Try To Surprise People This Way | Ask DS

He didn’t dress in fancy clothes. He didn’t support a large entourage. He liked to walk the streets of Rome, meeting his fellow citizens, being of use and helping them. As a politician, Cato traveled across the empire, again, without a large baggage train or an advance party to make sure he was treated with the respect accorded to his official position. --And in today's Ask Daily Stoic, Ryan talks stoics and answers questions for 300+ Risk, Safety, Compliance & HR Leaders from across the country for True North Companies. Overall the goal is to guide our clients and manage the complexities of risk management & workforce. Registration is only open until TUESDAY, NOVEMBER 7TH. Take the next step in your Stoic education today. Click here to sign up.⏳ You can view our entire Memento Mori Collection at dailystoic.com/mm✉️ Sign up for the Daily Stoic email: https://dailystoic.com/dailyemail🏛 Check out the Daily Stoic Store for Stoic inspired products, signed books, and more.📱 Follow us: Instagram, Twitter, YouTube, TikTok, 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

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

• 0:03Ryan Holiday?

  Welcome to the Daily Stoic Podcast, where each day we read a passage of ancient wisdom designed to help you in your everyday life. While on Thursdays, we not only read the daily meditation, but we answer some questions from listeners and fellow Stoics who are trying to apply this philosophy just as you are. Some of these come from my talks. Some of these come from Zoom sessions that we do with Daily Stoic Life members or as part of the challenges. Some of them are from interactions I have on the street when there happened to be someone there recording. But thank you for listening, and we hope this is of use to you.

• 0:43Ryan Holiday?

  Try to surprise people this way. Cato was a rich and powerful man. He came from a family that for generations had been rich and powerful in a caste society with all the privileges and norms that that entailed. And yet, Cato dispensed with most of this, at least in how he went about his day. He didn't dress in fancy clothes. He didn't support a large entourage. He liked to walk the streets of Rome, meeting his fellow citizens, being of use and helping them. As a politician, Cato traveled across the empire, again, without a large baggage train or an advance party to make sure he was treated with the respect accorded to his official position. Sometimes, arriving before the rest of his group, he would arrive in a small town and sit and wait, often without being recognized,

• 1:28Ryan Holiday?

  sometimes quietly enduring snubs or indignities from people who had no idea who he was. When his identity became known and that treatment suddenly changed, Cato would smile and remind them that not all future visitors would be Catos. Not every Roman would be so understanding or low maintenance. Needless to say, this was all very surprising. One of Rome's greatest men, walking barefoot and bareheaded without fear or favor, a representative of Rome's great imperial might, being kindly and patient and respectful and prudent. This just didn't happen. Cato could have gotten away with so much worse. Indeed, he was entitled legally and culturally to all sorts of pretentiousness and deference.

• 2:11Ryan Holiday?

  Perhaps your job affords you similar privileges. Perhaps you are used to being treated a certain way. The measure of who you are is how lightly you wear these honors, how approachable you are. Be the kind of person that surprises people. They were so nice, I was so surprised at how easy they were to deal with. Be the kind of person that surprises other people with how interested you are in them, how much respect you treat them with, how little use you have for formalities or status symbols. You'll be amazed at the kind of respect this affords you in the long run and how surprising this really is.

• 3:00Ryan Holiday?

  Hey, it's Ryan Holiday. Welcome to another episode of the Daily Stoic Podcast. Today, we are doing a Q... Let's try to break apart. Back in May, I guess, I did a little talk in Cedar Rapids, and I went for a run in a place that I'd never been before. I thought it was quite beautiful. And I thought it was weird. Cedar Rapids, like the cap... I guess it's the capital or the city hall of the whatever is like in the middle of the river. And I was talking to someone about it. I was like, I've never seen that before. It's pretty cool. And he's like, yeah, it does flood. And then I thought, oh, yeah, that's probably why I've never seen that before. I could see why that would be a bad place to put a municipal building.

• 3:40Ryan Holiday?

  But anyways, I had a good time and I gave a talk to some folks at a company called True North, which is a risk management and insurance company. And then we had a nice little Q and A session and then a sort of an informal working lunch with some execs. So I'm going to bring you the best of that Q and A now. Let me kick in some questions around. So thanks to all those folks. Enjoy.

