Pod Insights The Daily Stoic | Wondery+ BONUS | Ryan Holiday’s Office Tour: Books, Stoic Artifacts, and Daily Rituals About this episode In this bonus episode, Ryan is takes you inside his office and walks through the books, objects, notes, and reminders that shape how he works and lives.
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Transcript Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.
0:00 Ryan Holiday? Welcome to the Daily Stoic Podcast, designed to help you bring those four key Stoic virtues—courage, discipline, justice, and wisdom—into the real world.
0:15 Ryan Holiday? I'm Ryan Holiday. I'm an author. I have a bookstore here outside Austin, Texas, and I'm going to take you through my office today and show you a couple of things that I think explain how I work, how I think about what I do, and how I think about life.
0:38 Ryan Holiday? The most important reminder I have on my wall sits between two pictures of my kids, here and here. I don't show their faces, but that's Dr. Oliver Sacks, and behind him is a sign in his office that just said, "No." This was given to me by the sports psychologist, Dr. Jonathan Fader. "You develop a career by saying yes to everything, but you can only keep a career by getting good at saying no to things." And he told me that there's something similar in baseball. He's a team psychologist for a bunch of baseball teams. They have a saying in the Dominican Republic, for instance, with baseball players, that you don't walk off the island. You only get there by hitting, by swinging at pitches. But, once you get to the majors, you have to learn pitch discipline. You have to learn when not to swing.
1:21 Ryan Holiday? And so, this is a reminder to me that's really important. As I sit here, I check my email, I'm working on stuff, that I not only have to say no to be really good at my job, but that when I'm saying yes to stuff, I'm saying no to these two people, who I've already promised my best time to, who I've already promised my best self to. And actually, I have another reminder of this that I keep here from the great Hugh McLeod. He sent me this in 2020. It's just a little drawing. It says, "Like an asshole, I took him, her, it for granted." You've got to remember that when you're saying yes to things, you are saying no to things. And most importantly, when you're saying no to things—Mark Schurist talks about this in meditation—you are saying double yes to the things that actually matter.
2:03 Ryan Holiday? And I have two other kind of reminders to say no. These are kind of cool. This is a memo from the Truman administration. It's a—this is the inter-office communication the secretary's writing. "Since the president will be out of office when this celebration will be held, how do you think that we should answer it? Should we say that because of many similar requests, the president must ask to be excused?" And then here it is underlined by Truman himself. It says, "The proper answer is underlined." That they should say the president must ask to be excused. And then here's another one. "I regret that I cannot comply with your request. It is long been my policy not to respond to questions. I received so many similar requests to yours that I could not keep up with all of them. I hope you will understand." And it's signed Harry Truman. I actually have a third one that someone gave me from Truman.
2:47 Ryan Holiday? It says here, "Your question will be answered in the book I am getting ready to publish as soon as possible." So you let the books do the answering for you. I think that's a pretty good policy as well.
3:02 Ryan Holiday? I don't keep all my books in my office, but I keep some of them. These are all books for the book I am working on right now. Those are international editions of my books. Those are some signed books. These are all my philosophy books. And here is biographies. Books are made out of books, so I try to keep the books that I rely on or use the most here in the office. I keep most of my novels at home, so I like to reread them. But part of the attraction of setting up this bookstore and office space is I told my wife I'd take some of my books out of our house. We'd have a little more room. But I have books here on the balcony.
3:42 Ryan Holiday? Got Civil War and War books here. These are books you can see from downstairs in the bookstore, but you can't touch because they're just mine. E-books are nice. Audio books are great, but I like books that I can keep on my shelf as trophies. I like to be able to go back to them, pick them up, to be able to refer to them. I like the ongoing relationship with the physical form. These are books that I've pulled off the shelf and used over and over and over again when I'm looking for something, going through my note cards. So these are my philosophy books over here. These are biographies. If I don't want to keep the book, if I have no interest in keeping it, it says something to me about why I was reading it in the first place.
