Ryan Holiday on stoicism

Speaker Key:

RH              Ryan Holiday

AL              Andrew Leigh


RH              Festina lente, which just means make haste slowly. Sometimes the fastest way to get somewhere is by slowing down a little bit. Slowing down a little bit being balance, not rushing things, having some of that moderation, is often the fastest way to get where you want to go.

AL               Welcome to the Good Life, Andrew Leigh in conversation, a podcast about living a happy, healthy and ethical life. In this podcast, we seek out wise men and women who have lessons to teach us about living life to the full, with humour, pleasure, meaning and love. We’ll chat with musicians and athletes, CEOs and carers, about making the most of this one precious life. If you like this podcast, do take a moment to tell your friends or give us a rating. Now sit back and enjoy the conversation.

                   Ryan Holiday just might be the world’s best-known promoter of Stoicism. He’s authored around a dozen books with titles such as Ego is the Enemy, The Obstacle is the Way, and Courage is Calling. Ryan operates the Daily Stoic podcast and runs a bookstore in Austin, Texas, where he lives with his wife and their two sons. Ryan Holiday, thanks so much for appearing on the Good Life podcast today.

RH              Thanks for having me.

AL               What got you into Stoicism? Who introduced you to the Stoics?

RH              I was 19-years-old and I was in college, not reading the Stoics because they’re not super-popular with academics. I was just at this conference. I was a college journalist and I went to this little event. It was actually sponsored by a condom company, that was for college journalists, and the speaker was this guy named Doctor Drew, who I’d grown up listening to. He’s a radio host. He did a show called Loveline.

                   And he was talking about college stuff to kids, and I went up to him after and I just said, I’m really into reading. What books would you recommend? And he said, I’m reading this Stoic philosopher names Epictetus right now that you might like, and I went back to my hotel room and bought Epictetus and Marcus Aurelius and it changed my life.

AL               There’s these big Stoic thinkers that people may have heard of, but I imagine most people, even if they’ve read a bit about Stoicism, would think of them as a block. But tell us a little bit about the big figures in Stoicism, Marcus Aurelius, Seneca and Epictetus.

RH              You think about the Stoics, this is a lapse in nearly 600 years from the founding of Stoicism to Marcus Aurelius’ reign, which is by no mean the end of Stoicism, but it is the end of the big Stoic thinkers. Zeno starts in Stoicism as the founder. He’s a merchant who loses everything in a shipwreck. And then that goes to Marcus Aurelius at the end, who’s the emperor of Rome. And in between, you have Seneca, who’s a playwright and a political advisor, and you have Epictetus.

                   So, the big three, people call Marcus Aurelius, Epictetus and Seneca. You have a slave, a political advisor and the emperor of Rome. Then there’s Cato, who’s a senator. You have all these sorts of interesting, pivotal Roman and Greek figures, who were philosophers, yes, but they were also actual doers. They were engaged in public life at the highest levels in Roman…

                   To me, that’s what makes not just the Stoics so interesting, but so relevant today. Because they weren’t just white guys from a long time ago exploring intellectual ideas, although they were doing that. They were trying to solve the problems of life. Their experiences were the experiences not of academics but men and women of action.

AL               I don’t know whether it’s because I’m a politician, but I find myself most drawn to Marcus Aurelius because he’s writing about issues that he’s directly wrestling with. I’ve always struggled a little bit with Seneca on the riches side. It’s all very easy for Seneca to say you should throw away your riches, but he’s phenomenally rich. And in Epictetus, the mysticism I find a little distracting from the central messages. How do each of them speak to you? What do you take from each of those big figures?

RH              Marcus Aurelius speaks to me for the reasons you’re talking about, but I think he also speaks to me because Meditations is perhaps the only philosophical book, perhaps the only book in the Western canon, that was not at all written with an eye towards publication. It’s a work of philosophy for oneself. Marcus Aurelius, when he says…

AL               It’s a got a kind of Diary of Anne Frank feel about it, doesn’t it?

RH              Yes. When he says, when you have trouble getting out of bed in the morning, here’s how you should think about it. He doesn’t mean you as in you and me, although it does speak to you and I, he literally means him. He doesn’t want to get out from under the warm covers, and so there’s an immense authenticity and accessibility to Meditations that speaks to me.

                   You have a guy talking about losing his temper, and you have a guy talking about dealing with urges, and you have a guy dealing with depression and grief and pain, and all these very human emotions, as well as power and success and fame. He’s just working his way through that. Seneca, on the one hand, is kind of not accessible in the sense that he was very wealthy, and he also worked for Nero. So, not exactly the most stand-up of political advisors either.

