25. Ryan Holiday: Author of Lives of the Stoics

Book Thinkers family, we have a special one for you today. Today is episode number 25 of our brand new podcast, Book Thinkers: Life-Changing Books. During each episode, I interview one of the world's top authors, and as a listener, you can expect to discover new books, new mentors, and new resources that you can use to achieve more and live better. And so in this episode, I have the pleasure to interview the author Ryan Holiday. Ryan is one of the world's foremost thinkers and writers on ancient philosophy and its place in everyday life. Ryan's a lot of things. He's a sought-after speaker, a strategist, and the author of many bestselling books, including The Obstacle Is the Way, Ego Is the Enemy, The Daily Stoic, and the number one New York Times bestseller, Stillness Is the Key. So as a quick side note, Ryan is one of my all-time favorite authors. So I'm feeling extra special about this episode. One of the books I just mentioned, The Daily Stoic, is a book I've been reading every single day for a few years now, and so it's had a big impact on my life. And our conversation today is actually all about Ryan's brand new book, Lives of the Stoics. The subtitle is The Art of Living from Zeno to Marcus Aurelius. And as a lover of Stoicism, I devoured this book. So without further ado, please enjoy this amazing conversation with Ryan Holiday. Mr. Ryan Holiday, thank you so much for coming on the Book Thinkers Life-Changing Books Podcast. For those in the audience that don't know who you are, can you introduce yourself to everybody?

Yeah, my name is Ryan. I'm an author. I guess every author is sort of first and foremost a reader. So my life has been shaped by books, particularly ancient philosophy, and that's what I've you know, sort of come to write about the last decade or so. Basically, I feel like my books are the synthesis of ancient wisdom but applied to the context of modern life. Mm-hmm.

And your new book, Lives of the Stoics, just came out. It is a fantastic read. I've spent the last week and a half or so reading it. And, you know, I talk about Stoicism a lot on the Book Thinkers Instagram and sometimes on the podcast. Robert Greene and I just had a big discussion about confronting your own mortality and what some of the ancient philosophers thought about that. What is Stoicism and how does it differ from the modern-day definition of stoic?

Yeah. And this isn't my conception, but, but, uh, they sort of make a distinction between lowercase stoicism and uppercase Stoicism. So lowercase stoicism is, is what people think of when they think of stoicism. They think, uh, no emotions. They think really controlled. They think really disciplined. They think, you know, sort of gritting your teeth and bearing it. And there is an element of that in Stoicism, but Stoicism as a philosophy is sort of a vibrant, practical guide for living. The Stoics would say the purpose of philosophy is to live the good life. And that good life for them was, sure, not being ruled by your passions or your emotions, but it was It was so you could be better at whatever it is that you did, whether that was being the Emperor of Rome, as Marcus Aurelius was, or whether that was, you know, being a manual laborer, as Cleanthes was. So the Stoics were a really diverse group of real human beings in the real world who did real impressive things. So when I think of Stoicism as a philosophy, I think of it as a sort of an operating system or a way of going through the world that, that, that makes you not just good at what you do, but also makes you a good person inside of what you do.

When did you first start to read about some of these ancient philosophers? I mean, Stoicism has been around now for almost 2,500 years. And so what, what piqued your interest first? Was it working with Robert?

No, no, it was, uh, not unlike you talk about here, just, It's funny, Stoicism itself is a philosophy that is built around the power of a book recommendation. Zeno, the founder of Stoicism, was at a bookstore and he gets introduced to the works of Socrates. Marcus Aurelius is a young man in his 20s when he's given a copy of Epictetus's lectures. And so for me, I was in college and I asked a person I admired for a book recommendation. I read the book and it sent me down this whole rabbit hole of Stoicism. So sometimes the right book to the right person at the right time can, in my case, change the course of someone's life. But in the case of Stoicism, it can change the course of the world. And so I think Stoicism has always been there, just always sort of been discovered, been passed around. And that's something books are uniquely sorted to do, I think. As great as ebooks and audiobooks are, what a physical book has the power to do is be just a really effective gift, one way of spreading an idea from one person to another.

Yeah, that's an amazing way to put it. We had an earlier podcast guest, Vanessa Van Edwards, and she says that—

I know Vanessa, yeah.

Oh, perfect. Yeah, she says that her kind of like secret passion is book soulmates. She loves to interview people and then gift them the perfect book that can change their life. And so oftentimes that's what I try to find myself doing in the DMs on Instagram and other social media. Just like you're saying, a book is a unique opportunity for somebody to sit down, quiet the mind— stillness is the key— and reflect on what they're reading and participate almost in conversation and sometimes debate with the author. And so it's a really fun way to look at it.

