Rich Roll and Ryan Reflect on Stoicism (Live Talks LA)

Today’s episode features an interview of Ryan conducted by yesterday’s guest Rich Roll about Ryan’s latest book, Lives of the Stoics: The Art of Living from Zeno to Marcus Aurelius at a Live Talks LA event. They talk about the intersection of Stoicism and politics, the best way to live virtuously, and more. Live Talks LA: https://livetalksla.org/Event page: https://livetalksla.org/events/ryanholiday/This episode is brought to you by Four Sigmatic. Four Sigmatic is a maker of mushroom coffee, lattes, elixirs, and more. Their drinks all taste amazing and they've full of all sorts of all-natural compounds and immunity boosters to help you think clearly and live well. Four Sigmatic has a new exclusive deal for Daily Stoic listeners: get up to 39% off their bestselling Lion’s Mane bundle by visiting foursigmatic.com/stoic. Follow @DailyStoic:Twitter: https://twitter.com/dailystoicInstagram: https://www.instagram.com/dailystoic/Facebook: http://facebook.com/dailystoicYouTube: https://www.youtube.com/dailystoicFollow Rich Roll:Homepage: https://www.richroll.com/Twitter: https://twitter.com/richrollInstagram: https://www.instagram.com/Facebook: https://www.facebook.com/richrollYouTube: https://www.youtube.com/user/richroll66See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info. 📢 Share | ⚙️ Manage Subscription

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

• 0:04Ryan Holiday?

  Welcome to the Weekend Edition of The Daily Stoic. Each weekday, we bring you a meditation inspired by the ancient Stoics, something that can help you live up to those four Stoic virtues of courage, justice, wisdom, and temperance. And here on the weekend, we take a deeper dive into those same topics. We interview Stoic philosophers, we reflect, we prepare, we think deeply about the challenging issues of our time, and we work through this philosophy in a way that's more possible here when we're not rushing to work or to get the kids to school, when we have the time to think, to go for a walk,

• 0:46Ryan Holiday?

  to sit with our journals, and to prepare for what the future will bring.

• 0:53Ryan Holiday?

  Hey, it's Ryan. Welcome to another Weekend episode of The Daily Stoic. Yesterday, I had the privilege of interviewing my friend Rich Roll. Well, today's episode, the roles are reversed. Rich Roll is interviewing me. For the launch of Lives of the Stoics, Rich and I were supposed to get together in Los Angeles and do an awesome event for LA Talks Live. I was lucky enough to interview Robert Greene in the same format when Laws of Human Nature came out, and I thought it'd be awesome to get to see my friend Rich to do a big theater event for the book. But as you can imagine, that went by the wayside. So we did this remote when I was down at the beach in Florida. I was on my laptop.

• 1:36Ryan Holiday?

  Rich Roll was in his amazing shipping container office at his place there in Malibu. So we were not able to be in the same room together, but we had a great conversation. Instead of me interviewing him, he was interviewing me, but we go in-depth on some of the same topics that we did yesterday, but from the other perspective. As I said yesterday, Rich is just one of my favorite people. It was an honor to be interviewed by him. I think you will see just what an incredible interviewer Rich is. He'll put my interview with him to shame. I'm sure he's so good at asking the right questions. He's such a thoughtful guy. I think you'll love this. And of course, Rich has a new book out you can check out called Voicing Change. You can also listen to my interviews with Rich

• 2:19Ryan Holiday?

  on his podcast. I love Rich's book, Finding Ultra. It's one of my all time favorites. Love following Rich on Instagram and YouTube. Just a great guy. Love his podcast. His interview with George Raveling is incredible. Just a great guy. And I am planning, I just sent an email this morning, I am going to have Rich Roll's father, David Roll, who wrote a wonderful book about George Marshall on the podcast very soon as well. So enjoy this interview with me and Rich Roll.

• 2:49Speaker 01

  Welcome to another virtual Live Talks Los Angeles event. We welcome Ryan Holiday and Rich Roll to our series. We invite you also to visit our YouTube channel for over 300 conversations much like this, including an episode with Ryan interviewing Robert Greene. Today, they'll talk about Ryan's book, Lives of the Stoics, The Art of Living from Zeno to Marcus Aurelius.

• 3:10Rich Roll?

  Glad to be here and good to see you, Ryan. It would be nice to do this in person, but this is the world that we live in.

• 3:17Ryan Holiday?

  It'd be nice to do a lot of things these days, but that's not where we are.

• 3:22Rich Roll?

  Well, we're here to celebrate your new book, Lives of the Stoics, which I'm thoroughly enjoying. Congratulations on the review.

• 3:27Ryan Holiday?

  Thank you.

• 3:28Rich Roll?

  I will, as somebody who's known you for many years, though, my first, my sort of knee jerk reaction when I heard that you were writing this book was, was immediately like, really? Like, we're going to continue down this path? Like, what is this fixation on Stoicism that you simply can't seem to shake? You know, you're somebody who, no, obviously is credited with, with doing more to popularize this strain of thought than, than, than any other. But I'm interested in, in, you know, from whence this fixation, you know, originates. And you've spoken

• 4:07Rich Roll?

  about your introduction to this canon of thought by, by dint of, of meeting Drew Pinsky at an event. But I'm interested in what's behind that. Like, what was going on with you personally as a young man that magnetized you so completely about the Stoics in this particular vein of philosophy?

• 4:32Ryan Holiday?

  It was a weird experience. I bought this random book on Amazon as one does. I remember back then I had to wait for two day shipping because Amazon Prime didn't exist yet. Like I remember I had to buy another book so I could get the free shipping. Remember it was like if you spent $25 on Amazon, that's what like qualified you for for free shipping. So I think what so Marcus Aurelius arrives on my doorstep and or my P O box, whatever it was in college. And I remember opening it and just being struck with how sort of matter of fact and accessible and straightforward.

