These Are All The Ways Ryan Holiday Feels Poorer Than He Is

0:04Welcome 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.

0:43Hey, it's Ryan. Welcome to another Sunday episode of the Daily Stoke Podcast. You know, it's obviously a treat to get to interview people on this show, which I've been doing now for many years. And maybe you can tell a lot of times when I'm asking questions, I'm mostly asking for me. Like, I'm glad you guys are listening and I hope you get a lot out of them, but I'm chewing on the questions myself. And when I had Sahil Bloom on the podcast, You just wrote this book about different types of wealth, right? Obviously, we all think about financial wealth, but he's saying there's time wealth, like how much time you have.

1:14There's social wealth, like your relationships. There's mental wealth, how much knowledge you have. There's physical wealth too, right? How you feel, what you're capable of doing. And so I said, you know, you just wrote this book about wealth. Well, actually here, let me play that question for you. What are ways you think you're poorer than you would like to be? I have a tendency to get very narrowly locked in on things during short bouts. Like, and almost, I mean, I probably have a level of undiagnosed OCD where I get sort of obsessed with something and that gives me tunnel vision around that one thing.

1:51And so, my tendency is to have these seasons of unbalance that are sort of hopefully followed by seasons of balance, but I don't do that season of balance if I don't force it. Okay. And so what I've like had happen in my own life recently is I went through this season of unbalance as the book was coming out, all the push into that, as you know, well, and my whole intention was like, OK, coming out of that, I'm going to zoom out. I'm going to be home a ton, tons more time with my family, the people I care about. And that season of unbalance ended. And then there were all these new opportunities that came up.

2:22And so then I'm chasing another season of unbalance. So the area of my life that suffers the most when that happens is my social wealth. It is my relationships with, you know, namely those few people that I feel like are the most important. And that is a huge area that I need to work on. And yeah, I think his answer is pretty good. But I wasn't satisfied with like my own answer. I was thinking about like what ways am I poorer than I'd like to be. And in the weeks since the interview, we recorded it a couple months ago, actually. I've been thinking a lot about that. Because, you know, like financially, I'm doing pretty well.

2:57My books sell well. This podcast turned out to be an unexpected sort of business and contributor to the sort of whole daily stoic universe. My books certainly sell well for, you know, writing about an obscure school of ancient philosophy. And it turns out, you know, opening a bookstore was not a total disaster. It didn't bankrupt us or blow up our lives. You know, I was lucky to have a career in marketing. Before I became a full-time author, I've had some success as a ghostwriter. I made some pretty good investments along the way. And generally, I think my wife and I live within our means. So when I'm thinking about how I might be poorer than I'd like to be, I don't mean to imply that I'm not doing well.

3:41I think that's sort of insulting to like the single mothers out there, people who are crippled by medical debt, you know, the sort of people who are exploited by the modern economy. I'm thinking about it in the context that Saul Hill was talking about, right? Social wealth, time wealth, mental wealth, physical wealth. I've certainly met some billionaires who I would have no trouble as describing as poor. And I don't mean this just because they have this endless desire for more, as Seneca said. Seneca said poverty isn't just having too little, it's also wanting more. You could have a billion dollars, but if you're jealous of someone with two billion dollars, you're going to feel poor.

4:19And if you have insatiable endless appetites, you're going to feel poor. No, I would say that some of these billionaires I've met are poor because their lives were a mess, because they were preposterously insecure, because they were estranged from their families, because they didn't have friends, because they didn't take care of themselves, because they had bad values. And again, I don't mean this so judgmentally. I'm saying here that I'm poorer than I'd like to be, that I'm not as rich as I'd like to be in a few areas. I've said this before on this podcast and in articles that despite my success, I do feel often anxious and stressed out.

4:54Not so much about the state of the world, although that gets to me sometimes, but mostly about like needing things to go well. Like I get nervous when I fly and I fly a lot. And that nervousness is not like some people's where it's like you're afraid of crashing. I think for me, it's just like needing it to go well, to go a certain way, that that sense or need of control makes me feel powerless and impoverished, right? Like I'm thinking if I'm delayed, then I'll miss the talk. Or if I'm delayed, my schedule will get messed up, I'll fall behind. And I know on some level, objectively, this is very silly because I would be fine financially if I had to cancel something or if, you know, force majeure.