No, of course. Uh, you know, there's a Buddhist saying, you know, when, when the student is ready, the teacher appears. So there are certain books, like, it might be exactly what that person needs. It might be perfectly perfectly primed for what they're going through, but if they're not ready to hear it, it doesn't really matter. So there are books that I've tried to read when I was younger that didn't work, and Stoicism— I feel very fortunate in that not only was Stoicism exactly what I needed at that time, but I went on Amazon and I just bought this random translation, and that one arrived, and I feel like it could have turned out very differently for me. So one of the things for for instance, that I've tried to do in Daily Stoic was answer this question of like, well, I want to read about the Stoics, where should I start? And often what I think about with all my books is I really feel like it's the— like, to me, when a book doesn't resonate with a reader, it's the author's fault. It's never the reader's fault. And so I spend a lot of time thinking and crafting my books to be accessible, to be, you know, sort of grab you by the throat from the beginning. Because if they don't, you know, the idea that a reader is going to put up with something that isn't resonating with them is very unlikely. So it's not just the power of a recommendation. When Junius Rusticus gives Epictetus's lectures to Marcus Aurelius, had that translation been bad or had that edition been bad, or, you know, I don't think that would have been Marcus Aurelius's fault. I think it would have been Epictetus's fault. But the point being, had that not happened, history might have turned out very differently. And so I think there's a huge burden on the author to do a good job, and that's ultimately why you get paid the big bucks, which is a joke, which is the joke, but the point is you have to do the hard thing. You have to spoon-feed it to the reader because if you don't, they're just not going to get it.

Yeah. There are 2 things I want to unpack there. The first is my story with Stoicism, just the 1-minute version. I purchased Meditations by Marcus Aurelius, and I had a very difficult time getting through it. I had never been introduced to Stoic philosophy before. I didn't know anything about it. I think maybe I had read a couple of your other books like Perennial Seller and you know things that weren't related to Stoicism, and I had a very difficult time with it. But my friend Alec, and I'm so thankful for this, he gifted me a copy of *The Daily Stoic*, and he wrote a note on the inside. He's like, "Let's each read this passage every day and have a two-minute phone call about it." I think it'd be a great way to get into this, and so that's what we did, and that's how it started. And so you're right, it's all about the right recommendation. And I think that for people listening, I think Lives of the Stoics is a fantastic book, but I do think you should start with The Daily Stoic if you've never participated in any of this kind of thought before.

No, that's, uh, that, that's very kind and wonderful to hear. It's sort of one of the things, one of the things you, you have to realize as an author is like people are gonna say all sorts of different things about your book. Some people are gonna love them, some people are gonna hate them. The really— the only thing that should matter is when somebody tells you that you did exactly what you set out to do.

Hmm.

So the fact that that book has sold well is, you know, it's nice, it's validating, but like, what I set out to do in the book was solve the exact problem that you were talking about. So to me, that's where you have to define success as a writer, because, you know, Daily Stoic came out during the 2016 election. It could have very easily been swallowed up and not been successful. Lives of the Stoics is coming out into even a crazier time. Um, and, and so you have to detach from most of the external results. Really, you can only ask, like, did you do what you set out to do? But it's a tricky thing with Lives of the Stoics because I'm very proud of the book. It's very good. I like it. I think it's some of my best writing, and I think it's really important. But that exact thing that you just said is something I had to talk to my publisher about. I said, look, I'm going to go out and tell everyone about the book. That's what an author's job is. But I actually don't know if it's the best place to start as far as Stoicism. And then I said, the good thing is I've got a catalog of several other Stoic books, all of which are better. So yeah, if people are interested in Stoicism, they want to learn more, you can read Daily Stoic. I also do a daily email that's totally free. So if you don't even want to spend any money, and there's a podcast version of it too, That for me, the idea of Stoicism is something you have to start to sort of have a vague familiarity with to then really get what's happening when you read the biographies of the figures in this book. So it's not that this is a sequel to Daily Stoic so much as it's just— it's a slightly more advanced or deeper dive into Stoicism. And, and I think it could definitely work if you knew nothing about it, but It's, uh, I think you'd have better luck going into it a bit more familiar with the other stuff.

Well, having read a lot of your other work, and this is something I think we'll touch on a bit later, but I almost view it as a passing of the torch. And I'd love to understand a little bit more about how you see yourself in that role as history plays itself out as far as Stoicism. But the other thing that I wanted to unpack that you mentioned is that you start off each one of your books with an attention-grabbing, like grab you by the throat. And you did that here as well. The very first line of chapter 1, which is about Zeno the prophet, starts with, the story of Stoicism begins fittingly in misfortune. And I'd love to have you tell everybody a little bit about how it started and what— where is Stoicism rooted?

So Stoicism starts in disaster, right? The, the founder of Stoicism is a man named Zeno. His father had been a successful merchant. He'd followed in his father's footsteps. He's leading a convoy of ships. He's carrying precious cargo called Tyrian purple, which is this valuable dye that makes purple, which was the sort of most exotic, you know, fancy material that— color that clothes could be made of at the time. And we don't know exactly how he suffers a shipwreck, but what we're told is that he loses everything and he sort of washes up in Athens sort of penniless, you know, generation of wealth is wiped out. And, and, you know, that, that could have been the end of that story. He could have died, you know, he could have given up, he could have become a janitor somewhere, like he could have done anything. But instead, um, it sets him on this path that eventually turns him into the philosopher that he becomes and the founder of Stoicism. And it— and this little journey trickles all the way through world history. Um, so, but, you know, the key concept in Stoicism is you don't control what happens, but we control how we respond. And that story is a great example of Nobody would have chosen to lose everything in a shipwreck. It was nobody's fault, but it happened. And then what do you do about it? That's what we're all struggling with here in life. It's like shit happens and what do you do about it?

