a question. And you practiced the skill of marshalling your thoughts into a coherent argument, which you then put down on the page. And then you learned from the feedback you got, whether you did it or not. Right? These are all extremely valuable skills that have nothing to do with The Great Gatsby or Catcher in the Rye.
10:27 Speaker 01 Then how do people find the will or the determination?
10:32 Speaker 01 To really start practicing this, because everything that you're saying to us makes perfect sense, yet it's counterintuitive to what's happening in the outside world.
10:44 Ryan Holiday? Well, I think you've got to find how you make this interesting. Like, I mess around with AI with my kids. I'm trying to-
10:52 Speaker 01 You type in like, "Make Stoicism sexy."
10:55 Ryan Holiday? Well, that's a lost cause. They're just not interested in what I have to do at all. But I try to find the things that they're interested in, and I try to use AI and technology to go down the rabbit hole. Like, to me, that's the main skill in life. Like, the most powerful, one of the most powerful and transferable abilities is like, getting interested in something, and then chasing that all the way down. Watching movies about it, and reading books about it, and asking questions about it, and traveling about it, and making your own stuff about- that, that's what you want. And that's what changes history. I find it striking, as I talked about Thomas Clarkson, who was the founder of the abolitionist movement, and the justice
11:39 Ryan Holiday? book, and I talk about Lincoln a lot in this book. It's fascinating that two of the people who changed the world the most in the last 200 or so years, it begins, like, they have this moral sense that slavery is wrong, right? And it is. But they didn't just go, "Oh, it's wrong. I think it's wrong." So, they're both intellectually fascinated with it, right? Thomas Clarkson writes an essay about slavery in college, and as he wins, he takes the contrarian view that slavery is wrong, which in the 18th century was the contrarian view. And he writes this essay, and he wins this prize. After he accepts the prize, it occurs to him, he goes, "What if I'm right?" Like, this childhood exercise, this academic thing, he goes, "What
12:24 Ryan Holiday? if I'm right?" And then he says, "And then what if I'm right? Maybe someone should do something about it." And then he goes, "If someone should do something about it, maybe that someone should be me." And Lincoln, the same thing. He instinctively opposed to slavery almost his entire life. And it's not until the passage of the Kansas Nebraska Act, where suddenly it feels like slavery is now on the march, that he goes, "I don't really know anything about its roots." And they both go and they basically hit the books. Like Lincoln goes to the Library of Congress as a congressman
12:54 Speaker 01 Literally.
12:55 Ryan Holiday? To read books about the history of slavery. He reads congressional debates. He reads legal treaties. And the point is, both of them just do this deep dive into the subject. And they figure out not just what its roots are and its history, but they figure out a unique, take a unique angle on it that allows them to be effective as social activists. I guess what I'm saying is this meta-skill of like, "Hey, I don't know anything about that." Or, "Hey, that seems interesting to me." Or, "Hey, that doesn't add up to me." That force, to me, is what drives not just so much wisdom and creativity and art, but also like so much social change.
13:37 Ryan Holiday? Theodore Roosevelt is a state congressman in New York. And he's asked to vote on this bill, this cigar makers bill. Cigars were made in tenements, like on this individual level in tenements on the Lower East Side. And he's born blocks from there and he's never been. And the party line says, you know, basically people should be able to do... The Republican Party line at the time was for the bill. And Roosevelt just says, "Look, before I vote, I want to go see what the factories are like." And he goes and is never the same.
14:09 Speaker 01 He's never the same because he experiences empathy?
14:12 Ryan Holiday? He experiences the thing personally, not intellectually, right? Like Jacob Rees, who shows him around the tenements, famously talks about how the other half lives. He actually sees how the other half lives. So it's all rooted in this empathy, in this interest, in this curiosity, in this desire to explore. Seneca's motto was that we read like a spy in the enemy's camp. That is to say, we read and hear what other people think, what other people are doing. And I think that, if I could give young people or anyone any magical... It would be that desire, that interest to go, "I don't know anything about that. I'm not going to stop until that's not the case anymore."
14:57 Speaker 01 You know what's incredible about that Roosevelt example? And not to get political, but Doris Kearns Goodwin, the presidential historian, gives this example of when a president wins an election, the first thing he does, you really pay attention to their inauguration speech, because they are starting their journey of how do I learn about the whole country, not just my voters, how do I really experience it? And the thing that most presidents do is then travel the country, go see all different parts of the country, experience those people's lives, start to develop some sort of empathy, and once you see all of that, you can lead in a much different way.
15:33 Ryan Holiday? Yes.