• 5:14Ryan Holiday?

  The language is like, it really felt like like this was a human being writing to me. There wasn't a Roman emperor writing, you know, from 2000 years ago. And it, I don't remember exactly what was going on in my life. I don't remember being particularly happy. I was, it was in my sophomore year of college, it was going okay. But it just sort of was like everything that I needed and wanted. But funny enough, as I was writing Lives, I came across this story about Zeno getting this prophecy as a young man. Basically, the prophecy from the oracle Delphi says like, you will become wise when you learn to have conversations with the dead, which he later comes to understand means reading.

• 5:57Ryan Holiday?

  And I think what I was really struck by reading Marcus Aurelius was like, I'm, I'm talking to Marcus Aurelius. Like this is the most powerful man in the world, writing in such an accessible, straightforward way that all time and space and social hierarchy and all these things, it just completely falls away. And you're like, you're like inside this guy's mind.

• 6:19Rich Roll?

  Yeah, and it seems to be, you know, the gift that that keeps giving. And one of the things that that struck me about the new book. Is first and foremost that there's actually robust documentation about how these people live. Like, I was shocked at how much information you and Hanselman were able to unearth about these people. I would have suspected that it would be close to impossible to learn anything about the personal lives of these people despite their writings.

• 6:50Ryan Holiday?

  It's weird to think that these philosophers were like world famous in their time, like were, you know, sought out by kings. There was books written about them. They were, they were truly famous because philosophy, as it's being invented, is this kind of radically transgressive, earth shattering concept, just, just in the way of like, you know, obviously there's figures in the Bible. We have historical documentation about, and there's sort of independent confirmation about these things. It is interesting. We do have so much information about the Stoics, but it was tricky. I think, I don't want people to get the sense that like, when you're reading the book, that there's like a whole world about these other figures that you could like,

• 7:32Ryan Holiday?

  like, everything that's there is in the book on, on a lot of these figures. I mean, on Seneca and Marcus and some of the other characters, you could really write more, but some of these figures, you know, were, were what appearing is like an anecdote from a person, from a person, from a person. So it's kind of this mix of like myth and legend. I heard this great quote from Val Kilmer once when he was describing playing Doc Holliday in Tombstone, which I think is one of the great performances of all time. And he said that it, acting in that role was like putting clothes on a ghost, which I thought was a beautiful expression. And there was a little bit of that on the Stoics where we, we know this and that about them, but, but really

• 8:17Ryan Holiday?

  understanding how that fits into their personality and who they were, that was the tricky part on the book. And, and what I ended up trying to do was like, just get a sense of the essence of these people as human beings. Less, you know, like some of these figures, we, it's like Chrysippus or something wrote 700 books. I don't, I don't really know what he says in those books. And we don't know because a lot of it's lost. But I am interested in the kind of person who would write 700 books and what makes that person tick.

• 8:48Rich Roll?

  Right. It's a, it's a series of short biographies that are written in the Stoic tradition, meaning that in contradiction to kind of what we think of as the modern biography, which is a deep dive into somebody's life and every facet of it. This is an effort to illustrate some key things that, that kind of demonstrate this person's character, whether it's a simple action, or the way that they died, or an exchange that they had, that tells you essentially everything you need to know about how they embody these Stoic principles, for better or worse.

• 9:24Ryan Holiday?

  Totally. So Plutarch, who I think is probably the greatest biographer to ever live, ironically or coincidentally, Plutarch, who, who lives in the Roman period, his grandson is Marcus Aurelius's philosophy teacher. So it gives you a sense of how weirdly small this world was. But, but he makes this big distinction between writing biography and writing lives. And I thought that was really interesting. He said, lives is, and there's a reason this book is called lives, but he said, lives is like, an anecdote, it's a story, it's a quip, you know, it's, it's a, it's a, a split second in someone's existence

• 10:05Ryan Holiday?

  that captures or is reflective of the whole, as opposed to this sort of minute, detailed, you know, listing of every single thing that ever happened to a person.

• 10:16Rich Roll?

  What was interesting for me was, was learning, you know, I, I have like, a very kind of arms-length relationship with Stoicism, like, I understand the greatest hits, you know, Seneca, Epictetus, Marcus Aurelius. What I didn't realize is how robust the tradition was, and the length of time over which it spanned, and how many people were involved, how many leaders, how many factions, how many little groups, and, and the leverage throughout, you know, a pretty long period of history, these people exerted on public, everything from public policy to, you know, leadership and the battles that were waged.

• 10:54Ryan Holiday?

  Yeah, it's, it's, you know, it's 500-plus years of history, and not, you know, minor history. I mean, this is the history, this is the period that shapes. Western civilization, right? This is Greece leading into Rome, you know, ending sort of with the decline and fall of Rome. I think, I think what I found fascinating about Stoics, and I agreed, I didn't really, I sort of knew about the beginning and I knew about the end and I knew a couple of the people in the middle. I really didn't realize how active the Stoics were at the highest levels. Like, for instance, like, I knew about Cato, Cato being the sort of the resistance to Julius Caesar. And I thought

• 11:36Ryan Holiday?

  that kind of Stoicism dies out there. I didn't realize that the two teachers and primary political advisors to Octavian or Augustus, who's, you know, Caesar's direct successor, happens to be these guys, Athenodorus and Arius, who were Stoics. Like, I didn't, I didn't realize like how immediate the transition was. And what's fascinating about how immediate that transition was, is all the complex moral and ethical, you know, contradictions there. It's like you have a Stoic who's literally willing to kill himself, then be associated with the transition from Rome as a republic to an empire. And then,

• 12:21Ryan Holiday?

  you know, he's barely in the ground and two other Stoics are like, oh, sure, we'll advise the new emperor. It's sort of like a, the king is dead, long live the king, kind of a moment. And, and I just found that so complex and fascinating.