                   But there’s something to me about Seneca’s letters, where you have a guy writing notes to his friend who seems to be struggling, and there is a real accessibility and practicality to those letters, which I love as well. And he talks about, how do you deal with all the demands on your time? How do you deal with getting old? How do you deal with fear? How do you deal with the desire to travel, to just get away from it all?

                   And so, again, the Stoics are just constantly returning to these very down-to-earth, relatable ideas, and I think that’s just what makes them so different than all the other philosophers.

AL               At age 34, you’ve written four books on Stoicism alone, Obstacle is the Way, Ego is the Enemy, Stillness is the Key, and Courage is Calling. There’s four big Stoic virtues that people talk about, wisdom, justice, temperance and courage. Tell us about each of those virtues and how your four books about Stoicism map onto them.

RH              Now that I heard you say that, actually, I wrote two other books about Stoicism. I wrote a book called Lives of the Stoics, which is a biography of the different Stoics, and then I also wrote The Daily Stoic, which is one page of Stoic philosophy a day. And then I’m in the middle now of writing a series of books, as you said, on the four Stoic virtues, courage, temperance, justice, wisdom.

                   I’ve written the courage book, so that’s done. I turned in the temperance book on Monday, and then probably around June, I will start working on the justice book. I’m researching it now. So, that’s been the last two years of my life, and the next two years will be the other two books. But when I write about the Stoics, what I’m usually trying to do is take a person or a Stoic idea.

                   Like for The Obstacle is the Way, it was, how do we deal with the difficulties of life, the rocks that get rolled in our path? How do we overcome adversity? A book that goes, the enemy is about how you deal with that inner battle, the inner obstacles. And then Stillness is about where I happen to see Stoicism and Buddhism connecting with each other. I usually just take one thing that really I’m dealing with in my own life, that I’ve read a lot about as well, and I try to merge the Stoic thinking with stories, examples, ideas that bring the ideas in the book home to people in a way they can actually use or apply.

AL               Let’s go to a couple of favourite stories in there. In Obstacle is the Way, do you have a favourite tale that you think epitomises the sense in which an obstacle can be turned into a path forward?

RH              I was actually just thinking about this with Marcus Aurelius specifically. I’m doing a talk about him tomorrow. One of the ancient historians, Cassius Dio, says Marcus Aurelius does not meet with the good fortune that he deserved. He said almost, not only did Marcus Aurelius have bad health, but almost the entirety of his reign was beset by troubles.

                   There was a flood. There was an invasion. And then there was this little thing called the Antonine Plague which ravaged Rome, not for one year or two years like Covid, but for 15 years. It killed 10% of the Roman population, just a devastating, enormous plague that would make Covid look like a walk in the park.

                   But anyway, Cassius Dio was saying this. But, he says, it made me admire Marcus Aurelius all the more  because he never lost command of himself. He says, and because he never lost command of the empire either, meaning that basically because of Marcus Aurelius’ difficulties, he became the Marcus Aurelius that we know and admire, that he used this. Just as Marcus Aurelius says the obstacle is the way, so he actually lived that idea in the midst of the adversity that he faced.

                   My favourite story of Marcus Aurelius is actually, at the depths of the Antonine Plague, as Rome’s treasury is depleted, he leads a two-month sale of the imperial treasury. He sells off the palace jewels. He sells off their furniture. He sells off his wife’s robes, their perfumes. And he does this because everybody else was suffering. Why should he need all this stuff when other people could benefit from the money? To me, that’s just a great example. It’s like everything fell apart, and what Marcus did was step up, and to me, that’s what the idea of the obstacle is the way means.

AL               To go to the value of courage, I think this is one of the hardest for those who are living in a safe modern community. Unless you sign up for the military, you’re relatively unlikely to be putting your body in danger. But how do the Stoics see courage, and are their particular stories of people who’ve executed moral courage that you find particularly speak to you?

RH              That distinction that you just made is a really important one. There’s physical courage and moral courage, and it would be wonderful if everyone who had physical courage had moral courage, and everyone who had moral courage had physical courage. But unfortunately, they’re often not correlated, but yet both are very rare. Physical courage is running into battlefields. It’s also running into a burning building to save someone. It’s also a frontline worker in the middle of a pandemic. It’s putting your physical body at risk.

                   Moral courage though would be… I was thinking about this as well. There’s a woman named Katalin Karikó. She worked for 30 years, basically in the bowels of academia, on this line of research that everyone thought was fruitless. She never made more then $60,000 a year. She constantly had to re-apply for her own job. But previously, she came to America having escaped Communism in Hungary with $900 stuffed in her daughter’s teddy bear.