• 4:09Ryan Holiday?

  I just try to do something hard every day. That's sort of how I think about it.

• 4:14Ryan Holiday?

  I'm not like training for something or trying to do it. I just try to do something that pushes myself physically for some amount of time. And what I like about it is it usually means no screen time, usually means outside. And then it's also, probably also good for physical health, but I'm almost thinking about that is way down the line.

• 4:35Ryan Holiday?

  I got a cold plunge recently and obviously there's some science about what it does for you. But to me, the, the thing is, the benefit is the doing it. It's the, I'm gonna do this thing for however, I'm gonna push myself to see how long I can do this thing that is hard. That's the value of it, as opposed to does it help your circulation or your nervous, you know, maybe, hopefully. But weirdly, it's like, I think the doing the hard thing is the, is the thing of it.

• 5:08Ryan Holiday?

  So yeah, I, I just try to do something that pushes myself every, every day.

• 5:13Speaker 01

  Was that a part of why you chose your place?

• 5:17Ryan Holiday?

  Yeah, I mean, it's nice. I, yeah, it's nice. I, I can run on, you know, dirt instead of paved roads and stuff, although I have to worry about dogs, uh, for the most part.

• 5:29Ryan Holiday?

  But yeah, no, it's, it's, it's great.

• 5:32Ryan Holiday?

  I think, uh,

• 5:35Ryan Holiday?

  you know, are, are we meant to live in big, concrete jungles? Probably not. And so, and anything that gets you away from that is nice.

• 5:42Speaker 01

  Were you born and raised in that area?

• 5:43Ryan Holiday?

  No, no, I'm from California.

• 5:47Ryan Holiday?

  We just, uh, we just ended, ended up in Texas.

• 5:51Speaker 01

  How'd you meet your wife?

• 5:52Ryan Holiday?

  Uh, in college.

• 5:53Speaker 01

  Yeah.

• 5:54Ryan Holiday?

  Yeah. Um, yeah, in college. So we've been together a long time.

• 5:58Speaker 01

  Cool.

• 5:58Ryan Holiday?

  Yeah, it's fun. It's fun. She didn't want to come to Des Moines, or I mean to Cedar Rapids, as you can imagine.

• 6:06Speaker 01

  It's beautiful here now, dude. This is the best time of year to come.

• 6:10Ryan Holiday?

  I know, she probably would like it.

• 6:11Speaker 01

  Are your kids stoics too?

• 6:14Ryan Holiday?

  Well, they're six and four, so they're more like feral animals, but

• 6:21Ryan Holiday?

  especially living where we live, you know, we have to have uh, lots of discussions about where you're allowed to pee when we're out in public, stuff like that.

• 6:30Speaker 01

  Do you have a stoic, a stoic?

• 6:33Ryan Holiday?

  I do, actually, I did a boy, a book called The Boy Who Would Be King, which is about the story of Marcus Aurelius, and then I did a book called The Girl Who Would Be Free, which is about Epictetus, so sort of a boy and a girl one. I did, I actually did them during the pandemic. My kids are not interested in hearing them, about them at all, but other, other kids of life. I was writing about Marcus Aurelius because I think it's an interesting story in that Marcus is not born to any kind of royal family. Like, there was five Roman emperors in a row who don't have any male children.

• 7:15Ryan Holiday?

  And so each one had to choose an heir. And, and some did good, some did not so good. But in Marcus's case, he was very young

• 7:33Ryan Holiday?

  when the Emperor Hadrian sort of realizes that it's coming to the end. And so making a kid the emperor is probably a really bad idea. So he adopts this, he adopts this older man who's in his 50s, thinking that he'd live for like five more years or something, given life expectancy then. And in, he adopts this guy named Antoninus. Antoninus is, then has to adopt Marcus Aurelius, and they set in motion this sort of plan. But then Antoninus lives for 20 more years. And so Marcus basically gets this kind of leadership apprentice program that's very unusual in all of human history.

• 8:14Ryan Holiday?

