We Could Use More People Like This | How Ryan Holiday Is Challenging Himself Creatively

Summary

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Podcast Summary: The Daily Stoic

Episode: "We Could Use More People Like This | How Ryan Holiday Is Challenging Himself Creatively"

Date: June 5, 2026
Host: Ryan Holiday, joined by guest Austin Kleon

Overview

This episode of The Daily Stoic centers on the critical need for good, courageous people in a complex world and explores the personal and creative challenges of author Ryan Holiday. The conversation weaves in practical Stoic lessons—especially around service, courage, and ongoing creative evolution—and presents a candid look at how Holiday reinvents his approach to professional speaking and creative work. Special guest Austin Kleon, writer and artist, joins Holiday for an engaging dialogue on priorities, creative constraints, and staying energized mid-career.

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Key Discussion Points & Insights

1. The World Needs Good People and Public Service

• Theme Introduction:
  Holiday reflects on the prevalence of "cheats and cowards, liars and monsters" in the world, emphasizing the public service of being good and courageous.
  • “To be courageous, as Cato was, as Helvidius was, even as Marcus Aurelius was during the Antonine Plague, is a public service… When they see someone committed to justice… it gives them hope.” (00:38)
• Call to Action:
  He challenges listeners to fill the world’s need for more moral leaders, suggesting the first step is to study those who exemplify virtue.
  • “We can always use more leaders. We are in desperate need of good, courageous people. Can you fill that need?” (02:17)

2. Prioritizing Work, Family, and Creative Life

• Austin Kleon's Advice:
  Holiday recalls advice from Austin Kleon about the necessity of prioritizing among work, family, and “scene,” highlighting the impossibility of excelling in all at once.
  • “Work, family, scene – pick two… you gotta pick what your priorities are. And that stayed with me. It’s been life changing advice.” (03:21)
• Choosing Family and Work:
  Holiday discusses his own choice to combine work and family, referencing his upcoming West Coast speaking tour.

3. Taking Creative Control & The Joys of Touring

• Agency and Independence:
  Holiday talks about shifting from being “chosen” (waiting for invitations) to “choosing” by proactively planning his events in places that matter to him and his family.
  • “For me, the tour stuff is much more about not being chosen but choosing, if that makes sense.” (07:04)
• Engagement with Audience:
  The duo contrasts bookstore gigs (where people want to be present) with corporate talks (where people attend by obligation).
  • “It’s way more fun than the corporate stuff because the people actually want to be there.” (06:45, Holiday)
  • “You actually get to, like, talk to real people that chose to be there, as opposed to… doing it to people under duress.” (07:51, Holiday)
• Logistics of Speaking vs. Musical Touring:
  Holiday appreciates the simplicity and nimbleness of public speaking compared to music tours.
  • “Unlike music, which is a lot of work to tour... I could take a Southwest flight to any city… you speak into a microphone. There’s no logistics. There's no crew.” (09:42, Holiday)

4. Challenging Oneself Creatively

• Ditching the Slides:
  Inspired by Chris Williamson (Modern Wisdom), Holiday decides to give talks without slides, taking it as a personal challenge.
  • “I tried it at first as the challenge. And then second… when you step into a theater, there is something that feels somewhat off about, like, and then let me click over to the next slide.” (10:24, Holiday)
• Constraints as Creative Fuel:
  They discuss the value of new constraints—whether through format or circumstance—to spark new creative outcomes.
  • “I think the decision to go, hey, I'm going to do this in a different way... it's a new constraint… and that leads to new ways of doing stuff. It's generative.” (13:01, Kleon)

5. Avoiding Creative Rut and Minding the Audience

• Reinventing Content:
  Holiday cautions against the creative “death” of repeating a routine indefinitely, as seen with some musicians and speakers.
  • “There's probably some comfort in that. And there's also—that feels like a little bit of a kind of death, you know?” (14:25, Holiday)
• The Carlin vs. Seinfeld Dilemma:
  Kleon highlights the balance between new material and fan favorites in live performance, referencing George Carlin’s frequent new hours versus Jerry Seinfeld's more consistent set.
  • “It's kinda the Carlin vs. Seinfeld thing... finding a nice middle path between ‘shut up and play the hits’ and ‘here's the new stuff.’” (15:05, Kleon)