Mm-hmm. Yeah, it's a beautiful lesson. And so could you describe the Stoic aphorism? And I'm not even sure if I'm pronouncing this correctly, but amor fati to everybody.

Yeah, so amor fati is, is just this idea. It actually doesn't come from the Stoics, it comes from Nietzsche, but, but it's, I think, encapsulating the Stoic position, which is basically that not, not just that you have to accept what happens, but you actually have to see what happens as the best possible thing that could have happened because it did happen. So I carry this coin with me. This is the amor fati coin. It just says Amor fati in the front, and then on the back it has the quote from Nietzsche, which is, not merely to bear what is necessary, but love it. And the image, there's a fire on the front of the coin, it comes from a quote from Marcus Aurelius. He's saying, you know, he says, a strong stomach digests what it eats. What is thrown in front of a fire becomes fuel for the fire. And so the idea is, like, it's not just that Zeno endured what happened to him, It was the platform, the event with which assured his greatness. And he did that by not just accepting, but by leaning into it, by finding the best in it. And he equips, actually, he says, fortune did me a great favor by suffering me a shipwreck. He just means that his life wouldn't have been what it was had he not gone through this. And so this idea of amor fati, of using your obstacles as fuel, is just a really key Stoic concept. But it's also just a coping strategy because what else are we going to do? Mm-hmm.

Yeah, it's a beautiful way that Nietzsche put it. By the way, I have my memento mori.

I love it.

Yeah.

Nice.

I'm always rocking that with me. And crazier even still, I'm also just like you, a little tattooed. Could you, you know, and this is something I want to touch later, but because you brought up the coin, could you tell everybody a little bit about your tattoos and And maybe just a couple sentences about each of them.

So when I, when I write my books, I'm really trying to write about a concept or an idea that I want to build my life around, that I think is worth building a life around. And, and I want to distill them down to their absolute essence. So my first Stoicism book was a book called The Obstacle Is the Way, which I have tattooed on my arm here. This comes from a quote from Marcus Aurelius. He says, the impediment to action advances action. stands in the way becomes the way. But what he means is that nothing is so bad that there's not some good that can't come out of it. There's not some opportunity inside of it, that everything we face is an opportunity to practice virtue in some form or another. So that's what the idea of the obstacle is the way is. And then I have ego is the enemy on this arm. Again, I feel like there's no situation that ego is a positive element. You know, no one's sitting around a table and says, we need more egos in this room, right? Ego is a Thing That Makes Things Worse. And then more recently, I did Stillness Is the Key on my wrist, which is the 3rd book in that trilogy. These are, these are sort of, I think, deeply philosophic ideas backed by thousands of years of wisdom that obviously I'm not putting them on my arm for marketing purposes. I'm putting them on my arm because they're sort of aphorisms or mantras that I try to live by.

I do the same thing and I have been for the last 6 or 7 years. I have tattoos and I always— I think about neuro-linguistic programming and positive reinforcement. And I think about my subconscious catching the tattoos that are on my arms and on my body and reinforcing the things that I want to live. And so one of the big, one of the big, really important pillars of Stoicism is that this is a philosophy rooted in reality. All of these principles are things that should be lived and practiced and experienced. And I think that it was Antipater that the Ethicus that first brought it from the realm of debate in politics down into the average person's life. And so what are some of the bigger life questions that Stoic philosophy can help address in your day-to-day life or a listener's day-to-day life?

That's a good question. I mean, Seneca is saying, you know, the purpose of philosophy is to offer counsel. It's to be a guide. It's to help you solve problems of life. And Thoreau said this as well. He said, you know, the purpose of philosophy is not to found a school or to have subtle thoughts. It's, it's to solve the problems of life, not theoretically, but practically. So for me, Stoicism is, you know, a way of managing your temper. It's also a way of managing your fear of mortality. It's a way of, you know, deciding how you're going to treat other people. It's a way of discerning what our obligations to other people are. So when we think of Stoicism, we want to think of it as, as it's, you know, it's not a list of 10 Commandments, like do this, don't do this, do this, don't do this. But it is kind of a, like a set of values that are pretty elastic, pretty flexible, that allow you to translate these ideas into the practical decisions that you have to make in life. Yeah.

There's, there's a quote, um, that, that you have in the section about Panaetius. How do you, how do you pronounce his name?

I say Panaetius, but all these people are dead and they didn't exactly leave us a guide for how they like their name to be pronounced. So I just, people to wing it. Although one of the things that I did in the book is I put a phonetic spelling of each one because— and for people who don't know, you keep saying things like Antipater the Ethicist. That was the other thing is I wanted people to have a way, a handle to grab them by. So Zeno, I call the prophet because he's the one that comes up with the concept of Stoicism. Marcus Aurelius, who concludes the book, is the philosopher king. I just, I wanted people to kind of also understand just the role that each, like, what's the stereotype? What's the role? What's the, what's the quick summation of this person's work? Because to me, the purpose of the book is you read it and then you understand not just what Stoicism was and who the Stoics were, but how they all fit together to bring us to where we are today.

