The Rich Roll Podcast - Ryan Holiday Wants You To Do The Right Thing, Right Now

Episode Date: August 26, 2024

Ryan Holiday is a renowned author, modern Stoic philosopher, and the driving force behind the resurgence of ancient wisdom in contemporary culture. This conversation explores the intersection of Stoicism and Ryan’s iconoclastic perspective on personal ethics, which emphasizes actionable virtue over abstract philosophy. We discuss Ryan’s journey from a marketing prodigy to a philosophical powerhouse, his interpretation of Stoic justice, and the drivers of ethical behavior.  We also examine the importance of moral rectitude in a complex world, the role of individual choice in societal change, finding purpose through service and right action, and many other topics. Ryan is a luminary of practical wisdom. This conversation is a masterclass in applied philosophy. Enjoy! Show notes + MORE Watch on YouTube Newsletter Sign-Up Today’s Sponsors:  Peak Design: Get 20% OFF thoughtfully crafted sleek carry solutions 👉 PeakDesign.com/RICHROLL LMNT: Get a FREE Sample Pack with any drink mix purchase 👉drinkLMNT.com/RICHROLL Squarespace: Use the offer code RichRoll to save 10% off  👉Squarespace.com/RichRoll Seed: Use code RICHROLL25 for 25% OFF your first order 👉seed.com/RichRoll On: Enter RichRoll10 at the checkout to get 10% OFF your first order 👉on.com/richroll This episode is brought to you by BetterHelp: Get 10% off their first month 👉BetterHelp.com/RICHROLL Check out all of the amazing discounts from our Sponsors 👉 richroll.com/sponsors Find out more about Voicing Change Media at voicingchange.media and follow us @voicingchange

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People tend to come to Stoicism because they're going through something personally difficult. It's about getting rid of the destructive emotions, the emotions that wear at you, that are bad for the engine. Ryan Holiday is one of the most incisive young minds of his generation. Best known for popularizing the ancient philosophy of Stoicism and translating its timeless principles into actionable tools for modern living, Ryan is the author of a dozen books on philosophy, marketing, history, and how to live well, which have sold, astonishingly, more than 10 million copies worldwide. Stoicism isn't there to help you crush your enemies more efficiently and not have to feel bad about it while you're doing it. To me, this is all a very important way of sort of combating the nihilism and despair

that can so easily creep in, especially in the modern world. His counsel is highly sought by the world's highest performers across professional sports, business, entertainment, and politics. And he is the host of the wildly popular Daily Stoic podcast, which is housed in the Painted Porch, his independent bookstore in rural Bastrop, Texas. is an independent bookstore in rural Bastrop, Texas. Today's conversation canvases justice. We talk about moral rectitude, kindness, and compassion. And we do it through the lens of Ryan's latest installment on the Stoic virtues, his new book, Right Thing, Right Now.

Ryan is one of my favorite thinkers. He is a friend I myself turn to for perspective and guidance. And this, his fifth appearance on the show, does not disappoint. When you figure out how the other half lives, you are faced with the most essential question of your life, which is what are you going to do about it? Well, this latest book is your latest, you know, missive from the front lines of Stoicism. The third in this series on the Stoic virtues, it's of course about justice.

It's called Right Thing Right Now. And it's really about moral rectitude on some level, right? And of course, it's going to, in the Venn diagram of these virtues, they all kind of overlap to a certain extent. I mean, I found this book to have a lot in common with the Courage book because you can't have justice without courage, especially in light of people who are pursuing justice in the face of cultural, social, political resistance. And also courage without justice is a strange thing.

Yeah. When I started this series, I guess I wasn't fully aware of how inseparable the virtues were. But each time you try to look at one specifically, looking at courage or discipline or justice or wisdom, you go, oh, but it's so connected. You're kind of writing about the same thing. Yeah, and the same people doing the same things. And you can, how you choose to talk about each one, it's really just a choice. Are you putting in this bucket or this bucket?

But you're illustrating the same thing over and over and over again. Right, because if you're pursuing justice without wisdom or temperance, it's not gonna come out well. Or is keeping your word, doing what you say, honoring your commitments, is that the virtue of justice? Or is that the virtue of discipline? Is doing your best,

realizing your potential as a person? Sure, this is very obviously a matter of discipline and willpower, but to not give your best is to cheat someone, right? To not realize your potential is to deprive the world of something. And so they're all very, very related. I am fully convinced that justice has to be the virtue that the others orient themselves around. Because, yeah, courage in pursuit of an evil end, what's the point? And hardly admirable. And then there is this idea, of course, that like, because you're doing the right thing,

the world will just greet you with green and and tailwinds and they won't right so you need the discipline to to sort of bring that into fruition and then like wisdom is obviously the thing that helps you sure figure them all out in the mix of of trying to parse all of these uh from each other from a writer's perspective, the challenge then becomes, how do you not be sort of duplicative in your writing or tell the same stories again or highlight the same historical event that is relevant or germane to this virtue

just as it was to the one in the previous book? It was the first time that I've ever worked on a creative project related to other creative projects. So if you're just writing a book, you're writing a book, whatever you put it in, you put in it. I'd never had to think, well, if I put it in here, then I can't put it in there. And so it's forced me weirdly to sort of practice, I would say, forced me weirdly to sort of practice, I would say mostly discipline and wisdom that having to see the whole picture is harder than only sort of just thinking about what's in front of you right now. And so there was a chapter that I forget which one it was, but there was a chapter

that was supposed to be in the courage book that got cut and rewritten to go in the discipline book that got cut and rewritten and appears in the latest one. And so, yeah, it's been actually a great challenge. And it's like, I just have to be thinking more than one step ahead, which has been, has made me better. Yeah, there's sort of a puzzle aspect to this or an assembly aspect to putting these books together. You showed me your famous note card system and

each one of these cards gets numbered or delegated to its respective virtue. And it seems like that's a fluid thing where, well, yeah, maybe it could go there, but actually it's more applicable in this book about this virtue. Yeah. Like I'm working on the fourth one now and a good chunk of those note cards. So basically I do all my research on note cards. So I used to just grab like, you know, your standard note cards from the store. I use four by six ones. And then I was like, you know what, I feel like I'm financially at a point I could print my own note cards. So I went to a printer, there's one up the street from the bookstore. And so it just says courage, temperance, justice, wisdom at the top. So as I was researching, whenever I would be making a card, I would just write, I would just circle whichever virtue it was. And so there are cards that I'm

dealing with now, five years into the series, that courage was circled, crossed out, discipline was circled and crossed out, justice was circled and crossed out. So I've recategorized this four times. I've thought it would be in each one of the books and the ideas moved. Okay, actually now I can finally tell that story. When we talk about justice, obviously we think of the legal system. We think of balancing the scales, but you are coming at this from a broader perspective. How do the Stoics contemplate justice

and what's relevant for us to understand about where you're coming from with this? When the Stokes are laying out the four virtues, they're not like courage, discipline, wisdom, and then following all laws, you know, or like arguing in court. That's not what they mean by justice. What they mean is how do you act? What do you do and not do? You know, discipline is like, hey, do you, you know, do you go for the run or not go for? Discipline is like, hey, do you go for the run or not go for the run? Justice is like, how do you treat people? What's the code of ethics that you operate by?

Does this also intersect with the legal system and with politics and policy? Yeah, of course. But I really wanted to not focus so much on those questions and focus more on the phrase used earlier, which is sort of more erect to like, who are you as a person? How do you operate? And I think what I'm sort of excited by and challenged by these days is like, obviously there's all these big things that are happening in the world, but what's cool about

having a podcast or, you know, you have a little company, it's possible to like for individuals to taxes or not? But like, do you work with this supplier or that supplier? How do you treat your employees? Like these sort of questions that we get to, instead of, there was an impotence in us sort of going, well, how do we want those people far away who are in the positions of power influence? How do we want them to make decisions? the positions of power influence? How do we want them to make decisions? There's also a sort of return of a lot of agency to the individual in this sort of global interconnected, where like we actually get to make decisions of some consequence. It's not the same as Nike deciding or Apple deciding where their factory is going to be, but you get to decide, are you buying from this supplier or that supplier?

And that's of no small consequence, at least for the people directly affected by the thing they're making. My favorite part of the entire book is the afterword where you address this directly. I really was thirsty for and enjoyed like your own perspective of how these principles have applied in your life

or how you're striving to apply them and where you've needed to apply them in order to address like failures and weaknesses. And you're very specific with perspective what you just shared, like where did the coins come from? The Daily Stoke coins and who is manufacturing the leather bound, you know, covers to the books

and all that sort of stuff are decisions as a business owner that you have to make that have ethical, you know, considerations in terms of how they measure up with virtue and your own personal integrity. Or just like a, even like more mundane one, like, I don't know about you,

but I would always read about like Black Friday sales and people like lining up for, you know, like to buy like a plasma TV, like the day after Christmas or Thanksgiving or whatever. And I was like, this is gross. Like, why are you doing this? Right? Is this what we want to be as a society? And then, you know, you start a business and you sell things and then someone comes to you on your team and goes, so are we going to do like a Cyber Monday email? And suddenly you're faced with the decision that- Right, it becomes very real. The CEO of insert department store was also faced with and you have to go, oh, okay, so I think these things are gross, but they make a lot of money. Do I want to do that?