                   And if this name is sounding familiar at all, it’s because Doctor Karikó would go on to be one of the primary contributors to the mRNA research that’s now given us the vaccines that have saved hundreds of millions of lives all over the world. Moral courage is sticking to it. Moral courage is persevering down a line of enquiry that everyone is criticising and looking down upon. It’s avoiding the spotlight because there’s something important that you want to do. It’s being laughed at. It’s being criticised. It’s doing the right thing because you think it’s the right thing.

                   Moral courage to me is arguably more important and, unfortunately, rare. We see this in American politics all the time. Someone will be a military leader who enters politics, and then turn out to be a complete coward. They’re afraid to tell the truth. They’re afraid to lose their job. They’re afraid to risk criticism or controversy as a politician. This is a person who could run fearlessly into battle, have no problem being shot at, but doesn’t want anyone to angrily tweet at them. So, moral courage to me is the thing we need most these days.

AL               You mentioned in a conversation I was listening to that you’d been looking to try and publish something on the question of moral courage surrounding people who won’t take the Covid vaccine. You and I both totally believe in the science. You and I both think that that is a decision which endangers health. But yet you’ve got some views about how we ought to think about the moral courage of vaccine deniers. Do you want to share your thoughts on that very… I hope this is a topic that makes you as uncomfortable to answer as it does me to ask the question.

RH              I’ll give you an example. There’s a basketball star in the United States, Kyrie Irving. He plays for the Brooklyn Nets. 97% of the NBA has been vaccinated, and he has refused, and he’s refused even though it’s cost him now millions of dollars. He can’t play home games in New York City, in Brooklyn, which just tore apart the team.

                   James Harden, who was his team mate, asked to be traded. And so, Kyrie Irving is clearly willing to sacrifice for his beliefs. Kyrie Irving is clearly willing to be criticised, attacked for his beliefs, willing to be the lone voice amongst the overwhelming majority. Unfortunately, in America, it’s not such a lone voice. The minority in America is unfortunately a pretty sizeable block, so he’s not exactly the only one.

                   But he is, let’s say, even amongst his peers, he is willing to stand alone. So, this brings up an interesting question. Is this courage? Is that courage? Now, you might say that there’s a certain fearlessness to it, but is that what courage is? And I would argue that courage as a virtue, courage in the virtue sense, it’s very difficult to separate courage from the outcome, from the cause.

                   There’s a Lord Byron poem. He says, 'tis the cause makes all that hallows or degrades courage in its fall. To me, the question is, are you standing for something good? Or, in this case, are you standing for your right to inflict your fellow team mates and citizens with a deadly virus that’s killed, at this point, nearly a million of your fellow countrymen?

                   It’s hard to draw a clear line as to what counts as courage and what doesn’t, but I would argue that courage in pursuit of something that is intellectually incorrect, that’s based on misinformation or disinformation, or something that externalises the consequences of your actions onto other innocent people, is probably not what the ancients meant by courage as a virtue. And certainly Marcus Aurelius, who many suspect died of the plague, would maybe have a very specific opinion about people who refuse to take basic public health measures.

AL               Yet it feels to me a little bit like the way in which I look at Japanese kamikaze pilots. I can see the courage in their eyes, but I, in the end, can’t respect the entirety of what they’re doing.

RH              After 9/11, Bill Maher, the comedian, lost a television show because on Politically Incorrect, he had a discussion about whether the 9/11 hijackers were courageous. It is an interesting discussion, and in retrospect, it seemed like we were punishing the wrong person there. We’re punishing the guy talking about it which, of course, he didn’t do it. But it is an interesting question because, is it courageous to crash a plane into a building or a battleship in pursuit of a goal?

                   You can argue again, there’s a certain fearlessness there. But is it perhaps that the fundamentalism, the certainty, which is rooted in ignorance or brainwashing or whatever gets a person to that place, is it actually not that courageous because they have no doubt? Maybe it’s actually the doubt, the fear, and pushing past the doubt and the fear to do a thing that there’s a certain amount of risk to, that makes it impressive.

                   Again, they know they’re not going to walk away from the plane. They know this is the end of it. Is suicide itself brave? You’re leaping into the unknown, but also, you’re not leaping into the unknown because it’s the end of it. I think you could also make an intellectual argument that it’s cowardice embodied because you are essentially leaving the consequences of your actions to everyone but you.