  And they're basically sort of two good emperors in a row, which is pretty rare also. And so it's kind of a remarkable story. Because absolute power is supposed to corrupt absolutely. There's like a handful of exceptions in history, and this is, this is kind of two of them.

• 8:35Speaker 01

  Ego section was really good, I thought.

• 8:37Ryan Holiday?

  Oh, thanks.

• 8:38Speaker 01

  Really similar to Sid Leighton. She's done some stuff, "What's called no ego," it's very good.

• 8:43Ryan Holiday?

  Yeah.

• 8:43Speaker 01

  Check it out. I thought your mindset stuff reminded me of some of Carol's work.

• 8:47Ryan Holiday?

  She's great, yeah.

• 8:48Speaker 01

  Yeah, so I was just curious if you like anybody and kind of pay attention.

• 8:53Ryan Holiday?

  I love a lot of people. I actually have a bookstore in Texas, in this little town that we live in. And basically, the premise is it's only books that I like.

• 9:05Ryan Holiday?

  Which is one of the perks. There's not many perks to running a bookstore, but that is one of them. I like David Epstein a lot. He has this book called "Range," which I think a lot about. I like, I like a lot of biography, so there's a big biography section. I don't tend to read a lot of books like in the category that I write in, just as I try to sort of keep other people's work out of my head. But I like Cal Newport a lot. As I was talking about deep work in the talk, about focus and concentration. I like his books a lot.

• 9:45Ryan Holiday?

  I just was reading Gretchen Rubin's new book. She has this book on, I'm forgetting what it's called exactly, but it's on like exploring and improving each one of the senses, which is really interesting. But yeah, I like lots of contemporary authors. I try not to read in my own space as much, but yeah, there's tons of people I like.

• 10:07Speaker 01

  What prompted you to decide, with all you've got going on in life, to open a bookstore?

• 10:11Ryan Holiday?

  Well, it's all about the money, as you can imagine. That's why I opened a bookstore.

• 10:17Speaker 01

  Sure, that's why we own restaurants.

• 10:18Ryan Holiday?

  Yeah.

• 10:21Ryan Holiday?

  I don't know, my wife and I were sitting at this little restaurant in the town that we live, and we were looking at this building across the street that had been vacant for a really long time. She was like, that would be a cool bookstore. And I was like, yeah, it would be really cool if someone else did that. And I don't know, we ended up doing it. It was, I liked that it was her idea. So then if it went badly, it wasn't all on me. But it's usually the big bad ideas are mine. But it, you know, it's probably a crazy idea under ordinary circumstances. And then we started construction in the first week of March 2020.

• 11:00Ryan Holiday?

  So, you know, it was a little behind schedule and looked to be a really, really, really bad idea for quite a while. And now it's great. It's been really fun. And it was actually awesome to have like our own space that wasn't open during the pandemic, during like that first summer. But yeah, it's been, it's been really, really fun. And it's actually, as an author, it's been interesting to like really understand the business side of the thing. Like to see it like, oh, this thing that I thought my publisher was screwing up. All publishers are screwing up, you know? Or, or just the, the sort of economics of it have been really interesting. And then it's nice to have, like as an author, you can kind of work from anywhere.

• 11:44Ryan Holiday?

  You can work from your house, whatever. This is kind of also like a headquarters, like there's offices upstairs and stuff. So it's been nice to have like a place that all my stuff is rooted in and then to get that stuff out of my house. You know, so I go to the office, people that work for me are at that office and I go home and I'm not at that office. So that's actually been, been a really nice, nice part of it. So like a lot of people took from the pandemic, like working from home. And I went the exact opposite. I'd been working from home for a long time and I was like, I gotta get out of the house. So it's been, it's been beneficial in a, in a bunch of different ways. And then it's been a cool part of this, you know, little town.

• 12:27Ryan Holiday?

  Yeah, yeah, and it's called The Painted Porch. You can just look it up. But yeah, it's about 30 minutes from downtown Austin. About 8,000 people. The county is, the county is big. Uh, it's, the county's about 80,000, but this little town is 8,000. It's, uh, yeah, it's about 30 minutes from Austin. Now, now it's blowing up because Austin's blowing up and lots of stuff is moving there. But it's, it's still this little like sort of Disney-esque Main Street and it's pretty cool.