Yeah, I thought it was brilliant that you did that, and it's helped me reiterate and communicate some of the lessons to other people in my life. But the quote from that chapter of the book was, learn, apply, learn, apply, learn, apply. This is the Stoic way.

Yeah.

And so, you know, with Book Thinkers, my goal is to help people create real behavior change, to really make an impact on their lives, to take the lessons from these books and apply them ruthlessly. Reflect, you know, apply, kind of the same thing that you're talking about.

Yeah, that— I mean, look, that's the whole purpose of reading, right? We're not— Seneca says, you know, philosophy is not a parlor trick. It's a thing to alleviate suffering, to guide behavior, to make you help or to help you reach your potential. So the purpose of reading has to be a happier life, a wiser life, a more courageous life, you know, a a more generous life. So the purpose of the philosophy is you're learning, and then you have to be out in the world doing things, and then you have to apply what you've read to those things. Like, one of the, one of the things that I've been very deliberate about in my career— this is before I was a writer and then after— is that I've always been trying to have a couple different irons in the fire, different projects, even if those, you know, sometimes feel a bit onerous or they take a lot of time, because you don't want to be in a place where all you do is talk about things, right? If you're just a writer, it's very easy to get lost solely in the world of ideas. Even, you know, just having investments or having a business that you operate or volunteering at a charity or, you know, having this side hustle that you're doing, all these things, what they allow you to do is apply those ideas somewhere other than the— than to other ideas. And so you're allowed to test them, that you get real feedback, and that's just a really important part of it.

From that same section of the book, you talked about this philosophical club, the Scipionic Circle. Do you have something like that in your life? Are you talking about these concepts with the same people on a consistent basis?

Yeah, absolutely. I mean, one of the things I built at Daily Stoke, we built this program called Daily Stoke Life, which is sort of a membership group where people can join and they can hold each other accountable and we discuss philosophical ideas and we have a book club and stuff like that. But in my own life, I know I'm a product of the mentors that I've had and the relationships that I've had. And so I have a few different group text threads that I'm on. I'm in a few groups of different authors who get together a few times a year and go over stuff. There's a few conferences I attend. I'm a pretty introverted person, so I would prefer generally to be at home with my books writing, but if you're not also being exposed to different perspectives, not only are you cutting yourself short in that sense, but you're forcing yourself to learn a lot of things by trial and error that other people might have been able to save you trouble on. Every time I leave one of these events, I have a big list of things that I'm going to go do and then I do them. And then, like we're saying in the quote, you learn, apply, learn, apply. I apply them and then when I come back the next year, the next time we meet, I've got, okay, here's what I learned, here's the questions, here's what I tried. And that process of sharing and reciprocity is a really important driver.

Yeah. One of the reasons that Book Thinkers and my brand actually started is because the same guy that gifted me The Daily Stoic, we had both read Think and Grow Rich by Napoleon Hill around the same time. And he talks about this concept of a mastermind group and that, you know, 2 minds focused in the same direction, 1+ 1 can equal 3. A 3rd mind gets created that can help, I don't know, more fuel on the fire, if you will. And so, I think it's important for a lot of people to talk about these concepts as they're learning them and apply, apply, apply.

No, it's important. I mean, Napoleon Hill was a con man and a criminal. So, it's— there's sort of a blind pig can still find a few truffles. But the concept of masterminds is a great one and a really important one. And I think it doesn't have to be something in person, but you can have mentors who are not alive, but a mastermind has to be filled with real modern-day human beings who you're having discussions and you're sharing things. And EO, which is called Entrepreneurs Organization, is a great group like that. There's an event I've attended for many years called Mastermind Talks, which is really great. You know, TED is a version of that too. So yeah, it's like, it's got to be a multifaceted conversation, multidirectional conversation where people are putting— it's like everyone's putting all their stuff in a pot and then somehow magically what comes out is greater than the sum of its parts for everyone. And that sort of interchange between people is really effective. Mm-hmm.

A lot of the ancient philosophers, like, sitting on the porch discussing these ideas, you know, there's the adjacent possible that comes from 2 things being combined and kind of colliding, which is beautiful.

Yeah, Stoicism very distinctly is found— takes up shop in the agora, right? Not far from town. Epicurus famously starts this garden, which is this private space that people are not allowed into. But Stoicism, stoa just translates as porch. The porch was accessible. It was out in the open. It could hear the sounds and smells and energy of the marketplace. And so, yeah, as a philosophy, I think you have to see it as a collaborative exchange, and it makes everyone who's touched by the exchange better for having been involved.

I'd like to pivot over to something related to young professionals because my audience is primarily young professionals in the United States, and I'd love for more of my peers, I think, and your peers to take on Stoic philosophy and to understand it a little bit more. In your chapter about Cicero, there's a quote that says, that is the critical question of nearly everything Cicero did, as it is for so many young, talented, ambitious people. Were the motivations sincere? Yeah.

Or were—

or was it all part of some plan? Are they training or resume building? And so what advice do you have to young professionals who are deciding what career path to take or where to apply their time outside of maybe their main job?

