Pod Insights The Daily Stoic Premium (🔓) The Stoic Formula For Timeless Success | Ryan Holiday About this episode What separates the work that fades from the work that endures? In this episode, Ryan explores the Stoic wisdom behind lasting success and how to turn adversity into something timeless, meaningful, and built to outlive you. 📖 Preorder the final book in Ryan Holiday's The Stoic Virtues Series: "Wisdom Takes Work": https://store.dailystoic.com/pages/wisdom-takes-work🎙️ Follow The Daily Stoic Podcast on Instagram: https://www.instagram.com/dailystoicpodcast🎥 Watch top moments from The Daily Stoic Podcast on YouTube: https://www.youtube.com/@dailystoicpodcast✉️ Want Stoic wisdom delivered to your inbox daily? Sign up for the FREE Daily Stoic email at https://dailystoic.com/dailyemail🏛 Get Stoic inspired books, medallions, and prints to remember these lessons at the Daily Stoic Store: https://store.dailystoic.com/📱 Follow us: Instagram, Twitter, YouTube, TikTok, and FacebookSee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info. 📢 Share | ⚙️ Manage Subscription
Transcript Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.
0:04 Ryan Holiday? Welcome to the Weekend Edition of the Daily Stoic Podcast. On Sundays, we take a deeper dive into these ancient topics with excerpts from the Stoic texts, audiobooks that we like here or recommend here at Daily Stoic, and other long-form wisdom that you can chew on on this relaxing weekend. We hope this helps shape your understanding of this philosophy, and most importantly, that you're able to apply it to your actual life. Thank you for listening.
0:43 Ryan Holiday? Hey, it's Ryan. Welcome to another episode of the Daily Stoic Podcast. I hope you are having a good Sunday. I am having a great week. This is my last day in Ithaca, and then we are off to... Where are we going next? We're gonna go see the Temple of Apollo at Delphi, which is where Zeno, as a young man, is given a prophecy which would set in motion the creation of Stoic philosophy. I'm really excited about that. That's the traveling I'm doing now. But back in February, I was in Nashville. I got to speak at the Country Music Hall of Fame Theater, like, one of the coolest venues I've ever been in. I was talking a little bit about Stoicism, and I do tell the story of Zeno and his shipwreck. But mostly, I was talking about my experience
1:28 Ryan Holiday? taking what was then a relatively obscure philosophy and making it accessible and interesting to people, people like you. The idea of doing a daily podcast about Stoic philosophy would have been insane in 2012, when I went to my publisher and pitched them the idea for what became The Obstacle Is the Way. And I was talking to this group. It's this group called the Tugboat Institute. And it's a fascinating group. Basically, it's these sort of interesting companies from all over the world. But it's all about sort of evergreen companies, like, not like... Creating a company, getting a lot of hype, and then flipping it to someone else. It's not about trends or fads.
2:10 Ryan Holiday? One of the companies, I think they've been in business for like 300 years or something. It's not about getting big fast or getting rich quick. Tugboat is about building like sustainable, generational, persevering companies, which is of course, something I think Stoicism can teach us about. And something I've tried to think about as I've written my books. I obviously have a whole book about this called Perennial Seller, which is more from my previous life in marketing and consulting. But anyways, it was a short talk. I was only on stage maybe 20, 25 minutes. So I thought I'd just bring it to you. Maybe it might be interesting to you to sort of hear how I think about these things and then learn some of these lessons. Not just what the Stoics can teach us about life, but what can they teach us about building something that lasts? And I do think they can teach us a lot.
2:54 Ryan Holiday? So thanks to the folks at Tugboat for having me out. Thanks to the Country Music Hall of Fame for letting me, you know, grace their stage. Oh, man, it was crazy just looking at the people who'd been in the same green room. It was absolutely nuts. I think you'll really like it. And now I'm excited. We're gonna go have dinner last night here in Ithaca and then take the ferry back to the mainland tomorrow. So I'll talk to y'all soon.
3:19 Ryan Holiday? Stoicism is a philosophy that comes out of a disaster. The essence of Stoic philosophy is this idea of whether that tragedy, that event that befell you, whether it's going to be unfortunate or fortunate. The Stoics would say, we get to make that choice. We decide, not just in how we perceive it, but in how we respond to it, what we make of it, what it makes us into.