AL               Let’s go to something which is a little easier to tackle, the notion of stillness. You write in Stillness is the Key about a number of important leaders who have employed stillness, particularly Kennedy during the Cuban Missile Crisis. But you’ve also written more expansively about the way in which you’ve looked to build stillness into your life. Do you want to talk a little bit about nature, exercise and making, and how they can bring stillness?

RH              I just found that almost all of the moments of my life that mean anything to me, whether it’s some sort of creative breakthrough that I had, or if it’s time with my family, whether it’s some beautiful memory, at the core of it was a kind of stillness, a quietness, a focus, connectedness, an essentialness to that. So, I tried to design my life and my days around making that possible.

                   Last night, I worked out on my driveway under the stars. This morning, I got up early. I took my kids for a walk. We watched the sun come up. We encountered some deer that were running by. I spent some time with my journal. I didn’t touch my phone for the first hour or so that I was awake. And then I came to my office here and I wrote, without much in the way of interruption, until I’d done what I needed to do creatively for the day.

                   And then, of course, a life of complete stillness is impossible for anyone who is not a monk, who has responsibilities. But only then, after I had accomplished that, did I check the phone, did I make some phone calls, did I read some paperwork, the stuff that’s not exactly stillness.

AL               Have you looked to do more craft and making? You’re on a bit of acreage outside Austin, I understand.

RH              Yes, I live on a little ranch out here. There is something to physical labour that I do quite enjoy. Having two young kids, I’ve struggled and wrestled with. It may be wonderfully therapeutic for me to go out and fix this fence myself. Is that the best use of my time? I find some tension there, especially as my books have done well and I’ve got a number of other responsibilities.

                   I don’t have the time to do some of the meditative practices that I’d like as much as I had at different phases in my life. But I do find being active, being outside, being in nature, being intensely focused on what you’re doing, is the way to be though.

AL               As they get older, it will become easier for you. I certainly find making things with my boys is one of life’s true delights. Are there other ways in which you’ve looked to build stillness into your day, to carve out that thinking time that I know so many of us wrestle with? I spoke to Cal Newport on the podcast about his views on email and social media, and banishing those technologies. Are there things that you’ve looked to?

RH              It’s a tension for me, and I’ve talked to Cal about this myself. Social media is also the means by which I reach people with the ideas that I talk about, and so there’s a tension between what might produce the most personal stillness for me, and then, what allows me to get the ideas that I think are important out into the world? But I do try to delegate that stuff as much as possible and create as much insulation from those things as possible.

                   To me, the number one way to have stillness in your life is by saying no to things. I think we say yes to so many things. There’s a great passage in Meditations where Marcus goes… Sorry, there’s two actually. My favourite one is he says, are you afraid of death because you won’t be able to do this anymore, whatever that is? You’re afraid of death because you won’t have to sit in the DMV again? You’re afraid of death because you like doing your taxes so much? You’re afraid of death because you really love sitting in traffic? No, of course not.

                   So, just how much of the crap that we do in life, that we don’t actually need to do and don’t enjoy doing, is really sometimes important to remember. But he says, look, with everything you do and say, he says you have to ask yourself, is this essential? And if it’s not essential, by eliminating it, not only did you stop doing something that you didn’t need to do, but you then get the double benefit of doing the essential things better.

                   And so, my calendar had two things on it today. That’s it. And my calendar tomorrow has… I can look. My calendar tomorrow has one thing on it. I’m giving a talk from 12:50 to 2pm. That’s the only thing I’m scheduled to do tomorrow. That doesn’t mean it’s the only thing I’m going to do tomorrow. It just means all that time, all the working time I have tomorrow, with the exception of one hour, is for me. I’m in charge. I didn’t sign up for a bunch of stuff. I didn’t agree to do a bunch of stuff. I’m in control, which is really I think where you want to be.

AL               Your latest book, you said, was on temperance. It seems like the most un-Ryan Holiday virtue, as somebody who is extraordinarily intense, a dozen or so books by age 34, a whole lot of high-powered roles, the New York Times bestseller list and the like. How do you think about temperance, or moderation as it’s sometimes characterised?

RH              The book’s going to be more about self-discipline than that sort of traditional definition of temperance. But I have to be self-disciplined about my self-discipline. I know that sounds like a lot of books, and it was. There’s definitely an alternate universe in which I was more productive, in which I did even more. Now, would that be sustainable productivity? Would that have come at a personal or health cost? Yes. So, it’s obviously about figuring out what you’re capable of doing, where your limits are.