I have a chapter in my Ego book about John Boyd, who's one of the sort of great strategic minds of the 20th century. And he would— it was sort of a mentor of a lot of young officers in the Air Force. And as he saw them sort of making their way up through the ranks, he would eventually give them all what he would call the to-be or to-do speech. And this is essentially a fork in the road. He's saying, are you going to try to be an impressive— are you going to try to be an impressive person, meaning have a high rank, have a nice, you know, job, you know, be well-liked, or are you going to try to do impressive things, which is often going to put you at odds with the status quo. It's often going to mean you have unpopular views. It's often going to mean that you don't get the sexy assignments, but you get the ones where you can make a real difference. So this idea of to be or to do is really important, and it's something I've struggled with in my own life, in my own career. I was, you know, by the time I was 21 years old, I was running marketing for a publicly traded company, and I, I've built various different businesses, and I very easily could have continued down a lot of those roads and and would most likely still be on them and be quite well paid and maybe even well known for those things. But I took sort of a hard pivot at some point in my mid-20s to decide to become a writer because, one, that was what I really wanted to do. Two, I felt like that was where I could have the most impact. But even inside that decision, my first book was a very popular book about marketing. And I was actually— I just interviewed my editor I had her on the Daily Stoic podcast and I was talking to her and I said, what did you think when I came to you with this book about ancient philosophy? And she said, well, your first marketing book had been successful and you did this other marketing book. We kind of just hoped you would get this out of your system. And I had no intention of getting it out of my system. I was writing that book because I really cared about it. It's really what I wanted to do. It's what I thought would be the most meaningful and fulfilling, but also the most important. Really deciding where you want to go and what you want your life to be like. I remember I was at American Apparel. I wanted to be a writer. I'd done some writing, but I was also very successful as a marketer. I remember I was at Adweek in New York City, which is this big multi-day event across the city. Everyone goes and it's lots of big parties and you're launching new campaigns and pitching things and finding out about new technologies. And I remember I went the first year and I was a kid and I was the only one, you know, sort of not wearing a suit. And then the next year I wasn't wearing a suit. And then the third year I remember looking around and thinking, if I keep coming to this, eventually I will be in a suit, right? Like, I'm only going to be the kid who the rules don't apply to for so long. And I just— it just struck me that that's not who I wanted to be. I didn't want to be one of this 1,000 people that were in this room. I didn't particularly respect any of the work that these people were doing, and I definitely didn't think it mattered in any significant way. And so my decision ultimately to break off from that and to take this sort of hard left turn in my life came from, you know, that sort of similar crossroads. Who do you want to be? What do you want to do? What kind of impact do you want to have? It's just when you're talented, not only do you have lots of options, but there's often very real temptations or opportunities attached to those options that are hard to turn down. And that's certainly something that Cicero struggled with.

Yeah, you actually have a quote in the section about Cato the Younger where you say he was not playacting, he was practicing. And essentially resisting temptation. And so it seems like you're not play-acting this role of carrying the torch as a Stoic sort of observer. I mean, you really are practicing and acting.

I mean, I'd like to think so. I mean, I think I feel like I'm sincere. I feel like I care about it. It is deeply important to me. But I think the challenge that the Stoics present to us is is essentially the idea that just to write and think about these things, to live a sort of contemplative life, is not— is necessary but not sufficient to be a philosopher. That this is a title you earn, and you ultimately earn it with your results. So, you know, I mean, are there things I could do that could make me much more successful as an author that would be a violation of the philosophical principles? Sure. And I try not to do those things, or I don't do those things. But I don't give myself a lot of credit for what I don't do. So I feel like I'm sincere. I feel like I'm committed, but I'm always trying to grow and go, okay, what would— what's the next step in this? What's the next obligation? What's the duty, you know, once you've gotten this far along? So that's just something I'm always thinking about.

It's interesting. It's one of those kind of personal questions that I wanted to ask you. And it's because participating in social media, you have some people that, that I think they look at some of the original Stoic texts or the translated Stoic texts and they say, you know, Ryan Holiday is not a philosopher. And I say, he's not trying to be a philosopher. You know, he's trying to consolidate this history of countless, you know, philosophical representations. They all kind of boil into this one thing called Stoic philosophy. And he's trying to make it digestible for other people. And so I wanted, you know, I wanted your thoughts on that.

No, I appreciate that. So I'm a writer. So I— that's what I did before I wrote about Stoicism. That's what I've done even while I've been writing books about Stoicism. And ultimately, my books, even about Stoicism, are a platform for my writing. So I think society has much need and much less, frankly, interest in a philosopher, like someone who's coming up with ideas of philosophy, right? I have a skill as a communicator of ideas. I think my track record with my own books clearly proved that, but I've also sold and written huge projects for other authors and public figures. I know how to write. That's my skill. And the way that there might've been other Stoics who were woodworkers and there were Stoics who were architects and there were Stoics who were leaders of troops in battle, my skill is that I'm a writer. And so that's how I make my living. It just also happens that Stoicism, the philosophy that I try to practice, is one of the things that I write about. But if you were to remove every Stoic book that I've ever written, I would still be an author who sold hundreds of thousands of books, who's been on multiple bestseller lists, who would be like a successful working writer. So I think when people are going like, oh, Ryan's just writing about this, it's like, yeah, that's what I, that's what I do. That if I was a comedian who is a Stoic and you said, oh, he's just joking about the philosophy, he's not a philosopher, it'd be like, you're missing the point. I'm a comedian. My job is to tell jokes. and some of, if not a good portion of those jokes are influenced by or contain Stoic ideas, that's just because it's hard to separate those 2 things. Does that make sense?