5:31And I also know I'm way ahead on my deadlines. I have enough slack in the line to endure some setbacks. And yet here I am just stressing myself out like I'm on the razor's edge. I did an episode on this in an article about how anxiety is a very expensive habit, that it's cost me a lot. It's cost me misery and frustration and a lot of sleep. It's cost me to miss out on things that were important to me. Family dinners where my mind wandered, minutes of vacation because I was preoccupied thinking about this or that happening, opportunities that I passed up because I was caught in various fears or, yeah, again, nights that I laid awake in bed just worrying about what might happen.

6:13The thing about anxiety is it feeds on itself. That's why if you've seen the Daily Stoic anxiety coin, which I carry, I actually use it a lot when I travel, it's like a nice fidget. I'll link to that in today's show notes. But it's got the Ouroboros on the front, right? The symbol, the ancient symbol of a snake devouring its own tail. That's what anxiety does. But what anxiety does is it creates real problems from our obsession with imaginary ones. When you are worried about running out of money or luck, you know, where you feel like your career could end, it affects how you organize your life and your finances.

6:48You leave earlier for the airport than you need to, and then you just sit at the gate. You ruminate on the past or the future at the expense of the project you're working on now. You stress about money so much that you don't put it to use in ways that would make your life less stressful. My wife and I talk about this like, we should not be living this way. We have too much on our plates and not enough people helping us. We're doing too well financially to feel so anxious or stressed out. We're fighting about stuff that we don't need to be fighting about. Certainly, I'm adding tension or stress from how I think about things.

7:21And there's not an objective or a rational basis for this. It's not making things better. And when you live this way, it really doesn't matter what your income is because you're spending down your capital. You are depleting the accounts of your relationship and your own happiness. You're driving people away. You're driving yourself away. I'm not as busy as a lot of people I know, but I do think I'm too busy. Like just this week, I was trying to put a doctor's appointment in my calendar and I couldn't. Some people can't afford to go to the doctor, but for some of us, for other reasons, can't afford it either.

7:52I was like, well, I'd have to cancel this. I'd have to move this. I'm like pushing this appointment way off in the distance. But if you're too busy to take care of your health, is that success? Is that doing well? No. And I do also know that I'd be better off if I had more friends. I think that's a downside of success. It can isolate you and alienate you from others. Like fame is weird. Having an audience is weird. That you're listening to this is disorienting and alienating for me. It's cool and I'm grateful for it, but it has consequences too. I can see people watching me when I'm out in public, see people waiting to talk to me.

8:31Like if you're introverted, fame can make you a little suspicious, makes you a little more guarded. You're more inclined to stay home or in your office. There's a no new friends policy that makes a little bit of sense, right? And I think mostly though, what success does is it sucks up your time. My friend Austin Kleon has talked about this. We've done it a lot at Daily Dad, like it says work, family, scene, pick two. Like do great work. You can be there for your family, but like you're probably going to miss out on a lot of parties. Or if you go to a lot of parties, you're going to neglect your family if you're still doing work.

9:07Or, you know, if you're just hanging out at home and at parties, you're not at the office doing the work. I happen to love my family. I love my work. And that doesn't leave as much time for friends or socializing as maybe I would like. And actually, Austin and I talked about that the last time we hung out. Like, why don't we do this more? But we know why. It's because it's lower on the priority list. That's a shame. And there's a privileged impoverishment in that, I think. Like, it's weird for me to think that as a kid, when I had no money, I would just go over to a friend's house and we'd hang out.

9:36We didn't have anything scheduled. We didn't even have anything to do, but we'd spend hours together. And it's weird to think back and be jealous of that kid. But I am. He had something that I don't have anymore. Actually, when we put this up as an article, my friend Francisco sent me this message. That was someone I spent so much time with as a kid. And it's like, what, I'm going to fly across the country and just hang out at his house? Like, that's obviously low on the priority list. But if I had a billion dollars, would I be able to do that more? I don't know. Probably not. Probably if I had more, I'd have less time.

10:06But that's kind of the point.

10:15I'm recording this on a Monday and Monday is our grocery store day and our family. I usually pick my kids up from school and we go over to Whole Foods, get all our groceries for the week. Although here very shortly, we're going to go over there to get our Thanksgiving turkey because they've got a bunch of great options. Turkeys start at$149 a pound if you have prime with organic birds at$2.99 a pound. And they only carry no antibiotic ever turkeys that will bring quality to your table at a great price. Whole Foods has great everyday prices on all your Thanksgiving essentials, whether you celebrate with a massive family or just a few close friends.