• 12:59Ryan Holiday?

  Wow. Where? Not much Disney in Florida. Just about an hour and a half southwest of here. Texas has these sort of little perfect, almost look fake, Main Street towns.

• 13:12Speaker 02

  So what are you working on now, man?

• 13:14Ryan Holiday?

  Um, so I'm doing a series on the cardinal virtues. Uh, so I've done courage and discipline, those are the first two. And then, uh, the next two are going to be justice and wisdom. So I'm, I'm mostly done with the justice book, but I decided to space them out. So I, it was supposed to come out in September of this year, but actually took some discipline to pause it. So I'm sitting on it for basically a year. I'm trying not to work on it and then it'll come out the following year. I'll, I'll probably pick it back up in the fall. And then the following summer, I'll have to start the, the fourth book. So I'm, I'm doing those, those four, uh, and then that's, that, that gets me out of ways.

• 13:57Ryan Holiday?

  I, I can't think that much further than, much further than that. But, um, it's, this is the first time I've been working on books that are related to each other, which is, I'm, I, I always like to do something that sort of challenges me or makes me do what I do in a way that's different than how I've done it before. And so, you know, when I, I wrote The Obstacle Is Away, then I wrote Ego's the Enemy, and then I wrote Still This Is the Key, and they ended up being related to each other, but they were each independent, independently conceived projects. Whereas this was four books, you know, on similar kind of overlapping topics as part of one. Those are the four virtues of Stoicism. So they all kind of fit under this larger umbrella.

• 14:41Ryan Holiday?

  And so it's really forced me from a... Planning perspective to think about all of it differently because if I put, you know, a chapter that's encouraged that, you know, three years later, I wish is in discipline or something, it's too, it's too late. And so I've had to kind of, I've had to think about it in terms of a bigger chessboard, which has been really interesting and maddening, but also fun and rewarding. So I'm about, I'm a little bit past the halfway point on, on this thing that I conceived in 2019. So it's also the longest I've worked like on a single, uh, you know, a single project. So that's been fun.

• 15:21Speaker 02

  With all your references to like New Garrick and McQueen and Churchill, are you researching all of that?

• 15:27Ryan Holiday?

  For the most part.

• 15:28Speaker 02

  People on your team that are helping?

• 15:29Ryan Holiday?

  Uh, for the most part, I mean, I, I sort of pick who I want to be in, um, in, in the project. It's usually sort of, the way I'm doing these series is there's kind of like three tent pole characters in each book. And then there's obviously other characters running through it. But yeah, I have, I have to find all that. You really can't. I do use research, uh, a research assistant and research assistants, but it's, it's mostly on finding small stuff or very specific things like I need a quote about this or I need, I need to know more about this thing, but most of the heavy lifting stuff, I, I, it's not that I have to do. I mean, I like doing it. It's, it's my favorite part of it, but, um,

• 16:12Ryan Holiday?

  yeah, that, that's, that's, I, I try to outsource everything but that.

• 16:16Speaker 02

  Yeah.

• 16:16Ryan Holiday?

  But the, the research and the writing of, of the books for the most part.

• 16:20Speaker 02

  So you're a sports fan? You get really detailed histories of Kyrie?

• 16:23Ryan Holiday?

  Yeah. He's, he, he's like one of my least favorite people in the whole world. So I may have, I may have gone overboard there, but, uh, yeah, yeah. I love sports. And I think what I, what I've found is if I go, Too in-depth on the philosophy stuff, people are like, "What are you talking about? Where does this come from?" But if I connect it to things that a wider base of people are familiar with, that can illustrate the ideas. So I try to look for, you know, sort of contemporary or modern examples of kind of timeless problems. And guys like that have always existed, and they always do what they do. And there's a certain amount of people who think they can fix them, or it'll be different with them, and it, you know. I mean, that's a very old, just as a sports story, that's an old sports story.

• 17:08Ryan Holiday?