• 12:34Rich Roll?

  Right. In thinking about Arius, I mean, we have Arius is to Augustus as Seneca is to Nero.

• 12:42Ryan Holiday?

  Yeah.

• 12:43Rich Roll?

  Fill in the blank is Trump. I mean, there's some questions about these complicated relationships of these philosophers to leaders that is highly relevant to what we're enduring right now.

• 12:56Ryan Holiday?

  Well, and what's so complicated about it is that Augustus is a pretty good emperor. I mean, he's a, is an all authoritarian king. So, you know, obviously, within, within whatever the sort of the bounds of absolute power corrupting absolutely, like, but, but as far as being Decent emperor, like no one thinks that he did a bad job, right? Like he did a good job. I imagine the those two Stoics rationalize their sort of cavorting with an autocracy as hey, we, this is the least bad version of this scenario, right? So then you flash forward several generations.

• 13:37Ryan Holiday?

  Seneca, who lives through the life of five emperors now gets called into the service of Nero. The idea of restoring Rome to a republic is probably a fantasy at this point. It's all he's ever known and two of his heroes seem to have done a good job mitigating the worst impulses of of an emperor. You know, he's telling himself, hey, this is, this is what my duty is. And, and there's, I'm forgetting the phrase, I think it's quinquennium, neuronium or something. But the first five years of Nero's regime are considered kind of a golden age and Seneca gets most of that credit.

• 14:18Ryan Holiday?

  So, so then you flash forward 2000 years and these people who've spent their lifetime in DC and Republican politics, and now they have a chance to be the head of the CIA or the, you know, Secretary of Defense. You know, as an outsider, you might go, oh, that's a morally incomprehensible, you know, sort of choice. But it's complicated, you know, because somebody's got to do the job. And, and I think that's what's, I think that's, in one sense, that's where they get you. And on the other hand, the Stoics would say, but isn't that your duty? And, and it's, I don't have a good answer.

• 14:55Rich Roll?

  Yeah, it's a very complicated sort of algorithm to solve that a lot of people in the administration are going through right now. This idea of is the institution that I serve better off with me here trying to stabilize it with some, you know, anchor or ballast? And what is my obligation to my colleagues and my peers in this institution versus taking the kind of implacable ethical stand and departing, knowing that that spot's going to get filled with someone else who might do a greater disservice to the greater good?

• 15:31Ryan Holiday?

  And so, again, the Stoics being famous, Tacitus is the most well-known Roman historian of this imperial age. And Tacitus is talking about the Stoics. Tacitus is also where we get historical confirmation of Jesus Christ, right? So Tacitus is talking about this Stoic opposition. That's what they called Helvidius and Thrasse and Seneca and Musonius Rufus and a handful of the other Stoics who defied and fought against Nero. And actually, his argument against them is that they made almost no difference. He said that they paid quite

• 16:14Ryan Holiday?

  dearly and accomplished nothing, except for basically being difficult. And so I think that is another wrinkle in it. And I remember I was, I'm trying to not name too many names here, but I was in, I had breakfast in the Senate dining room a few years ago, shortly after, I guess it was midway through Trump's first term, hopefully last. But anyways, and I was asking, they were privately expressing to me their doubts or frustrations with Trump. And I brought up Jeff Flake, and they said, "Look at Jeff Flake now. He's not going to run for reelection. He's not going to be a senator anymore." And they're like, "What

• 16:58Ryan Holiday?

  difference can he make now?" And so that, I was...

• 17:04Ryan Holiday?

  Both as a citizen, I'm a little, you know, I have one set of feelings, but as sort of a historian philosopher, you're like, oh, that's the exact same dilemma that Seneca was thinking about. Seneca, you know, begins to push back against Nero and then he gets pushed out. And then shortly thereafter, he has to commit suicide. So on the one hand, you could say he went out, you know, insisting on what he believed in, but it didn't do anything. And, and so I think this is the, this is the sort of, there's a pragmatic side to the Stoics and there's a sort of a principled side of the Stoics. And, and those things are often in tension with each other, just as I'm sure you are with your audience or with my audience.

• 17:47Ryan Holiday?

  It's like, I can say what I think, uh, you know, but let's say you and veganism, obviously the more strident you are in your beliefs, you perhaps end up alienating people who are on the fence or who are not interested. And then you cease to be able to have influence or impact with those people. So it's, it's this weird tension. And I don't think there's a clear cut answer, but I think it was something that even 2000 years ago, the Stoics were struggling with.

• 18:15Rich Roll?

  Yeah, it's this idea that, um, it is through storytelling that we learn. This is how these principles really, um, you know, find weight in the human condition. Like you, you can post these quotes on Instagram or, or, or talk about, you know, the philosophy from 10,000 feet, but placing these people in context and what they're actually struggling with is when they really become resonant. And it's amazing how these, you know, ancient historical figures were struggling with the same things that we're dealing with now. There really is very little difference. And I, we talked about this before, but isn't, I, I believe it was Marcus Aurelius,

• 18:58Rich Roll?

  where he's writing down his thoughts and there's a, there's like a gym downstairs and they're making all kinds of noise and he can't clear his mind. And it just, it, it really, it's a very short leap to, you know, the struggles that we have, turning our phones off or trying to find that ability to focus to do the deep work.

• 19:16Ryan Holiday?