And then you have to decide. And, you know, and so like for Daily Stoke, we don't do Cyber Monday or Black Friday. I just, I was like, this isn't what I like. So we do like a food drive every year. And it's been cool. But like, how do you, I'm saying that not to pat myself on the back,

but this idea of like justice, not this abstract theoretical thing, but justice as something that results from the decisions that you make in your life in the sphere in which you happen to operate. So some of us are the CEO or the founder of Patagonia and we make a decision that can impact tens of thousands of employees. And then some of us own a little bookstore in Texas and we go,

hey, do I want to give my employees the day off to be with their family? Of course, it seems awesome. But the cost of that is this number. Are you okay with that? Like, justice is that. It's wrestling with that. I don't want to hold myself up as someone who's always making these great moral decisions. But the idea of principles being a thing that costs you money or things that challenge you or that you are allowed to do, and in fact, may even be like an industry practice. But whether you should do them, whether it's the kind of person you want to be is an entirely separate question. On some level, it feels like you're wrestling with the outer boundaries of agency.

Stoicism is so much about controlling the controllables and letting go of what you don't have control over, right? It's a serenity prayer sort of exercise where you realize like all I can do is, you know, have domain over my actions, my behaviors, to some extent, my thoughts, how I respond or react to, you know, the external world. And within that, there is a sort of circumscribed sense of agency. Like I really don't have any control over all these people. And as much as I would like all these people to arrange themselves

to my liking, like this is a, not only a fruitless exercise, it creates misery and wrong and ethics, et cetera, does have repercussions that spill out into the external world. And you actually can have some level of impact. It shouldn't be about that. You should do the right thing because it's the right thing. And this is the kind of recurring mantra or theme, but it's worth considering that you're not an island, like you're not operating

in isolation here. And that does feel a little, maybe not different, but a broadening of kind of where your own head is at with respect to stoicism. Yeah, I think so. Look, the stereotype of the stoic is that they're resigned, accepting, indifferent, and kind of self-contained, which I think there is a part of that in Stoicism. But then what was the job that the most Stoics had? They were politicians. They served in or they retreat from public life. And the Stoics said, no, no, you actually have to get involved. Someone has to do it.

And that if you don't do it, someone worse will do it. I was thinking about this. So all these sort of explanations we've come to understand, like the different there's structural racism or systemic problems. These are all very real, right? Like, yeah, the vast majority of pollution or things contributing to climate change are, you know, huge corporations or entities or developing nations. But one of the things that happens when you look at problems that way is it kind of lets you as the individual off the hook because you get to say, well, I don't really matter. I am this infinitesimal inconsequential thing.

And that's what's really powerful about stoicism is that there is this repeated meditation on how small and insignificant we are but then with equal measure, this repetition of how your choices matter to you, they matter because if you don't make those choices, then who are you? This is now intersecting different schools,

but Confucius said like every individual should act as if the fate of humanity was on their shoulders. Like people don't vote because they think their vote doesn't matter. And as a result, their votes don't matter. And so how do you make individual decisions as if they are of moral consequence? And there's something constraining about that, but there's also something super empowering about that because it means things have significance. And you're not just doing it because you're doing it because you're making money or what you're, you make the decisions

based on this set of values you have based on your, your sense that these things cumulatively have an impact. And then that gives you like, it sounds weird to say, because you have a reason to wake up in the morning and it gives you a reason to go through the world. It's deciding that things matter and that there's a thing there's right and wrong, and there's things that you won't do. There's things that you don't think people should do. To me, this is all a very important way of sort of combating the nihilism and despair that can so easily creep in, especially in the modern world. There's the intrinsic reward of practicing this discipline, which is a sense of self, a crafted identity that adheres to a certain sense of values and the self-esteem that that will kind of gather for yourself. Like you feel good about who you are

because you're true to your word and this is what you believe in and your actions correspond to that, right? But there's also this extrinsic thing, like externally, it does matter whether or not, like you talk about how karma doesn't come around, you know, for people that are, you know, practicing this form of justice because they're doing it for the right reasons. Maybe it comes around way later, maybe it never does.

Nonetheless, it still matters because whether or not you're aware of it in some, you know, perhaps even too subtle to notice way, it does make a difference how you show up. Yeah, yeah. Mark really says this, he writes this in meditations. He says, stop asking for the third thing. And I'm like, what's the third thing?

And he says, you've done something good and someone benefited from it. The third thing is the recognition, the parade, the appreciation, the credit, the payback. That's such a powerful concept. And I think about it not just in when you do someone a favor, but when you do anything. So, you know, you went to the gym and you had a great workout. The third thing is you check the mirror in six months and you have a six pack or you work really hard on a project and then a large check comes into your bank account or you find out where you land on the bestseller list or whatever. That's the third thing. But if you can get to a place where you do the thing

and you get the enjoyment, the satisfaction, the appreciation, the landing of the thing, it is received by the world, it benefits someone, and you just go, that's enough. If this third thing happens, if karma is real, if it does come back to you, if it does make a positive difference, if you do end up winning or whatever, fantastic. But the more you can detach from needing that

third thing to justify one or two happening, you're in a really wonderful place and you're very free. Because the thing that can happen is you do this thing, you slave away at it, you work so hard on it, or you do this thing that costs you that you didn't have to do, and then it's not appreciated or it's rejected or you're made fun of or it flops. And if you had an expectation that that's how it was gonna go

and then you don't get it, you're devastated and you're probably not gonna do it again. And this idea of not needing the reward is a very powerful place. The doing is its own reward. Yeah. Right, always and every time. In the case-

Basically every school says that. Yeah, of course, this is not a new idea, right? Oh my God, I had this epiphany. I wrote a book about it. In the context of justice though, you highlight all of these examples. Of course, there's Harry Truman, there's Harriet Tubman, there's the women's suffrage movement.

There's all these sort of characters that populate the narrative as they always do in your books. In this particular one though, these are people who not only are not getting the satisfaction for being recognized for their, you know, acts of justice and courage, they're in some cases reviled or, you know, on some spectrum between just being dismissed and unrecognized to, you know, outright pilloried for their actions and their behaviors. Yeah, I mean, Martin Luther King Jr.

for their actions and their behaviors. Yeah, I mean, Martin Luther King Jr. was disliked by a majority of the country. He was disliked by a significant percentage of black people, even in that time. And then he was murdered, right? So like this idea that like, because you're right, because your cause is morally righteous,

because it's good, it's gonna be received with open arms. It isn't, which is another thing I really wanted, I think is a problem we have today. I think it's wonderful, particularly with younger people, just how idealistic they are and their notions of like fairness

and equality and equity and all these things are huge leap forwards. And it's kind of embarrassing that they're not commonly shared beliefs. But there is attached to that a kind of expectation that once it's been articulated, it will just become policy or law. And it's really important that people understand that every change is by definition bad for the people currently in power. Like that it's a hostile act, you know, you wanting to change things or redistribute things or recalibrate things. It's bad for people who have gotten successful in said system. And so there will be opposition, often very intense opposition. And the ability to be right about a cause is one thing. To be able to execute said cause or bring that thing into being requires,

again, this is where these virtues come in, not just courage, because I think a lot of activists are very brave. They're willing to go to jail. They're willing to risk criticism, whatever. But also we're talking competence. You know, a cause is not raising money. A cause is raising and then deploying and deploying effectively said money. And so that's something I wanted to, I think a lot about. It's not just like being right about the thing, but then doing something about it. Persistently, consistently over a very long period of time. Yes. In a sort of war of attrition with power. Yes. Yeah. Yeah. The civil rights movement was not a series of marches that changed people's minds. It was a series of marches designed to generate an overreaction by police and local officials who would then inflict bodily harm and arrests, which would raise public sympathy and generate headlines. And then there was also an incredibly effective legal movement behind that, an incredibly effective policy

movement behind that, an incredibly effective, like sort of lobbying movement. You know, there was all these things happening. It was this comprehensive reimagining of society with quite a bit of strategy thrown in there. The women's suffrage movement is another one. It's like a hundred plus years of organizing and protest and challenges and ballot referendums and prison sentences over, you know, multiple generations that finally bring this thing into effect. I really was fascinated by the suffragette movement because it's not a thing you like, okay, you go, women wanted the right to vote and men didn't want them to have the right to vote.

But of course, there were many, many, many women who were what they called anti-suffragettes who didn't feel like women. And so the battle that these activists had to engage in for so long, it was incredible, you know. And the coalitions that they had to organize around with like you had black women and white women, you had poor women and rich women. There's this big debate in the suffragette movement about whether Mormons were allowed to be suffragettes in a time when polyamory was still illegal in parts of the United States. And so you had these people who disagreed on so many things, having to effectively come together to make this thing work. I also think it's worth noting that it's easy to look in the rear view and just assume that everybody in the moment realized that this was a problem, like this was a wrong that needed to get

righted, right? And that is not the case. And so those who pursue justice for the sake of whatever particular cause it is in the moment of that struggle are not perceived as warriors for justice. They're sort of like, this is not a problem we need to solve. Yeah, they're crazy people. They're maligned and kind of cast aside.

Yeah, yeah. So it's like there's the women who were suffragettes and there were anti-suffragettes and they were the minority on both ends because the vast majority of people didn't give a shit at all. And that's the first hurdle that you have to give over. I tell the story of Thomas Clarkson, who basically single-handedly creates the abolitionist movement, which destroys slavery first in the British Empire, then in sort of globally. And 12 people get together in a meeting and decide, hey, maybe the slavery thing is like not okay. And that seems crazy that there was a meeting about that.