                   And then, when you are driven or ambitious, being balanced with that. One of the ancient emperors, actually the first emperor of Rome, Augustus… When he was younger, his name was Octavian, and he was actually tutored by two different Stoic teachers that I write about in Lives of the Stoics. One of the pieces of advice he gets from them, I think it’s a piece of advice I think of lately as encapsulated in the Latin expression Festina lente, which just means make haste slowly. Sometimes the fastest way to get somewhere is by slowing down a little bit.    

                   In the military they say, slow is smooth and smooth is fast. Slowing down a little bit, being balanced, not rushing things, having some of that moderation, is often the fastest way to get where you want to go.

AL               Yes, I’m often struck by… In my former profession of academia, a lot of the most productive academics were not those who would finish things in a flurry for the deadline, but those who would often get their material in early and then just move onto the next project, and they’re relentless. Do you have a word target in your writing?

RH              A word target like a daily word target?

AL               Yes.

RH              No, I think about it more as, what do I have to write today? So, I break all my books down into smaller pieces, and then I’m just working on that small piece until it’s done. I think less about, is it 1,000 words or 2,000 words or 500 words? And think more about, today I’m working on this section and I hope to make as much progress as possible.

                   There’s a great writer who I love… With just a couple of crappy pages a day, if you’re just making some forward progress every day, eventually you’ll get there. The problem is a lot of people say that they’re writing a book, but if you actually filmed them, you’d notice they spend very little time sitting down and writing.

AL               You must have challenges too because you’ve created a bit of a Stoicism machine around you. I’ve got here on my desk one of your [unclear]. You’ve produced all kinds of leather-bound editions. You’ve got your own bookstore. You’ve got Daily Stoic, which presumably means, on a daily basis, or at least every few days, you’ve got to be producing content. Are you finding that that machine is cutting into your core writing time?

RH              No, this goes to what we were talking about earlier, delegating or building systems around you. I wake up every day and I write because that’s the driving engine of all of that stuff. If I don’t write books that are at the standard to which I write books, not only am I not creatively fulfilled, but the whole thing falls apart. It all breaks. Everything I do comes from that.

                   So, you have to know what the main thing is. The GM of the Los Angeles Rams, who just won a Superbowl on Sunday, he’s a student of Stoicism and he said, the main thing is to always keep the main thing the main thing, and I love that expression. So, what is the main thing?

AL               It’s got a Yogi Berra feel about it.

RH              Yes. What is it that you do? What is the main thing that you do? Because it’s really easy to get caught up in all these other things, or to do other people’s jobs, or to do the fun things. The main thing for me is writing. Everything comes from there. And then I just try to schedule the other stuff in blocks. I write a certain number of Daily Stoic emails during the week. I shoot a couple of videos. I try to use the little in between moments to do stuff here, there. But most of the things that I accept or choose to do, I do only if I know that they won’t impede on the main thing.

AL               In terms of the craft of writing, you came to it in an almost old-fashioned kind of way. I think of your time with Robert Greene as being a bit of an apprentice kind of relationship there. How valuable did you find that, and to what extent do you recommend that to other people looking to become writers?

RH              I don’t think I could possibly put a valuation on it because it was essentially priceless. It was the thing that made me. He taught me not just how to think, but how to actually make a book, from a craftsmanship perspective, not just how to have an idea. But then how to make that idea into a real book?

AL               It was worth dropping out of university for?

RH              Of course. That was my real education. That was my grad school.

AL               I think we’ve got to talk about gender because the Stoic thinkers we talked about are all blokes. Early on in your Stoic books, your stories are mostly men, although I noticed that that’s changing in recent times. And your early mentors, particularly Tucker Max, is from a kind of strand of, I suppose you’d call, toxic masculinity. How has your thinking on gender evolved? What do you think Stoicism has to say to women? And is there a kind of overly masculine side to Stoicism that you’ve reflected on?

RH              I think those are two separate questions, which I’m happy to address both of them. The role of the male-dominated view of Stoicism is I think, one, a reflection of the fact that the ancient world was inherently a patriarchy. It’s not that there weren’t Stoic women in history. It’s that Stoic women throughout history were deprived of their voice.

                   Now, there were a few of them, and in Lives of the Stoics, I talk about Porcia Cato, who’s Cato’s daughter. Musonius Rufus, who is Epictetus’ philosophy teacher, is stunningly progressive in the ancient world, and controversial for it at that, for saying that men and women should both be taught philosophy. So, there’s nothing that says women can’t be interested in Stoic philosophy, just in the ancient world, women were cut out of certain things, and you do have to compensate for that as you tell stories.

