The Daily Stoic - We Could Use More People Like This | How Ryan Holiday Is Challenging Himself Creatively

Episode Date: June 5, 2026

We are in desperate need of good, courageous people. Can you fill that need?📚 Grab signed copies of Austin Kleon's books at The Painted Porch: Don’t Call it ArtSteal Like An Artist Show Your WorkKeep Going 🎟️ DAILY STOIC LIVE | Ryan Holiday is coming to a city near you! Grab tickets here | https://www.dailystoiclive.com/🇺🇸 USA dates:Portland, Oregon - June 8 San Francisco, California - June 11Minneapolis, Minnesota - August 18 Chicago, Illinois - August 19 Detroit, Michigan - August 20 🇳🇿 NEW ZEALAND:Auckland, New Zealand - October 13 🇦🇺 AUSTRALIA dates:Sydney, Australia - October 16 Melbourne, Australia - October 18 Brisbane, Australia - October 20Perth, Australia - October 21 🎙️ AD-FREE | Support the podcast and go deeper into Stoicism by subscribing to The Daily Stoic Premium - unlock ad-free listening, early access, and bonus content: https://dailystoic.supercast.com/✉️ FREE STOIC WISDOM | Want Stoic wisdom delivered to your inbox daily? Sign up for the FREE Daily Stoic email at https://dailystoic.com/dailyemailSee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Welcome to the Daily Stoic Podcast, designed to help bring those four key stoic virtues, courage, discipline, justice, and wisdom into the real world. We could use more people like this. It's a dark world. It's a world with cheats and cowards, liars, and monsters. It's also a world of busy people with a lot going on, people who don't have time or energy to get involved. That is why it is such a public service. as we said, to be courageous, as Cato was, as Helvidius was, even as Marcus Aurelius was during the Antonine

play. A public service to whom? To those people who are not cheats and cowards, liars, and monsters, to the busy people, the people who have a lot going on, the people who don't know what they can do, let alone what they ought to do. When they see someone committed to justice, when they see someone speaking out when they see someone getting involved, when they see someone doing good, it sends a powerful message. It shows them that not everyone is dark, that not everyone is afraid. It gives them an example to follow, gives them hope, gives them a practical set of things that they can do. We can always use more leaders. We are in desperate need of good, courageous people. Can you feel that need? If you want to be one of those people, well, start by studying them. It's what courage is calling and

right thing right now is all about people who chose to step up when it mattered whose actions helped inspired others who were not too busy who were not too scared who were good and courageous and didn't back down who showed that the best way to fight back against a dark world is to be a source of light hey it's ryan welcome to a another episode of the daily show podcast i remember when i first moved to texas i got lunch with austin cleon who had lived in austin a little bit longer. We were sitting out in East Austin at a restaurant that no longer exists, and he said, work family scene, pick two. He was just telling me that, like, I had to get my priorities straight as a creative and as a person I didn't have kids yet, but I was sort of thinking about it,

that, you know, you could be a sort of a trendy, cool sort of person about town and maybe get good work done, but that would come at the expense of your family. Maybe you could party and have a family and your work would suffer. His point was you've got to pick what your priorities are. And that stayed with me. It's been life-changing advice. I do try to mostly choose work and family. And sometimes I combine the two. I'm hitting the road here. Actually, tomorrow we're flying out to do a little road trip down the West Coast because I have two speaking dates. I'm going to be in Portland on June 8th giving a talk. And then I'm going to be in San Francisco, I believe, on the 11th. You can grab tickets to come see me if you want. daily stoic live.com.

But it's funny, Austin was just here. We have the fuller episode of the podcast, but as we were sort of settling down, he was asking me about the tour and how it's going, if he's having fun, you know, how I think about it. And we kind of riffed on it a little bit.

I don't know. I just thought it would be interesting. Austin is a great dude. He has a new book out called Don't Call It Art, which is lovely. It's sort of a sequel to his previous trilogy. Still like an artist, show your work and keep going. keep going has been a long time favorite and sort of resource for me. And I think this new one

has some really great stuff in there about creativity and kids. So anyways, I'm going to bring you a fuller episode about that. But I wanted to riff this out just in case you didn't know I was going to be in Portland. Maybe you want to come see me in San Francisco or Boston, Detroit, Minneapolis, Chicago, D.C., a bunch of other cities. I'm going to be in Australia with my family to do some dates in October. You can grab all those at Dailystoke Live.com. And of course, grab sign copies at Boston Cleon's new book, Don't call it art. I don't know if you've ever done any live shopping,

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And it's real people selling. Like if you're going to an estate sale or a really cool, trendy shop, not, you know, overpriced stuff, not produce stuff. There's no ads, no marketing. And people are on there explaining their stuff, why you'd like it, what's cool about it, where they got it. Like, I love buying stuff on auctions. So I think I'm going to like WhatNot. And I think you will, too. There are people making over a million dollars a year on What Not. That number has doubled in the last year. Whatnot is the largest dedicated live shopping platform, whether it's beauty, collectibles, electronics, luxury fashion, even cookies.