But for effectively all of human history up until that point, everyone had either agreed or not thought that much about whether you could own and control the labor of people who looked differently than you or people who had lost a war to you or people in another country that you didn't care about. Like, you know, this great man of history theory that like individuals change the world is not popular in academic circles. It's not popular, particularly amongst the kind of the people

we were talking about earlier, you know, people who believe in structural explanations or intersectional explanations. And these things are true and they're lenses that we have to understand the world through. And yet there are individuals who have fundamentally changed our understanding

of what's possible, what's right and wrong. Like Gandhi wasn't just this guy who kicks the British out of India. He effectively invents, that Thoreau had written a bit about it, Tolstoy had written about it. He sort of combines them. But he effectively invented the idea of nonviolent resistance. Like up until the mid

1800s, if you objected to something and wanted it to go away, you had to kill a lot of people. The anti-slavery movement is one of the first sort of modern political movements. Here you have, you know, states, sort of state operations. And he goes, hey, we don't have to overthrow a government by violent force. You can resist passively and change a policy. And so these are things I think it's worth pointing out. The Stoics could not have conceived of. These are inventions. These are modern inventions that are incredible,

as impressive as any of the technology we've come up with. The idea that, hey, we can get together and pressure the systems of power or business and make them do things differently is one of the most profound human contributions that have ever existed. Your point about organization and competence and structures is really important. But at the helm, you do need a leader. And these leaders who are flawed human beings, they are symbols, they're like avatars for a different way of thinking about something, right? Like in the case of Gandhi or MLK or, you know, choose your whoever, you know, you highlight many of these in the book, they become a representation of an idea and they have the sort of charisma and

fortitude to, you know, hold fast to that idea and pursue it. But the change only happens because structures emerge around that avatar. And this also comes right back to personal rectitude. Like what's so impressive about Gandhi is here you have this incredibly powerful person through untraditional means that Orwell writes this amazing sort of eulogy to Gandhi. And he goes, you know, what a clean smell he leaves behind. And that there weren't any abuses of that power. There's a couple of weird things, but like the problem also is these individuals

become avatars for these movements. They lead huge things and then they end up undermining or destroying said movement through personal corruption, dishonesty, ego, selfishness, right? And so this code of conduct, it's not just, hey, I'm going to try to do good in the world, but also then how, when I have this responsibility, power, influence platform, what are the standards that I hold myself to? Again, not what I can get away with. Martin Luther King on the road decides, hey, this is what everyone's doing. I'm going to do it.

And that's obviously, it's not just a shameful thing, but it was leverage that the FBI and other government agencies attempted to exploit over him. I don't know if you've ever read this, but there's this crazy letter that the FBI sends Martin Luther King where they're like, we know you're having these affairs. Here's our proof, blah, blah, blah. Our expectation is that you will kill yourself. And you could imagine a less strong person. That's the end of the Martin Luther King story. Obviously, a stronger Martin Luther King would have never put themselves

in that position to begin with. But the idea is, you know, on top of all of this, like first off, how many people have ever led movements or tried to positively change the world? And then how many of those people proved themselves worthy of the respect and faith and- Very few. Earnestness that the crowd put in that person when we said, we believe you, we have faith.

Yes. And then those stories always seem to end so sadly also. And what does that look like in 2024? Yeah. You know what I mean? Like who among those people actually maybe slipped by because all eyes were not upon them 24 hours a day and broadcast to the world constantly. So the bar, the ethical bar is even higher to meet. It can be unforgiving. Because it often forgets that human beings are fallible.

Yeah, it's always disappointing. You're like, you really admire somebody. You think they have all this potential. They're doing this change. And then they blow it all up to have an affair or for this, you know, suddenly they open themselves up to a bribe or something, you know, like it happens. Right. And so, so again, it's not just, Hey, I'm in support of a good cause, but what's the personal standards that I hold myself to? And do I also, on top of that, have the discipline to stick with them, to live within my means, you know, all that? This podcast is brought to you by Squarespace. In today's digital age, having a strong online presence is just crucial.

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And whether you're an insider or not, you can still get your free Element sample pack with any drink mix purchase at drinklmnt.com slash richroll. Speaking of the modern moment, what is your sense of where we're at in terms of our relationship to justice and our facility to kind of stand up to our own convictions as a culture? on what algorithm you live in. But the algorithm I see, social justice warrior is like a slur

you would throw at someone. Like, what does that say about our society that like, that's how you would dismiss someone as being an idiot or annoying? Like of all the things you would want someone to be a warrior for, what's a better thing, right? Yeah, it's become a pejorative. And you even say to the book, like virtue signaling. I mean, that's like a better thing, right? Yeah, it's become a pejorative. And you even say to the book, like virtue signaling.

I mean, that's like a slur, right? But wouldn't you want to be signaling virtue? Like you write all these books about virtue. Like you're the ultimate virtue signaler, you know, Ryan. Like you are this, you know, laser beam, this lighthouse, like emitting this, you know, high wattage bulb of virtue, you know, to the world. And look, just because someone doesn't live up to the virtues that they're talking about, it doesn't mean that the things they're saying are incorrect. Sure.

And there's a difference between, you know, doing your best to model virtue and performative virtue for the sake of, you know, kind of extrinsic reward or the approval of strangers. Yeah. And look, I think there's also a difference between falling short and being like a disgusting hypocrite. You know, the idea of like social justice warrior is a pejorative, virtue signaling is a pejorative. And look, if you have a problem with those things, I get it. But what do you saying they should be doing? There's something weird about our society where it's very good at tearing people down as being impractical or idealistic or whatever. And what we should be doing is this. It's more like, well, here's why that doesn't actually matter. actually matter, right? Here's why this is all, and so what you're left with is kind of like a nihilism. You're left with just this kind of cynical selfishness that I don't think leads to a world that anyone wants to live in. Maybe it's not full-blown nihilism, but on some level, it's a self-centeredness. it's a self-obsession because the distinction really is,

I mean, okay, what we would call a virtue signaler used to be called a bleeding heart liberal, right? It's sort of, this is the new version of that. And fundamentally, these are people who spend their time thinking about and concerned about other people and trying to make sure that they're provided for. Yes. Whereas, you know, the opposition force to that is like, I'll worry about me, you worry about you.

And if you have a problem, you should just solve that on your own. So it's like- I'll worry about me, you worry about you and fuck those people. That's kind of some version of the, I think the dominant cultural ethos, unfortunately. And what does that say about our relation? We talked about this last time, like our relationship to liberty and our relationship to collective responsibility.

The founders were all sort of steeped in stoic philosophy. They were steeped in classical virtue, classical philosophy. And so it's important that we understand that as they laid out a society that empowered the individual and protected them from the state. They were reacting to an oppressive sort of religious structure that tried to dictate how people lived because the religions differed, people had different beliefs about different things. It's great that so many rights and choices are delegated to the individual. That's the society you want to live in.

But part and parcel of that, and certainly the fundamental assumption of the founders, the fundamental assumption of the founders was that all this freedom would be counterbalanced by personal virtue. Adams has a line about something like how we would go through it like whales through a net. That the system of government we set up was not fragile, but insufficient to handle an immoral, fundamentally self-absorbed, cruel society. And so it was these classical ideas layered on top of these innovations in how government was structured. And I think we've neglected that. I did this piece for The Economist a couple years ago where I was talking about how we have a statue of responsibility. This is a line from Viktor Frankl, but he's talking about how there's a statue of liberty in New York Harbor, but there is no corresponding statue of responsibility. And the idea that you're

free to do it, but that doesn't mean you should do it. And what kind of world would it be if everyone did what was good for them in this moment? And we're not checked by a consideration of how their actions affect other people or the commons. Liberty can't exist without a collective sense of responsibility to one another. And I think we are in a moment or we've arrived in a place where we over-index on the importance of our personal liberty at the cost of the collective responsibility

that's required to enjoy those liberties. And I think, you know, when you think about liberty, which is like a core precept of being American, right? It's protected by the judicial system and the legislative system that creates, you know, dictates and constraints around, you know, to protect our personal liberty. But we don't have that for collective responsibility. That's sort of a voluntary thing that we're just relying on people and their better nature to practice, I guess. I think I've seen this a lot in the discussion

about free speech. And I think you and I both know a lot of people sort of in this space that are very sort of like that we shouldn't be mandating these things. We shouldn't be forbidding these things. We shouldn't be punishing these people. And I agree for the most part that people should be free to say what they want. Legally, they should be free to say what they want. Does that mean that if you own a company, you should allow your platform or your product to be weaponized by people to do things that are like incredibly damaging to society? Probably not, right? Or there's a difference between a lawyer protecting somebody in court

from legal consequences for something they said and whether that person should be shunned or held accountable by their friends. So like I was thinking about this the other day. I keep hearing people go, this is free speech, right? But they don't seem to be prefacing it with, I mean, look, it's obviously wrong and horrible to say, and no one should be saying it.

But if you want to protest as a neo-Nazi, you're free to do. Do you know what I mean? Like, there's this kind of reaction to political correctness where people are going, this is free speech, this is free speech. And they're not understanding that, yeah, the whole point is there's a big difference between whether someone should legally be allowed to do something and whether that thing should be condemned or disputed or corrected. Do you know what I mean?

And these things don't exist in a vacuum. I think what's unique about this moment, though, that makes it different from decades past is that we have a new incentive structure that encourages and rewards bad behavior that agitates people because it attracts attention. Yes. And attention means dollars, right?

Yes. And so, although there are no like legal constraints on this type of behavior, it used to be that if you engaged in it, you would be embarrassed or you'd feel guilty or be shamed by your, you know, your brethren or whatever. And now it's, it's kind of encouraged and applauded. And there's been an erosion of kind of social mores and each social more that's sort of broken, everyone sees it.