  Well, I love, I think Seneca is the source of the sort of scene you're talking about, but but both Seneca and Marcus Aurelius, they talk about like sort of wanderlust or the desire to travel, like the desire to get away from it all, to, you know, to head to the mountains or the beach or the or a country retreat. And and there's that feeling we get when we're stressed, or when we're unhappy, or when we're sad, and we think, I just need to go on a trip, I just need to go somewhere. And I think one of the things that pandemic has has been both a rude awakening and a sort of a nice bit of training is like, as as our ability to distract ourselves with busyness goes away,

• 19:57Ryan Holiday?

  you're sort of forced to sit there and wrestle with a lot of these things. And to connect that back to the sort of moral dilemmas we're talking about earlier, I think one of the reasons, one of the ways Seneca is able to navigate that key sort of series of contradictions is probably not by not thinking about it at all, by being so busy, by dealing with one crisis, one, you know, this is a guy who was a senator, a political advisor, and a famous playwright, and a philosopher all at the same time. I've got to imagine part of that busyness is, you know, built around not ever having to stop and think about what the hell you're doing.

• 20:38Rich Roll?

  It would be as if Lin-Manuel Miranda was also the president and Tom Brady, like in one person.

• 20:46Ryan Holiday?

  So James Rahm, who's a great biographer of Seneca, he was talking about it, like Seneca was so talented that there's, for most of history, we thought Seneca the playwright and Seneca the philosopher politician were different people, because everyone in Rome has the same name, like every member, every female member of Julius Caesar's family is named Julia, for instance. So it like, the idea that they they were the same people is, is, you know, was incomprehensible. And he says, this is the equivalent of if Emerson, the philat, the transcendentalist, had also written Faust, the play. And actually, as I say in Lives, that's actually not true. It'd be like if that were true, and Emerson

• 21:31Ryan Holiday?

  had been in Lincoln's cabinet, you know, like if Emerson had also been vice president. So just the sort of sheer brilliance, but also the sheer busyness of Seneca, I think, begins to Shed some light on how he found himself in the, you know, moral quandary that he found himself in.

• 21:55Rich Roll?

  Well, given the pandemic that we find ourselves in, and the kind of, you know, challenging political climate that tends to monopolize our focus at the moment, there's never been a better time in our lifetime to flex these Stoic principles, you know, for so many people, the world feels very out of control. You know, there's an incessant news cycle that's fueling anxiety and vitriol and conflict and confusion. We're seeing a breakdown of trust in institutions and in journalism and our ability to productively communicate. And so there is this sense that the principles, these ancient principles of Stoicism are needed now more than ever. Like in this, you know, there's a call to

• 22:38Rich Roll?

  return to rationality, to, you know, to a place of nuanced discourse and, you know, our respect for centrism. So how do you think about all of these things in this post fact world that we're in?

• 22:52Ryan Holiday?

  It really hit me at the beginning of this pandemic. Obviously, you know, Marcus Aurelius and I have had this sort of love affair now. I guess it's a one-sided love affair for, for a decade and a half. And I, so I knew it objectively, but it never quite struck me fully that he was writing during a pandemic. Like, like Marcus Aurelius, shortly after Marcus Aurelius takes power, the Antonine, what we now known as, now know as the Antonine Plague hits Rome. And, and it lasts for 15 years, longer than that. He eventually dies of it. So, so for his, you know, for his part, it was the death sentence ultimately. But just, just the idea that what he was going through in the second century

• 23:36Ryan Holiday?

  AD was very similar to what we're going through right now. There was political division. There was, you know, a public health crisis. There was an economic crisis. You know, there were all these things happening at the same time. And that the full weight of that never sunk in with me until, you know, our lives started to resemble that, which is a really weird thing. And, and I think. The ability to wrap your head around what's hap- like, he has this great quote, and again, it's like you get it, but then you don't get it till you really get it. You know, he says like, "A plague can destroy your life, it can take your life."

• 24:21Ryan Holiday?

  But he's like, "It only harms you if it hurts your character." And I, so I, I thought that was a beautiful idea, obviously, when I first read it. And then it didn't, I, again, it's like, oh, he was also literally speaking of a plague, right? And it struck me the other day, I was, I, I'm, I'm thinking about writing this. A, a friend of mine, actually a mutual friend of ours, I was, I was talking to them and, and all of a sudden, they started saying like some crazy kind of conspiratorial stuff, like about masks and, you know, all, all this. And I, it was like, oh, this person is infected, like not with COVID, but infected with another sort of dangerous, you know, like idea of virus.

• 25:06Ryan Holiday?

  And, and so I think this, these sort of, and that struck me as very sad, but you know, in some ways inevitable. It's just, I guess, I guess the, the sort of, the idea of being able to think clearly, of not being distracted or, or, you know, corrupted by the mob, of not losing your good-heartedness, of not losing your civic-mindedness. Like, the Stoics were struggling with those things, just as we're struggling with those things. So I take a lot of heart from their teachings, especially lately.

• 25:40Rich Roll?

  So then, in more specific terms, how have you doubled down or applied these principles to, you know, what is unique about right now?

• 25:51Ryan Holiday?

  I, I mean, I think the civic-mindedness one is really a big part of it. So obviously, you and I are doing, you know, this remotely, because it's the right thing to do. Just a few days ago, I got an offer for a talk, like an in-person talk. I don't know if you've started to get these requests sort of creeping back up as well. And so on the one hand, it's sort of a temptation, it's sort of a temptation in that like, you know, we've been- Forced to sort of stay at home and be productive and focus and not get distracted. And it was easy to say no and to sort of zoom in on what I have to do when no one was asking me to go do things. But it's also easy to say like, hey, you know, like, people should be safe. People should not expose others. People shouldn't take needless risks. People should think about the common good.

• 26:34Ryan Holiday?

