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31 Jul 2025 · 14m

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There Is Hope Within Despair | Ask Daily Stoic

In short

The Daily Stoic podcast, hosted by Ryan Holiday, draws on the teachings of Stoicism to guide listeners through modern life challenges. In this episode titled "There Is Hope Within Despair," Holiday reflects on the pervasive feelings of despair and how Stoic philosophers found hope within their struggles.

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0:05Welcome to the Daily Stoic Podcast, where each day we bring you a Stoic inspired meditation designed to help you find strength and insight and wisdom into everyday life. Each one of these episodes is based on the 2 ,000-year-old philosophy that has guided some of history's greatest men and women to help you learn from them, to follow in their example, and to start your day off with a little dose of courage and discipline and justice and wisdom. For more, visit dailystoic.com.

1:09What is working well? Not the economy, not the government, perhaps not even your own business or your own day-to-day life. Despair is so easy, even reasonable, in moments like this. And the Stoics knew that feeling well. Seneca in the time of Nero. Epictetus chained to slavery. Cato watching the Republic fall. Marcus Aurelius at the beginning of the end of the empire. But they did not despair. They did not give up. They knew that there was hope within despair. Where? Marcus Reilus notes that it was within us. It did not matter how much dung you threw on top of an underground spring, he noted. Fresh water was still there.

1:51He said we needed to dig for it. If we want to live in good times, he said the solution is easy. Do good things. Hope is there. It is within you. It is up to you.

2:10Hey, it's Ryan. Welcome to another Thursday episode of the Daily Stoic Podcast. I was out for a walk last night. I was taking the dog for a walk. The sun was setting, the weather had cooled off, and I was eating a plum cot. Do you know what that is? It's like a combination between a plum and an apricot. And it was so good. It made us a little epicurean of me. It just occurred to me, I was like, I don't think Mark Surrelius knew anything better than this. I mean, he might have been incredibly rich. He might have been incredibly powerful. He might have believed he had the divine right of kings. I don't know.

2:45But it was pretty amazing. And it's those simple pleasures, too. When I said Epicureanism, that we sort of gave Epicurus a bad rap, he wasn't a hedonist. He took delight in these small pleasures. And then the thing I thought about as I'm enjoying this is I said, when I get home, am I going to have another one of these? And I thought, you know what? No, I'm not going to feel good if I have another one of these. So I didn't. Anyways, that has nothing to do with the Q &A today. I was down in Palm Springs back in June, right before we left for Greece for a trip. And I gave a talk at this conference.

3:23It's called Freedom Fest. sort of, I would say libertarian, they say nonpartisan, but I would say it's more sort of the libertarian right. I don't necessarily agree with the politics of the folks there. I have no problem, though, going to places and talking to people who are not going to be super inclined to agree with me. I ended up talking about how the founding of America was built around the idea of liberty, yes, but it went in concert with the idea of responsibility and virtue. Anyways, I did a little Q &A after on why stoicism still matters. Daniel Richards was the moderator, asked a lot of lovely questions.

4:03I think you'll like this. I'll bring you some of this. And then next week, I'll bring you the rest of it. We'll break it up a bit. In any case, here we go.

4:19Thanks to Toyota Trucks for sponsoring this episode. When I bought my ranch in 2015 out here in Bastro County, I drove my car about halfway down the dirt road that we live on, thought this isn't going to work, stopped, parked it, walked the rest of the way home, borrowed my wife's car, drove into Austin and bought a truck. What I bought was a Toyota Tacoma. And this truck wasn't just transportation getting me to and from my house. It unlocked a whole different style of living for us, not just on the ranch, but in our little Texas towns. There were places I could go now that I couldn't go before, especially out here in the piney forests, through the fields, and on the unpaved roads like the one that I lived in.

5:04We got to go deep into the hill country's wild beauty. We've driven all the way out to East Texas. We've driven across the country. And by we, I mean not just my wife, but both my kids who I drove home from the hospital in that truck. Toyota trucks are built for those who understand that the best adventures happen when you're willing to veer off course, because you never know when you'll end up on a Toyota adventure detour. And of course, this is stoicism, too, because every detour, every obstacle is an opportunity. But it's helpful if you can handle the difficulty inherent in that. If you've got the resilience and the right companion to make it wherever the road takes you, discover your uncharted territory.