It makes complete sense.

Yeah.

And I think that, not that I need to play the role of advocating on behalf of anything, but it helps me to articulate, I think, when I receive questions about that, because Stoicism is incredibly powerful. I'm obviously an for practicing the philosophy in my day-to-day life. And so I will stumble upon people who have questions about that. I'm happy that, that you articulated it in that way because I think that I can also use the way that you just articulated that to explain my own involvement in the practicing of this philosophy.

Well, one of the things you discover as you, as your work goes out into the world and it reaches people is that at a certain point or eventually, there's a percentage of people who just don't get what you do at all, and it rubs them the wrong way, or they hate it, or they disagree with it, or they just have generally very strong opinions about you. This is true for all the Stoics, but it's been true for every artist and creator and public person of any kind for all of history. You have to get to a place where you're okay with that. And more importantly, when you were— we talked about this earlier where you were sort of describing exactly what I tried to do with, with The Daily Stoic. One of the reasons that has to be your notion of success, like, did you do what you set out to do, is you have to be able to come to terms with the fact, even if certain members of the audience can't, that it's not for everyone. So oftentimes when I'll hear from people who really don't like what I do, or they're upset, or they're, you know, writing some angry thing about me on the internet, is they're often explaining quite upfront, whether they know it or not, why they are precisely the person that I was not intending this book for.

Mm-hmm.

So, of course, they don't like it. Do you know what I mean? Like, if someone is doing a very specific kind of art, you know, if someone is doing a beautiful dance and I don't like dance, why would I have my opinion about that dance is incapable of judging whether it's a good or bad version of that thing. And so, once you kind of really figure out who you're for and what you're trying to do, it allows you to be much more secure as an artist because the person who thinks that they're criticizing you is actually telling you that you're on the right track. Brian Koppelman told me this once. He was You know, he was saying that the movie Rounders is supposed to have a lot of dialogue that people would quote to their friends. So when people would read the script and go, it's just full of quotable dialogue, he's like, that's the whole point. You know, that's all we were trying to do. And so when you get there, you're able to parse feedback effectively, which is a difficult thing to do, but ultimately very essential.

Yeah, we all, you know, everybody in the audience, I think, has made certain decisions in the way that they want to represent themselves to the world. that will, you know, that will cater to a very specific group of people. And then that, you know, that means by default that there will be other people that don't agree with them. And so, you know, Stoicism as a philosophy does teach you how to care a little bit less about the people that you're not intending to reach, you know, which is—

Yes.

It's fun to put it that way. Stoicism has 4 virtues. And before we go into, you know, some of my final questions about some of the more popular Stoic philosophers, I'd love to have you explain the 4 virtues to everybody.

So the 4 virtues of Stoicism are really the same 4 virtues in Christianity and a lot of different philosophical schools. It's courage, temperance, sometimes rendered as self-discipline or moderation, then justice and wisdom. And so obviously these are virtues that are difficult to separate from each other, but are all kind of interrelated and yet somehow distinct. And so, you know, what, what, when Marcus Aurelius is saying the obstacle is the way, What he means is that you, you know, you set out to do something, you know, you were trying to help someone, right? So that's the virtue of justice. Well, now all of a sudden you're besieged by people who are trying to prevent you from doing that. And now you need courage to push through that resistance. So when he's saying the obstacle is the way, what he really means is that everything is an opportunity to implement or execute one of those virtues. It's not always the easy one. It's not always the one that you intended, but nothing can prevent you from doing that.

Yeah, it makes total sense. I love it. And I also love how you— I've seen your reading lists. You read a lot of other schools of thought and religious thought and things like that. So what role have those other philosophies played in your understanding of Stoicism?

Well, I've always been of the mind that the Stoics are dead. And so they didn't pass on the word of God. They passed on the best that they knew at the time they knew it. And the vast, vast majority of that has been validated over thousands of years, but some of it hasn't. And I take my cue from Seneca. Seneca, the most quoted author in Seneca's works is Epicurus, who's ostensibly the head of a rival school of the Stoics, the Epicureans. So I think the Stoics were always open-minded. They were always looking for wisdom wherever they could find it. So I'm trying to do 2 things. I'm trying to read things that illustrate the Stoic principles, whether it's biography or history, and then I'm also looking for disagreement or new ideas. And it's all sort of going into the mixer and hopefully coming out in some, you know, either material for one of my books or, you know, something that teaches me and that I can apply in my own life.

You just mentioned Seneca. Could we transition over to a little bit more about Seneca specifically and how Seneca represents this philosophy?