10:52Everything they sell has high standards to help you shop with confidence. Enjoy so many ways to save on your Thanksgiving spread at Whole Foods Market. We just took our kids to an outdoor performance at the Nutcracker. They had a snow cone, and then they went insane in the car ride home. And one of the things I try to remind myself when that's happening is that I don't control my kids' behavior, especially when they're too far gone like that, but I do control how I respond, right? That's stoicism, but it's also what Dr. Becky talks about. Dr. Becky is a clinical psychologist and a best-selling author, and she founded Good Inside, which is there to give parents practical, actionable tools for handling those everyday challenges with confidence.

11:35My wife introduced me to Dr. Becky's books. I love them. I've recommended them a million times. I've had her on the podcast. And as it happens, Dr. Becky is hosting two live Q &A events for Good Inside members. I am one of them. She signed me up for it about a year and a half ago. I've loved it ever since. On December 1st, you can join Dr. Becky for her How Not to Raise Assholes event, which is about avoiding entitlement and raising kind, empathetic kids. And on December 15th, she's hosting her How Not to Lose It over the holidays event, which I'm sure we could all use. As I said, I'm a big fan of Dr.

12:12Becky. She's been a great influence for me as a parent and just as a human being. And daily Stoic listeners can join for 15 % off with code STOIC15. You just got to head over to goodinside.com to catch the events.

12:32you know i love where i live this little ranch outside austin just pulled up after picking my son up from school and it's funny to think of what a huge swing it was financially when we bought it and this is like well before the austin area blew up the way that it did and getting the mortgage was nearly impossible like banks weren't exactly lining up to lend money to a self-employed writer at the beginning of their career, let alone a writer trying to buy farmland in rural Texas. But we managed to get in. It's been one of the best things we've ever done. It's been a great investment too. We're tucked away from the noise, the city.

13:10We live on an unpaved road. It's pitch black at night, surrounded by thousands of trees. I'm looking out right now at the window at this lake. It's more of a pond. In ranching terms, It's a tank, but it looks like a beautiful lake. There's fish in it. There's ducks on it right now. There's thousands of turtles. I've got cows and donkeys. I know they're over in the other pasture. I can hunt deer and hogs whenever I want. And I love standing out there at night, just watching the sunset. I love watching the stars. But if I'm being honest, I don't spend enough time there. Rather, I don't spend enough time on it.

13:47I used to do most of the repairs myself. Samantha and I would go out and feed the cows every day. I delivered the hay each week. I checked the fences after a storm. I don't do that as much anymore. You know, I think part of it's because we fixed a lot of the problems we got at operating in good shape. That's like what you do when you know how to run a business or you're good at systems is you fix some of the need for that day-to-day-ness. But we also bought out one of our neighbors. And instead of dragging away the mobile home on the property, we found a wonderful family that lives in it. and they help us with the chores in exchange for, you know, a good chunk of the rent.

14:23And this is a relief, means the animals are always taken care of. It's something not to stress about, but I also miss it. Like weeks will go by and then I realize I haven't walked on more than a few paces from the house. We walk every night, but that's usually on the road. I just go like, man, I haven't seen the pastures in a while. I haven't been over here in a while. When was the last time the donkeys came up and ate carrots out of my hand? Whenever I feel that feeling, I think of this beautiful passage in one of my favorite books by John Graves called Goodbye to a River. He says, a rooting, poking dog-trailed child turning over stones in a creek bed, or a broke old man wandering back from a pulp mill in Oregon to toe-nudge rusty cans and shards of crocks at the spot where his father's homestead once stood, or a drifter in a boat on a river can all own it right out from under you if you don't watch out, can own it in a real way, own it with an eye and a brain and a heart.

15:19He's talking about how who owns the note on it is not that important. It's who's there, who's present for it, who soaks it in. I guess what I'm saying is reminding myself that if all I'm doing is looking at it from the back window, do I really own it? Do I really need to own it if I don't own it in that way? When I think about a rich life, to borrow a phrase from my friend Ramit Sethi, who's been on the podcast a bunch. It's not money that you value it in. In fact, kind of the point of having money is not to think about it. It's to have a life where you feel good, where you feel secure, where you think about what you want to think about and you do what you want to do.