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7:24You have made a 2000 year old philosophy feel urgent and relevant and useful for millions of people. How the heck did you do that? Yeah, needless to say, my publisher was not super excited when I came to them after writing a couple of marketing books and said that I wanted to write about an obscure school of ancient philosophy. But I knew that it had worked for me, and I knew that it was interesting. And I also knew that if you can understand where the audience is, and you can be real honest about that, you can do the work to try to bring them where you want them to be. And so, you know, I think I understand most people wake up and don't think, you know, what I really need today is ancient philosophy.

8:05But as it happens, the ancients were not that different than us, and they dealt with problems that feel shockingly modern when you read it. And so I feel like my work as a writer, I'm not translating from Greek and Latin into English. I'm translating from academic philosophy and jargon and the preconceived notions that people have about philosophy, I'm translating it from that to where people are. So what I do in my books is I tend to take stories from history, pop culture, business, sports, and I use them to illustrate the ideas. And then those ideas make sense to people. So it's really about understanding that what lights you up is not what necessarily lights the audience up.

8:49And then you've got to do the work of explaining that actually it's just because they haven't learned it the same way that you have or they haven't seen the things that you have. And that's what gets me excited. It's taking things that maybe don't seem interesting and make them accessible and exciting. Yeah. That's fantastic. So I'm also a marketer by trade. Yeah. And so there's a lot of discussion in marketing, obviously, about the audience or the customer. Did you have an audience in mind when you went into this or did you discover an audience along the way? Well, I mean, your audience is always partly yourself.

9:20And in the 80s and 90s, there'd been some books that sort of had popularized Machiavelli and Sun Tzu to like the Wall Street crowd. So it's always helpful to have sort of a comp title, like, hey, I want to be this for that. So I had some sense. And so I was thinking like the business world might be the first place that's where I was coming out of myself. And then, you know, it sort of, I saw with the first book, it started to resonate with sports in the military and then in different communities. So it's really about, I think, how do you make the, and I do think about as I'm writing, do I have examples that cover a wide swath of different professions, personalities, experiences?

10:01Like one thing you won't find in my books is me. Like I don't go, hey, so yesterday I was talking to my friend Steve and this is the problem we had and this is how I use stoicism to solve it. That just strikes me as super boring and not that compelling. So what I'm doing is, as I said, I'm drawing from things that people have heard of. I want to tell stories that maybe the names have a little bit of resonance or they saw it on TV and they remembered that. But I'm actually showing something that's going on a little bit beneath the surface. So the way I think about it is like diversity here is not so much about like quotas or anything like that or affirmative action.

10:39Diversity here is you want every potential kind of person to see themselves in your work. So it's not just a justice thing, although I do think that's actually essential. It's more like I don't want it to only speak to dudes. I don't want it to only speak to people who love sports. I don't want it only to speak to military circles. So I'm picking a breadth of examples and stories and situations that everyone's going to see themselves in it. And I'm trying not to exclude because I want it to include anyone that I think could benefit from it. I do find it interesting that in so much of your work, there is so little of you in it.

11:20One of the things we talk about when we're marketing ideas is before you even consider audience, as you noted, your audience has to be yourself to some degree. But you also have to have this really deep passion that you're doing. It has to come out of you and exude and be authentic. And you said your publisher wasn't super excited about stoicism. like how did how did that come about for you it doesn't seem like it was just a random I'm gonna pick stoicism no no uh I was introduced to it when I was in college I went to a conference like this and I asked actually Dr. Drew he was one of the speakers and I went up to him after and I said hey you know have you read anything interesting recently and he said you know I've been reading the stoics and that as it happens is a how stoicism has been spread for something like 25 centuries it's like this worked for me maybe it'll work for you and what I think I've done is just make that process a little bit easier, a little bit more accessible.

12:08Here's what Stoicism has to say about overcoming obstacles. Here's what Stoicism says about, you know, creating stillness in a crazy world. Here's what Stoicism says about discipline. So I'm kind of breaking it up as the Stoics were, you know, somewhat disjointed and all over the place, and we only have fragments of what they said and believed. So I knew that it had worked for me. It was exciting to me. And my first book had been a marketing book. I did one more marketing book, and I sort of sold what became the obstacles away in between there. I thought it would resonate. I thought it was something I was excited about doing.