And they're like, oh, I guess that's not really kind of like a rule anymore. And we don't have to feel bad about, you know, behaving badly in this way because so-and-so over here did it and look at all the attention he got. So-and-so had this person on their podcast and look how many views it got. So like, I should do it too. Instead of going, that person's a monster. No thanks, bro.

Like, again, he should be allowed to do what he's doing, but it doesn't have to do it through me. There's an expression I heard, you probably heard it in law school, where it's everyone's entitled to a lawyer, but it doesn't have to be you, you know? And I don't think I was good enough at that early in my career.

But the idea that like, there's this difference between these sort of abstract legal principles and then the decisions that you're going to make as an individual about what you're going to make as an individual about what you're going to be a party to or not. I don't think we're seeing enough people draw those lines and I don't think we're talking about drawing those lines. Look, should you be able to endorse cigarettes and appear in a cigarette commercial? Sure. Is that a thing that everyone should pat you on the back for

and no one should criticize you for? Of course not. It's a shitty thing to do that has real consequences for people. And so, you know, the decision to decide what you're personally going to be a part of and then what you're going to be a party to is important. Yeah. A very concrete example of this is something that we contend with every day, which is who are we gonna invite on the podcast, right? And to your point, like you look out there and there are certain people out there. It's like, I know if I invite that person on here,

it's gonna get a lot of attention, blah, blah, blah. But I find this person morally reprehensible. I'm not going to do that. But then it's a sliding scale. And then you're like, well, would it be okay to have that person? And then what happens, and I've seen this happen with other people,

you begin to make excuses around your own personal responsibility. It becomes, I'm just asking questions. We're having a conversation. What's the harm in that? But I feel very strongly that with this, it's not power, but when you have a platform and there's a lot of people paying attention, that that comes with a responsibility and it's just not okay to just say, well, I'm just, I'm just, I'm just asking this person questions.

I just want to understand this person. Like, I really believe that you have to, you know, basically own that and, and really decide, you know, really decide who you are and what you stand for in terms of the people you're going to engage with and the content that you're gonna publicly put out there. This is kind of a digression, but the only time I've really ever gone and done the like deep, deep library research

about like where I was doing original reporting on something, My favorite novel is Ask the Dust by John Fonte. Did I tell you this story? So he wrote this amazing history, this amazing novel about downtown Los Angeles in the early 1930s. And so he publishes this book. It's received to wide acclaim. It's sort of an incredible early book from a promising young writer. So why does it become basically lost to history until Bukowski rediscovers it like 50 years later? It's because his publisher, Stackpole and Sons, published in 1933 also a translation of hitler's mein kampf they were horrified by what hitler wrote in mein kampf and hitler was published in the u.s the official u.s translation was done by

houghton mifflin who's still a publisher today but they published like a very edited version of mein kampf like a more palatable, acceptable translation of Mein Kampf, basically with all the horrible stuff. And it's very successful. People don't understand Hitler. How does Hitler go from a failed art student, briefly imprisoned? Where does he get the money to become

a professional politician and lead this movement? It's from his book royalties. And so anyway, so Stackpole and Sons is horrified by this. They think, why should a dictator in a foreign country have publishing rights in America? They publish it. And Hitler sues them. Hitler's agents sue Stackpole and Sons in US federal court and he wins. His agents and Houghton Mifflin and Hitler win the lawsuit. And the cost of fighting the lawsuit, the urban myth was that it bankrupted the publisher. Really, it just, this huge legal fight squashes this promising young novel they're also publishing

and it's forgotten from history. And it's not until Bukowski rediscovers in the Los Angeles Public Library that this book is recognized as the classic that it becomes. It's an amazing book. It's one of my all-time favorites. But the point is is this free speech discussion about whether people should be allowed to say or do whatever they want is inseparable from uh like one argument about mein kampf was like if more people had read mein kampf

we would have known what hitler was up to and uh maybe the things would have been prevented and the irony is when houghton mifflin, they mail a copy of their edition to FDR. And FDR had read it in German already. And he writes back this letter, which I talk about in the piece that I wrote. He's like, this is morally reprehensible what you've done here. Like, this is not, these are not the same books.

You're taking the edges off this monster. In any case, yes, more people should have read Hitler. And at the same time, the platforming of Hitler is what allows Hitler to become Hitler. And so these discussions about free speech, they don't exist in a vacuum. They are morally vexing issues. Whether someone should or shouldn't be allowed to say something is very different

than whether them saying it on a social network reaches millions of people and then people make bad decisions based on this information, as we just saw during the pandemic. Or conversely, if they become so enriched by the scam or the con that they're running in what they're doing,

that they use that money for nefarious purposes, right? So I just think we have these kind of very naive discussions about these issues that seem to ignore the actual consequences for people in the real world that are affected by that thing. The worst job in the real world that are affected by that thing. The worst job in the world has to be content moderation on a social media platform.

That is a job I would not want to have. I can't imagine why someone would spend billions of dollars to acquire a social network. It sounds like a nightmare. It is. I mean, and so many smart people have written about what a vexing problem it is and how basically even the best sites are doing a bad job. And even despite their best efforts, it's sort of this imperfect science. wrestle, like our reluctance to think about the downstream consequences of the choices we're

making or our businesses making or our brand is making. To go back to slavery in the British Empire, it's interesting. Slavery was illegal in Britain, but not in the empire. So it was this really convenient way for British people to literally never see the horrible thing that their incredibly prosperous society was based on, right? And so we all have this tendency, and I'm not excusing myself here, we all have this tendency to just put things just out of sight so we don't have to think about them

and then wrestle with them and then make the expensive or painful decisions that they create an imperative for. When you think about justice and how we're conceptualizing it in this and practicing it in this moment, I can't help but think about, you talked about how we all have our own kind of bespoke information silos driven by these algorithms. You know, this results frequently in people, you know, pursuing justice, but pursuing justice under the delusion of a bad idea or some insane conspiracy theory. Like every man is right from his own perspective. Yes. And there are people who are like, I am doing what Ryan is telling me to do,

right? But they're chasing a misconstrual of reality in some way. And I can't help but despair a little bit about where we're headed with this because to their mind, they are behaving with moral rectitude. Yeah. Yeah. I'm thinking a lot about this for the wisdom book. I'm doing a chapter on our timeless tendency to fall prey to demagogues and scams and cons and fanciful self-serving thinking. And so this is where these virtues are so inseparable because your protest, if incorrect, it doesn't matter. Like there were obviously in the Civil War, people who thought they were defending themselves from invasion. This was obviously preposterous

and they couldn't have been defending a worse, more morally unjustifiable cause. But it is interesting how Southern society was set up to perpetuate and suppress the information that would have allowed people to see things differently. Do you know what I mean? Like, there was a reason slaves weren't allowed to be taught to read. It wasn't just that they would become smart and escape. It's that then if you kept people stupid, then you didn't have to see them as human beings. Anti-slavery activists were lynched or driven out of the South. Their newspapers were burned down. There was this whole, you want to talk about like a snowflake culture. There was this whole, you want to talk about like a snowflake culture.

There was this culture designed not just to prevent people in the South from thinking that slavery was bad, but designed to teach them from cradle to grave that slavery was a positive good and that every other society was either participating in the same thing or that the abuses and life of black people in the North was so much worse. And so, yeah, the ability to think for yourself. You have to think for yourself and you do need to do your own research.

And yet that is an imperiled pursuit now as well. Yeah, to actually understand things. There's a definition that wisdom is knowing what's what, right? Like wisdom is like actually seeing things as they are. And that's such an important part of justice. There's a story I tell in the book where Theodore Roosevelt's being asked to vote on this bill. There are protections for the cigar making industry. And he's sort of a laissez-faire capitalist. His father had been, his family came from this long line of industrialists. industrialists. And so his inclination was, well, what does my party think about this thing? That's what I'm going to go with. And this activist, Jacob Rees, says, why don't you come actually look

at where they make these things? And he goes down there to his credit. He had the curiosity to do it. And what he sees scars him for the rest of his life. And that's something Jacob Priest said. He said, he's the guy who wrote the famous book, How the Other Half Lives. He says, when you figure out how the other half lives, you are faced with the most essential question of your life, which is what are you gonna do about it? I think we at some level know

that if we discovered this or saw this or knew more about this, we would have to do some things we don't wanna do. And so the ability to get out of your bubble and go see the thing for yourself is such a powerful, powerful thing. Sure, we all would like to believe that, if we were in 1934 Germany or in the, that we would have made the right choice,

right? But we would have acted, you know, in accordance with the circumstances of the day, most likely without, you know, an extreme amount of courage and wisdom and all of the things that you're talking about, right? So with that, like, what is the version of that that exists right now that's right under our noses where there are people who are speaking out against a certain injustice who are not being welcomed as heroes but are instead being maligned as pariahs? Yes. Yeah, I mean, I'm thinking about this. What's the climate movement that's like defacing all these monuments? Their cause is almost certainly correct. The methodology by which they're going about it,

you could start to have a discussion about it. The suffragettes would break windows and destroy things. So I guess the jury's out. But what we know from studying the past is that the vast majority of people were okay with a thing that seems incomprehensibly evil to us today. And so I think first of just the open-mindedness that just because something's okay now doesn't mean it's actually okay. And you probably just don't know enough about it. But I mean, obviously, you're one of the sort of leaders in this space.