Yeah, so Seneca is one of the great Stoic thinkers. He's not just a philosopher, he's a senator. He's also Rome's— one of Rome's greatest playwrights. And then he happens to be Nero's tutor, which is— so he ends up sort of as the advisor to one of the most controversial and sort of unstable emperors in history. So he sort of, you know, got his hand in a lot of different things. But he primarily survives to us today in the form of his writings. His Letters of a Stoic is one of the most beautiful collections of letters I think ever published. Some of his essays on anger, on the shortness of life, on tranquility are just sort of beautiful, deeply provocative explorations of these Stoic ideas. And so I'm fascinated by Seneca, and we spent a good chunk of them on the— good chunk of the book on him because He embodies the best of Stoicism, but then also poses all sorts of morally vexing questions. You know, how could someone who believes in moderation have become so fabulously wealthy? How could someone who believes in virtue and ethics be an advisor to one of the worst dictators in Rome's history? And I think obviously if Seneca was here, he'd probably render a really articulate, persuasive answer. All we can really do is speculate, but he's a fascinating, fascinating figure.

I did read on the shortness of life, and I love confronting mortality because I believe it's something— and I just talked with Robert Greene a lot about this subject— I believe it's something that in 2020, coming into 2021, we've sort of taken death as a subject and we've shelved it. We try to ignore it. We don't pay enough attention to it. What does, you know, what are some of your thoughts and how do you confront your own mortality and reflect on it?

I don't know if I totally agree with that. I would maybe argue that 2020, of all the, you know, years of the modern era, has, you know, outside of, you know, let's say World War II or Vietnam or Korea, has forced, especially in America, but all over the world, has forced us to reckon with our mortality you know, in ways that we obviously have chosen not to, but have tried to avoid having to do for a very long time.

Mm-hmm.

I think the United States, as we're recording this, yesterday passed, you know, 200,000 COVID-19 deaths. It's probably, you know, closer to 250,000 or 300,000. It's, you know, this pandemic that we're in, you know, it feels abnormal, but the reality— Marcus Aurelius survived 15 years of the Antonine Plague before ultimately dying of it. So, In Rome, death wasn't this abstract, distant thing. You know, people died all the time. They died young. They died in their own houses. You know, they died tragically and suddenly, often violently. And so death was ever-present. And yet even then, the Stoics talked constantly about death. James Rahm has a translation and edited collection of Epictetus— or sorry, of Seneca— just called How to Die, and it's like 300 pages. It's one of the common themes from the Stoics. The other coin I have in my pocket is the Memento Mori coin, which you were pointing out earlier. The idea of Memento Mori just means remember your mortality. Marcus says, and this is on the back of the coin, he says, you could leave life right now, let that determine what you do and say and think. How we manage the little bit of life that we have, which really, and all we have for certain is this present moment, defines, I think, who we are. And sure, it's easy to wish things were otherwise. It's easy to deny it. But Cicero says, to philosophize is to learn how to die. The whole point of philosophy is to wrestle with the unfair, unnerving, unpleasant reality that we don't have unlimited time.

Yeah, it's a great point on COVID-19. I wasn't looking at it through that lens, but I'm happy you brought it up. I think a lot of people are being faced with death a lot more than they were a couple of years ago. So that's it.

I mean, look, mayors and governors are having to call up freezer trucks because they're running out of burial space in some cases. That feels shocking, almost third world, but that was the reality of— the Spanish flu, they think, killed 50 million people 100 years ago. There was a— there was an outbreak of influenza in 1967 that killed tens of thousands of people. This building that I'm talking to you from was built in 1888. It survived not just, you know, the Spanish flu, but, you know, typhoid epidemics, you know, all sorts of different epidemics, smallpox, whooping cough, you know. people just didn't live the same amount— didn't live as long as they do now. But more importantly, the average lifespan was cut short because young people, you know, Marcus Aurelius lost something like 7 children, which is just, you know, unfathomable, but not particularly abnormal for ancient Rome.

Mm-hmm.

And so, you know, death was just much more present in the ancient world. And I think we can learn from their sort of dance with it. And there's, I mean, there's a whole form of art called the Danse Macabre, which means the dance of death. You know, there's all these paintings of dancing skeletons and, you know, the idea of memento mori as a reminder was just, you know, a much more common thing.

Yeah, for me, it's been one of the easiest ways to communicate some of the more popular aphorisms and, you know, To get people interested in Stoic philosophy, like this documentary just came out, The Social Dilemma on Netflix. Did you have a chance to watch it?

No, I've heard a lot about it though.

So, you know, the— I guess boiling down the main theme is that big tech is mining for our attention. And so as we become zombies to our phones, prioritizing our life by realizing it's not that we don't have a lot of time on this earth, like Seneca says, it's that we're not using the time the right way. And so that, for me, the reason that I have that tattooed is so that I can look in the mirror every day And think to myself, I need to make the most of my time. You know, I need to make sure that I'm practicing. You mentioned Marcus. I'd like to kind of wrap up with a conversation about Marcus. He to me is the most popular of the Stoics. I think the name that is most easily recognized. Who is Marcus Aurelius and why was Meditation such a profound book for you?