3:45 Ryan Holiday? A little over 10 years ago, I'd just written a bestselling book about marketing. It was doing well. I had a whole career trajectory in front of me. And I went to my publisher with what I thought was a good idea. I said, hey, for my next book, I'd like to write about an obscure school of ancient philosophy. And, you know, their response was...
4:14 Ryan Holiday? Are you sure? In fact, my editor would tell me later that they were just humoring me and they hoped I would get this philosophy thing out of my system and go back to writing marketing books. I certainly didn't expect, they didn't expect, that these books would go on to sell millions of copies and Stoicism would be this sort of resurgent force and way of living to people all over the world. In retrospect, though, it does make sense. That first book, The Obstacle is Away, was just celebrated its 10-year anniversary. Not that I feel like someone who could have a 10-year-old book.
4:56 Ryan Holiday? I realize in retrospect it was a classic blue ocean, right? We tend to focus on what everyone else is doing, what is established, what makes sense. But in fact, most successful businesses, most enduring businesses, most lasting creative works were transgressive, or new, or unexpected, or they had a field totally to themselves. I wrote a book many years later about the venture capitalist Peter Thiel, and he had this line that I think about all the time. He said, "Competition is for losers." And his point was, you want to go where there is no competition. It's scarier at first, but if you can establish yourself, if you can do it right, you have
5:40 Ryan Holiday? that space totally to yourself. And in retrospect, it actually does make sense that Stoic philosophy would make its way through professional sports, it would make its way through entertainment and pop culture, it would become part of the toolkit of Super Bowl-winning teams and elite companies, special forces, military leaders, heads of state. Again, this isn't what I was thinking, but of course, it was what Stoicism was in the ancient world. There were Stoics who... Were in the Olympics, there were Stoics who ran businesses, there were Stoics who led armies into battle. And so as The Obstacle is the Way made its way through not just the business community,
6:23 Ryan Holiday? but all these different groups, I spent a lot of time thinking about why. Why did it work? And why did it become, actually, the New York Times Bestseller List explicitly excludes this thing that they call perennial sellers? So you look at the bestseller list every week and it tells you what is selling in that moment. But that list is heavily edited to exclude things that have been selling for long periods of time. It excludes basically the bulk of where the income from the publishing industry comes from. And the reason is that no one would check the bestseller list every week if it just showed
7:04 Ryan Holiday? the same 10 or 20 or 50 books that have been selling basically since books were invented, right? And so there's always this newness bias when we look both literally at the news and then any kind of rankings. Actually, if you went on the New York Times or Fox News or any website, and you know, there's the little list on the center that says our most read articles. Almost all of those most read articles would also be older articles. It's the perennial pieces, the how to's, the instructions, the classic long reads pieces that do the majority of the traffic cumulatively. But they want you to read the new thing, so you'll come back over and over again. So how does The Obstacle is the Way and my books on so, and how did it become what we would call a perennial seller?
7:49 Ryan Holiday? Wrote a book on this, that's my cow, Domino. But as I think about why it worked, it's ultimately because the idea was timeless, right? Stoic philosophy has endured for 25 centuries for a good reason. It is based on the trial and error, the sum total of human wisdom. And it was tested in this laboratory over and over and over again. And the ideas were winnowed down into their essence. It was boiled into a kind of truth. And in fact, Stoicism originates 25 centuries ago from a businessperson. Zeno, the founder of Stoicism, was a merchant in what was called Tyrian purple.
8:33 Ryan Holiday? This was the dye that would make the cloaks of the wealthiest Greeks and Romans. And as he traveled in this convoy of ships, he suffers a shipwreck sometime around the 4th century, and he washes up penniless in Athens. And there, at rock bottom, he's walking through the Athenian agora and trying to figure out what to do next. And he comes across a bookseller. They had book merchants. Then he comes across a bookseller, and the bookseller is reading aloud one of the stories from Socrates. It's the story of Hercules at the crossroads. Do you go the easy way or the hard way? This is what the parable is supposed to demonstrate.
