Try To Surprise People This Way | Ask DS

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0:54I'm picking my kids up from school today and then doing our weekly routine, which is I take them over to Whole Foods. and we get all our groceries for the week. Then we have dinner. It's one of their favorite things to do. It's one of my favorite things to do. And then my wife loves it because she doesn't have to take care of it. This holiday season, whether you're a guest or hosting the big dinner Whole Foods Market has what you need to delight everyone at your table. They even have heat and eat sides from the prepared foods department. You can make Whole Foods your one-stop shop. Everything follows Whole Foods Market's strict ingredients standards so you know it'll be delicious and good for you.

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1:41Welcome to the Daily Stoic Podcast, where each day we read a passage of ancient wisdom designed to help you in your everyday life. Well, on Thursdays, we not only read the daily meditation, but we answer some questions from listeners and fellow Stoics. We're 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.

2:21Try 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 advance party to make sure he was treated with the respect accorded to his official position.

2:59Sometimes arriving before the rest of his group, he would arrive in a small town and sit and wait, often without being recognized, 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 Cato's. 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.

3:39This 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. 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.

4:37Hey, it's Ryan Holiday. Welcome to another episode of the Daily Stoic Podcast. today we are doing a cute or let's scratch it apart i um 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 uh i thought it was weird cedar rapids like the cap i guess is 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.

5:13I could see why that would be a bad place to put a municipal building. 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 &A session and then sort of an informal working lunch with some execs. So I'm going to bring you the best of that Q &A now. with me kicking some questions around. So thanks to all those folks. Enjoy.

5:47I try to do something hard every day. That's sort of how I think about it. 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 as way down the line. I got a cold plunge recently, and obviously there's some science about what it does for you. But to me, the thing is, the benefit is the doing it. It's the, I'm going to do this thing for however, I'm going to push myself to see how long I can do this thing that is hard.

6:31That's the value of it, as opposed to, does it help your circulation or your nervousness? Maybe, hopefully, but weirdly, it's like I think doing the hard thing is the thing of it. So yeah, I just try to do something that pushes myself every day. Was that part of why you chose your place? Yeah, I mean, it's nice. Yeah, it's nice. I can run on dirt instead of paved roads and stuff, although I have to worry about dogs for the most part. But yeah, no, it's great. I think, you know, are we meant to live in big concrete jungles? Probably not. And so anything that gets you away from that, it's nice. Were you born and raised in that area?

7:21No, no, I'm from California. We just ended up in Texas. How'd you meet your wife? In college. Yeah. Yeah, in college. So we've been together a long time. Yeah, it's fun. It's fun. She didn't want to come to Des Moines, or I mean to Cedar Rabbits, as you can imagine. It's beautiful here right now, dude. This is the best time of year to come. I imagine you probably would like it. Are your kids stoics, too? Well, they're six and four, so they're more like feral animals. but especially living where we live, you have to have lots of discussions about where you're allowed to pee when we're out in public, stuff like that.

8:08Do you have a stoic children? I do, actually. I did 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 actually did them during the pandemic. My kids are not interested in hearing about them at all, but 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. There was five Roman emperors in a row who don't have any male children. and so each one had to choose an heir and some did good, some did not so good but in Marcus's case he was very young 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 older man who's in his 50s, thinking that he'd live for like five more years or something, given life expectancy then.

9:29And he adopts this guy named Antoninus. Antoninus 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 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 kind of two of them Do you like any contemporary authors? I thought your ego section was really good.

10:15Oh, thanks. Similar to Cy Lakeman. She's done some stuff. The whole book called No Ego is very good. Yeah. Checked it out. I thought your mindset stuff reminded me some of Carol Dweck. She's great, yeah. Yeah, so I was just curious if you like anybody and kind of pay attention. 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, 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.

10:57I like a lot of biographies, so there's a big biography section. I don't tend to read a lot of books in the category that I write in, just as I try to keep other people's work out of my head. But I like Cal Newport a lot. I was talking about deep work in the talk about focus and concentration. I like his books a lot. 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 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.

11:45What prompted you to decide, with all you've got going on in life, to open a bookstore? Well, it's all about the money, as you can imagine. That's why I opened a bookstore. Sure, that's why we own restaurants. Yeah. 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. And 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. I liked that it was her idea.

12:21So then if it went badly, it wasn't all on me. But it's usually the big bad ideas are mine. But, you know, it's probably a crazy idea under ordinary circumstances. And then we started construction in the first week of March 2020. 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 really, really fun. And it's actually, as an author, it's been interesting to, like, really understand the business side of the thing.

13:05Like, to see it like, oh, this thing that I thought my publisher was screwing up, all publishers are screwing up. You know? Or just 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. You can work from your house or whatever. this is kind of also like a headquarters like there's offices upstairs and stuff so um 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 um so i go to the office people that work for me 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've been working from home for a long time and i was like i got to get out of the house so it's been beneficial in a bunch of different ways and then it's been a cool part of this you know little town

14:05yeah yeah 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 big the county is about 80 ,000 but this little town is 8 ,000 Yeah, it's about 30 minutes from Austin. Now it's blowing up because Austin's blowing up and lots of stuff is moving there, but it's still this little sort of Disney-esque Main Street, and it's pretty cool. I grew up in about a thousand. Wow. Where? Not much Disney. Just about an hour and a half southwest. Texas has these sort of little, perfect, almost look fake Main Street towns. So what are you working on now, man?

14:53So I'm doing a series on the cardinal virtues. So I've done courage and discipline. Those are the first two. And then the next two are going to be justice and wisdom. So I'm mostly done with the justice book, but I decided to space them out. So it was supposed to come out in September of this year, but I 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 probably pick it back up in the fall. And then the following summer, I'll have to start the fourth book. So I'm doing those four.

