The Daily Stoic
We Could Use More People Like This | How Ryan Holiday Is Challenging Himself Creatively
05 Jun 2026
Transcript generated automatically by AI and may contain errors.
Chapter 1: What challenges does Ryan Holiday identify in today's world?
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 Plague. 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 fill that need? And 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 another episode of the Daily Stoke Podcast.
I remember when I first moved to Texas, I got lunch with Austin Kleon, who had lived in Austin a little bit longer. And 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 family and your work would suffer. His point was you got to pick what your priorities are. And that stayed with me.
It's been life changing advice.
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Chapter 2: How can courage serve as a public service?
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, dailystoiclive.com. But it's funny, Austin was just here. We have a 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 it'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 longtime 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 rip 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 dailystokelive.com.
And of course, grab signed copies of Austin Kleon's new book, Don't Call It Art. I don't know if you've ever done any live shopping, but it's blown up. And some of the kids, I don't know if I call them kids, but some of the Gen Z kids on my staff had to tell me about it. They really love it because you can find vintage stuff and collectible stuff.
I was looking at some videos of people selling vintage band tees and records and watches. 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 produced 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.
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Chapter 3: What priorities should creatives focus on according to Ryan?
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So when's your floor 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. Well, it's also just way more fun than the corporate stuff because 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. Yeah, sure. 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.
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Chapter 4: How does Ryan balance work and family while touring?
Or just like, wait, why is this? Like, you know, you do enough things at like 9 a.m. in Las Vegas. Yeah. 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. Yeah, 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. To meetings, yes. Exactly. This is like torture. You're the extra meeting. Yeah, yeah. One more thing on their plate. Exactly. And so anyways, the gigs have been fun and sort of touring around and then trying to like pair.
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 aversion of the moment to be deciding whether you get to do your job or not? Yeah. 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 Econo. 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, and then you walk on stage and you speak into a microphone. There's, there's like, you're using a house PA system and there's no, there's no logistics, there's no crew, there's nothing.
And so it's like, do you have an HDMI cable for my laptop? Okay. 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, no, I just, he's like, I just taught. And I was like, oh, I'll try that. And so that's the other thing is like, it's a, 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.
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Chapter 5: What insights does Ryan share about live performances?
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. 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. 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 uh let me click over to the next slide so anyways i've been 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 gotta i have 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 audiences. 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. And then deciding to do it. It's actually funny.
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