← The Daily Stoic
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- [00:00]
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. 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 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 Doar, 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, Doar 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. 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 Doar 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. We've just been feeling, like, a little claustrophobic in our house lately, like, as our kids are getting older and our stuff is getting older. It's just like our space is not working. So we're kind of reorganizing not just at home, but at the office. We've been making some room for some.
- [02:52]
New employees here at the office and.
- [02:53]
Then also just redecorating a little bit. And the first place we checked was Wayfair because it is a one stop shop for all kinds of decor stuff. Office furniture, organizers, bookcases, even blankets and pillows. Wayfair's huge selection makes it easy to find exactly what's right for you. And their site is super easy to use and you can navigate with all these different filters to find exactly what you're looking for down to the exact size and material you want. And that's how we found all the stuff that is now decorating our house and the bookstore. Get organized, refreshed and back on track this year. For way less, head to Wayfair.com right now to shop all things home. That's W a y F a I r Wayfair. Every style, every home. 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 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 budget and save and it's bringing her a little bit closer every day to being debt free, which I can only imagine would be a huge relief. Monarch shows you exactly where your money is going. It helps you redirect it towards what matters. With automated tracking and clear projections, you can actually see yourself getting closer to being debt free or hitting your savings milestone instead of just hoping it happens. Unlike most other personal finance apps, Monarch is built to help make you proactive and not just reactive. And Monarch helped users save over $200 per month on average after joining. You can set yourself up for financial success in 2026 with Monarch, the all in one tool that makes proactive money management simple all year long. And you can use code stoiconarch.com for half off your first year. That's 50% off your first year@monarch.com code stoic. 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 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 for 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 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 it just thousands of entries a day, just Arnold Schwarzenegger existing in the world and my tangential connection to him.
- [06:04]
I don't know, I thought it was.
- [06:05]
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 Streetwide to do this Q and 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 and A now. And here we are talking stoicism and wisdom. Enjoy.
- [06:35]
Stephanie Rule
Can you learn wisdom?
- [06:37]
Ryan Holiday
Well, I see wisdom as a. As a methodology as opposed to like.
- [06:41]
Stephanie Rule
A thing you have Explain.
- [06:43]
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.
- [07:05]
Stephanie Rule
How concerned are you about people not reading? David Rubenstein says alliteracy is one of his biggest concerns. The antithesis of stoicism is those who are not reading, who are not participating.
- [07:17]
Ryan Holiday
So the founding of stoicism goes back to Zeno. As I said, Zeno is traveling the Mediterranean as it's merchant, and he stops at the temple of Apollo, where the Oracle of Deli 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 has no idea what this means.
- [07:41]
Stephanie Rule
I don't either.
- [07:42]
Ryan Holiday
That's the. The oracle was obviously, was. 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 them that. 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 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. It's reading. Reading is a way to talk to people who are no longer alive. So if you think about reading as this superpower, this way of. I mean, I'm talking to you about Zeno and Marc, 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 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. And so I think it's deeply alarming that we're living in a. In a. 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.
- [09:23]
Stephanie Rule
I'm like, please say a. I mean, 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?
- [09:41]
Ryan Holiday
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 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.
- [10:16]
Stephanie Rule
Okay? That's what's amazing. Because conventional wisdom is telling young people the opposite.
- [10:23]
Ryan Holiday
Right now, AI hallucinates 10 to 20% of the time.
- [10:27]
Right.
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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.
- [11:00]
Right.
- [11:01]
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, I 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.
- [11:36]
Stephanie Rule
But doesn't I 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. Yes, 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.
- [12:01]
Ryan Holiday
Well, not 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 were forced to think very hard about a question. And you practiced the skill of marshaling 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.
- [12:38]
Right.
- [12:38]
These are all extremely valuable skills and that have nothing to do with the Great Gatsby or Catcher in the Rye.
- [12:45]
Stephanie Rule
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.
- [13:02]
Ryan Holiday
Well, I think you've got to find how you make this interesting. I mess around with AI with my kids. I'm trying to.
- [13:10]
Stephanie Rule
You type in, like, make stoicism sexy.
- [13:13]
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. 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'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 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, 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.
- [14:18]
Right.