4:29 Ryan Holiday? I keep some little note cards here on my wall, one of which is kind of my why. To me, this is like a guiding principle that I want to think about. This says, "Am I being a good steward of Stoicism?" Like, I didn't invent the philosophy that I write about. It's not mine. I possess no ownership of it. But I am associated with it because of the success of the books, because of social media. I just try to remind myself that like, somebody else will be sitting in this chair at some point, right? Somebody else will be associated with the philosophy in the future. That it's a long tradition. I think it's important that you take the job you do seriously, but not yourself. And I just try to remind myself that like, this isn't mine. I don't own it. I have to represent it as well as I can. I have to try to live up to it. Martin Luther talks about fighting to be the person
5:14 Ryan Holiday? that philosophy tried to make you. That's what I'm doing here. This guides the kind of content I will and won't make, the kind of products I will and won't make, how and when I publish my books, the effort that I put in. Am I living up to the expectations and the standards of what I talk and write about? That's one of the things I want to think about. And then I have a couple more that sort of guide me. I try to have a why or a through line on each of the projects that I'm working on. Somehow, this one got wet. This is Hemingway. It says, "Do not worry. You have always written before, and you will write again. All you have to do is write one true sentence, write the truest sentence that you know." That was one on a project I was struggling with. Another one from Martha Graham, "Never be afraid of material. The material knows when you are frightened and will not help." This is, I'm doing this work in nonfiction right now.
5:57 Ryan Holiday? "Historical writing, which is not literature, is subject to oblivion." That's Paul Horgan. This is from a different novelist. "The side lights on the life of every great man are interesting." It's a reminder to me to go down different rabbit holes. This is an Italian writer. "Who in our day can penetrate the hearts of the ancients? Who can bring life and light again to a mind long since removed in death? Who can elicit their meaning? A divine task that not human." And it says, "It is therefore my plan of interpretation first to write what I learned from the ancients, and when they fail me or when I find them inexplicit, to set down my own opinion." I feel like that's kind of what I'm doing. And then here, I have one. This is an exchange with me and the great General Mattis. I was writing him at some moment when it felt like the world was coming apart. He said John McCain used to joke to him
6:42 Ryan Holiday? that it was always darkest just before it turned darker. "Keep the faith. Hold the line." So I try to have some, like a sports team. I try to have reminders of the values and principles that I'm trying to live and write with.
6:56 Ryan Holiday? Okay, so this is technically in my office. We keep it in the studio because someone asked me about it on the podcast. In 2017, I was a producer on an album. I worked on the liner notes. I'm not good at music at all. But I was a producer on an album that won a Grammy. Like, I literally went to the Grammys, walked the red carpet, and then our album won. We went on stage and accepted it. They only gave us one Grammy, and then you could apply for like a certificate. There are so many producers, they don't give everyone a Grammy. And also, there's two different Grammy awards. There's like all the ones you see on TV, and then there's a smaller ceremony for the hundreds of other Grammys before. The point is, I could have gotten this paper Grammy and put it on the wall. Instead, I was like, you know what? I'm gonna get my own Grammy, and I'm gonna say what it actually means. And so it says, "National Academy of Recording Arts and Sciences, Ryan Holiday, Best Large
7:40 Ryan Holiday? Jazz Ensemble Album 2017." And then I says, "When you die, this will go in the trash alongside all your other accomplishments." You know, it can be easy. My publisher sends me little plaques and things, right? Like, this is, um, this is from my UK publisher. When I sold a million and a half copies in the UK, this is spring 2023. Like, I think it's cool. It's a cool accomplishment. But like, what are my kids gonna care about that? Maybe it's one of the ones they'll keep, but maybe it won't. Right, here's a hundred thousand orders from Daily Stilex Store, or, you know, there's my YouTube plaques. I guess my kids were vaguely impressed when I got YouTube plaques, so maybe they would actually keep those if something happened to me. But the point is, when you achieve and accomplish things, it's a very privileged problem to have, but, but the things start to stack
8:25 Ryan Holiday? up. Okay, you hit the bestseller list, and then they send you a framed thing. Like, I literally have more of them than I know what to do with. My wife does not want any of them in her house. And so, I was just trying to remember as kind of a joke that, like, all these things are cool. And it is cool to walk down the hall and go, "I did that. That accomplishment was a lot of work, and there was payout for it, and that's great." But it's also a reminder that, that at the end of the day, not only is it junk at some level, it's forgettable. It doesn't mean as much as you think it means. And that if that's why you did it, if that need to be recognized and remembered and celebrated for the thing, that was the, the motivating factor. The Stoics would say, "You're gonna be sorely disappointed when you realize what it's actually worth," which is not much.