  It's easy to say this, like, in a debate about whether, you know, college football should have crowds in the stands or not. And then when someone is then offering you tens of thousands of dollars to go do a smaller version of a dangerous thing, now this is like where the rubber is meeting the road. So I've been, that's just something I've been thinking a lot about. It's like, it's very easy to be sort of pure about these things, to be very strident about them, to be very insistent on what you know is right. And then when your livelihood is on the line, suddenly you're different. So I think one of the things I've been thinking a lot about is just like, what, what are your obligations to your family, to other people, to your country?

• 27:16Ryan Holiday?

  And then how do you kind of navigate that, you know, amidst the various obligations that you have as a human being?

• 27:23Rich Roll?

  Yeah, in 12 step, they would call it practicing these principles in all our affairs.

• 27:28Ryan Holiday?

  Yes.

• 27:29Rich Roll?

  It's when you're faced with that challenge yourself, do you show up and live those principles? Or do you make some kind of excuse so that you could do what you want to do?

• 27:40Ryan Holiday?

  Well, I heard a great line where it was like, it's not a principle unless it costs you money. So it was like, I'm not absolutely opposed to doing anything in person, but I had, my wife and I had to sit down and go, okay, so here's, here's what, here's, here are the constraints under which we would feel comfortable, like, getting from place, you know, point A to point B, right? Like, here's how we would do it. Like, we're, we don't feel comfortable travel, like, flying or staying in hotels. So here's how we would do that. But then it was like, okay, what are, what are the safety protocols that I would insist on? And here they are. Now, you can say that to those, to the event organizers, and then they could say, no, we're not going to do that.

• 28:21Ryan Holiday?

  And then you have to go, okay, well, then I'm going to say goodbye to that amount of money. You know what I mean? Like, you actually have to, like, it's, it's, again, it's easy to say, hey, everyone should wear masks. It's harder to say, if you can't guarantee that everyone in this event is going to be wearing masks, or that, you know, the attendance is going to be below this level, or that everyone's going to be tested beforehand. I'm willing to walk away from X. And I think at a different point in my life, I think I would have had a lot more trouble doing that. And even now, it's a hard thing to do. I don't need it, but it's still a hard thing to do. And so that, again, I think one of the things I've tried, the standard I've tried to hold

• 29:06Ryan Holiday?

  myself through the pandemic is, have I kept my family safe? That's obviously your first obligation. But second, have I done that without exposing or harming other people as well? Do you know what I mean? Like, I think, and I think that's something that we as a society have really struggled with. Like, again, we were talking about this, just telling you about someone who is sort of passing forth some conspiratorial thing. And we might be getting too off in the weeds here, but there was a discussion about masks and they were saying, you know, a lot of the people who have been exposed or who have tested positive were wearing masks.

• 29:48Ryan Holiday?

  And so to them, this was the argument, this was, you know, evidence that they don't, they shouldn't have to wear a mask, which fundamentally is not just wrong scientifically, but they're missing the entire moral argument for masks, which is that you wear the mask to not, to help other people, not to yourself. There is science that mask reduces your viral, the viral load you could pick up. But the argument for mask, the stoic argument for mask, and Stephen Pressfield, I think, expressed this very brilliantly. He was, he was saying that the Spartans, if you lost your helmet or your sword in battle, the Spartans would get you another one. But if you lost your shield in battle, the Spartans would punish a soldier with death

• 30:31Ryan Holiday?

  because the shield was not for you. The shield was for protection of the entire Spartan line. If each person held, if each Spartan holds their shield in the, in the, in the, in the phalanx, everyone is protected. But if someone drops their shield, the, the, the person on the right and the left of them becomes exposed. And so again, like, I think what I've really taken from the Stokes, especially lately, is just a much stronger sense of what our obligation is to other people, especially, you know, even and especially people you will never meet and never know and never even have any idea whether you negatively impacted them or not.

• 31:13Rich Roll?

  Yeah, of course, the the shield just being a proxy for the mask, right?

• 31:18Ryan Holiday?

  Yes, yes.

• 31:21Ryan Holiday?

  Right, the mask, the mask is to reduce your spread of the virus, not to protect you from getting the virus, but that's, that's almost the exact opposite of the way our brains are wired these days, is we think about, like, James Stockdale, who I don't really talk enough about in the book, we decided to cut it off at the modern, you know, the, the, at Marx's really being the last Stoic, but I did kind of a bonus chapter on him, he has his, he said, "The flip side of what's in it for me," he said, "is I am my brother's keeper." The idea that it's not about whether this helps you or not, but it's about what your obligation is to other people or not, and, and we seem to, we seem to struggle with that.

• 32:07Rich Roll?

  Right, well, there's something, I think, very American about our struggle with that, because rugged individuality is so bred into the genetic material of who we are as a country, and that's at odds with being more communitarian and oriented around our neighbors, and the fracture that we're seeing has to be traced back to that on some level, but it's metastasized to such an extent that it's really fractured us in a way that it's difficult to see our way back.

• 32:40Ryan Holiday?

  Yeah, there's this great Huffington Post article, the headline, I think, is just perfectly captures where we are today, and it's from a few years ago, but it's, the headline, and I think about it all the time, almost on a daily basis, because I do feel like I'm constantly bumping up against this with people I know, with my readers, even with my own family, but the headline is just, "I don't know how to tell you that you have to care about other people." And I really feel like that, you know, that is something that people seem not to understand, just at a fundamental level, like, they don't, they don't understand why they're supposed to care.

• 33:27Rich Roll?

  When you look at Stoicism, these principles emerge courage, justice, temperance, wisdom, I'm sure there's a bunch more.

• 33:37Ryan Holiday?

  No, those are the big four.

• 33:38Rich Roll?