9:18 Ryan Holiday? And as Zeno hears this story, his introduction to philosophy, he asks the man, "Hey, where can I find a man like that? Where can I find a philosopher?" And he's introduced to his philosophy teacher, who happens to be walking by at this very moment, a man named Kretes, a cynic philosopher who is known as the door opener, which is what great teachers do. They open doors for us. But the reason that this experience so strikes Zeno is that as a young man, he'd received a prophecy, and that prophecy had said that wisdom will come when you begin to have conversations with the dead. And he realizes that that's what books are. That's what philosophy is.
10:02 Ryan Holiday? Stoicism then is the great conversation, as the Western canon is sometimes referred to, right? The great conversation. He's talking with the dead. "I am telling you a story about a man who died thousands of years ago, and yet it resounds to us to this day."
10:29 Ryan Holiday? But Zeno, his life is changed in this instant. From the shipwreck comes his introduction to philosophy. And he would actually joke that he made a great fortune when he suffered a shipwreck. So he loses everything, of course, but it opens a different door, literally and figuratively, that not only changes his life, but changes the course of history. Again, here we are, all these centuries later, talking about him. And so Stoicism is a philosophy that comes out of a disaster. Sometimes these disasters are personal, sometimes they're political, sometimes they're very, very small, and sometimes they're very, very big. But the essence of Stoic philosophy is this idea of whether that tragedy, that event
11:13 Ryan Holiday? that befell you, whether it's going to be unfortunate or fortunate. The Stoics would say, "We get to make that choice. We decide." Not just in how we perceive it, but in how we respond to it, what we make of it, what it makes us into. That's what Zeno was saying. "I made a great fortune when I suffered a shipwreck." The same event, the same experience, could have been the worst thing that ever happened to him, but he turns it into the best thing that ever happens to him. That's what the obstacle is the way is. It's not that every obstacle we face in life is an opportunity to make a little bit more money in our business, or to acquire an extra client, or to even do something fun.
11:57 Ryan Holiday? The idea of the obstacle is the way is that we can transform these events into experiences which, in retrospect, we see as significant and meaningful and positively directing the course of our lives. And Marx really ruminates...
12:15 Ryan Holiday? On this idea repeatedly in meditations, he says that, yeah, our actions can be impeded, our plans can be disrupted, our life can be blown apart, but we always have the ability to accommodate and adapt. He says, "The mind adapts and converts to its own purposes, the obstacle to our acting." And then the famous phrase is, "The impediment to action advances action. What stands in the way becomes the way." Or as I said, "The obstacle is the way." That in any and every situation, no matter how big, or small, or unfair it is, or undesirable it is, we always have the opportunity to practice virtue. And I think it's important that, it's not just the Stoics who said the obstacle is the way, but there's
12:57 Ryan Holiday? a Zen saying too, that the obstacle is the path. It's that we have the chance to practice excellence in response to this situation, this obstacle, this disruption, this problem. We have a chance to practice excellence. And in practicing that excellence, in struggling with this thing, in adapting and adjusting and accommodating this thing, we have the opportunity to grow and improve and be made better. Effectively, we don't control what happens, we control how we respond to what happens. We don't control other people, we control how we respond to other people. As it happens, that quote from Marcus Aurelius
13:38 Ryan Holiday? about how the obstacle is the way, he's specifically talking about assholes. He's talking about jerks. He's talking about the people that get in our way, right? It would be wonderful if we were all aligned, if we always worked together, if we always helped each other, if nobody ever tried to prevent anyone from doing what they were trying to do. But that's not life. Life is filled with difficult people and obnoxious people. In fact, he opens a beautiful passage of meditations with this very idea. It says, "The people you meet today will be difficult, and frustrating, and annoying, and dishonest, and jealous." And he lists all the things that we inevitably face in the course of the day. But he says,
14:21 Ryan Holiday? "Hey, you're meant to work with these people." He says, "You can't let them implicate you in their ugliness. You have to figure out how to do good with and through them. That's the purpose. That's the struggle." And- And in that way, you become better and you have the choice, of course, not to become worse. We control who we are in each situation, who we are in life, whether we get green lights all along the way, or we hit a frustrating amount of stop signs and stoplights. So the obstacle is the way is this sort of timeless thing that comes to us from the Stoics that our trials, our tribulations are a chance for us to triumph. Again, we're not always