                   Part of the reason I tell modern stories in a lot of my books is that I want to be able to highlight people that were, if not intentionally Stoic, at least exhibiting Stoic traits, in the books. And if you only focus on the old, dead white guys from history, you can’t do that. And one of the things Robert taught me, it’s not just that diversity is morally important. But as a creator, if your book is only attractive to a certain sub-set of the population, that’s like a bad business decision.

                   He was like, all cultures, all genders, all ethnicities, all backgrounds, should be in the book. So, that’s a journey that I’ve been on, and I think it’s always something I’ve been intentional about. But I do think I’ve gotten better at it as I’ve gone, and it’s something I’ve looked for more in each of the books. Now, my own history, I’ve had the unique experience of having worked for some controversial, provocative figures, Tucker being one.

                   I was the director of marketing at a company called American Apparel. One connects towards the end of the MeToo movement and another one predates it a little bit. But it always was kind of a surreal experience for me because I never quite understood that. I’ve been with my wife for 15 years now. We met when I was 19-years-old. I’m not someone who parties. I’m not someone who’s interested in these lifestyles that I think have gotten people in trouble.

                   So, it’s been a strange experience for me because it’s so inexplicable to me that one would use one’s power to mistreat someone, or that people would treat people as less than, or not as good as. How did I keep finding myself in these different environments? I don’t have a good answer for it, but it’s something I’ve certainly been puzzled by in my own life.

AL               There’s nothing really Stoic about defacing a Tucker Max billboard so that you can provoke a feminist backlash and sell more of his books, is there?

RH              No, there isn’t. And my first book was wrestling with, just because one’s profession calls for certain things, or just because incentives are aligned in a certain way, or just because one could be very well paid to do a certain thing, is that really what one should be spending their life doing? And I saw that book as… It’s been interpreted different ways by different people, and it’s now coming up on it’s ten-year anniversary, so I’ve seen it go in different waves.

                   But that book, for me, was always supposed to be the end of a chapter of my life. Sometimes it’s interesting when you write a book and you publish…

AL               This is Trust Me, I’m Lying you’re talking about?

RH              Yes. When you publish a book, when it comes out, that’s people’s first interaction with you, even though you’ve moved on from that thing, and that’s why you wrote the book about it. So, I have a strange relationship with that book.

AL               Do you have regrets about that phase of your life?

RH              Yes. Regret is a hard word in that I think it’s impossible obviously to learn from things, in some cases, without having done them, and I wouldn’t be here without the collection of those experiences. I’d say at the beginning of Trust Me, I’m Lying that I was disintegrated. We think disintegrated means falls apart, but disintegrated means also not integrated.

                   Obviously, I’d been introduced to Stoicism. I was writing about Stoicism. I was reading about Stoicism. And then when I look at my day-to-day life, it was so different than those ideas. And that lack of integration is obviously something that baffles me a bit more in retrospect, and something I’ve wrestled with, and tried to become more integrated as I’ve matured and gotten older and had more experiences.

                   But yes, I think I think back to that period and I just go not just, who were these people that I was working for? But who was I? And what brought us together? And what do you learn from that?

AL               Do you believe in free will?

RH              The Stoics would say that we’re these dogs tied to a cart. They talk about the Logos, the Logos being the rhythm of the universe, that we’re like a dog tied to the cart. The cart is the Logos. And that we have some freedom, here or there, but at the end of the day, we’re not fully in control. I’m probably somewhere close to that. So, the universe where I didn’t end up working for those people, I never had those experiences, I would be in a very different place now.

                   And so, I think there is a part of me that just, it’s like, this is how it’s shaking out. What matters is, do you learn from it? Do you grow from it? What changes do you make because of it? I think you don’t have total control, but you have some control is maybe how I think about it.

AL               Drawing you back to that theme of being disintegrated, do you want to talk a bit to the success of Iron Maiden, and whether there’s anything that they teach us about success?

RH              Iron Maiden’s my favourite heavy metal band, also my model for an artistic… Actually, Bruce Dickinson, the lead singer of Iron Maiden, is in Austin for a spoken word tour that he’s doing next week that I think I’m going to go to. Iron Maiden has 100 million albums in 50 years, which is just incredible to think about, considering they’ve basically never been popular, never been on the radio, and they write 11-minute songs about Alexander the Great and poems like the Rime of the Ancient Mariner.

                   It’s an absurd band in some respects, and yet they’ve had this enormous impact because they carved out a niche. They care about only that niche. They do what they do extremely well, and they don’t care if it’s on trend or not. They have a platform. They speak to that platform. And that’s their universe. And I do hope that I’m building something at a smaller scale than that, that stands the test of time and builds a community or a group.