  Those are the big, okay. But it is very much, it's kind of ephemeral, like when you contrast it to, say, the 12 steps as an example, or the eight-limbed path, like, these are, these are, you know, ideas or not necessarily philosophies, but like ways of living that are, that are, you know, kind of distilled into very practical steps or practices, whereas Stoicism is, I think you're the one who said, you know, it's, it's kind of a choose your own adventure way of living. And I find myself struggling to figure out, like on a day-to-day basis, how to take these

• 34:23Rich Roll?

  ideas and put them into tactical practice.

• 34:28Ryan Holiday?

  It's tricky. And so for, for, for the Stoics and Christianity, the cardinal virtues are the same, right? Courage, justice, temperance, and wisdom. But Christianity, and I think this is a brilliant, I don't want to call it invention, that sounds patronizing, but, but it's, one of its sort of critical features, one of the reasons it becomes such a dominant sort of way of living and guide, is, is that Christianity also gives us the 10 commandments, right? Like the very clear do and don't lists. And, and one, one of the, the chapters in the book is about a Stoic named Aristo. And Aristo, I don't want to say he screwed it up for everyone, but he sort of creates

• 35:11Ryan Holiday?

  this early Stoic backlash against what they call precepts, like the rules that you're talking about. He says, like, you should just know, that it should just kind of be obvious, that once you study, you should know what's good and bad, and then sort of intuitively, naturally always do it. He sort of likens this to an athlete, he says, you know, a javelin thrower, just, you know, from, from their practice knows. What to do, but I sort of push back on that, not just in the book, but in my, my own thinking. It's like, actually, you know, athletes have coaches and the coaches are telling them exactly what to do and not do, and they have very specific game plans. So that I think as, as

• 35:52Ryan Holiday?

  Stoicism evolves, it gets closer to precepts, but we, we have to, the tragedy of Stoicism is that the vast majority of the writing does not survive. Um, for, for most of the Stoics, excepting basically Seneca, Musonius, Rufus, Epictetus, and Marcus Aurelius, all that we have from them are a handful of fragments. So we have quotes of quotes of quotes. I think in the actual Stoic texts, there probably was a lot more specific instructions and a lot more, a lot more in the way of clear guidance. So I think what I try to do in my writing is then to still illustrate these sort of more ephemeral ideas in stories

• 36:37Ryan Holiday?

  or examples or rules. Um, because I, I, I agree with you. I think that's ultimately what we need. It's like, look, uh, someone can tell you the 12 steps of, of Alcoholics Anonymous. That's not really the process. The process is that you then go to meetings multiple times a day, in some cases where they're reviewing it constantly over and over and over again. Just like, you know, it's not about reading the Bible once. It's about, you know, 80 years of going to church and hearing about it and talking about it and dissecting it. So I think where Stoicism has struggled is that, uh, it, it hasn't had, it, it hasn't been brought to people in the form of a practice or a sort of a, in a, a

• 37:20Ryan Holiday?

  thing you're engaged with. And that, that's what I try to have, that's what I've tried to make for myself, but that's also what I try to do in my writing.

• 37:28Rich Roll?

  Reading the, uh, the, back to this idea of, of, you know, you being a person of influence and, and trying to figure out how to articulate your perspective and often a perspective on current events and the impact of that on this audience that you've built has created an interesting experience of diving into your comments section.

• 37:54Rich Roll?

  Highly entertaining and and reveals a sort of moral confusion, I think, not only about the essence of Stoicism itself, but also its responsible application to action. It's like there's a there's a blindness in certain people to the fact that the Stoics, by and large, were were people of the world, that they were integrated into public life at the highest level, literally themselves politicians. And to see people frustrated or upset that you would express perspective or an opinion on things that are going on right now is kind of amazing. Like, do they not know, you know, what you what it is that

• 38:35Rich Roll?

  you're talking about? Like, how very articulately, but I think you know what I'm talking about.

• 38:42Ryan Holiday?

  I know exactly. I know exactly what you're talking about because it's consumed way too much of my mental and emotional bandwidth lately. It's it's it's rather surreal, right, to to hear from someone, you know, and I've seen this comment a thousand times, like, what would Seneca or Marcus Aurelius or Cato think of you bringing politics into this? And it's like, as professional politicians, I think they'd probably be okay with it. You know what I mean? What are you like, what are you talking about? But it's it's been it's been hard because I think you know this. It's like you work so hard to build an audience. You have an affinity for the audience. You are loyal to the audience.

• 39:23Ryan Holiday?

  You feel obligated to the audience. You're proud of it, you know? And then you you think you have one set of connections, or you think you're on a similar wavelength, then you then you go, oh, maybe not. Maybe maybe we're not even existing in the same reality. And and that's been that's been hard. I sort of go back and forth between being sad about it and finding it absurd, heartbreaking, and then also, you know, sort of galvanizing. I kind of go back and forth. But it is, it's like Arianna Huffington is a modern Stoic. She's very liberal. James Mattis is a modern Stoic. He's a lifelong Republican who served for a time in the Trump administration. James Stockdale, you know, a relatively

• 40:08Ryan Holiday?

  modern Stoic. He's a political independent. He runs for vice president as a political So I don't think the Stoics are necessarily going to have a bunch of specific policy views. But it seems undeniable and indisputable to me that the Stoics would be opposed to a whole swath of things that are happening right now. And we know this because we saw them oppose very similar figures at very high personal cost. And we see them talk over and over again about our obligations to other people, about their obligation to goodness and decency and kindness.

• 40:50Ryan Holiday?

  And so it's just, you know, it's just incredible when you see people sort of using Stoicism to justify or rationalize like just completely heinous things.

• 41:03Rich Roll?

  Yes, I would agree with that. I think we only have a few minutes left. So I do want to pivot a little bit.

• 41:10Ryan Holiday?

  Yeah.

• 41:11Rich Roll?

