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

Episode Date: May 25, 2025

In today’s episode, Ryan opens up about how despite his career success and net worth, he still struggles with anxiety and stress, not so much about the state of the world but about the constant pressure for things to go right.🎥 Watch Ryan's interviews with Sahil Bloom and Robert Rosenkranz on The Daily Stoic YouTube Channel Sahil Bloom episode: https://www.youtube.com/watch?v=BKCA2ymdQtcRobert Rosenkranz episode: https://www.youtube.com/watch?v=IvzsEopZ94Q📚 Pick up signed copies of  The 5 Types of Wealth: A Transformative Guide to Design Your Dream Life by Sahil Bloom at The Painted Porch📕 Grab a copy of The Stoic Capitalist: Advice for the Exceptionally Ambitious by Robert Rosenkranz at The Painted Porch💡The Wealthy Stoic: A Daily Stoic Guide to Being Rich, Happy, and Free explores how stoic ideas can be applied to personal finance, wealth-building, financial mindset, and how it can help you overcome common financial obstacles and challengesGet The Wealthy Stoic: A Daily Stoic Guide to Being Rich, Happy, and Free & all other Daily Stoic courses for FREE when you join Daily Stoic Life | dailystoic.com/life🪙 We are the creators of our anxiety. Which means we can also be the ones to do something about it. Gain a powerful tool in your fight against anxiety and get the Daily Stoic Anxiety Coin today! https://store.dailystoic.com/🎙️ Follow The Daily Stoic Podcast on Instagram: https://www.instagram.com/dailystoicpodcast🎥 Watch top moments from The Daily Stoic Podcast on YouTube: https://www.youtube.com/@dailystoicpodcast✉️ Want Stoic wisdom delivered to your inbox daily? Sign up for the FREE Daily Stoic email at https://dailystoic.com/dailyemail🏛 Get Stoic inspired books, medallions, and prints to remember these lessons at the Daily Stoic Store: https://store.dailystoic.com/📱 Follow us:  Instagram, Twitter, YouTube, TikTok, and FacebookSee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

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Welcome to the weekend edition of the Daily Stoic podcast. On Sundays, we take a deeper dive into these ancient topics with excerpts from the Stoic texts, audio books that we like here, or recommend here at the Stoic texts, audiobooks that we like here, 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.

Hey, 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 Sal Hill Bloom on the podcast, he just wrote this book about different types of wealth. Obviously we all think about financial wealth, but he's saying there's time wealth, like how much time you have, there's social wealth, like your relationships, there's mental wealth, how much time you have, there'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. And 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, okay, 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. And 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 my own answer. I was thinking about what ways am I poorer than I'd like to be? And in the weeks since the interview,

we recorded it a couple of months ago, actually. I've been thinking a lot about that. Because financially, I'm doing pretty well. You know, my 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. I 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 Sal 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. And Seneca said poverty isn't just having too little, it's also wanting more, right? If you could have a billion dollars, but if you're jealous of someone with $2 billion, you're gonna feel poor.

And if you have insatiable endless appetites, you're gonna 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. Not 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. And I also know I'm way ahead of 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 and an article about how anxiety is a very expensive habit. That it's cost me a lot. You know, 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. You know, 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. The thing about anxiety is it feeds on itself.

That's why if you've seen the Daily Stoke anxiety coin, which I carry, I actually, I 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. You 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. Or certainly I'm adding tension or stress from how I think about things. And 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 were 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. I was like, why 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. Like 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 a lot at Daily Dad, like says work, family, scene, pick two. Like do great work. You can be there for your family,

but like you're probably gonna miss out on a lot of parties. Or if you go to a lot of parties, you're gonna neglect your family if you're still doing work. Or 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. We 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 gonna 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. But that's kind of the point. ["The Last Supper"] Shopping local might seem like a tough cookie, but truthfully, finding Ontario-made products and we'll see you next time. Support Ontario manufacturers of all sizes. When you choose Ontario Made, you're supporting your neighbors, strengthening our economy, and celebrating the incredible products

Ontario sells with pride. Discover what's made right here. Visit supportontariomade.ca. You 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. 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

and it's been one of the best things we've ever done. It's been a great investment too. You know, we're tucked away from the noise, the city. We 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 standing out there and at night, just watching the sunset. I love watching the stars.

But if I'm being honest, like I don't spend enough time there. Rather, I don't spend enough time on it. Like I 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-dayness. 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. And 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 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. He'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 is 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 wanna think about and you do what you wanna do. Like 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 would change my whole day around for some, you know, 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. So why don't I keep the day that I've planned? Why don't I focus on what I wanna 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 ever watched the show Billions, it's in the first episode, the main guy, Axe, 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. Not right now. This is something we talk about in the Daily Stoke Wealth Challenge, which is I think one of the best challenges we did for Daily Stoke. You can all 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 more than a decade working for this deranged evil man. He becomes rich in the process, but he pays a price for that. Many 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, just as happy to live without it. Wealth consists not in having great possessions, he said, but 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, 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 workday 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. I 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. 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. And 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 dailystoke.com slash wealth, or if you join daily Stoke life, you'll grab it for free. I'll link to all that. It's something we cover in the Sal 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. 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. I think you'll like all those. And I hope some people liked 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 you all soon. Have a good weekend. Thanks so much for listening. If you could rate this podcast and leave a review on iTunes, that would mean so much to us and would really help the show. We appreciate it. I'll see you next episode.

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