15:02 Ryan Holiday? going to win. We're not always going to end up exactly where we wanted, but we can be made better for having dealt with it. We can be driven in some new way. We can make a fortune out of this misfortune. I'm traveling a bunch this summer. I've been traveling a bunch recently, but I really love sleeping in my own bed because my own bed is in Eight Sleep. I have the Eight Sleep Pod, which cools my bed, it heats my bed, it tracks my sleep, it even can raise the bed up or down. And so when I travel, I go to cool places. The only downside is that I miss my bed. Sometimes if I forget to turn my Eight Sleep off, I get a little message and it says, "Your Eight Sleep is warming up or cooling down." I go, "Ah, I wish I was
15:47 Ryan Holiday? home." And look, the Pod 5 is the newest generation of Eight Sleep's signature products. It's a smart mattress cover you put on top of your existing mattress. The result, they say, is up to one full hour of additional quality sleep per night. And actually, with the Pod 5, sleep optimization goes even further. They've got a bunch of preventative health tracking with their autopilot health check, which gives you visibility into your heartbeat, your breathing, even sudden changes in HRV. And right now, you can head over to eightsleep.com/dailystoic and use code DAILYSTOIC to get 350 bucks off your own Pod 5 Ultra. And you still get 30 days to try it at home and return it if you don't like it. But I think you will love
16:29 Ryan Holiday? it and your body will thank you for this investment in better sleep. Shipping to many countries worldwide. You can see details at eightsleep.com/dailystoic. And so I think the reason that Stoicism resonates, the reason is my book, my
16:44 Ryan Holiday? resonated is not because I'm such a great writer, although I do my best. It's it's that it's rooted in this fundamental part of the human experience. It's rooted in the fact that we don't control the world around us, that Murphy's Law is real, that people are annoying, and we have been having to deal with this for as long as we have been conscious as a species. Jeff Bezos said at Amazon that you try to build the business around focusing on the things that don't change, right? People like things cheap, they like them fast. That doesn't mean that Amazon doesn't also try to take advantage of trends and doesn't
17:28 Ryan Holiday? try to to to wield, you know, the greatest and latest technological breakthroughs. But ultimately, it's got to be built around assumptions or truths about customers and people and best practices that are going to remain true no matter how much the other situations change. And I think the great businesses do this. Zildjian Symbols was started in the 1600s. They made symbols for Napoleon's army, right? But but what a symbol does hasn't changed that much. Now, are they always refining and improving and trying to make things cheaper and last longer? Of course. But fundamentally, what they do doesn't change.
18:13 Ryan Holiday? How do you do it better? That changes, but what you do doesn't change. Fiskars scissors, also 1600s, pretty simple business. This is what a very old pair of Fiskars scissors look like. Same basic idea, now they use plastics and better metals and all these different things, but but fundamentally, the business is basically the same. I'm wearing Red Wing boots. Red Wing boots started making boots for the US Army in World War I. This pair of boots I bought 15 years ago for $300. I thought, wow, $300, that's a lot of money for boots. 15 years later, it seems like a pretty good deal.
18:52 Ryan Holiday? Also, I went hunting in them a couple of weeks ago, so I'm glad I cleaned them off. I'd be getting this carpet very dirty. But this is probably the third or fourth pair of soles that I put on them. You take them to a cobbler, you can send them back to Red Wing, and they'll put new laces and a new sole on them, and then the boots will ostensibly last forever, right? They're functionally the same thing as they've always been, and the need for something like this pair of boots remains unchanged as well. Nashville has a number of businesses that have been around for a very long time. Here's 1907. The Hermitage Hotel predates the right to vote for women.
19:32 Ryan Holiday? And I know this because during the passage of the 19th Amendment, that's where the suffragettes and the anti-suffragettes and the politicians from the Nashville State House, or the Tennessee State House, went and lobbied each other. It was the scene of one of the most pivotal moments in American history. But you can walk into that lobby today because what a lobby is supposed to do hasn't changed that much. Nashville's got a couple of businesses, like a lock and safe business, basically a window and door business, that both date to the Civil War. You know, doors haven't changed that much. They've changed a little, but not that much. I sometimes say this about books. Like, people go, "What about eBooks and audiobooks? You think in the future, books will all be digital?"