  To explore a little bit more deeply this idea of what it means to live and examine life, to be devoted to lifelong learning and also packed into it, this Stoic idea of life being a training ground for death, like learning how to live your life to prepare for death. And, you know, death throughout the new book is so prominent, like the way that these people die and the sort of intentionality that they put into the choices that they make around surrounding their death is very unique and is not something that I think we think much about at all.

• 41:52Ryan Holiday?

  Well, spoiler alert, all the Stoics in the book die. None of them are still alive. That's a reality of the human existence. I think Edmund, was it Edmund Wilson said, "Death is the one prophecy that never fails." And so all this, it's a book of the lives of the Stoics, but it's, you know, by definition, also a book of the deaths of the Stoics. I think, I don't know about you, but I do feel like the pandemic has brought mortality much more into focus for people, even myself. It's like, I mean, you could argue that the risk of dying of coronavirus is probably similarly low to a bunch of other things that we regularly don't think about or take for granted.

• 42:35Ryan Holiday?

  And that's because we can't just get those things going outside and being breathed on by someone, right? So with the

• 42:44Ryan Holiday?

  You know, or you sort of see this argument, people go, but you know, X amount of, you know, 100,000 people die every year of the regular flu, as though that somehow makes the pandemic not serious. What I've taken from a lot of those arguments is like, oh, man, there's been a lot of, you know, horrible public health crises that we have just not been paying attention to because we assume that we're invincible and it doesn't affect us. So I think what the Stoics wanted us to realize is that death is sort of ever-present and it's always there. And that rather than being scared or intimidated by this, it should shape how you live. I think the most beautiful thing I've taken from Seneca, he has this idea that don't think

• 43:25Ryan Holiday?

  of death as something that looms in the future, but think of death as something that's happening right now. So, you know, all these people, we went into quarantine or we went into this weird limbo that we're in. And they were like, oh, I'll just wait to do this until we get back to normal. And Seneca would be like, but you just died eight months waiting for things to get back to normal. Like you'll never get those eight months back. And so I think one of the big things you take in living a life that is prepared for death is that you don't waste the life that you have.

• 43:54Rich Roll?

  In the process of doing your own examination around this, like where do you find yourself struggling? Like where's your inflection point as you, you know, continue to evolve? There has to be obstacles that you have self-awareness around that continually trip you up. And this is where you need to put your time and effort into.

• 44:14Ryan Holiday?

  Well, I think it's relatively easy to get to a place where philosophically you're okay with death, you know, provided that you're not like a sort of a raging narcissist or something, right? Like it's, but it's then when you have attachments or obligations to other people that it gets very tricky, right? Like Marcus Aurelius talks about when you tuck your kids in at night to say to yourself that they could die before morning, which on paper, you know, reading at 19 years old, I was like, that's an interesting way to think about it. Well, when you're cuddling with a four-year-old, that's a, that's a heavy thing to do. You know what I mean? And, and even, you know, writing this book, really trying to wrap my head around the fact

• 44:57Ryan Holiday?

  that Marcus Aurelius loses multiple children before adulthood. You, you realize it's like, okay, it's one thing to sort of be philosophical about death because it's involving you, but what about when your death affects other people? Or what about, you know, your love or, or care or commitment to other people is affected by, you know, the, the, the reality of death? So I think, you know, it's like, look, uh, I don't want, you know, you, you don't want to say goodbye to your family. You don't want anything to happen to them. And so I think wrestling with the real implications of nothing being certain and mortality being

• 45:39Ryan Holiday?

  real is, is just another thing entirely when it affects innocent other people.

• 45:45Rich Roll?

  So in the book, you profile, what is it, like 26 of these Stoics? It had to be a process trying to figure out who's in the book, who's not in the book. But who, in the unearthing of all this research, surprised you the most? Like, what was the, you know, as somebody who's been steeped in this for so long, what were the kind of happy accidents or surprises in the writing?

• 46:11Ryan Holiday?

  The one character that, one of the things I really wanted to do is I wanted to make sure it wasn't all men, which is not an easy thing to do because the ancient world was, you know, sort of heavily biased towards men. And so the exploration of Portia Cato, I mean, I knew who Portia Cato was, and I think I vaguely understood that she was married to Brutus. There, there's this scene where basically she, and, and again, the idea of just how real the stuff is, like, she gets the sense that her husband is Up to something and she doesn't know what. And she gets the sense that he doesn't want to tell her, not because he's ashamed of it, because he doesn't want to harm her.

• 46:53Ryan Holiday?

  And so she realizes, oh, he has a secret that he's afraid if he tells me it will put me in danger. And so she stabs herself in the leg and, and then just sees how long she can, she can deal with the pain before, you know, she breaks. And the reason she's doing this is that the punishment for, you know, secrets, conspiratorial secrets in Rome was, was the punishment of torture. So she's basically torturing herself just to see if she's got it. And she does. And, and ultimately this is what lets her in on and, you know, makes her a major component of the conspiracy to assassinate Julius Caesar. And you're just like, okay, I get why we mostly talk about men historically, but like, this is such a badass story.

• 47:37Ryan Holiday?

  How did I not, how is, how has this not been taught in every school? You know, it's like, I, I read Julius Caesar in, in high school and we didn't spend a couple of days talking about Portia, but that would have been fascinating, you know? So I think just how central she was and how central her identity was as far as the Stoics being very unanimous about their belief that virtue had nothing to do with gender. I, that was just a wonderful discovery.

• 48:09Rich Roll?

  Yeah. And, and her being the daughter of Cato and, you know, her, where she kind of sits in the lineage. And then when Brutus goes off, you know, to do what we all know that he was setting out to do, the confusion around like, who died first? Did she die? And the anxiety that she had about where he was in the world and whether he was going to make it back is fascinating.

• 48:31Ryan Holiday?