15:34 Speaker 01 And her fear is now that we're living in silos, and we don't need to see anyone else, so there's a soundbite of it, we never get to actually experience that thing, so we'll continue to judge from up high. And you have to dig down deep in order to be a true leader.
15:51 Ryan Holiday? Well, I would say not only is the technology an obstacle, but then it seems to be this cultural backlash, like that famous Elon Musk interview with Joe Rogan, where he says, you know, empathy is going to be the downfall of Western civilization.
16:03 Speaker 01 Empathy is now, there's a campaign against it.
16:05 Ryan Holiday? Yes, exactly, it's a sort of deliberate closing of the mind, of the interest of how things are for other people. And I think the reason for that is, this is what Jacob Rees said, he says, you know, when you learn how the other half lives, then you're presented with this question of, like, what are you going to do about it? And we all do this, right? We all close our minds, they're all things that we don't want to think about, because we know...
16:31 Speaker 01 If you're exposed to the human condition, you're more likely to care about it.
16:34 Ryan Holiday? Yeah, there's a reason we don't think about where our food comes from, or, you know, what it's like to live in, you know, this country, or that country, or how our clothes are made. But we don't think about these things, because when we think about them, it puts a great weight on our conscience, or it puts a great onus on us to change our behavior, and we'd rather maybe not do that.
17:06 Speaker 01 You're talking about, you know, historical figures and how they behaved and how they led. Where does Elon Musk land in this map for you?
17:15 Ryan Holiday? Well, he's a figure in the book as...
17:18 Speaker 01 A cautionary tale.
17:19 Ryan Holiday? Yes, as both one of the smartest people in the world and then one of the most profoundly stupid and misguided people in the world. And I think that he is a figure right out of the ancient texts or a Greek play or Shakespeare, where you have someone who's considerable genius and drive, when pointed in the right direction, can literally make a dent in the universe. And then, when pointed in the wrong direction, can be destructive at a scale that we won't be able... Just as it's unfathomable to calculate just the sheer reduction of carbon emissions
18:01 Ryan Holiday? that like Tesla cars have done, it will take future historians many years from now, doing some very painful, dark math on the sheer amount of death and suffering that the taking a chainsaw to the federal government and foreign aid will have inflicted on the world.
18:24 Speaker 01 But in real time, it's easy for people to ignore that because it's not right in front of their face.
18:29 Ryan Holiday? Yes, yeah. What's that Stalin thing about how, you know, one death is a tragedy and a million deaths is a statistic?
18:37 Speaker 01 Yes.
18:38 Ryan Holiday? And there are things moved around on paper, and so it doesn't feel real. And part of empathy, also part of wisdom and perspective, is the ability to sit down and go, okay, what does that mean? What if this was happening to my children or to someone that I loved? Do you know about the veil of ignorance from John Rawls? The idea of like, if you were redesigning society or reimagining society and you didn't get to choose where you landed, so there's a pretty high probability you would end up not better off than you are, but worse off than you are, would you want to live in that world? And I think, you know, it's crazy that the richest country in the world...
19:19 Ryan Holiday? Is arguing over whether it should spend less than 1% of its budget on foreign aid and
19:25 Speaker 01 Helping people survive.
19:26 Ryan Holiday? Yeah, it's like, we should be fighting over how that number should be way larger. I mean, that's just, that just seems to me to be one of the most basic notions of
19:36 Speaker 01 But it's hard for people to do that, right? If people are struggling in their day-to-day life, it's understandable, right? It's understandable that people would say, "Why not me? I'm struggling."
19:48 Ryan Holiday? I think that is understandable, but that's not what's happening. It's not like there was this giant groundswell of people and energy against saving people from dying of AIDS in Africa. This is the richest man in the world acting as a demagogue to turn that energy away from people like him, where it should probably be rightfully directed, and at the poorest, most vulnerable people in the world because they can't fight back. And so, again, when we talk about the study of history, though, like, that figure, that betrayal is something as old as time.
20:28 Speaker 01 I'm going to share some of our audience's questions. What, if at all, is there a dark side to Stoicism?
20:34 Ryan Holiday? Certainly Stoicism can be used and can be popular with people who are dark or have a dark side, right? You could use it theoretically to be a better sociopath if you ignore, if you ignore, you know, the stuff about justice and...
20:51 Speaker 01 No, but Stoicism on its face, Stoicism is very much, or it seems like, don't judge people's past, don't judge what you've heard, take people at face value. So that would give one the ability to put blinders on.
21:05 Ryan Holiday? Yeah, I mean, look, if you're saying like, "I've, I've got my own stuff to focus on, just going to focus on what's in my control," if you do that too much, what you've basically just done is made yourself the center of the universe. And that's fundamentally not what Stoicism...