20:16 Ryan Holiday? I go, "Here's the thing: Books are a pretty good form of technology." You know? Like, in the movies, like a sci-fi movie, all the doors are like, you know, they hit this code and it opens automatically. But like, in truth, here we are, living in 2025, and doors are pretty much the same as they were 100 years ago and 200... Because a door is a pretty good form of technology. A lock is a pretty good form of technology. A book is a pretty good form of technology for delivering an idea that you want to have a physical manifestation for, that you want to carry around. There's someone here today whose business is basically three centuries old. How cool is that? Now...
20:57 Ryan Holiday? These businesses have to change and adapt how I would buy these boots on the internet instead of in a store or out of a catalog. That might change, right? I might be able to use AI to sketch out where I want my door to go. Or my lock might have a code that I type in now. But fundamentally, it is the same thing. And so what we're trying to do as we root our work or our business is we want to find both what is timely and timeless. And when these things intersect, that's when you have something that I think is powerful and something that endures. Like Star Wars, when it came out, was obviously a cutting-edge sci-fi movie with really cool
21:41 Ryan Holiday? special effects that people hadn't seen before. Fifty years later, that's not why people are watching still the original Star Wars. And that's not why the series has lasted so long. My eight-year-old, when he watches Star Wars, is not blown away by the special effects in the first movie. He's captivated, however, by what George Lucas based the Star Wars franchise on, which is the idea of the hero's journey. And this is also why my eight-year-old is obsessed with The Odyssey and still gets the jokes in The Odyssey about the Cyclops, how he's, you know, he asks Odysseus his name, and he says, "My name is nobody."
22:23 Ryan Holiday? And then when they ask him, you know, "Who did this to you?", he says, "Nobody did it to me." And my eight-year-old thinks that's hilarious because the timelessness of that joke transcends language and centuries. And the myth, the story of Odysseus, is as captivating as the story of Luke Skywalker. The arc, the hero's journey, is what he rooted this in. And the fact that it has spaceships and lasers and Wookiees and whatever is secondary to the journey it's taking you on. One of my favorite movies is Greta Gerwig's Lady Bird, which is actually based in the town and the year that I graduated from high school. Now, that resonates with me specifically.
23:07 Ryan Holiday? But that's not why the movie won Best Picture and why it's still so many people's favorite movies. It's because it's rooted in what so many great works of art is, in that idea of the coming of age story, another kind of archetype or myth. A story that you can resonate with however old you are, whatever your circumstances are, whatever language you're in, whatever race you are. The idea of a person struggling to become who they are, to make sense of the world, to choose their path in life. That's also the story that Zeno resonates with Socrates and the choice of Hercules. Do I go this way or do I go that way?
23:50 Ryan Holiday? And that's why that movie is not just amazing and was trendy and cool in the moment it came out, but every year it not just retains its resonance, it resonates with a new group of people who are themselves coming of age. There's a lovely book by Guy Kawasaki called Enchantment. We have the same publisher. This is sort of a perennial title that sells every single year. It's about how you sort of create like this love affair with your customers and with your branding and marketing. He worked with Apple and I worked with Canva. He knows what he's talking about. I just love to contrast two of Guy's books. So he writes this book, which is a perennial seller. And then he also wrote this book, which is less of a perennial seller.
24:35 Ryan Holiday? When you're rooting what you're doing so much in the moment, you lose the chances of it being tight. I mean, look, if he'd written this about Facebook, obviously, Facebook lasted in a way that Google Plus didn't. But Facebook or Instagram or Snapchat, when it was published versus where it is now, has also changed so much. So how are you thinking about what you're going after? And what's the half-life of the relationship or the connection or the truth you're speaking to? Is that going to continue to be true? What he should have written about, what I wish I'd written about is, or what I wish I'd written is, of course, this book, one of the bestselling books of all time. Because people get pregnant every day and they have no idea what to do about it. And they need a book, right?