  Yeah. And I just love the idea of like a husband keeping a secret from the wife, but of course the wife immediately knows, like, I just, I just loved how modern that felt as well.

• 48:41Rich Roll?

  Speaking of modern, if, if Marcus Aurelius or, or Seneca were around today and, you know, made their appearance on. CNN or Fox, you know, what it, what is it, what does that talking head look like?

• 48:58Ryan Holiday?

  Well, I don't know if you've seen this, but if you Google it, a bunch of really interesting artists have been doing this thing where they kind of reconstruct what people look like from statues. They've like put sort of skin on the statues. And I've got to say, I'm going to send you this photo. You've got a Marcus Aurelius thing going on right now.

• 49:15Rich Roll?

  I'll take that as a compliment.

• 49:17Ryan Holiday?

  But yeah.

• 49:18Rich Roll?

  The hook on the question.

• 49:20Ryan Holiday?

  No, I don't know what they'd be saying exactly, but I think they would. I mean, I think they would be, they'd be doing, I think it'd be a Lincoln-esque kind of a moment, appealing to the better angels of our nature. You know, that, that, that a divided house can't stand. Marcus says like, the fruit of this life is good character and acts for the common good. They'd be talking about sort of being in this together. They'd be talking about what our obligations are to ourselves, to other people. And I think they'd be, you know, those four virtues are, are of courage, justice, moderation and wisdom are as relevant and in desperate short supply as they ever have been. So I'd, I'd like to think it'd be a reminder of that.

• 50:01Ryan Holiday?

  And sadly, I also think they'd probably get, you know, mocked on social media almost immediately as well.

• 50:08Rich Roll?

  And how would they, how would they manage that mockery? What, what are they engaging with the comments and the trolls?

• 50:15Ryan Holiday?

  I don't know. I think, I think Seneca, I think Seneca would be a much more astute sort of player of information and, and understand how persuasion and sort of political realities operate. Marcus Aurelius, you kind of get this sense that maybe he was a little bit too pure for this world and sort of struggled. So I don't, I don't know, but, but I, I certainly know they would be involved, right? Because that's, that's the, the, the fundam, in the ancient world, the fundamental distinction between the Epicureans and the Stoics is that the Stoic believed you had to be involved.

• 50:50Rich Roll?

  Yeah, the Epicureans being more, there's a little bit of like an eastern bent to that, right? Like it's your relationship to yourself and you're kind of opting out of that discourse that's happening publicly.

• 51:03Ryan Holiday?

  Yeah, the Epicurean is turning inward and the Stoic is, which is ironic as we think of the Stoics as being resigned, the Stoic is saying, no, you gotta, you gotta go into the strife.

• 51:13Rich Roll?

  All right, as we, as we wind us down, I think it would be instructive for somebody who's listening or watching, who's new to these ideas, they haven't, you know, read any of your books, this is their first introduction to the idea of Stoicism. What is it that you want the reader to take away from this newest book? Or what is most fundamental to understand about Stoicism and its applicability to, you know, how we live our lives currently and how we engage with our communities?

• 51:44Ryan Holiday?

  Although there are, there are certainly philosophers alive today, I would argue almost nobody cares what those philosophers are doing. They don't care what kind of car they drive. They don't care, you know, what they think about this or that. They exist in, in almost a purely academic setting. That was not what philosophy was in the ancient world, and that's not what philosophy is supposed to be. To me, what is so powerful about the Stoics, why I wrote this book, was that the purpose of philosophy is to improve yourself as a human being, to improve yourself as a citizen, as a, as a, as a spouse, as a child, as a, as a leader, as a, you know, whatever, right? And, and that the, so the

• 52:28Ryan Holiday?

  purpose of philosophy is to get better as a human. And that, that the reason we look at what the philosophers, we should look at what the philosophers did more than what they said, is that we want to see how they manage to measure up and what lessons we can learn from that struggle between theory and application. So I don't think the world needs more people having clever thoughts. The world needs more people who manage to put these good ideas into daily practice in their lives. Now, I mean, I'm not saying I've mastered that. I'm saying I'm struggling with it, but I think that struggle is what philosophy is really here for.

• 53:10Rich Roll?

  Right. And I think you've, you've done an amazing job of not only being an astute shepherd of these ideas, but also being, you know,

• 53:19Rich Roll?

  How do I say this? Like, in the ancient tradition, there were these groups that would get together, right? They would congregate, and they would talk about these ideas. And you've kind of created a digital version of that by virtue of The Daily Stoic, which allows people to congregate virtually around these ideas to propagate them. And I think, what you've created is a service to humanity. Thank you for doing that. And I look forward to the next book about Stoicism.

• 53:48Ryan Holiday?

  I appreciate it. Thanks again, man. It's always good to chat.

• 53:51Rich Roll?

  Right? You're well into your next book, I would imagine.

• 53:55Ryan Holiday?

  Yes, I'm actually, I've sort of finished one, and I'm on to the next one.

• 54:00Rich Roll?

  And you're going to be predictably tight-lipped about what that's about?

• 54:03Ryan Holiday?

  Of course, of course.

• 54:04Rich Roll?

  All right. The book is Lives of the Stoics. Thank you, Ryan. I look forward to seeing you in person when this thing lifts. And when it does. And so, then, everybody watching and listening, thank you for your attention. And check out The World of Ryan Holiday, ryanholiday.net. You can sign up for your, it's ryanholiday.net, right? You can sign up for Ryan's monthly email newsletter, where he talks about all the books that he read that month. And it's, I recommend it.

• 54:37Ryan Holiday?

  Thanks, man.

• 54:38Rich Roll?

  That's it.

• 54:40Ryan Holiday?

  If you like the podcast that we do here, and you want to get it via email every morning, you can sign up at dailystoic.com/email.