You talk a lot about it. At some level, unless there's something profoundly wrong with you, you know that our food system is a moral abomination. Sure, I mean, I'm leading you to water here, right? You know, it's like the elephant in the room, like the sort of glaring injustice is that of factory farming.

It's just perpetrating, you know, unspeakable harm and suffering right under our noses. And it's shrouded with a lack of transparency and all these things that you've talked about. It's like illegal to film inside one for a reason. Yeah, you can't even go in. So you can't inspect the cigar factory because they won't let you in. And those that break in and create these videos and share them, you know, are like crucified for doing it and

prosecuted also. There are laws to prevent this and those laws exist for a reason, which is to maintain the status quo and keep those in power, you know, remaining in power. But I have to believe that in, I don't know how long it'll take, 50 or 100 years, we're going to look back on this systemic way in which we, you know, provide food for humans as being just utterly inhumane and reprehensible in so many ways. Yes. And I think I always try to catch myself when I am being deliberately ignorant of something. We all know the videos exist and there's a reason we don't watch the videos. It's because one, we know they're gonna be deeply disturbing and then it's gonna make it hard

for things to go back to normal. Yeah, it's confronting because it's asking you to measure up your behavior and your agency with a level of willingness to take action on that. And nobody really likes to have that internal conversation with themselves. It's easy to just go about your way, especially when no one's asking you

to do anything either, right? But I think the reason that we don't like looking at those is because inherently, fundamentally, we are all compassionate people and we don't like seeing that. And we don't like the fact that we're participating in it. It doesn't sit well with us because we know that creates dissonance with our own virtues and our own set of ethics. And so

if we dismiss these people or call them crazy or shut the laptop down and refuse to look at it, it's just an easier way to not have to really think about that too much. And it's even easier because of these laws that, you know, shroud it in mystery and inhibit our ability to have a transparent arm's length understanding of what's actually going on. And this is what's so fascinating about Thomas Clarkson's campaign against the slave trade is like, I'm sure you've seen that famous graphic, like of a slave ship. It's this detailed schematics of an 18th century slave ship and where all the slaves went. It's all labeled.

I saw it in a history book when I was a kid. He commissioned that drawing. People didn't know. And they would listen to the propaganda or the lies of the people coming back to some port in Birmingham or whatever going, oh, it's all fine. You know, the horrors of what was happening was obscured. And Clarkson really figured out a way, not just to detail that very effectively, but so on the one hand, he's showing like, here's how it's operating on these people. And he creates probably the first political, I don't want to call it a cartoon, but like sort of like an advertisement. He has this famous image of a black man and over it says,

am I not a man and a brother? He humanizes slaves. Like he's asking this question that people were not asking then, like, is this person with different hair and skin, a human being like you? and skin a human being like you. But he also does, like, he publishes the math on the crews of the slave ships, right? Something like 20% of the crew members on slave ships wouldn't return, they would die. So he's showing like, oh, it's not just bad for these people that you don't really care about, it's bad for the people you do, it's bad for your sons and husbands. And so he was really effective at sort of understanding that different people are going to be persuaded by different things. Some people see the horror of something and they get it.

Other people, I think this is where the sort of food activists have like, some people are going to be persuaded by the climate impact. Some people are going to be persuaded by the sheer horror of the video. Some people are going to be persuaded by the climate impact. Some people are going to be persuaded by the sheer horror of the video. Some people are going to be persuaded by the health arguments, the ability and willingness to weave all these different arguments there and to nudge people a little bit here, a little bit there is ultimately what gets public opinion to go from 100% in one direction to sufficient in another direction to bring about legislative change. Sure, in the food industry context that you just shared,

there's of course, the sort of animal rights, suffering, compassion avenue or on-ramp into that. There's the climate impact of our food system. There is the health considerations, maybe not so great to eat this stuff that shot up with hormones and was treated horribly. And then there's also a human rights aspect to it, which is like, this isn't great for the people that are working in these places.

And then also the people in the surrounding areas, when they're just spraying all kinds of chemicals and refuse everywhere, it's just, you know, it's causing health problems and it's degrading, you know, the environment. There's like the point being like, there are all these different aspects to issues like this that are interesting to different people for different reasons. And there is of course, a variety of ways

to be an activist around this or to communicate these ideas. So while one person might respond to somebody throwing fake blood on a fur coat or, you know, spray painting the Mona Lisa, more people might be sort of motivated by, you know, someone who can appeal to, you know, what it is that's meaningful to them that gets them interested

in thinking differently about that. And I think you need all those forms of activism to create that kind of systemic shift. And each and every one in their different ways of communicating kind of contribute to a greater whole, like a congealing of an idea that then has enough resonance to actually produce change.

Well, I actually even think about this in stoicism, right? So people tend to come to stoicism because they're going through something personally difficult, right? They got a cancer diagnosis or they got fired. They're going through a divorce. They're having some tough thing in their life. And so they tend to come to stoicism for the sort of personal side of things. As did you.

Of course. And yet once you get into the universe of it, there's these other things that it can start to be appealing and attractive to you. So the core exercise in stoicism, which again, I'd probably been reading and writing about it for a decade before I even knew about this. There's this stoic named Hierocles, who's a sort of a middle era stoic. And he had this, he says, we're born self-interested, like as babies, we're just fundamentally selfish. All we're after is what can we get? And then, you know, we start to care about our parents and we start to care about our family, our extended family. It's these sort of series of circles

that get bigger and bigger and bigger. And the goal of philosophy, he said it was this beautiful madness of pulling the outer rings inward, that that was the work of philosophy. And it's funny, I was talking to Peter Singer and I told him this and he was like, you know, I wrote a book called

The Expanding Circle, right? And he's like, and I didn't even know about this idea from the Stoics because we don't think of Stoicism as an ethical philosophy. We think about it so much more as a sort of a personal set of tools, like a way to survive the blows of fate as opposed to sort of a personal set of tools, like a way to survive the blows of fate

as opposed to sort of a recipe for a meaningful, significant life. But this was a big part of it too. This idea of like, hey, no, I'm a citizen of the world. I have this obligation to other people. I can't control most of what's happening, but the more I can try to exert positive, you know, feelings outwards and then pulling actions inwards, that that's like this journey

that we're on. But if you start there, I mean, one of the laws in the 48 laws of power, which I think about all the time is never appeal to mercy or gratitude, always appeal to self-interest. never appeal to mercy or gratitude, always appeal to self-interest. And so much of what activists try to do or people who really care about a cause is they just try to shame people into caring as opposed to pulling these other levers that can get people closer.

I tell the story in the book of Harvey Milk. Harvey Milk gets his start as a politician by basically favor trading with the Teamsters Union. They are trying to boycott these beer companies to get a new union contract. And Harvey Milk is the most connected guy in the Castro. And he offers to help them make inroads with the gay bars. And he says, I'll do it if you hire some gay drivers in your union. And that starting there, and it was the relationship between him and these, you know, 1950s, 1960s teamster, California teamsters that begin this whole movement and collaboration.

But like these people had never had an interaction or a connection prior to this thing they managed to come together on. Yeah, there's a practicality to it. It takes it out of idealism and into action by appealing to self-interest. Yes. And that self-interest is motivated by a certain idealism as its goal, but it's rooted in like reality and how you actually get things done. Yes. Right. And so I think there's, yeah, I think there's plenty of lessons in that. But the thought that I had as you were sharing that is a broader kind of a more meta thought on your writing and perhaps your relationship with stoicism as a whole, because as you mentioned,

you originally got interested in it for selfish reasons. It gave you a sense of connection with something more meaningful that was very practical and can kind of direct your life in a moment in your life when you needed it. A sense of maybe not identity, but a belonging to something. But it is a very kind of inward looking thing, right? And I think it is attractive for a lot of people, you say in your afterword also, like particularly young men, right? As this sort of guidebook to help them make sense of their life. But like anything,

the more that you steep yourself in it, it starts to become something else, right? And what I'm seeing in the evolution of your writing, subtly a little bit, but perhaps most directly in this book is a real shift from that inward approach to how these principles and this philosophy can improve your life into the more important aspect of it,

which is how it can improve the lives of others. Yeah. And so, it's like this gradual kind of evolution that I see you going on. And even, especially in the latter parts, like the later chapters of the book, it becomes like you're softening at the edges, dude, big time, and I wanna talk about this.

But it really does become about like, look, don't just think about yourself. Like this is really a roadmap as much for self-improvement as it is for the improvement of others. And that is something to be not only considered, but like respected as like the core of what this philosophy is really all about. Yeah. And look, I don't think some of those self-improvement people, whether they're talking about Jordan Peterson on one end or Admiral McRaven on another, yeah, make your bed, like start, get your shit in order,

get your house in order. That's of course where you have to start. But if that's where you stop, or if all you're thinking about is this endless self-improvement, self-optimization, I think it's kind of empty. Like stoicism shouldn't be this recipe for being like the best sociopath that you can be. You know, that strikes me as very sad. Yeah, or like the manual for the that you can be. You know, that strikes me as very sad.

Yeah. Or like the manual for the assassin CEO, right? I don't know if it's been used that way, but it's certainly, there's a certain narrative around it that's been kind of perpetrated out there. Stoicism isn't there to help you crush your enemies more efficiently

and not have to feel bad about it while you're doing it. Because you're this emotionless stoic, right? Exactly. Getting rid of these pesky feelings of empathy or understanding or connection. Ironically, like we have these stories of Marcus Aurelius crying, weeping, feeling sad, loving other people.