9:14 Ryan Holiday? So I sit in a little bit of magic every day. This is Joan Didion's chair. Next door, I'll show you, I also have Joan Didion's table. She's from Sacramento, I'm from Sacramento. I just like objects where they have a story to them, something with a little bit of history and sacredness to them. And it so feels good to sit every day in the chair of someone who is one of the best to ever do it. I know it doesn't really mean anything. It doesn't convey any magic, but it went up for auction and I thought it was pretty cool. So it's not the most comfortable chair, to be perfectly honest, but maybe there's a little stoic lesson in that. Mark Schrillis would famously sleep on a hard mattress. I sit on this hard ass chair and I try to think about who sat in it before me.
9:54 Ryan Holiday? So I do all my research on note cards. I'm doing a book on Stockdale right now. These are the note cards from that. When I did my Four Virtues book, I printed out these note cards. And for almost 20 years now, I've kept a commonplace book in these note cards. Each book I do has note cards. So like, this is the project I'm working on now. My stuff's here laid out on the table. This is the book I'm doing. This is the layout for the book. Every time I read a physical book, I go back through it. I put the ideas that I need to take out from it onto my note cards. And then those note cards come with me when I'm traveling and I'm writing. Or those note cards sit on my desk here and I'm writing. So for me, the note cards are the building blocks,
10:39 Ryan Holiday? the pieces of the puzzle that go into each book. And I have one for each book here. I'll show you next door. This is Future Projects. Here's the Courage book. Here's the Justice book. Here's the Discipline book. There's Ego is the Enemy. Wisdom books down there. But that's Stillness. That's Growth Hacker, I think. Trust me, the line's in here somewhere. So each one of the books is one of these boxes. And there's even a beautiful Joan Didion essay called On Keeping a Notebook, where she talks about that she would keep note cards, not when she's doing a script or a screenplay, but she would write down things that she found in the course of her life. And she talked about how a journal or notebook is a way to keep in touch with who you used to be. Right? And sometimes I go back through these note cards,
11:24 Ryan Holiday? some of these books, like this one here. These are note cards. Some of these are... Twenty plus years old of just different notes that I've kept since I was in my early twenties. I pick up these cards and I see things that I took pains to write down. How long ago and what I was thinking about, why I was thinking about it, why I decided to write down this note about dogs? Or the animals killed at Nero's Games in Rome? Or this is a plenty. It's true that what he wrote will not be eternal, or at least I didn't think so. Still, he wrote them as if they would be. It's a great line. These are notes about writing. This is Marshall, the Roman poet.
12:07 Ryan Holiday? "Forgive me, it's not worth my while dying to earn your critical smile." Oh, here's Joan Didion. That's so funny. "People tend to forget that my presence runs counter to their best interests," she was saying as a journalist. "And it almost always does. That is the one last thing to remember. Writers are always willing to sell somebody out." Maybe she wrote that down sitting in that chair. Kind of crazy.
12:31 Ryan Holiday? So I have this print here. We actually made this for the bookstore a couple of years ago. I don't know if we still sell it, but it's a great line from Hemingway. He famously said that the first draft of anything is shit. And here it is, sort of illustrated as an idea. It's very tempting or easy to accidentally compare the thing you're in the middle of to something that's finished, either that you've finished or that somebody else has finished. And this is not fair. That's not how it works. You have to remember that everything was terrible at some point. Everything was partially done at some point. Everything was a blank page at some point. And if you remember that first drafts are supposed to be crappy, you're supposed to be working the stuff out on the page. I try to remember where this bookstore or Daily Stoic or the YouTube channel,
13:14 Ryan Holiday? where it was at the beginning, where it was for the first several years. You're getting better as you go. And this Ira Glass talks about the taste and talent gap. Often your taste is better than your talent in the early days of what you do, or even in the early days of a project. And so you have to get comfortable being bad. You have to trust the process. And if you can't, you get stuck. And that perfectionism becomes a kind of paralysis. Those high standards actually prevent you from getting better and better because you're so convinced that what you're doing right now isn't good. It's not supposed to be good. So I try to remember what a first draft is supposed to be, which is a part of the process, a step along the way to getting to where I want it to go.