6. The Challenge of Keeping It Fresh

• Different Sets, Different Cities:
  As filming and streaming talks becomes easier, Holiday plans to vary his presentations to provide value both for live and remote audiences.
  • “I also try to think, okay, how am I making sure each time I'm telling a chunk of new things? Otherwise… what's the point of the videographer, right?” (16:55, Holiday)
• For Both In-Room and Remote Audiences:
  The duo explores the unique challenge and opportunity of serving two audiences—the ones present and those watching later.

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Notable Quotes & Memorable Moments

• "The best way to fight back against a dark world is to be a source of light."
  (01:30, Holiday)

• "Work, family, scene—pick two."
  (03:21, Austin Kleon's advice, as remembered by Holiday)

• "It’s not about being chosen, but choosing."
  (07:04, Holiday on planning his own tours)

• "There's something about, like… do you want whatever the trend of the moment is or the aversion of the moment to be deciding whether you get to do your job?"
  (09:10, Holiday on independence)

• "Slides are props in the sense of, they're propping you up a little bit."
  (10:42, Holiday)

• "By creating those borders, there’s infinite combinations inside… Sometimes also it’s good to be like, okay, I'm gonna do something totally different this time."
  (13:15, Holiday)

• "There was a kind of exhaustion, you know?...what happens when that just isn’t enough anymore?"
  (13:43, Kleon on creative midlife)

• "It's kind of the Carlin vs. Seinfeld thing, you know...finding a nice middle path between 'shut up and play the hits' and 'here's the new stuff’.”
  (15:05, Kleon)

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Timestamps for Key Segments

• 00:00–03:00 — Opening: The call for public service, historical Stoic examples
• 03:21–05:00 — Priorities in creative life ("Work, family, scene—pick two")
• 06:33–09:15 — Touring: Independence, engagement, and audience connection
• 10:08–13:15 — Dropping slides, creative constraints, and performance challenge
• 13:43–16:00 — Avoiding creative staleness, Carlin vs. Seinfeld performance philosophy
• 16:32–17:49 — How new technology changes what it means to perform and record live events

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Takeaways

This episode offers a rich blend of wisdom for anyone feeling the need to serve, the desire to stay creatively vital, or the struggle with mid-career inertia. It underscores the Stoic ideal of courage in action while advocating consciously chosen constraints and renewal as an antidote to stagnation. The conversation remains light, honest, and practical, providing a rare window into the evolving creative process at the heart of modern Stoic practice.

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Transcript

[A]

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. It 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 show 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, but 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 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. Cause 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. Come see me if you want. Daily stoiclive.com but it's funny, Austin was just here. We have the fuller episode of the podcast, but as we were of settling down, he was asking me about the tour and how it's going, if I was 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, Steal 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 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. bunch of other cities. I'm going to be in Australia with my family to do some dates in October. 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[B]

So when's your four stuff?

[A]

I think the first one is Monday. So we're flying to Seattle on Friday.

[B]

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.

[A]

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.

[B]

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.

[A]

And it's also more of like a performance than a. Yeah, it's like a show than a, like, like a presentation. You know what I mean? And this is a show.

[B]

Yeah.

[A]

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.

[B]

Yeah, somebody asked.

[A]

Like, and. 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.

[B]

Yeah.

[A]

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.

[B]

The real story is Sam wants to do something.

[A]

It's more like, hey, I want to be in this area.

[B]

Yeah.

[A]

So, like, well, why don't I just work while I'm there?

[B]

Right.

[A]

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 per. Like, you know, you do enough things at like, 9am 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. Like, they're at work. Yeah, they're at work.

[B]

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.

[A]

You know, like, they're 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.

[B]

This is like Torch.

[A]

You're not only. You're the extra meeting.

[B]

Yeah, yeah. And so, like, one more thing on their plate.

[A]

Exactly. And so. 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.

[B]

So it's like your version of a maiden show too, right?

[A]

Well, I would say the other thing is, like, so being chosen versus choosing is. 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.