What we don't have is stories of him like losing his temper, right? So when he was talking about mastering his emotions, that's what he was talking about. He was talking about not getting angry at strangers. He wasn't talking about feeling nothing towards them, right? It's about getting rid of the destructive emotions, the emotions that wear at you, that are bad for the engine.

He says he learns from this philosopher named Sextus, who may have been Plutarch's grandson. He says, I learned from Sextus to be free of passions, like free of emotions, but full of love. Like the idea was getting rid of jealousy and anger and fear and anxiety and entitlement and, you know, these other forces and to be driven by something deeper and more profound and more meaningful. We're brought to you today by On. Being a gearhead, I'm all about testing the latest sports tech. But you know what often gets overlooked? Apparel. Apparel is crucial to performance, and that's why I was blown away by the folks at ON's Swiss Labs. Their cutting-edge approach from sustainability to precision testing for performance enhancement is next level.

It is truly Swiss innovation at its best. Visit on.com slash richroll and use code RICHROLL10 at checkout to get 10% off your first purchase. This show is sponsored by BetterHelp. Do you remember when you were a kid and learning was nothing but joy? We had this sense of wonder. Why do we lose that as we get older, as we become adults? When you think about it, learning should be something that is joyful, that inspires awe and wonder. that is joyful, that inspires awe and wonder. Because in truth, learning a new language or honing your cooking skills

or, I don't know, beating a friend at chess, these are fun things. And they shouldn't be reserved for the joy that we experience as kids. It's back to school season. But again, this also isn't something that's just for kids. We can all go back to school anytime. And sometimes we need a little bit of help to reconnect with that curious inner child.

And let me tell you, that is where therapy comes in. Because therapy isn't just for major crises. It's this really powerful tool for growth, helping us to rediscover those passions and overcome barriers. Therapy is about learning coping skills. Thank you. no problem, no extra charge. Rediscover your curiosity with BetterHelp. Visit betterhelp.com slash richroll today to get 10% off your first month. That's betterhelp, H-E-L-P dot com slash richroll. The issue that I've always had with stoicism the struggle that i've had is that it seems to be one of kind of practiced self-circumscription like how do you how do you

hold yourself back from your inner demons and you know kind of keep them compartmentalized in at bay so that you can behave and show up as your best self. And obviously there's great practicality in that, but at the same time, I've often like found myself like thinking, where's the soul in all of this? Like what is the kind of deeper connection with something bigger, you know, within this kind of world of stoicism? And to be honest, I've sort of found it somewhat lacking. Like where is the appreciation of awe and wonder? And when we, I've been thinking a lot about like happiness and love, I just got back from traveling to India

to see the Dalai Lama with Arthur Brooks. And the Dalai Lama will tell you that our purpose is to be happy. And Arthur Brooks will say that happiness is love and that love is a decision. But Arthur will also say that happiness demands a relationship with the transcendent. And I think the reason I find stoicism somewhat cold

is that I feel like it's missing that appreciation or prioritization of having a relationship with something, you can call it transcendent, you can use whatever word you want. Essentially, it's a word that means the ability to see outside yourself and a humility to embrace the fact that we might not be able to know all the answers and that maybe something else is going on here.

And I think stoicism does answer those questions in practical context, but I think it's missing that kind of faith piece that I'm yearning for. And I know you just talked to Pete Holmes, right? I'm sure he probably wanted to talk to you about this as well. I think it's in there. I think it's in there.

I know. And here's the point that I wanted to make. I said you were softening around the edges. Like in the final kind of couple chapters of the book, you're talking about Gandhi and you did something I've never really seen you do before, which is like, you're actually talking about love and you're talking about how, you know, kindness is really the underpinning of all of this. And you're sort of flirting with these ideas for maybe the first time. I know you talked about Buddhism and some other kind of faith traditions in the Stillness book,

but this felt a little bit new and within it, an appreciation for like oneness. Like you're talking about how we aren't separate. We all share this. I'm sure this is gonna dovetail into temperance. Like how do we treat others? How do we treat the planet? All of these sorts of things.

And I guess I've just never seen you kind of grapple with those larger ideas. I haven't had as much space in the books. The previous two books were about very specific things, right? How to overcome obstacles, how to beat back your ego, etc. And so there wasn't, I think, as much room to explore these ideas. But to me, they all fit very clearly under the virtue of justice. But it's interesting to think like, we only know some of what the Stoicsics said because only some of it

survives to us they're doing this cool thing so it pompeii there were these libraries people had libraries of all these ancient texts in their houses in pompeii and then this volcano comes and it flash freezes them right and so we can see like these rolled up scrolls that we know contain lost philosophical works. They can now scan them. They can like shoot x-rays in them and see what's inside. And they're now running this contest. You can, they're feeding them

through these massive AI computers and they're able to decode some of what's in there. And they've already gotten one that they can tell is an Epicurean text and they have like one sentence from this thing already. So like we could wake up a year from now, 20 years from now, and you could be pretty embarrassed because the Stoics apparently are speaking all about this. I don't know. What does your intuition tell you about what might be discovered? I think there is going to be so much more, the Stoics are going to come off as so much more well-rounded than we thought they were.

Because what meditations is, it's this incredible work of literature, you have the most powerful man in the world, notes to himself about what he's specifically struggling with in that moment. So it's a lot about his temper. It's a lot about his fear of death. But there is also, you know, he talks about, he says, your soul rejoicing in perfect stillness. So he thinks he has a soul. He's talking about it. He's talking about his connection to other people. He's talking about how history is the same thing happening over and over again, and that we're all

part of this continual tradition. I think it's there. I think the oneness is there, the connectedness is there, the love is there. It's just not as specific and spreadable and immediately understandable as, hey, when you wake up tomorrow, remember that people are obnoxious and annoying and what he opens meditations with. But that passage itself, which is sort of book two, passage one,

Mark says, you know, when you wake up in the morning, people are gonna be annoying and stupid and strange and mischievous, he lists all the things. And like, that's always struck people as this like encapsulation of stoicism because it's like prepare in advance,

grit your teeth, don't get angry about it. And that's part one of that message. But the next sentence is, and he says, and why are people like this? And he says, it's because they don't know any better. And he said, these people are your brothers. You are made to work together. He says, you share like a body and a blood with each other. And that to write them off is to go about this the wrong way. You were meant to be here together. And he says, the important thing is that you don't let them implicate you in their ugliness. So we see that as this ugly passage.

And really the whole point, he's writing something that he knows is nasty and saying don't let this nasty fact of reality make you a nasty person and so there on the surface level there is this kind of detachment and disassociation with stoicism but why what are they doing they're trying not to be sucked in to the evil and darkness and violence of what it must have been. Like, imagine you live in a society where anytime you can just walk into this big giant auditorium and watch them like rip slaves to shreds or slaughter an elephant in front of you, it would have been like horrendously violent and awful. People died of diseases and starvation. And so what I actually think Mark Cerullo is doing in meditations is trying to protect some of those beliefs and the innate things you're talking about,

oneness and love, compassion and happiness from just this oppressive, like nastiness that must have been ever present. I get that. But when you're on the receiving end of so much nastiness and awfulness and oppressiveness and evil, like what is that doing to you inside? And what are the kind of traumas that you're experiencing and the demons that are festering as a result.

And this is a time before there was any understanding of mental health, right? So what are we gonna do? Let's compartmentalize it. We're gonna push it down there and just make sure you behave this way and don't let those things dictate your behaviors. And I think now we're in a place where we understand

like maybe not the best strategy, perhaps it might be good to talk to somebody about what's going on. And I think, I guess what I'm getting at is, you know, is there no appreciation or room for the power of like vulnerability, right? I think so. I mean, one of the things I find myself recommending from the Stoics the most is these three essays that Seneca wrote. And it was a common situation then, it's a common situation now. Someone he knows is deep in grief.

In one case, it's a daughter of someone he knew. In another case, it's his own mother who is grieving her son who's just been sent into exile. He writes these, the literary form then was known as a consolation. And he writes this beautiful moving essay that is not saying your emotions are invalid, shove them down, pretend they don't exist, don't be a little bitch.

He's not saying that. What he's trying to do is walk them through the grieving process as best he understood it. He's saying, look, you're not going to fool your mind out of feeling this way. You've got a process. You've got to think through it and make your way through it. And there are these essays that hold up incredibly well because that human experience is so fundamentally timeless. I love them. I read them every time I lose someone. And here you have a thoughtful, considerate, compassionate stoic helping someone with what they're going through.

So again, this idea of the stoics being like hard asses about everything, it's not true. One of the stories we have with Marcus Aurelius weeping is like over the loss of this tutor that he has, his favorite teacher. And some other philosopher supposedly comes up to him and, you know, tries to say, hey, you shouldn't do that. And Antoninus, his stepfather, is this wonderful man, says, you know, let the boy be human for once. And so there is whatever the writings of the Stokes, there is a push and pull in the reality of them. And I think they were like us. They had good days and bad days. They were overcome by things. They tried to process them. They probably understood at some level that just stuffing your feelings in a closet makes they explode outwards on you one day. So I don't know, maybe I'm projecting, but the more I

read the Stokes, the more I find those sort of deeper, more meaningful themes in them. They're just not what you're looking for at first, because what you're looking for is how can I stop getting distracted or whatever? You know, we're looking for these really practical things, which philosophy doesn't help us enough with. So the Stoics are really unique in that regard, but they also have, I think, a wonderful set of tools for just like being a good and thriving person. Is there any aspect of Stoicism that has failed you

or to which you've turned for counsel and it has like let you down or led you astray? Well, you know, I don't rely much on the Stoic physics. There's a whole bunch of things. I'm talking about your personal decision-making and how you're relating to your life. Yeah, look, the stoics don't have that much great parenting advice.