  But the cool thing about the books going their way through sports is that I get to be like, the ultimate bandwagon fan, because I just get to be connected to all these different teams and, you know, sort of follow them in different ways. But, um, yeah. There's basically, like, Bill Belichick's the only coach that's ever rehabbed a terrible player and not come, lived to regret it, for the most part, it seems. But I think what happens is most people, most organizations, think their culture and their system is stronger than it is. I mean, you could argue this is what America is doing now, too. Like, we think that the norms and the system and the rule of law, or whatever, that it's all always going to be there.

• 17:53Ryan Holiday?

  Instead, these things are really, really fragile. And if you have one person that's, you know, you either raise above those rules, or you make exceptions too many times, you know, what you get is, you know, rot or destruction that really either takes a very long time to fix, or it, you never, you can never fix it, you know? And, uh, so I think, yeah, most coaches are always going, "Hey, you know, we'll work them into our system." And it's like, "Sure, maybe." Um, but yeah, it'll be interesting to see what happens. I always think what you, what you tend to find in companies is like, whatever the thing that ultimately sinks them, or causes problems for them, or whatever, like the fatal flaws...

• 18:40Ryan Holiday?

  It's not like it's a secret. Like, it's not like it's like some, you know, it's not like that Challenger explosion or something where it turns out it's this really, you know, my, you know, freak thing. It's like, everybody knows, the information is just not working its way up. Right? And so, you know, how do you create the channels or the culture or the communication where the thing that, you know, you need to know, or the feedback you need, or the idea, like, the new idea, or the, like, how do you make it where that makes its way up? To me, that's, that's, that's the thing, an ego tends to shut that down, or, you know, doesn't want to hear it, or, you know, whatever, whatever that is. So, I, that, to me, that's like, sort of, the killer variable there.

• 19:21Speaker 03

  Writing professionally is hard. I've got friends who try to do it. You know, they join these writers' clubs and help each other, but you just...

• 19:28Ryan Holiday?

  Yeah, I mean, I, I wanted to be a writer. That's what I wanted to do. But I knew it'd probably be better to go do other stuff first, just to experience things and learn things. Like, I think if all you do is write, then, you know, how do you, how do you know that you know what you're talking about? So, I, I just took a bunch of different, interesting opportunities in my twenties. And one of those was, I was a research assistant for a writer named Robert Greene, who wrote Forty Laws of Power and Mastery and a bunch of other amazing books. So, I was sort of doing both of them simultaneously. Uh, and then, um, I was just sort of waiting for my shot. And I did a marketing book first, actually, I did two marketing books first, and then, when I had a little bit of leverage, I was like, well, here's what I really want to write

• 20:13Ryan Holiday?

  about. And they were like, "That sounds like a really bad idea. No one will be interested in that." And, um, you know, they weren't really at first. It's kind of been a slow, but steady, uh, sort of word-of-mouth, word-of-mouth thing. It took, The Obstacles Away was my first Stoicism book, and it took six years for it to hit a bestseller list. So, yeah, it's kind of been a, a slow process, but it's been, it's been really cool.

• 20:42Speaker 03

  So you own a bookstore.

• 20:43Ryan Holiday?

  Yes.

• 20:44Speaker 03

  African border, only books that you enjoy.

• 20:46Ryan Holiday?

  Yes.

• 20:47Speaker 03

  And you're also a top seller on Amazon. What's your love is in love?

• 20:51Ryan Holiday?

  Yeah, I mean, part of the reason I wanted to open my own bookstore was I realized like the that so about

• 21:01Ryan Holiday?

  seventy five percent of most book sales are through Amazon in one form or another. And then almost fifty to sixty percent of sales are digital. So eBooks, audiobooks. And so I'm just like a physical books person. That's what I love. And the idea that you just don't know the vast majority of your customers because there's you sell your book to a publisher and then the publisher sells the book to a wholesaler. And then the wholesaler sells the book to either a retailer or to Amazon. That's sort of like how the the book market works. And so, I don't know, I just thought like, why not cut out some of the middlemen?

• 21:46Ryan Holiday?