[B]

Right.

[A]

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. 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.

[B]

Yeah, it's very like. You know, the Minutemen used to call it Jam and Kano. You know, it's like you get in the van and you do the show. Gigs and flyers, you know.

[A]

Yeah.

[B]

There's a simplicity to it.

[A]

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, you got a mic. 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. But there's no. No, there's no logistics. There's no crew. There's nothing. And so I was like, do you

[B]

have an HDMI cable for my laptop? Okay, we're good.

[A]

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 saw. And I was like, oh, I'll try that.

[B]

Yeah.

[A]

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.

[B]

It's like a lecture more. It's more like you're.

[A]

You're.

[B]

Or like a standup set, even, you know, like, you don't have props. You don't have the props of the slides and this.

[A]

And the slides are props in the sense of, like, they're propping you up a little bit. Like, you. You can get away with not being as good because you have a funny picture.

[B]

Oh, yeah. I do that all the time. I'm surprised that you would get rid of that.

[A]

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. Your slides are in their world.

[B]

Right, Right.

[A]

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. Let me click over to the next slide. So anyways, I've been. I've been doing it without it, which

[B]

is more of the campfire thing. Like, we're all.

[A]

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.

[B]

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. Cause it's like, oh, I'm gonna clean up and whatever. This is like an. Interestingly, like, this is a new challenge for me. This is something that would be cool.

[A]

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 wanna give my same handful? Cause I have, like, different talks for different audiences. But do 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.

[B]

Right. They know you. They have a relationship with you.

[A]

I think by putting yourself in different contexts, you have to sort of rise to meet the occasion. Yeah, but. And then deciding to do it, it's actually funny. There's a line in Meditations where Marcus Grealis talks about how long that take.

[B]

10 minutes.

[A]

Where are we at? Yeah, let's see. Why don't I see if I can kn. Mention the rest? That will be my challenge for today.

[B]

We're old friends. I get to do this with you. Of course.

[A]

No, no, He. He talks about using the reins of the horse with your opposite hands. Like, he's just.

[B]

Oh, right.

[A]

So it'd be like, hey, I'm going to try to draw this with my other hand.

[B]

Exactly.

[A]

And. 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.

[B]

You know, it's a new constraint, like what David's writing about, 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.

[A]

Right. Even with these. This is, I guess, four books, similar size, similar title, approach. Like, so there's something. Cause 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 gonna do something totally different this time.

[B]

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? Cause 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? Cause Keep going was like, about showing up and showing up and showing up. You know, the Marshawn lynch just run through a face, you know, and then. But like, this book is like, what happens when that just isn't enough anymore, basically.

[A]

Well, I want. And 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. It 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, yeah, 40 years. Yeah. And. 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 got to figure out new ways of mixing it up inside there.

[B]

Yeah, I mean, it's kind of the.

[A]

The.

[B]

The Carlin vs. Seinfeld thing, you know, Like, Carlin did a new hour every year.

[A]

Right.

[B]

And that was the challenge. But Seinfeld's a little bit more like, hey, I want your best stuff.

[A]

Yeah.

[B]

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.

[A]

Yes.

[B]

And every, you know, every band has to deal with that. Uh, 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.

[A]

Yeah.

[B]

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.

[A]

Yes.

[B]

So, like, how do you find a way to make sure you're delivering the good stuff and then also, like, challenging yourself?

[A]

It's new. But then I've also been thinking, okay, am I doing the same one each time?

[B]

Yeah.

[A]

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 standup 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 gonna film that, and that's gonna be the live album. Or that's gonna be the special.

[B]

Yeah.

[A]

And part of the reason they. They didn't just film every date is because it's expensive.

[B]

Yeah.

[A]

But as the costs of filming drop and then also the value, 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. Cause you're mostly giving it away. You're not, like, selling it on Netflix or something. But the point is, if you do the same thing every night, you can't take advantage of.

[B]

You can't chop it.

[A]

You can't. Because you're just like, okay, now you have. You did 10, and you have 10 shots of you telling the same story in a different shirt. Like, there's no. Yeah, that's a. 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, 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.

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