- [14:19]
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 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 literally 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. 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 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. 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.
- [16:28]
Stephanie Rule
He's never the same because he experiences empathy.
- [16:30]
Ryan Holiday
He experiences the thing personally, not intellectually, right? Like he. Jacob Riis, 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. 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 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.
- [17:15]
Stephanie Rule
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. 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.
- [17:51]
Ryan Holiday
Yes.
- [17:52]
Stephanie Rule
And her fear is now that we're living in silos and we don't need to see anyone else or there's a sound bite 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.
- [18:09]
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 society.
- [18:21]
Stephanie Rule
Empathy is. Now there's a campaign against it.
- [18:23]
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 Riis said. He says, when you learn how the other half lives, then you're presented with this question of what are you gonna do about it? And we all do this, right? We all close our minds. They're all things that we don't wanna think about because we know if you're.
- [18:49]
Stephanie Rule
Exposed to the human condition, you're more likely to care about it.
- [18:52]
Ryan Holiday
Yeah. There's a reason we don't think about where our food comes from or what it's like to live in this country or that country or where our clothes are made. 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.
- [19:21]
New year, new systems.
- [19:22]
Right.
- [19:23]
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- [21:38]
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- [22:01]
Stephanie Rule
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?
- [22:10]
Ryan Holiday
Well, he's a figure in the book.
- [22:12]
Stephanie Rule
As a cautionary tale.
- [22:14]
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, that he is a figure right out of the ancient texts or a Greek play or Shakespeare, where you have someone whose 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 to. Just as it's unfathomable to calculate just the sheer reduction of carbon emissions 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 would, will have inflicted on the world.
- [23:19]
Stephanie Rule
But in real time, it's easy for people to ignore that because it's not right in front of their face.
- [23:25]
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?
- [23:32]
Stephanie Rule
Yes.
- [23:33]
Ryan Holiday
And these 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 love? Do you know about the veil of ignorance from John Rawls? The idea of 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 were. Would you want to live in that world? And I think, you know, it's just, it's, it's crazy that the, 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.
- [24:31]
Stephanie Rule
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.
- [24:43]
Ryan Holiday
I think that is understandable. But that's not what's happening.
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It's not like There was this giant.
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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.
- [25:23]
Stephanie Rule
I'm going to share some of our audience questions. What if at all, is there a dark side to stoicism?
- [25:30]
Ryan Holiday
Certainly stoicism can be used and can be popular with people who are dark or have a dark side.
- [25:36]
Right.
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You could use it theoretically to be a better sociopath if you ignore, you know, the stuff about justice and.
- [25:46]
Stephanie Rule
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.
- [26:00]
Ryan Holiday
Yeah, I mean, look, if you're saying like, I 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.
- [26:15]
Stephanie Rule
Say that again. Say that again. I think this is so important.
- [26:17]
Ryan Holiday
If all you're doing is focusing on what's in your control, what's up to you? All the limitations if you're just making yourself the center of the universe. And stoicism was actively trying to. There's this Roman stoke named Hierakles 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 that 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 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.
- [27:03]
Stephanie Rule
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.
- [27:21]
Ryan Holiday
Yeah, it takes work.
- [27:22]
Stephanie Rule
Oh, I like this. What does stoicism say of heartbreak?
- [27:26]
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. 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? Am I 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 kind of processing the emotions and dealing with them as opposed to just being overwhelmed and enslaved by them.
- [28:52]
Stephanie Rule
What are the exercises to get started on becoming a Stoic?
- [28:55]
Ryan Holiday
Oh, well, I would say stoicism and the practice of journaling are inseparable from each other. Mark Cerealius's Meditations, one of the most unique and wonderful books ever produced, is. Is not a book like, it's not for us. Mark Cerealius is. 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.
- [29:33]
Stephanie Rule
Your dumping them on the page and doing what with them, working through them.
- [29:37]
Ryan Holiday
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?
- [29:45]
Stephanie Rule
When you journal, what do you do with those pages?
- [29:47]
Ryan Holiday
Nothing.
- [29:48]
The page doing them is what I do. Yeah, I keep them because I struggle to throw anything away. But I spoke 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 it 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 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 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.
- [31:12]
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