21:20 Speaker 01 Say that again, say that again. I think this is so important.
21:22 Ryan Holiday? If all you're doing is focusing on what's in your control, what's up to you, all the limitation, if you're, you're just making yourself the center of the universe. And Stoicism was actively trying to, there's, there's this Roman Stoic named Hierocles, and he said, "Yeah, sure, we're all at the center, right? We care about ourselves the most. Then we have these concentric circles around us." Our family, our neighbors, our fellow citizens. And he said, actually, the work of the philosophy, this idea of caring for the common good is how do you pull those outer rings inwards? Peter Singer, the modern day philosopher, talks about it in the exact opposite terms. He talks about expanding the circle of who you care about.
22:03 Ryan Holiday? But this is the ancient virtue of justice, caring about people other than you.
22:09 Speaker 01 But it's the opposite of the veil of ignorance. It sounds like what you're asking again of people is to read more, is to not take things just at face value and say, it doesn't matter what you did, here's how it affects me, is to actually understand the environment that you're in and all the people that you're interfacing, and that takes homework.
22:26 Ryan Holiday? Yeah, it takes work.
22:27 Speaker 01 Oh, I like this. What does Stoicism say of heartbreak?
22:31 Ryan Holiday? Ooh, the Stoics would have a lot to say about heartbreak. I guess it would depend on, first and foremost, what kind of heartbreak are we talking about? Are we talking about getting dumped? Are we talking about the heartbreak of grief and loss because, you know, someone you know has passed? Seneca writes these beautiful essays, it's his consolation series, and he writes three essays, one of which is to his own mother when he's exiled by the Emperor Claudius. So he's writing to his mother who's lost her son, or a mother who's lost her son, that son just happens to be him. You know, I think there is this perception that the Stoics are unfeeling, that they just don't have any emotions. And that's what the lowercase word stoic means, just like lowercase epicurean means loves food, and that's not what Epicurus was talking about at all.
23:16 Ryan Holiday? But I think the Stoics are saying, look, you have the emotions, you have the feelings, it's just, it can't rule your life. So oftentimes, you know, you're going through the heartbreak of a breakup and you're like, my world is over, I'm never gonna love again. A little bit of perspective helps you see, first off, everyone's suffering, everyone goes through these things, and then also it allows you to go, am I gonna feel the same way in five years? Am I gonna feel the same way in 10 years? By the way, What do I think about the last time I got dumped? You know, and you go, oh, wait. So Stoicism, to me, is this framework for a kind of processing the emotions and dealing with them, as opposed to just being overwhelmed and enslaved by them.
23:57 Speaker 01 What are the exercises to get started on becoming a Stoic?
24:00 Ryan Holiday? Oh, well, I would say Stoicism and the practice of journaling are inseparable from each other. Marcus Aurelius's Meditations, one of the most unique and wonderful books ever produced, is not a book, like, it's not for us. Marcus Aurelius's Meditations is a book for the author, not for the reader. He is writing to himself what he needed. And from the incredible specificity of that comes its general and universality. And so, for me, the idea of sitting down and working on your thoughts, working, like, dumping your thoughts on the page instead of on your colleagues or your family.
24:39 Speaker 01 Like dumping them on the page and doing what with them?
24:40 Ryan Holiday? Well, working through them. Why, why am I angry? What caused this? What can I do about it? Why am I depressed? Why am I struggling? Why am I sad?
24:50 Speaker 01 When you journal, what do you do with those pages?
24:52 Ryan Holiday? Nothing. The page, doing them is what I do.
24:55 Speaker 01 But do you keep them?
24:56 Ryan Holiday? Yeah, I keep them because I struggle to throw anything away, but I...
25:01 Speaker 01 Speaking like a true bookshop owner, yes.
25:03 Ryan Holiday? I, to me, I'm getting 95% of the benefit in the moment itself, and any kind of review later is just extra. To me, the benefit of journaling is in the journaling. It's not in the journal. It is the act of reflection, of taking the thing that was bouncing around in here and putting it on the page, and in having to articulate it and then think it, giving yourself even just a few feet of distance. Writing is a contemplative act.
25:38 Ryan Holiday? Hey, it's Ryan. Thank you for listening to the Daily Stoic Podcast. I just wanted to say we so appreciate it. We love serving you. It's amazing to us that over 30 million people have downloaded these episodes in the couple of years we've been doing it. It's an honor. Please, spread the word. Tell people about it. And this isn't to sell anything. I just wanted to say thank you.
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