25:21 Ryan Holiday? And so when you go to these kind of perennial needs, these things that don't change as far as the human experience goes, you've really tapped into something timeless and important and powerful. As Drake says, it's not about who's popular now, but who's going to be here 10 years from now. And that's what Meditations is. Marcus Aurelius writes one of the greatest philosophy books of all time. He's not intending for it to be published. He talks over and over again about the worthlessness of posthumous fame. He says, because you're not going to be around to enjoy it. And he says also, the people in the future will be just as stupid as the people alive now. But in making something very specific and very personal, but also very timeless,
26:04 Ryan Holiday? he creates something incredibly universal and ultimately enduring. And in chancing upon that book at 20 years old and being so inspired by it and deciding to root my own writings in that, instead of coming up with something myself, I said, how can I translate and adjust and popularize these ideas, which are tested and true? I fell into something that seems timely now, but ultimately is part of this tradition that goes way, way back. That's what The Obstacle is the Way tapped into. And as I wrap up, I would say one other thing that I want to add here is like, when you make something, how do you tell people about it?
26:46 Ryan Holiday? Right? What platform do you have to speak to it? And I was struck by the story of Winston Churchill, who was thrown out of power after the First World War, after a number of mistakes. And he spends roughly 10 years in what he would call the political wilderness. But Churchill isn't sitting there passive at all. In fact, in the course of the 10 years that he spends out of political power, he writes multiple books, multiple articles, gives hundreds of speeches and pioneers. He has one of the first, what we would, I guess, today, call a syndicated radio show. And in the course of this radio show, reaches millions of people all over the world. But particularly in America, he builds this enormous platform, which allows him to promulgate.
27:31 Ryan Holiday? His ideas, test his ideas and develop this back and forth that he ultimately draws on when he comes back to power. And and this form of having a platform, having distribution through direct access to your customers, to the people you need to influence is one of the most powerful things that you can have, particularly in this busy technologically driven world where you can't buy distribution the way you once could. And this is ultimately, I think, not just why my works have gone on and succeeded. It's not just because they're rooted in something timeless, but I'm also trying to take advantage of these very timely technologies. So I wrote this book called The Daily Stoic and I decided at the end of it, you read one page a day.
28:15 Ryan Holiday? I said, well, what do you do after you finish the one page a day? After you get to the 366th entry in the book, so you got to write an extra one for a leap year because you don't know what year people are going to be reading the book in. After you finish the 366th entry, what do you do next? And I started this email and every day for the last eight years, I've sent out the Daily Stoic email. I also do a parenting one called The Daily Dad. I've sent these emails out for free. So I've written basically eight or nine books totally for free now that people get piece by piece over email. But that platform, so it's a podcast version, all these, that platform is what has allowed the books to reach all these people all over the world. We have a YouTube channel where we do a video every day. We have Instagram, of course, and all the different platforms that you can imagine.
28:58 Ryan Holiday? We're doing stuff and it's something like it's become this almost incredible machine. We do something like 50 pieces of content or thousands per month. The vast majority of it is free, does something like 50 million views a month. And it's all spreading these ideas that are, again, timeless ideas in sort of very timely formats or mediums. And I'm thinking about how am I being a steward of this philosophy? How am I not just writing something, putting it out in the world and hoping people find it, but actively running and engaging with a community that I am in direct contact with? In fact, I started this on my first book.
29:41 Ryan Holiday? I just put a little note at the end. It said, hey, I send out an email every once in a while. You want to sign up? And when I sent it out on my first book, it had about 10,000 people on it. The Daily Stoic email now goes out to a million people every single morning. Probably the largest community of Stoics that have ever existed, maybe even cumulatively in the last 25 centuries. And this is something I've built over time. But it's essential. Stefan Zweig, a great 20th century novelist, would say that the most valuable success you can have as a writer, but I think in any form of art, or business, or commerce, is a faithful following. People who look for what you're doing next, who buy what you make, they're subscribers effectively, right?