Marcus Aurelius is the, is maybe the only example of a philosopher king ever in history. Um, this was a young boy. His father was not emperor. He was chosen. The Emperor Hadrian senses some, some, you know, almost, uh, supernatural, uh, ability in this boy. And he, Hadrian adopts a man who in turn has to adopt Marcus Aurelius to set him in line for the throne. And, and when Marcus does eventually take over in his, in, I think, his late 40s, early 50s, He, you know, proves to be like one of the few exceptions to this idea that absolute power corrupts absolutely. Now, it would have been wonderful had Marcus lived in a time of peace, in a time of plenty. You know, what— we can only speculate what sort of social reforms he might have put in place. Would he have freed Rome's slaves? Would he have restored the Republic? There's any number of things that he might have done, but Even the historians, even some of the ones that are not a big fan, sort of laments just what ill fortune he was met with. You know, Rome spent most of its time at war. They were invaded. There was the Antonine Plague. You know, there was all sorts of incidents. So Marcus's reign isn't necessarily one of sort of towering greatness in all its, you know, wonderful achievements, but But he manages to survive and thrive within incredible adversity and sort of prove himself a worthy opponent of all of it. And just in his own time was worshiped as perhaps the greatest leader to ever live.

I have a little bust, I guess, this shoulder of Marcus. Me too.

Let me find it. This is a bust I bought when I was writing Obstacles Away. It's from the the 1840s. And it was much more common 100 years ago, 200 years ago, 500 years ago, 1,000 years ago, a person was expected to have some— he was such a great leader, such a symbol of greatness, that he was one of the people that people would have in their houses. And it wasn't in a sort of sycophant way that a lot of the worship of other emperors was. It wasn't out of fear, It was that he really just embodied the best of what people are capable of becoming. And that's what I think of when I look at it.

Yeah, me too. It's a really good way to look at it. Have you ever been to Greece? Or have you visited Rome?

I've been to Rome many times. I've unfortunately never been to Greece. I was supposed to go for the launch of this book. And that didn't end up happening. But I was— one of the last trips I took before the pandemic, I was in Budapest, which is where Marcus wrote a good chunk of Meditations. And so it really is incredible. You can walk some of the same city streets that, you know, these figures, you know, would have seen on a daily basis, which is always a sort of humbling thing to do.

Yeah, I had my entire family, my mom, my dad, my brothers, some girlfriends, we were all supposed to go to Rome. as well as visit Pompeii during the pandemic. And that's been canceled or rescheduled. But I couldn't wait to sort of walk some of those streets and feel what you were just talking about. It's probably a very humbling experience.

Definitely.

Yeah. Something that I really love that you talk about, and this question I get all the time, people ask me about putting down a book. And so in your conversation, where you actually interviewed Tim on his, on his podcast, you talked about the rule of 100.

Yeah.

Talk about that with everybody.

It's definitely not my rule, but I've definitely stolen it and spread it a lot. The idea of like, you owe a book 100 pages minus your age. So as you get older, again, this idea of memento mori, you have less time to waste. I am very, very strict with the books that I read, or with the authors that I give my time to. If they're not doing a good job, I'm out. There's too many books to read. To me, the cost of reading a bad book is quite high, and I'm definitely not going to spend time, too much time with an author that I think hasn't been doing their job. Ultimately, the job of an author is to make ideas both accessible and interesting and then practical.

Understanding that a book recommendation is in most cases, very personal. Are there some general books, books that you've gifted the most to people that you'd like to mention right now?

Yeah, I mean, I'm obviously a huge fan of Robert Greene, has been sort of the guiding sort of influence in my life. His book Mastery is incredible. 48 Laws of Power is a must-read. Meditations by Marcus Aurelius, I usually recommend the Gregory Hayes translation. I think it's, it's the most accessible of them. I'm a big reader of biographies, so I've written about that before. There's not like one biography I'd read, but like, the Lyndon Johnson series by Robert Caro is incredible. The William Manchester series on Churchill is incredible. The Edmund Morris series on Theodore Roosevelt is pretty incredible. So I'm a big believer in those epic biographies. I find you just learn a a ton from them. It's funny pitching a new book, but I tend to read older stuff. I like stuff that's been validated by the test of time. So those are my rules for books.

In that same podcast discussion, which I listened to earlier this year, you guys were talking about that concept of you need to wait until something has been validated before you really know whether or not the impact or the author lived out what they were trying to Yeah, I think that's right.

Like, let's say I'm looking for a biography of someone. I don't read the newest one. I try to read the best one, or maybe one from a generation or two before. It might not have as much cutting-edge stuff in it, but it will also be as, you know, un— it will be as detached from the current moment as possible and allow you to get a little more perspective.

For For people who are looking to learn a little bit more about you and your works, they're interested in Labs of the Stoics, where should they go? What should they do?

So, uh, ryanholiday.net, that's where I write. That's where I do my reading newsletter. And then Daily Stoic is the sort of, uh, hub for all my Stoicism stuff. We do a free email there every day. There's a free podcast every day. Um, on Instagram, we do a quote and videos every day as well. That's just @DailyStoic. So basically @RyanHoliday, @DailyStoic, pretty much anywhere and you'll find my stuff.

That is a wrap. Thank you so much for taking the time to listen to this week's episode of Book Thinkers, Life-Changing Books. To discover more books, more mentors, and more resources that you can use to achieve more and live better, make sure you check out our website at www.bookthinkers.com. There you'll find links to our mobile application, more podcast episodes, our shop so you can get some Book Thinkers swag, and our socials. With that, I'm signing off and I'll see you for next week's episode of Book Thinkers Life-Changing Books.