AL               I wanted to ask you too about your book on Peter Thiel, Bringing Down Gawker. The fascinating observation that you make in that book about the fact that when you went to their apartments, Nick Denton, the founder of Gawker, had Seneca on his bookshelf. Whereas Peter Thiel had Machiavelli. How do you think about these two figures? You clearly, in the end, sympathise more with Thiel than Denton, but how did the Stoic lose?

RH              The interesting thing about that book is how much I ended up liking both of them, Nick Denton being the founder of Gawker, Peter Thiel being the billionaire that destroyed it. It was just a surreal experience on every level, and I enjoyed it so much. The weird thing I don’t think I would have expected is that I think I connected with Nick more on the human level and Peter Thiel more on the strategic level, and I might have thought that would have been exactly flipped.

                   Thiel, I’m just fascinated with. I don’t agree with everything that he did. I certainly agree with him less now than I did then as he went on to be a prominent Trump backer, and now he’s backing a number of very reactionary, extreme figures in US politics. But I was impressed by the competence of it all. I feel like in a time of extreme incompetence and ineffectiveness, there was something remarkable about someone setting out to do a thing that no one thought was possible, and then pulling it off without anyone noticing.

                   Again, you can be appalled by it and also impressed by it. Sometimes I feel this about things that Israeli agents do, like they’ll assassinate a world leader or they’ll destroy something in Iran or something. They just pull off these things that you’re like, I’m not really sure you’re supposed to do that, but holy shit, that’s pretty cool that you did it. There’s a certain aspect of that to Peter Thiel that I feel.

AL               But that does go to the central difference between Machiavelli and the Stoics, doesn’t it? Machiavelli is all about tactics and strategies regardless of the end, whereas the Stoics very much, as our conversation beforehand about courage highlighted, the Stoics are very much about the ends as being critical.

RH              But I think you need both. Obviously you need your leaders to have a moral compass, and the ends can’t justify all means. And yet, the argument against Cato as a politician would be that he was not very effective, that he was so morally pure and so unwilling to compromise that he brings about the end of the Roman Republic just as much as Caesar does.

                   I’m of two minds of this and I could argue it both ways with equal sincerity. But there’s a line in Meditations where Marcus Aurelius says, don’t go around expecting Plato’s Republic. You don’t live in Plato’s republic. You live in the real world. And I was telling you about Octavian earlier. Octavian takes power after Rome’s second civil war. He’s the emperor of Rome.

                   There’s a slight problem, which is that Caesar likely had a male heir with Cleopatra, named Caesarean, who lived in Egypt. And Athena Doris and Arius, his two Stoic advisors, they go, you can’t have too many Caesars. You can’t have two rival heirs to the throne. It doesn’t work that way. And Octavian has him murdered.

                   Now, this is obviously unjust and cruel and unsavoury, and at the same time, should Rome have been plunged into a third civil war because he didn’t want to do that? Machiavelli focuses on those questions. The Stoics focus on the higher, elevated questions of meaning and purpose and virtue, but when you’re running the world, what do you do? I’m not saying they can be integrated with each other. I’m just saying that it’s tricky.

AL               That was a stronger defence of Machiavelli than I expected. You, like me, Ryan, are an introvert playing an extrovert’s occupation. What advice do you have for people who consider themselves fundamentally introverted, but would like to have an impact on the world? And look around and see extroverts who they regard as basically pretenders, but who don’t want to go through the almost physical pain of putting themselves out there?

RH              In the US, there’s a rule for that. I forget what it’s called, but it’s basically embodied in the example of Eisenhower, that we need for instance more politicians who don’t want to be politicians, who don’t like politics. And I would say, precisely the fact that you don’t want it, that you would rather be quietly, reflectively thinking about things by yourself, is why we need you.

                   I think the problem with the introvert/extrovert distinction or whatever is that we end up deferring a lot of things to the extroverts because they want it more than we do, even if they’re not more qualified for it than we do. And in some cases perhaps are disqualified precisely by how badly they want and need it. So, you’ve got to put yourself out there.

                   Look, as a writer, of course I would love not to be doing this interview. I would love never to have to get on stage and talk to people. The irony of being a writer is that you became a writer because you like to sit quietly alone in a room and think about ideas as text. And then you succeed at it, and they go, we would like to pay you a lot of money to come do the opposite of that.

                   I just gave a talk to a group of people in Miami, and I was just thinking, this is the exact opposite of… I had to leave my house, go to Miami, which is like another universe, and get up and talk about these ideas in a compelling, extroverted way. It’s so different. But if I don’t do it, it’s not like some different Stoic enthusiast or writer is going to take my place. Do you know what I mean? If someone else could do it better than me, I would gladly defer to them.