30:25 Ryan Holiday? That's what Guy Kawasaki was talking about with Apple, right? You'll just buy the next thing from Apple because they always make amazing stuff. When you want a car, you go to this dealership, or you buy from that car manufacturer because you are that, you're a loyal insert, whatever it is. How do you develop that? And how do you have as few intermediaries between you and that customer as possible? My wife and I, at the beginning of 2020, we actually broke ground on the first week of March 2020. So it was amazing timing. We decided to open this small bookstore in the town that we live in. It's actually called The Painted Porch, which is a nod to Xeno on the Stoa Pokile, the painted
31:09 Ryan Holiday? porch in the Athenian agora. We decided to open this small bookstore because I didn't like the idea that when you write a book, you sell it to a publisher, who in turn sells it to a wholesaler, who in turn sells it to Amazon or other bookstores. I wanted to go as direct as possible. So we opened this little bookstore in the town we live in. It's been quite an experience. It took longer than expected. It cost more than expected. You know, it was a lot. Elon Musk, who moved all his stuff to this little town also. So that's been an interesting wrinkle in it. He said that starting a business is like eating glass and staring into the abyss of death. It was definitely like that, you know? But coming out of the other side, it's been... Wonderful experience. Of course, I had to remember the obstacle is the way I didn't
31:54 Ryan Holiday? control what happened. I controlled how I respond to what happens. And I wrote this note card to myself as I was looking out over this seemingly disastrous decision to open the bookstore in the middle of a pandemic. And I said, look, this is a test. What make you a better person or a worse person? It will make you better or worse. That's what it means when we say that the obstacle is the way. That's what what Zeno is saying. Hey, yeah, sure. I lost the family business. I don't get to be a die merchant anymore. But it opened up this new door. It took me in a new direction. I became better for what I went through and the bookstore did open. My wife and I are still married, so that's a success. And and we had to, of course, reimagine what a bookstore would be.
32:38 Ryan Holiday? We learned a whole bunch of interesting lessons along the way. And we're always pivoting and changing. But the idea is here we are in this space, this bookstore that's this building that's well over 100 years old, doing a business that is thousands of years old. If if Zeno is bumping into a bookseller in the Agora. And we have to take advantage of things like e commerce. And of course, you know, sometimes we piss people off because we don't accept cash. It's only only use credit cards. But but so we want to take advantage of the current things, but also root it in the timeless things. And most of all, though, it is a direct relationship between me and my fans. When I have a book coming out, I don't say, hey, go buy this from a multi billion dollar conglomerate, please.
33:23 Ryan Holiday? I say, hey, you can buy it from me and I'll sign your copy. And then, when I put out the next book, I know who my fans are because we have an exchange. We have a relationship. We do business with each other as opposed to having all these intermediaries between you and the people who like what you do. And yeah, sometimes that means I have to take them to the post office to ship, which isn't always the most fun. But I'm reminding myself what this is doing is it's rooting me. It's connecting me to the people that I want to have, not just a short term transactional relationship with, but a long term relationship, one that lasts. ...over the course, not just of my writing career, but their lives as well.
34:05 Ryan Holiday? And as I said, the town's growing faster than ever, so that's nice. But success brings its own obstacles and difficulties. And the idea in Stoicism is that, does this make you better or worse? How do you adapt and adjust to that? And as I wrap up here, I would just say, look, making something that lasts for a few minutes or a few weeks or a year, it's difficult. Making something that lasts for 20 years or 100 years, also difficult. But why do it if it's not going to last? Why do it if it has an expiration date on it? Art, life and work, it's all difficult. Try to make it as not ephemeral as you can. Try to make it as enduring and sustaining as you can. You might as well do it right.
34:49 Ryan Holiday? You might as well root it in what is timeless and true and significant and meaningful. That's what I'm trying to do with the bookstore. It's just a reminder that life is very brief, right? There are other things I could do that would make more money than opening a bookstore in 2021. I understand that. But it's meaningful to me. It's what I want to spend my time and energy on. Because ultimately, the Stoics would say that life is brief, but art is long. And as some of the businesses we were talking about here, and some of your businesses, it can last for a very long time. So, thank you all very much. I appreciate it.
35:29 Ryan Holiday? Thanks so much for listening. If you could rate this podcast and leave a review on iTunes, that would mean so much to us and it would really help the show. We appreciate it, and I'll see you next episode.
Previous This Conversation Will Make You Rethink Everything You Create | James Altucher (PT. 2) Next Are Your Excuses Any Better? | Made For Working Together Page updated September 29, 2026 · transcript and summary are machine-generated