12:39I didn't want to be just going around talking about marketing for the rest of my life. I wanted to talk about something more substantive. But I think you would like to think that everyone's going to see the potential, the potential market. They're all going to support you and advocate for you. My publisher's been great. But I mean, when I went to them with what was then my second book for, you know, to do about socialism. I think they offered me, you know, significantly less than half I've gotten offered for my first book. So it was a big step down. That was their objective analysis of what that idea was worth.

13:14But it was worth more to me. And I was excited about it. And I thought, you know, the downside is what? Nothing. Upside is it could work. And it did work. And so you have to understand that it's going to be an uphill battle for a while, and it's going to be against a headwind for quite some time. And now I get requests to blur books about stoicism from other people that would not have been possible 10, 15 years ago when I was going out with The Obstacles of the Way. That's great. That's success. I wanted stoicism to be more popular. It always takes longer than you would expect, even when you take that law into account.

13:50Do you hear that, all of you? It takes longer than you expect. So stick to it. One thing I find really remarkable about your work is how approachable it is. It's very digestible and easy to read for either the novice or someone who's more studied in the ideas. The emails, the tweets, the newsletters, the books, the journaling sort of and how it all works together. How was it sort of discovering that system for you? Like, was it a lot of trial and error? Well, I learned from one of the masters, we're talking about wisdom. Obviously, the idea of an apprenticeship is not so in vogue anymore. But that's how I learned.

14:27I was a research assistant to an amazing writer named Robert Greene, who wrote The 48 Laws of Power, who, by the way, did this version of what we're talking about himself first. He took these seemingly obscure texts from ancient history and medieval history and all over the world, like all these, and he made it accessible and practical to the point where I'm pretty sure the 48 Laws of Power is the most requested book in the federal prison system. And it is, by and large, the most shoplifted book every year, all of which is quite an endorsement. It is. It's quite an endorsement to the accessibility to that book.

15:02These are people who are not shoplifting other books on a regular basis. So I learned from him the art of story and crafting. And I learned the process from him. But then, obviously, I've also just been doing it a long time. The Daily Stoic email started in 2016. It was going to be one bit of Stoic wisdom every single day. I think it started with about 10 ,000 people, which is from all my different platforms. And it now goes out to almost a million people every day. But that's a result of me writing an email every single day for, you know, going on nine years. That's nine free books. You know, that is a lot of engagement with the audience, like seeing what works, seeing what doesn't work.

15:50Just the stage time of doing it over and over and over and over again. And I feel like I'm just getting the hang of podcasting or YouTube videos or even public speaking. You know, you can be serviceable if you're decent at the beginning. And there are things you can do to sort of get up to speed. But it takes, you know, thousands of hours to get good at a thing that is hard. Yeah, absolutely. And making things accessible is one of the hardest things that there is. Or else everyone would do it. Yeah. I forget who said it, but they said, excuse the length of this letter, but if I had more time, I would have written you a shorter one.

16:28Totally. Yes. And the other thing is anyone that does it well tends to make it look easy. So you see someone with a huge YouTube following or a big social media. Look, sometimes these people have been blessed by the algorithm and there's not really much there there. But a lot of times it is, you know, just incredible amounts of repetition and experience and trial and error, seeing what works and you sort of hone a sense of how you do what you do.

17:00Hey, it's Ryan. Thank you for listening to the Daily Stoic podcast. I just wanted to say we so appreciate it. We love serving you. It's amazing to us that over 30 million people have downloaded these episodes in the couple years we've been doing it. It's an honor. Please spread the word. Tell people about it. And this isn't to sell anything. I just wanted to say thank you.

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18:58So if you want to support a show but not listen to ads, well, we have partnered with Supercast to bring you an ad-free version of Daily Stoic. We're calling it Daily Stoic Premium. And with Premium, you can listen to every episode of the Daily Stoic podcast completely ad-free. No interruptions, just the ideas, just the messages, just the conversations you came here for. and you can also get early access to episodes before they're available to the public. And we're going to have a bunch of exclusive bonus content and extended interviews in there just for Daily Stoic Premium members as well. If you want to remove distractions, go deeper into Stoicism and support the work we do here.

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From the publisher

Despair is so easy, even reasonable in moments like this. The Stoics knew that feeling well.


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