They don't get too specific about that. They don't talk about women too well. There's like whole aspects of it, I think that we can, we were saying earlier that like, we should understand, you know, nonviolence was an invention. And so was the consumer boycott,

which Thomas Clarkson pioneers in the anti-slavery movement. Like understanding the effects of trauma, understanding how the brain works, understanding even like nutrition. These are all like inventions that did not exist. And I think we're seeing legally in the United States, the abysmal preposterousness of like originalism as a legal doctrine. I'm not an originalist when it comes to the Stoics either. Like, what did they say about these things?

Like, let's take that and then let's give them the benefit of the doubt that had they known about these other things, they would have incorporated the ideas into their philosophy. That's something that hit me somewhat recently, kind of a mind-blowing realization that Stoicism was ancient philosophy

to Marcus Aurelius too. Zeno founds it around the 4th century BC. Marcus Aurelius is writing meditations in 160 AD. It's older than Shakespeare is to us. Like this is a multi-century evolution just between Zeno and Marcus Aurelius, the A to Z of it. The idea that we should have just stopped, you know, in the next 18 centuries, I mean, that seems silly to me. How are you shouldering this responsibility that you've

taken on to be this steward of stoicism for the modern age. Like I'm thinking about an experience we had last year where we both found ourselves in Arnold Schwarzenegger's office at the same time. You were back in the Austrian room doing a podcast with him and I was waiting for him to finish so I could do it. And then in between, we kind of all met in the middle and he's, you know, you're holding the Conan sword and like where he's telling us about all, it was like the crate. It's like, that was a wild experience, right?

Unbelievable. But I'm sure most meaningful for you is when you talk to him about the fact that like Meditations is the book that's on his bedstand, right? Or he has like- No, is it Daily Stoic? Oh, is it a Daily Stoic? He reads Daily Stoic every day.'s on his bed stand, right? Or he has like- No, is it Daily Stoic? Oh, is it Daily Stoic? He reads Daily Stoic every day.

He had it there too, right? Did he have it there? I think so. It was strange and surreal and certainly not what I expected. I was thinking about this the other day. Like if people ask me like, did you have any idea that this is how it would go?

And I realized like, if I had, I don't think I should have been allowed to write a book called Ego is the Enemy. Like, because it would have been delusional. It would have been totally delusional. I was just really interested in this thing. And I thought I would write a book about it. And I thought, I mean, I didn't think it would do badly, but I certainly didn't anticipate any of this. And it should be said that you were at the time, the guy who was writing about marketing and that's what your publisher wanted you to write about. So then you're like, I want to write about stoicism. They were like, let's back up the Brinks

truck. Nobody thought it would do well. I'm doing the 10 year anniversary of Obstacle right now. And the idea that it would still be selling 10 years later seems insane, that it would sell what it sold is insane. The idea that people would be talking about stoic philosophy at the level they are, like it's unreal. And it's strange because like I am associated with it, but I know I didn't invent it. So like people credit me with things that are not mine. And I have to for my own sanity and just to not spin off the planet, I have to constantly remind myself that it is a reflection of a 2000 year old philosophy. That's why it's working. And it has very little to do with me because if you take credit for stuff, it fucks with your head, you know?

And I have this very common occurrence where people will be like, you know, I was on death's door and someone gave me the book or like people tell me these incredibly heavy things that the books have helped them through. And I mean, obviously when I was writing them, I didn't think I was wrong, but the idea that I would be so presumptuous as to think I could tell anyone who's going through something that I

can't even conceive of going through, you know, going through. So it's a kind of a strange thing that I try. I try not to think anything about except in so far as any kind of success confers a responsibility and an obligation to not make it about you, to not fuck it up, to not fuck it up and to try to use it to do good as you see it. Which means you then have to turn to it itself in order to help guide you through the stewarding of it, right? Because I imagine you get some pretty crazy phone calls too from CEOs and NFL coaches. And like, I mean, I don't even know like who's calling you,

but I know that, you know, probably some pretty interesting people are calling you. What are those phone calls like? What is the, you know, typical question that they're asking you? And like, what is the guidance that you're giving them? Well, I think we both know some people who have sort of been gurufied,

like the success or influence or the questions have kind of pickled their brain. It's funny because Marx really is in meditations. He has this great expression. He says, try not to be Caesar-ified or dyed purple. The emperor wears this purple cloak. He's saying like, don't be changed by what's happening. And so there has been this element.

Translation, you know, don't be a victim of audience capture. Yes. Basically what he's saying. Or don't let success, material reward power, chain, you know, inflate the ego,

make you think you're superior, make you think the rules don't apply to you, make you, you know, inconsiderate or whatever. And so having to think about that on a much smaller scale is sort of giving me an insight of why he's writing. Like meditations is the process by which he's trying not to lose his mind amidst opulence and stress and success and disorientation. And yeah, there's been some very surreal moments. I spoke at the NFL owners meeting

like right before the pandemic. That was strange to say the least. We were like, I am addressing not just like 30 billionaires, but people who employed tens of thousands of people across countless industries. They own city blocks. And then how do you, you know, how do you use this opportunity? I've done the last four years, I've been doing this standing series of lectures at the Naval Academy. So you're talking to these men and women who are going to go on to be admirals and fighter pilots,

and in some cases, like senators and congressmen and women or presidents. And you go, okay, are you going to tell these people, are you just going to talk about the discipline side of stoicism or the courage side of stoicism? Are you going to try to get in some of these other things? Are you going to try to plant in some of these other things? Are you gonna try to plant the seeds that might take a long time as they even did with me to bear the sort of more ethical fruit of the philosophy? How are you gonna do that?

I think about that with the daily stoic email, which goes out every day. It's like, okay, I know if I just talk about these things, it'll grow at this rate. I talk about these other things, it'll not just not grow, it'll get smaller. And the tension between not blowing up the audience because who does that serve?

But then also not just giving the audience what it thinks it wants over and over and over again is this tension you have to wrestle with. But that forces you to confront your own relationship with the virtues and your personal ethics. Like what is right? Do I have the courage to say the thing that I believe in when I know it's going to land with a thud or it's going to be unpopular or ruffle some feathers of the people that follow you and are looking to you for guidance? And also, I think as an artist, you wrestle with this.

It doesn't matter what size your audience is. There's always this tension between what's creatively interesting to you and what will do the best commercially. And as an artist, you can build the muscle of like, I follow my interests, or you can build the muscle and the skill of like, I follow the commercial interests. And, you know, probably best served at some overlapping Venn diagram of the two, but that's not a thing that you just automatically do. But as a artist and as a person, do you think that you'll reach a day where you're like,

I've said everything there is to say, like, I'm so tired of talking about stoicism. I wanna talk about Bitcoin or, you know, like what, you know. I definitely don't. I would not be honoring myself if I didn't, you know what I mean? Like how much can there be said? Do you feel like you can continue to do this?

I just know for myself, like, like for example, if all I was doing was talking about endurance training and like a plant-based diet, I would go insane. Like I couldn't do it, you know. Speaking of those scrolls, there was an early Stoic named Chrysippus who supposedly wrote 700 books, none of which survived. So that's a pretty high number. I'm not really close there. So if this AI starts to decipher all of these texts, you're good.

You have a lifetime. No, no, I'm saying he wrote, he didn't get bored of it after 700 books. So, you know, like 15 is probably good. The Stoics talk about this idea of like, you never step in the same river twice and that you are changing and it is changing. And as unchanging as a, you know,

2000 year old philosophy is, who I am in relation to it it is changing. And as unchanging as a 2,000-year-old philosophy is, who I am in relation to it is constantly changing. And the world that we're living in is constantly changing and helping me understand these other things. So as it stands, I don't feel bored by it. But if someday I come to the end of that creative road, I think ethically, you have to admit you came to the end of the road. You don't just continue grinding it out. I could probably just turn the Daily Stoke email on repeat and it would take another eight years for anyone to notice that it started over again.

But I don't feel that right now. It remains very stimulating to me. And I take on different projects that challenge me in different ways. So right now, I don't feel bored. Right, like you wrote the conspiracy book kind of in the midst of all of this. Yeah.

And that's certainly something that, like when you've completed this virtue series, do you see a book that's a little bit different? To kind of like, you know, reset the palette a little bit. Yeah, or just something stylistically that's different like even okay obstacles away ego's enemy so this is a key similar in size and style in some ways to this for virtue series but the fact that one is a series and the other isn't was creatively a huge challenge that I've been wrestling with for five years. So I think you wanna pick your challenges

inside of what you're doing also. So even if you're doing it the same way, it's like you think about someone who's trained in martial arts for many years, like it's the same cycle of lessons, but they go every day and they try to find something else to be challenged with. And I think every day and they try to find something else to be challenged with. And I think every day you

get older. So you, you're who you are in relation to these ideas. It's so different than who I was at 19 reading meditations in my college apartment. What is the biggest challenge that you have or what is the stoic idea that you struggle the most to master? Well, I talk about the virtue of discipline, which is a core stoic virtue, but the other word they use for it is temperance or moderation or balance. And I think anyone that's becomes successful at something, a performer at something, is by definition a bit compulsive about it, right? And so I think I struggle with not a deficiency of discipline or drive or willpower, but probably a surplus of it. And so I think, you know, who I was 15 years ago and who I am today,

I'm much more balanced. So it's like, on the one today, I'm much more balanced. So it's like on the one hand, I'm much more balanced. Could I honestly describe myself as balanced? No, those are very different things. So I think I'm making progress, but I struggle with what I write about and who I am as a writer, professional doing the thing. these things are somewhat in tension with each other by definition. It's like, I, the person am attempting to be stoic. I write about stoicism, but the profession is itself not.