14:00 Ryan Holiday? Okay, so this pine cone, this is a pine cone from a lodgepole pine. And it looks like an ordinary pine cone. That's because it's opened up. It's called a serotonous pine cone. It's covered in this waxy resin. For it to work as a pine cone is supposed to work, it has to be exposed to heat. I don't just mean like everyday heat. I mean like the heat from a forest fire. So basically, the thing that you would think would be the worst thing to happen to a tree, which is a fire, is actually necessary for this tree to recreate, for the next generation of trees to come. It is, to me, a perfect metaphor of both creative destruction and the idea that the obstacle is the way. You think you want to avoid adversity and difficulty. You don't want to be put to the fire. But in fact, the fire is there to help you open up,
14:44 Ryan Holiday? to melt off that covering, to make new growth and new things possible. This is just a lovely reminder. I also think it's funny, I bought this. I've never actually seen a lodgepole pine in person that I know of. Some lady just sells these on Etsy. She puts the pine cones in the oven, they open up. I just think that's hilarious. So I bought a couple of these just as a reminder. So this is also, to me, a great embodiment of the Stoic idea of amor fati, right? Marx realist talks about how what you throw on top of a fire becomes fuel for the fire, right? That it turns everything to flame and brightness and heat. Can also turn it into something beautiful and new and fresh.
15:27 Ryan Holiday? This is a picture of me and my grandfather. I may be 12 or 13 there. I had some other pictures, let's see. I have some other pictures in my house and in my office of me as a kid. My therapist told me I should do it. She says, you know, it's easy to lose touch with your inner child. And part of what we're trying to do as adults is heal that inner child, be a better parent to ourselves, so we can be a better parent to our kids. Because you so easily lose track of who that person was, what they looked like, what they felt like, what it was like to be five or six or 15. And those reminders are helpful to me. So I have a couple of those. And then it's also, to me, a reminder of the passage of time, how recent that was and also how long ago that was. And that's a powerful reminder as well.
16:15 Ryan Holiday? Okay, so this is a reminder on the way up to the office. I took this from the creator of Per Se. It says, "Sense of Urgency", which is his reminder that, look, you don't want to rush things, but you also don't have unlimited time. To me, that tension of "fistina lente", like make haste slowly, and then also like hustle, hustle. I think about this going into fulfillment and stuff like, how long are we going to make people wait before we put their package in the mail? How long am I going to wait to answer that email that I need to respond to? How long are we going to wait until we ask the best for ourselves? As Epictetus talked about. So a sense of urgency is something that's got to shape who you are and what you do. That's one of our values here at Data Stoic.
17:01 Ryan Holiday? I have this chunk of a tombstone here to keep behind my desk. I used to keep this on the mirror in my bathroom, but we changed our bathroom and there wasn't space for it anymore. I don't know how this came to be so old on the internet. I don't want to know. I just know that at some point, a dad, a parent, a living person, they passed away and this is all that remains from that memorial. It's a memento mori, right? The Stoics want to remind us that life is short, that life is unpredictable, that none of us are here forever. That's what memento mori means. And in ancient art and in philosophy, these reminders are everywhere. Here's an illustration by Salvador Dali of Montaigne doing a memento mori, staring at death for a second. The idea is that you reflect on your mortality.
17:46 Ryan Holiday? You put up things that humble you and remind you of the fragility and the shortness of life to give you perspective, to give you urgency, a sense of urgency, and that these reminders are important and powerful. And this is, to me, a reminder in the end of all the things that really matter to you as well.
18:06 Ryan Holiday? So anyways, that's my office and a dozen or so objects. I thought as I wrap up, I'll give you rapid fire, some other cool ones. Maybe we'll do another video about this if you guys like it. What do we have here? This is the last page of Steven Pressfield's manuscript for Gates of Fire, which is pretty incredible. This is the first manuscript page from Walker Percy's Lancelot, one of my favorite novels. That's a memento mori, a ticket from General Grant's funeral. There I've got a... Print or a wax painting of Sherman, one of my heroes who I wrote about in Ego is the Enemy. The great Garland Robinette, who was on the David Stone podcast, painted me this little portrait of Walker Percy, one of my favorites.
18:49 Ryan Holiday? There's my Marcus Aurelius one. Marcus Aurelius reminder, waste no more time arguing what a good man is like. Just be one. This is a fossil my son found. I got some money. This is the first little bust I bought of Marcus Aurelius. It's from the 1800s. This is a hand chipped tool or axe from a Paleolithic man. Think about the passage of time. That's pretty cool to hold. This is a Roman penknife. Just think about somebody opening mail or a package or cutting something with this. 2,000 years ago, that's pretty cool. That's a chunk of a White House that Truman took down to the studs. This is a signed edition of The Road Not Taken by Robert Frost. And then the final thing.
19:34 Ryan Holiday? I have like in a locker room or right before you run out on the field in a sports stadium, you have the four virtues of Stoicism. Courage, discipline, justice, wisdom. I like to see it as I go up and down the stairs every day.
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