15:58Like I remember early when I first started writing, this is before I had my office, I'd be here, I'd wake up, I'd see an email, oh, this radio show wants you on. I'd throw everything out to go rush and do this interview. That's what you're supposed to do. That's your obligation to promote your work. And I've changed my whole day around for some radio interview in some spot or some podcast or some reporter would have a question. And it was only with time that I got to realizing that I don't have to do any of this. Like even if the appearance sold 10 ,000 books, which it never does, sells like 10 books, that doesn't change my life.

16:37So why don't I keep the day that I've planned? Why don't I focus on what I want to focus on? Why can't I say no? And that realization, realizing that I could say no, it changed my life more than any single check I ever got. That's the life that I want. To me, that's what being rich is, that ability. And you realize there's people with enormous fortunes who don't have that freedom. If you've ever watched the show Billions, it's in the first episode. The main guy acts. He says, you know, what's the point of having fuck you money if you never say fuck you? I don't think you have to say that. You could just say, no, thanks.

17:10Not right now. This is something we talk about in the Daily Stoic Wealth Challenge, which is, I think, one of the best challenges we did for Daily Stoic. You can link to that. It's great. It's not about money. It's about this kind of wealth. You might think that Seneca is the richest of the Stoics, but he's our model of a poor Stoic throughout the challenge because he's under the thumb of money and ambition and power and status. That's what dragged him into Nero's orbit. And he spends, you know, more than a decade working for this deranged evil man. He becomes rich in the process, but he pays a price for that.

17:43Many people, Seneca himself would write, have riches just as we say they have a fever, when really the fever has us. The fever that Seneca had, it trapped him in a gilded cage that he never was able to buy his way out of. But Epictetus, who claws his way out of slavery, was richer in a way that Seneca was not, that other powerful people, men and women of the time, were not. Because these people, despite everything they owned, were themselves owned by Nero or by their ambition or their fame or their jobs or their insecurities or their possessions. There's an amazing story about Epictetus being robbed of a prized lamp, but he shrugs it off because he doesn't care about stuff.

18:26Just is happy to live without it. wealth consists not in having great possessions he said but in in having few wants it's about having the life you want that's wealth i was in my office like a year ago and i called samantha i was like hey what's up and she said hey like the kids and i are over at the park and i said oh i'll just come over and see you guys and i got up from my desk in the middle of the work day and i walked over and we played at the park now i can do that for financial reasons i can do that for lifestyle and logistic reasons, because I live in this small town and work for myself.

18:57I can do that because my wife and kids want to be around me and I want to be around them. And I can also do that because I'm in good physical shape. And I can do that if I do the work on myself and remember that I don't have to be stressed about this or that deadline, like if my priorities are aligned. And as I walked over to that park, it sort of hit me like, this is what I work for. Like, this is so great. I'm so lucky. I could be a billionaire and not be able to do this. I could be the president of the United States and not be able to do this. And if I could stay in that state of mind more of the time, well, then I'd really be doing well.

19:31And that's the message of today's episode. It's a theme we've obviously been covering a lot, something we dive deep into in the wealth challenge that you can check out. I think that's dailysoak.com slash wealth. Or if you join Daily Soak Life, you'll grab it for free. I'll link to all that. It's something we cover in the Saul Hill episode of the podcast. I'll link to that. And obviously, this is something we talk about in the episode with Robert Rosencrantz. He is a self-made billionaire. He just wrote this book called The Stoic Capitalist and talks about some of these things. And we talked about that in our interview on the podcast.

20:03I think you'll like all those. And, you know, I hope some people like this article. Some people got a little mad at me, but I'm not perfect at this stuff. I'm struggling with this stuff as well, as the Stoics did themselves, Seneca being a very real example of that. But we're all trying to get better. We're all working on ourselves we're all trying to get to that rich life to that true definition of wealth trying to get past those things that make us feel impoverished that steal from us trying to curb those expensive habits like anxiety status anxiety comparison worry inadequacy the more you push those away the richer the life you'll have that's today's episode enjoy talk to y 'all soon have a good weekend

20:50Thanks 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. I'll see you next episode.

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