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So when's your four stuff? I think the first one is Monday. So we're flying to Seattle on Friday. I just think that whole industry, it's like when you have an audience like you do, you might as well book your own shit and like... Well, it's also just, it's way more fun than the corporate stuff because, like, the people actually want to be there. Yeah, they want to be there. They bought the ticket and they want to hear from you. It's like doing a bookstore gig versus a corporate. And it's also more of like a performance than a, yeah, it's like a show. Than a like a presentation. You know what I mean? And this is a show. Yeah. So I like it better. For me, the tour stuff is much more about not being chosen but choosing. If that makes sense. Like there is something weird about like, why are you going to. X, Y, or Z. It's like, well, somebody asked. Yeah, somebody asked. And so you sort of get to this place in your career and then you're just like, probably like an actor, just sitting around waiting to be asked to go to a certain place

to do it on certain terms. Yeah. And it just occurred to me that like, it would be much cooler to be like, like, Samantha wanted to do a road trip on the West Coast. So I was like, well, why don't I just tell the promoter that we'd like to do that we were planning on doing this? So the real story is Sam wants to do something. It's more like, hey, I want to be in this area. Yeah. So, like, well, why don't I just work while I'm there? Right.

And then, you know, you actually get to, like, talk to real people that chose to be there as opposed to, like, I work here. Yeah, or just like, wait, why is this? Like, you know, you do enough things at, like, 9 a.m. in Las Vegas. And you just, you're like, oh, not only am I getting up there to talk about an obscure school of ancient philosophy, but I'm doing it to people under duress. Yeah. They're at work. They're at work. I remember the first time I got like a gig at Google and I was like, oh, Google, whatever.

And I got in there and it's just a job to these people. They're all like, I wonder what's in the cafeteria today. You know, like, they're not. The sports one, you think sports is going to be this crazy cool audience. And then you're like, they got into sports to not have to go to meetings. Yeah, exactly. This is like torture. You're not only, you're the extra meeting.

Yeah, yeah. And so like one more thing on their plate. Exactly. And so anyways, the gigs have been fun and sure touring around. and then trying to like pair it. It's like, oh, I'm already going to have to be here, so let's do that. It's like your version of a maiden show too, right? Well, I would say the other thing is, like, so being chosen versus choosing is important.

But there's also, like, would you rather be dependent or independent? And I think there's something about, like, the audience can cancel you, but like by not being interested. Right. But there is something about going, like, do you want, like, whatever the trend of the moment is or the, a version of the moment to be deciding whether you get to do your job or not. And so I like, I just thought it was important given where we are politically and culturally to have an avenue that is not dependent on other people choosing you. So that's what I've been doing. Yeah. It's very like, you know, the Minutemen used to call it Jam McConnell. You know, it's like you get in the van,

they do the show, gigs and flyers, you know. Yeah. There's a simplicity to it. Well, and unlike music, which is a lot of work to tour, that is the nice part. It's like, I literally, it's like, I could take a Southwest flight to any city in the country. And then you walk on stage and you speak into a microphone. There's, there's, like, you're using a house PA system. But there's no, there's no logistics. There's no crew. There's nothing.

And so, it's like, do you have an H.T.MI cable from my laptop? Okay, we're going to. So actually, and it's talking about, like, challenging yourself, which I want to talk about, you know, Chris Williamson? He's a podcast, modern wisdom, he's based here. He was telling me he did it, he did a tour of Australia or something. And I said, so, like, do you do slides or whatever? And he's like, I just talk.

And I was like, oh, I'll try that. And so that's the other thing is like, it's a totally different kind of. I took it as a challenge at first, but then it also, it does require you to be better at it. It's like a lecture more. It's more like you're, or like a stand-up set even. You know, like you don't have props. You don't have the props of the slides. And the slides are.

props in the sense of like they're propping you up a little bit. Like you can get away with not being as good because you have a funny picture of you. Oh yeah. I do that all the time. Me too. I'm surprised that you would get rid of that. I think I did it first as the challenge. Yeah.

And then second as a like I think like when you're talking to a corporate audience, you're like here, let me speak. Slides are in their worlds. Right. Right. Like they're doing Zoom presentations and keynotes and whatever. But I think when you like step into a theater, there is something that feels somewhat off about like, and then let me click over to the next slide.

So anyways, I've been doing it without it, which is more of the campfire thing. Like we're all. It's nice. It's also scarier because it's like, oh, wait, I got to come up with an hour presentation to do on Monday. I think it's really interesting because from the outside, you're someone who's kind of like mastered a lot of things.

And I think it's interesting to hear you talking about how, you can make things interesting for yourself. Like you're not doing it out of necessity. Like you're not doing a tour because it's like, oh, I'm going to clean up and whatever. This is like an interestingly, like, this is a new challenge for me. This is something that would be cool.