  Not as a whole, but just in in this one instance, like, why not, you know, have some direct access to people in the physical world? And, you know, was in a position financially that I could sort of take that risk or do that mostly as a hobby than as opposed to like a really sound business decision. But it's been, you know, it's been really, really cool. And I think coming out of COVID, we are also reminded and remembering why physical spaces are so important. And so it's been this sort of cool community thing. It's been a cool place to meet people. But it's also been just a way to do what I do a little bit better. So like when my books come out, like I can, I can say, don't, don't go buy these from this multi billion dollar conglomerate.

• 22:31Ryan Holiday?

  Like you can, you can buy it from me. And yeah, I don't care where you buy it, but if you want to support me more, you can do that. And that's been a really. Cool part of it. It's been, it's been fun. And I think it's such a small number that Amazon, Amazon doesn't care. I mean, Amazon, if they could, would probably get out of the book business altogether. They sort of can't because it's what they're known about and people get mad at them and it's probably not. The only reason Amazon hasn't closed its book business is probably, is probably because it's not worth the public relations headache. But it is a rounding, a rounding error of rounding errors for them. And so, you know, they're, they're like, whatever.

• 23:17Ryan Holiday?

  Yeah. They, I mean, they opened some bookstores, which were actually really cool and better than I think a lot of bookstore chains out there. And then they, even though they were doing great, they were just like, whatever, it's not worth it. And they closed them all. But the Amazon bookstores were similar. If you, if you ever went in one, they were all, they, they only had a couple hundred books and they were all face out. Which is very different, you know, you go even to a Barnes and Noble, there's 20, 30, 40,000 titles in a, in a large Barnes and Noble. And they're all, you know, side in. And, you know, it's hard to see what you want, hard to see what's good. And so, our thinking was, let's just sell books.

• 24:01Ryan Holiday?

  Like a few books that were really behind, it'll be way easier. So you don't have to carry all this inventory. And, you know, my thinking is actually if people know what book they want, they will buy it from Amazon's cheaper and faster. But if they're going to a bookstore, it's because they don't know what they want. They would like to find something that they don't know about. And that's sort of what we built the bookstore around.

• 24:27Speaker 04

  You're coming on physical spaces. If you think about your store and your town, you know, all the talk about commercial real estate now, do you sense? Good movement back physical spaces compared to free folk?

• 24:42Ryan Holiday?

  I don't know, I mean, it's probably a very different story. New York, Los Angeles, San Francisco, these major cities and office space is obviously very different. But I, I do know a lot of the people that I know that make, that do all their stuff on the internet, whether they're like a social media influencer, or an artist, or they're, they are like, I want some kind of physical space. So like, they want to, they need a place to film stuff, they need a place to, you know, they need like a podcast studio, they, they need a space to do what they're doing. And, um, since the margins of what they do are like a hundred percent, because it's a digital product, you know, the, the, in my case, you know, space in a small town

• 25:27Ryan Holiday?

  is like, not, not, like, I couldn't, I couldn't have this bookstore in Manhattan, but in Bachelor, Texas, it's like, sure, you know? And so I, I do see people, especially with some freedom of movement, just going and doing their sort of dream project or some cool thing, um, just because they can. And then, they, you know, like, for me, the videos that we shoot in the bookstore, the podcasts that I recorded, but all that stuff means that like, actual sales of books to customers walking into the bookstore are like the third or fourth, you know, revenue

• 26:09Ryan Holiday?

  stream for the, like, in terms of priority, right? And so, you know, the space pays for itself and then you have the mixed uses or the cool stuff you want to do with it.

• 26:20Speaker 04

  It's just an interesting balance.

• 26:22Ryan Holiday?

  Yeah.

• 26:22Speaker 04

  Because you comment on it and then, not just commercial words today, but like AI. Feels like it continues. There's so many pressures driving people

• 26:32Ryan Holiday?

  Sure.

• 26:32Speaker 04

  into themselves and into

• 26:35Ryan Holiday?

  Yeah.

• 26:35Speaker 04

  less interaction. So I'm curious what you see as you travel around.

• 26:39Ryan Holiday?

  Yeah, I don't know. I mean, the town's been there 150 years. It's probably not going anywhere in my lifetime. You know, that's sort of how I think about it.