The Daily Stoic - You Have to Fight for It | Is There A Dark Side To Stoicism?

Episode Date: February 10, 2026

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/👉 Support the podcast and go deeper into Stoicism by subscribing to The Daily Stoic Premium - unlock ad-free listening, early access, and bonus content: https://dailystoic.supercast.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 FacebookSee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

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

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 once passed were then often ignored

by southern politicians and law enforcement officers. But the reason the cause eventually prevailed was encapsulated by the legal philosophy of John Doer, 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, Dore filed hundreds of motions, sat before multiple judges, appealed and appealed and appealed. He never lost hard. 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. 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. Kato knew this. He was dogged in his determination to keep Rome a Republican, 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 Doer 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 happened at all had they not kept going back, had they not made it happen. Look, this is the time of year. We try to get our health in order, try to get back on track, try to have better habits, put better things into our bodies. So maybe you're thinking about supplements. If you are, you know it's a confusing space. There's a lot of brands out there. It's a low trust category. Not a lot of regulation, a lot of scammers, a lot of big, unpronounceable ingredients. It's hard. And that's where momentous comes in. And it's also what makes them stand out. They become

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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've read 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 his poster 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 the caption says Arnold Schwarzener 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's words are 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 say, 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 90s Second Streetwide to do this Q&A with Stephanie Rule. She was nice enough to interview me. It was a lovely conversation.

I'm going to bring you some of that Q&A now. And here we are talking stoicism and wisdom. Enjoy. Can you learn wisdom? Well, I see wisdom as a methodology as opposed to like a thing you have. Explain. 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. How concerned are you about people not reading? David Rubinstein says, illiteracy is one of his biggest concerns. The antithesis of stoicism is those who are not reading, who are not participating. So the founding of stoicism goes back to Zeno. As I said, Zeno is traveling the Mediterranean as its merchant, and he stops.

at the Temple of Apollo, where the Oracle of Delphi sits. And he asked 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's no idea what this means. I don't either. 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, 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 a 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 talks about. talking with the dead is. 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 Mark Surrealist 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're a, you know, if you 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. 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 illiteracy with AI. I was just, I'm like, please say AI. 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? I am not a Luddite. I have spent hours and hours reading about AI, messing with the different platforms. I've 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 experience, 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. Okay, that's what's amazing because conventional wisdom is telling young people the opposite right now. AI hallucinates 10 to 20% of the time, right? 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, right? And so again, if you're not, if you were 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, or 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 for you.

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. 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. Well, that just disrespects the effort.

But it's actually depriving you of the real benefit of doing the effort. Like 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 we're 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. Then how do people find the will or the determination 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.

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... Do you type in like make stoicism sexy? 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. To me, that's the main skill in life.

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 and that's what changes history i i find it striking as i talked about thomas clarkson who's the founder of the abolitionist movement and the justice book and i talk about lincoln a lot in this book it's fascinating that two to 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 his 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 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 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 activist. 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. Theodore Roosevelt is a state congressman in New York, and he's asked to vote on this bill, this cigar maker's 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. Like he... He's never the same because he experiences empathy? He experiences the thing personally, not intellectually, right? Like he, Jacob Rees, who shows him around the tenements, is famously talks about how the other half lives. He actually sees how the other half lives. So it's all rooted in this, in this empathy, in this interest, in this curiosity, and 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, 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. You know what's incredible about that Roosevelt example, and not to get political, but Darrys-Kirn's Goodwin, the presidential historian, gives this example of when a president wins an election, right? 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. Yes. 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 lead to be a true leader. 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. Empathy is now, there's a campaign against it. 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 mind. They're all things that we don't want to think about because we know. If you're exposed to the human condition, you're more likely to care about it. 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 where our clothes are

that 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. So we have a little place down in Florida that we go when I do some writing there. We go there for spring break sometimes for Christmas. It's one of my favorite places to be. We just did some remodeling and refurnishing. And part of that, we needed all new mattresses. And now I'm I am seeing why people love their Helix mattresses. We got all new mattresses for the house, and they are amazing. They did not disappoint.

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Make sure you enter our show name at checkout so they know we sent you at Helix sleep.com slash stoic. We've got an employee here at Daily Stoke. I won't say who because it's kind of private, but they've been using Monarch, today's sponsor, to track their progress as they try to pay off their student loan. own debts. I'm a college dropout, so I don't have any debt, thankfully, but I can only imagine how overwhelming it would be to have this thing hanging over you. And she's been using the app to

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and you can use code Stoic at Monarch.com for half off your first year. That's 50% off your first year at monarch.com code stoic. 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? Well, he's a figure in the book as... A cautionary tale. 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, 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 emission, 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.

But in real time, it's easy for people to ignore that because it's not right in front of their face. Yes. Yeah. What's that Stalin thing about how, you know, one death is a tragedy and a million deaths is a statistic? Yes. 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 how you, 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 were, would you want to live in that world? And I think, you know, it's crazy that the richest country in the world is arguing over whether it should spend less than 1% of its budget on foreign aid and... Helping people survive. 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 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. 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, uh, 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 this study of history, though, like that figure, that betrayal is something as old as time. I'm going to share some of our audience questions. What, if at all, is there a dark side to stoicism? 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 the stuff about justice and... No, but stoicism on its face, 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. Yeah, I mean, look, if you're saying, like, 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's... Say that again. Say that again. I think this is so important. If all you're doing this is focusing, on what's in your control, what's up to you, all the limitations. You're just making yourself the center of the universe. And stoicism was actively trying to, 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 the exact opposite terms, he talks about expanding the circle of who you care about.

But this is the ancient virtue of justice, caring about people other than you. 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. Yeah, it takes work. Oh, I like this. What does stoicism say of heartbreak? Oh, 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? We're talking about getting dumped? Or 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 Epicureus was talking about at all. 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 going to 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 going to feel the same way in five years? I'm going to 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. What are the exercises to get started on becoming a stoic? Oh. Well, I would say stoicism and the practice of journaling are inseparable from each other. Mark Surrealis' Meditations, one of the most unique and wonderful books ever produced, is not a book. Like, it's not for us. Mark Shurulius' 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. But dumping them on the page and doing what with them? Well, working through them. 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? When you journal, what do you do with those pages? Nothing. The page, doing them is what I do. Yeah, I keep them because I struggle to throw anything away. I'm spoken like a true bookshop owner, yes. 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 and think it, giving yourself even just a few feet of distance. Writing is a contemplative act. Hey, it's Ryan. Thank you for listening to the Daily Stoag 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 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.