I do think whatever you're doing, you should always be finding a new way to do it. It's like, okay, did I just want to give my same handful? Because I have like different talks for different lines, but did I give essentially the same talk just in a different location? That doesn't seem that interesting. And then also, like, By nature of these people choosing to be there, they don't need an introduction to what I talk about or they wouldn't be there.

Right. They know you. They have a relationship with you. I think by putting yourself in different contexts, you have to sort of rise to meet the occasion. Yeah. And then deciding to do it. It's actually funny. There's a line in Meditations where Marks Reelis talks about. How long that take? Ten minutes? What are we at? Yeah, let's see. Why don't I see if I can not mention it the rest. That will be my challenge for today. We're old friends. I get to do this with you. Of course.

No, no, he talks about using the reins of the horse with your opposite hands. Like he's just... Oh, right. So it would be like, hey, I'm going to try to draw this with my other hand. Exactly.

And so I think the decision to go, hey, I'm going to do this in a different way. Like, hey, I'm going to do this from memory this time or I'm going to do it, you know... It's a new constraint. Like, what David's right. Like, David Epstein, his new book, like, talking about constraints.

It's like a new constraint for you. And then that new constraint... leads to new work and new ways of doing stuff. And it's like generative. Even with these, this is, I guess, four books, similar size, similar title approach. Like, so there's something, because I've done that where you're sort of like, this is the, this is like the Law and Order episode. It starts with this and it ends with this.

And David's totally right. There's by creating those borders, there's infinite combinations inside. Right. And then sometimes also it's good to be like, okay, I'm going to do something totally. Totally different this time. That's my big question with David is just like, what do you do when your constraints are not generative anymore that they're constraining you? Because I think that's what this new book is about for me is like I hit a point mid career where it's just like, I don't even remember why I got started. I don't even remember what was fun about this.

I don't even really remember what it was like to start making things and putting them out in the world. And so like to me it was about like there was a kind of exhaustion. You know, because Keep Going was like about showing up and showing up and showing up. You know, the Marshawn Lynch just ran through the face, you know. And then, but like this book is like, what happens when that just isn't enough anymore, basically? Well, I want to talk about that. But I think it can be really easy to just do like, I remember a couple years ago, more than a couple years ago. But I was doing some talk.

He was in Buffalo. And, you know, sometimes you see the people talking before you. This guy gave this talk. And it was like, how to lead like Reagan. and he was like a Reagan speechwriter and I was like, for 40 years. And I think you can see that probably musicians too where it's like the same set.

They probably have the same jokes. And they just, and so, you know, there's probably some comfort in that and there's also that feels like a little bit of a kind of death, you know. And so you've got to figure out new ways of mixing it up inside there. Yeah, I mean, it's kind of the Carlin versus Seinfeld thing. You know, like Carlin did a new hour every year. Right.

And that was the challenge. But Seinfeld's a little bit more like, hey, I want your best stuff. Yeah. Like when you come. So it's like finding a nice, like, I guess middle path between that shut up and play the hits and like, oh, here's the new stuff. Yes.

And every, you know, every band has to deal with that. It's kind of, yeah. But the thing I always try to keep in mind is like most people, it's cool that you're doing these talks where it's your audience showing up because they probably are familiar with your work. Yeah. When you do that, hello, Purina, and you're like, whatever, like, hello, Indiana. And, like, you get on stage, like, those people don't know. They haven't ever heard you before.

And so it's fresh for them. And I also think that's, like, something that's hard, like, as a, you know, as a performer is that it's new to them. Like, they've never heard the stuff. It's just not new to you. Yes. So, like, how do you find a way to make sure you're delivering the good stuff and then also, like, challenging yourself? it's new, but then I've also been thinking, okay, am I doing the same one each time? Yeah.

And like, there's some things that I keep and there's some things I swap out because in a world where it's suddenly like, okay, a band might do, or in the stand-up model, like a band's going to do a tour and then they're like, we're going to pick the best city and then we're going to film that and that's going to be the live album or that's going to be the special. Yeah. And part of the reason they didn't just film every date is because it's expensive. Yeah. But as the cost of filming drop and then also the vexed.

like it's this weird thing where it's like the cost of it is dropping but then also the demand for it is infinite because you're mostly giving it away you're not like selling it on Netflix or something yeah but the point is if you do the same thing every night you can't take advantage of you can't chop it you can't because you're just like okay now you have you did 10 dates and you have 10 shots of you telling the same story in a different shirt like there's no there's a waste of that opportunity so I also try to think okay how am I making sure that each time I'm telling a chunk of new things because otherwise, like, it's not what's the point of doing it because you're also doing it for the people there, but like everything now you're doing

it for the people in the room and then the people not in the room who are able to watch it. And so there's a challenge there of like, like, so I'm doing Portland and San Francisco like three days apart. I'm not going to do the same shows because I mean, I'm then like, what's the point of the videographer? Right. Like, you know, so I'm going to, I'm going to try to tell different stories.