And how do you smooth that out? Yeah. I appreciated the honesty around how that surplus of discipline that you have, like you were frank in the afterward about your awareness of how that impacts other people, right? Like this realization, like everybody wants discipline, everybody's chasing it.

I too, like this is not my problem, but the problem is that that discipline then isolates you from the people you care about because you have this goal and you're in pursuit of it and other important buckets of your life get less care and attention. When you think about like, if you see an athlete

who can do these incredible things in the field and you hear about their training rituals and their routine and however, like, unless they're like a lone wolf, which we very rarely are, other people's lives are orienting or orbiting around this, you know, planetary sort of force. And as my wife pointed out, you know, we were talking about something and I was talking about how sort of, how hard it is for me, you know? Like, I'm like, you know, this isn't like fun. It's like exhausting and it's hard work

and, you know, whether you're traveling to media or you're grinding yourself down on a book and she was saying like, sure, but you get like also the rewards of it, you know? And she was saying like, sure, but you get like also the rewards of it, you know? And she was saying like, it's also hard and disruptive for us, but it's like not our dream. Like we're supportive of you because we're supportive of you, but we're not all in this together in that way. And that was like an interesting way for me to think about it that I hadn't conceived.

It hadn't been fully part of my consideration that like, and like the irony is, I'm also not that interested in the rewards, right? Like that's not what's getting me out of bed. It's more the process of it

that's rewarding. But the process is also taxing and disruptive and exhausting. You're not the only one who's paying that tax. Yeah. Yeah, yeah. Yeah, yeah, I mean, yeah, it's like, hey, this is everything that's pivoting around this,

but like you're the one that gets to go on the court and play. Well, the good news is now you get to write the book about temperance and you get to learn about yourself in the process, Ryan. Is that the next one? Is that the one you're doing now? Temperance is the discipline one.

Oh, it is. So I did that. Oh, okay. So the next one is wisdom. All right, wisdom. But like the- I read that book. What? I read that book.

It all bleeds together, Ryan. Thanks. Wisdom is the next one. When I was in New York, this is actually a similar insight. So I was in New York to do all the press. I was there for like a week. And my wife and I were on the phone and she said, you know, do you think if I wrote a book,

like I would go to New York for a week and you would, you know, just take care of all this stuff. And I was like, of course, you know, of course I would. And then I was like, but I have to be honest. I think after 16 times, I would be like enough, this is enough, you know? And then realizing like, okay, yeah, because I'm always lost in the thing, the cumulative toll of it is less apparent to me. And that's one of the things I was wrestling with at the back of the book is just going like, what is it, you know, what is it like to live with me? I don't know if I would like, I don't, people go, is your wife a writer? And I go, I wouldn't want to live with one. It sounds horrible. You know, I think we can always do better thinking about how, who we are and what we're going through, the consequence that has on

other people. Sure. Sam used to put these Instagram posts up though, about like the real Ryan, like, here's the Ryan you think he is. And like, let me tell you about who he really is. I haven't seen any of those in a while, but you know, maybe it's time to resurface that. I don't think they were all bad. No, they were all fun, you know? Anyway, I made two sojourns, pilgrimages out to Bastrop

to the Painted Porch Bookshop. The first of which was great because you hosted my dad to talk about Harry Truman and his book that just came out, Ascent to Power. And that was so, like, it was a meaningful experience. It was very cool to like sit in the back room and kind of watch it on the screen. And I was like, wow, is my dad talking to Ryan about that?

I would not have guessed that your dad would, that Rich Roll's dad would end up in the acknowledgements of one of my books. I noticed that. But he gave me very nice notes on the trip. I was like, you know what? He had just asked me to do a blurb and I was like, I don't need a blurb, but will you just like tell me

that I didn't get like way off base on this trip? And he gave me some very good notes. I forget what they were, but he was like, I don't know about this. And he made me tighten some stuff up. That's cool. Yeah. He's very, speaking he was like, I don't know about this. And he made me tighten some stuff up. That's cool. Yeah. He's very, speaking of old school,

like he's the guy who like goes to the presidential libraries and holds up for days at a time. And it's like going deep into the archives and uncovering letters and old stuff that nobody's ever read or cited before. I know, I'm very indebted to those people because my books are based on a lot of that research and I've only done it a couple of times,

but the painstakingness and attention to detail you would have to have to read through hundreds of documents to find one line you would use in a book, that's not in my personality. I know, he loves it though. Yeah, that's probably the lawyer in him. Yeah, for sure. What was interesting though was the intersection

between the two of you, because he's approaching it from a pure historical perspective and you're approaching Truman, who plays a big part in this new book through the lens of how stoicism impacted his decision-making and the way he comported himself. And that was sort of news to my dad, despite all of his research, he was seemingly unaware of this aspect of Truman. Well, I'll get to that, but I had this interesting

experience. I was talking to this, she's sort of my bonus grandmother, not technically related, but she's 94. And she had read the book and she was talking to me about the Truman chapter. And I was like, it's weird to me that Truman's not a historical figure to you. He's a person you remember as a politician when you were about my age. You know, that blew my mind. She was like, I just remember him as being kind of not that interesting. And like, she was interacting with him in the way that I would interact with the current president. Right. Not as a historical figure, a thing set in stone, but just like a person you're hearing about on an ongoing basis. But speaking of going into those libraries, there is,

there's this great biography of Truman called Plain Speaking. Sort of like this, there's this reporter named Merle Miller who did like this hundreds of hours of television interviews with Truman for a special that nobody ended up wanting. And so he turned it into this kind of oral history book. So it's a very unusual presidential biographer. And in it, they're at like either the presidential library or they're somewhere. And Truman goes and gets his copy of Marcus Aurelius' Meditations from

the other room. And he shows it to Merle Miller. And this is the only other mention. I've asked around. No one seems to know where this book is but at one point the he probably got it from a you know a subscription book service or something you know 1911 it's his hand noted copy of right but you've never actually seen it but it must be lingering in the depths of his presidential library somewhere, right? Or it'll come up for auction at some point. Nobody currently that I could find knows where it is. But that was not something that appeared in your death book that I was very excited to see when I first heard about it.

Speaking of auctions, you purchased a few auction items yourself. And after that experience, you took my dad up to your office and you were pulling things off your wall, like his letters or whatever. Can you share a little bit about those? Well, yeah, another Truman. So when Truman was president, he basically gets into the White Houses and he realizes it's been a dump because FDR has lived there for 12 consecutive years, not taking great care of it. It's just an old historical house that has had hundreds of people or thousands of people traipsing through over. Anyway, so he orders basically a total gutting and remodel of the White House. And part of the way he paid for it was he sold off like

chunks of wood and mementos from the White House. And so those sometimes go for auction. So I have now over the door in my office, I have like a piece of trim that would have gone over a door in the White House from that remodel. Like Truman spent most of his administration in Blair House across the street because the White House was uninhabitable.

That's like my one vice. The one thing I collect, like I don't collect like cars or fancy things. Yeah. But what is it? You have that letter too. What is the letter? Oh, the letter.

Oh, I have a couple Truman letters. Yeah. So I have one that's right next, I guess if I'm sitting here, it's right here on the wall. It's right next to two pictures of my kids. And it's a letter. Truman's sort of besieged

with all these requests to do things. And it's a memo and it's from one of the secretaries. And she says, you know, because of all the president's, you know, inquiry, should we say to these people like he must beg to be excused? And Truman must have looked at this memo because he underlined, must ask to be excused. And he wrote, the proper response is underlined HST. And I have that next to my desk as a reminder of like saying, here's you have the president of the United States

just struggling with this thing that we all struggle with, which is that we have too much stuff on our plate. I have another letter where he's responding. It must have been a form. He says, I'm sorry, it's my policy. I don't answer questions. Right. That's my favorite one. Yeah. And then there's another one that I have. So I have three, I guess it is. It says, I appreciate your question. It will be answered in a forthcoming book. And I think about that because it's like, if I answer every question that comes in, I'll never get anything done. But if I actually put the time in to make a video or a book or whatever, it will not only answer your question but it'll answer this question for lots of people.

And so I- Right, but they'll still ask you, even when you put the book out, they'll still want you to answer it personally. Yes. Congrats, man. Thank you. Number one, New York Times bestseller, first week out.

Is that the first time you've hit one? No, Stillness hit number one also. Stillness did, yeah. Unbelievable. But who's counting? Unbelievable. You crank out a book a year. You're running a bookstore. You do the Daily Stoic podcast.

You got the newsletter. You travel for speaking. And you're married and you have two sons. It's a lot, man. It is. It's a lot. I'm trying to figure it out. Well, you're doing a good job.

And I think the work that you're doing is vital and important. And I'm always here to support you, my friend. So thanks for coming in, sharing today. Right thing right now. Get it right now in the right thing place. Right?

Or actually, people should go to your website to get it, right? Yeah, you can get it from Daily Stoic or thepaintedporch.com. Yeah, absolutely, man. All right, well, until next time, dude. What was this? Was this five times, six?

I don't remember how many times you've been on, but it's a lot. Yeah. But it's been a while. Well, you're always very gracious. Cool. Thanks, man. Peace. We're brought to you today by Peak Design.

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