AL               Ryan, what advice would you give to your teenage self?

RH              Teenage self? I don’t know what I’d give my teenage self. A little older, I’d just say, relax. You’re taking whatever it is way too seriously. I was just too intense about things, and that’s probably why I ended up in some of the messes that I was in. I was just too focused on winning and not focused enough on asking myself whether it was even a game worth playing.

AL               What’s something you used to believe but no longer do?

RH              That’s a good question. I think Covid has strained some of my faith in certainly people I know and am/was friends with. But just even my understanding of the social contract. Do you know what I mean? It’s strange enough when people won’t do something that’s in their obvious self-interest. And what do you do when they also won’t do it when it would be utterly painless and costless to them, but be demonstrably beneficial to the entire world, and they can’t do it?

                   And not only can they not do it, but they can, as we were talking about with Kyrie Irving, contort themselves into a position where they think it’s actually heroic that they won’t do it. It’s been baffling. There’s a passage in Meditations that I’ve of course read many times where he says, look, there’s two types of plagues. There’s a plague that can take your life, and he’s like, there’s a plague that can destroy your character. And it was only in the pandemic that I came to understand what Marcus was actually referring to there.

AL               When I asked you about loss of belief, I was half expecting you might talk about religion. You’re an atheist, I understand. Have you been that way all your life?     

RH              I don’t know if I would categorise myself as an atheist. I grew up Catholic, and then we transitioned to a more, as a lot of Americans now do, to a sort of non-denominational evangelicalism. Just like, basically, white people Christianity in the United States, which I found increasingly shallow and meaningless. Especially as I went to college, and then went through the young male atheist phase of Richard Dawkins and all these other writers.

                   I’d probably categorise myself as more agnostic today. I certainly don’t think that there is a God or that I have a clear conception of who God is, but I am no longer remotely so presumptuous as to say that I definitely know that there isn’t. I’m very sure that it’s not the God that a lot of people think that it is. You know what mean? I can safely say, you’re obviously wrong or you’re at least doing it wrong. But I don’t know what the answer is.

AL               When are you most happy?

RH              With my kids on that morning walk, or with my wife on the couch in the evening, and then when I’m writing.

AL               What’s the most important thing you do to stay mentally and physically healthy?

RH              Some form of strenuous physical exercise every day.

AL               Mostly running?

RH              Running, biking, swimming. I haven’t swum as much as I’d like to. If I lived in Australia, I would swim every single day. Those rock pools I think are one of the Seven Wonders of the Earth. We have something called Barton Springs here in Austin, which is pretty incredible. It’s basically a rock pool, but it’s a natural spring. But just nothing quite like the ocean, and I don’t live anywhere near the ocean.

AL               I’m training for a half-iron. It’s next weekend. And the swim is in the ocean at  Huskisson where you can just see right down to the bottom. You can see the fish below you. It’s the most glorious course to do. Do you have any guilty pleasures?

RH              Crappy TV like re-runs of The Office or Parks and Recreation or Law and Order. I like just procedural… I like to watch Seinfeld 1,000 times. I like to watch the same hilarious sitcoms over and over again.

AL               Seinfeld rather than Friends, right?

RH              Yes, Friends is garbage.

AL               And that goes to your point before about timelessness. I’ve heard you make this observation, that Seinfeld will endure in a way that Friends just wasn’t designed to.  

RH              I think so, although Friends is having a huge Gen Z resurgence here in the United States because of some of the streaming platforms. But yes, in the long run, what is better art? Friends is garbage.

AL               And finally, Ryan, which person or experience has most shaped your view of living an ethical life?

RH              What person? I think the Stoics have certainly changed me in so many different ways, so I’d probably just put the Stoics in general. I don’t know if there’s a specific person I’d credit though.

AL               Ryan Holiday, thanks so much for taking the time to share your wisdom on the Good Life podcast today.

RH              Thanks for having me.

AL               Thanks for listening to this week’s episode of the Good Life, Andrew Leigh in conversation. If you liked this episode, please tell a friend or mention it on social media. It really helps others find the podcast. If you liked the episode, I reckon you might also enjoy my chats with Martha Nussbaum and Massimo Pigliucci, both of which touched on Stoicism. Next week, we’ll be back with another inspiring guest to discuss living a happier, healthier and more ethical life.


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Cnr Gungahlin Pl and Efkarpidis Street, Gungahlin ACT 2912 | 02 6247 4396 | [email protected] | Authorised by A. Leigh MP, Australian Labor Party (ACT Branch), Canberra.