15:31And then that gets me out of ways. I can't think much further than that. But this is the first time I've been working on books that are related to each other, which is 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 wrote The Obstacle's Away, then I wrote Ego's Enemy, and then I wrote Still This Is The Key, and they ended up being related to each other, but they were each independently conceived projects, whereas this was four books, you know, on similar kind of overlapping topics as part of one.

16:14Those are the four virtues of Stoicism. And so they all kind of fit under this larger umbrella. And so it's really forced me from a planning perspective to think about all of it differently. Because if I put a chapter that's encouraged that three years later I wish is in discipline or something, it's too late. And so 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 a little bit past the halfway point on this thing that I conceived in 2019. So it's also the longest I've worked on a single project. So that's been fun.

16:59With all your references to New Gehrig and McQueen and Churchill, are you researching all of that? For the most part. Or are there people on your team that are helping? For the most part, I sort of pick who I want to be in the project. It's usually sort of the way I'm doing these series is there's kind of like three tentpole characters in each book. And then there's obviously other characters running through it. But yeah, I have to find all that. You really can't. I do use research assistant and research assistants. But it's mostly on finding small stuff or very specific things. Like, I need a quote about this, or I need to know more about this thing.

17:41But most of the heavy lifting stuff, it's not that I have to do. I mean, I like doing it. It's my favorite part of it. But yeah, I try to outsource everything but that, but the research and the writing of the books for the most part. So you're a sports fan? You get a really detailed history of Kyrie? Yeah. He's like one of my least favorite people in the whole world. so I may have gone overboard there. But yeah, yeah, I love sports. And I think what I've found is if I go too in-depth on the philosophy stuff, people are like, what are you talking about? Where is this coming from? But if I connect it to things that a wider base of people are familiar with that can illustrate the ideas.

18:25So I try to look for 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, you know, I mean, that's a very old, just as a sports story, that's an old sports story. 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 yeah, there's basically like Bill Belichick's the only coach that has ever rehabbed a terrible player and not lived to regret it for the most part, it seems.

19:10But 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. We think that the norms and the system and the rule of law or whatever, that it's all always going to be there. Instead, these things are really, really fragile. And if you have one person that you either raise above those rules or you make exceptions too many times, what you get is rot or destruction that really either takes a very long time to fix or you can never fix it. 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 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 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, freak thing.

20:26It'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 ground, like how do you make it where that makes its way up? To me, that's the thing. An ego tends to shut that down or doesn't want to hear it or whatever that is. So to me, that's sort of the killer variable there. Writing professionally is hard. We've got friends who try to join these writer's clubs and help each other.

21:06Yeah, I mean, I wanted to be a writer. That's what I wanted to do. but I knew it would probably be better to go do other stuff first just to experience things and learn things and 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 just took a bunch of different interesting opportunities in my 20s and one of those was I was a research assistant for a writer named Robert Greene who wrote 40 Laws of Power and Mastery and a bunch of other amazing books so I was sort of doing both of them simultaneously. And then I was just sort of waiting for my shot.

21:44And 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 about. And they were like, that sounds like a really bad idea. No one will be interested in that. And they weren't really at first. It's kind of been a slow but steady sort of 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 slow process, but it's been really cool. Another question comes to mind. So you're in a bookstore.

22:21Yes. A brick and mortar, only books that you enjoy. Yes. And you're also a top seller on Amazon. What is it love? Yeah, I mean, part of the reason I wanted to open my own bookstore was I realized, like, so about 75 % of most book sales are through Amazon in one form or another. And then almost 50 % to 60 % of sales are digital. So e-books, audio books. 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.

23:14That's sort of like how the book market works. And so, I don't know, I just thought, like, why not cut out some of the middlemen? not as a whole, but just in this one instance, like why not, you know, have some direct access to people in the physical world and, you know, is in a position financially that I could sort of take that risk or do that mostly as a hobby 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.

23:54It'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 say, don't go buy these from this multi-billion dollar conglomerate. Like you can buy it from me. And 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 fun. And I think it's such a small number that 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 will get mad at them.

24:35And it's probably not. the only reason Amazon hasn't closed its book business is probably because it's not worth the public relations headache. But it is a rounding error of rounding errors for them. And so, you know, they're like, whatever. Yeah. 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 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 ever went in one, they only had a couple hundred books, and they were all face out, which is very different.

25:17You know, even to a Barnes & Noble, there's 20, 30, 40 ,000 titles in a large Barnes & 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, like a few books that were really behind. It'll be way easier. So you don't have to carry all this inventory. And my thinking is, actually, if people know what book they want, they will buy it from Amazon. It'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.

26:01And that's sort of what we built the bookstore around. Yeah. You're coming up 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 to physical spaces compared to people? 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 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 are like, I want some kind of physical space.

26:42So like they need a place to film stuff. They need a place to, you know, they need like a podcast studio. 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 is like not not struck like i couldn't i couldn't have this bookstore in manhattan but in baster of texas it's like sure you know um and And so I do see people, especially with some freedom of movement, just going and doing their sort of dream project or some cool thing just because they can.

27:27And then they, you know, like for me, the videos that we shoot in the bookstore, the podcasts that I recorded, 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 stream for the company, 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. It's just an interesting balance. Yeah. Because you comment on it and then not just commercial or you say, but like AI feels like continues. There's so many pressures driving people into themselves and into this interaction.

28:14So I'm curious what you see as you travel around. Yeah, I don't know. I mean, the town's been there 150 years. It's probably not going anywhere in my lifetime. That's sort of how I think about it.

28:31so

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