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

We are in desperate need of good, courageous people. Can you fill that need? 📚 Grab signed copies of Austin Kleon's books https://www.thepaintedporch.com/search?type=product&q=austin+kleon* at The Painted Porch https://www.thepaintedporch.com/search?type=product&q=austin+kleon*: Don’t Call it Art https://www.thepaintedporch.com/products/dont-call-it-art-10-ways-to-create-like-a-kid-again-signed?_pos=9&_sid=2462dbc08&_ss=rSteal Like An Artist https://www.thepaintedporch.com/products/steal-like-an-artist-10th-anniversary-gift-edition-with-a-new-afterword-by-the-author-10-things-nobody-told-you-about-being-creative-signed-by-austin-kleon?_pos=5&_sid=2462dbc08&_ss=rShow Your Work https://www.thepaintedporch.com/products/show-your-work-10-ways-to-share-your-creativity-and-get-discovered-signed-by-austin-kleon?_pos=1&_sid=2462dbc08&_ss=rKeep Going https://www.thepaintedporch.com/products/copy-of-keep-going-10-ways-to-stay-creative-in-good-times-and-bad?_pos=4&_sid=2462dbc08&_ss=r 🎟️ DAILY STOIC LIVE https://www.dailystoiclive.com/| Ryan Holiday is coming to a city near you https://www.dailystoiclive.com/! Grab tickets here https://www.dailystoiclive.com/ | https://www.dailystoiclive.com/ 🇺🇸 USA dates: Portland, Oregon - June 8 https://www.etix.com/ticket/p/80444483/onstage-with-ryan-holiday-portland-revolution-hallSan Francisco, California - June 11 https://www.eventbrite.com/e/daily-stoic-live-onstage-with-ryan-holiday-tickets-1984559640307?aff=oddtdtcreatorMinneapolis, Minnesota - August 18 https://www.dailystoiclive.com/Chicago, Illinois - August 19 https://www.eventbrite.com/e/daily-stoic-live-onstage-with-ryan-holiday-tickets-1984473140584?aff=oddtdtcreatorDetroit, Michigan - August 20 https://www.eventbrite.com/e/daily-stoic-live-onstage-with-ryan-holiday-tickets-1984473550811?aff=oddtdtcreator 🇳🇿 NEW ZEALAND: Auckland, New Zealand - October 13 https://au.thinkable.events/ryan-holiday-tour/ 🇦🇺 AUSTRALIA dates: Sydney, Australia - October 16 https://au.thinkable.events/ryan-holiday-tour/Melbourne, Australia - October 18 https://au.thinkable.events/ryan-holiday-tour/Brisbane, Australia - October 20 https://au.thinkable.events/ryan-holiday-tour/Perth, Australia - October 21 https://au.thinkable.events/ryan-holiday-tour/ 🎙️ AD-FREE https://dailystoic.supercast.com/| Support the podcast and go deeper into Stoicism by subscribing to The Daily Stoic Premium https://dailystoic.supercast.com/ - unlock ad-free listening, early access, and bonus content: https://dailystoic.supercast.com/ https://dailystoic.supercast.com/ ✉️ FREE STOIC WISDOM https://dailystoic.com/dailyemail | Want Stoic wisdom delivered to your inbox daily? Sign up for the FREE Daily Stoic email at https://dailystoic.com/dailyemail https://dailystoic.com/dailyemail See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.

• 0:00Ryan Holiday?

  Welcome to the Daily Stoic Podcast, designed to help bring those four key Stoic virtues, courage, discipline, justice, and wisdom into the real world.

• 0:15Ryan Holiday?

  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. 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,

• 0:59Ryan Holiday?

  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? 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 are not too busy, who are not too scared, who are good and courageous and didn't back down, who showed that the best way to fight back

• 1:44Ryan Holiday?

  against a dark world is to be a source of light.

• 1:57Ryan Holiday?

  Hey, it's Ryan. Welcome to another episode of the Daily Stoic 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 family and your work would suffer. His point was, you gotta pick what your priorities are.

• 2:40Ryan Holiday?

  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, come see me if you want, dailystoiclive.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 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.

• 3:24Ryan Holiday?

  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 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, DC, 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 dailystoiclive.com. And of course, grab signed copies of Austin Kleon's new book, Don't Call It Art.

• 4:08Speaker 01

  So when's your tour stuff?

• 4:09Ryan Holiday?

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

• 4:14Speaker 01

  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.

• 4:20Ryan Holiday?

  Well, it's also just, it's way more fun than the corporate stuff because like the people actually want to be there.

• 4:23Speaker 01

  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.

• 4:29Ryan Holiday?

  And it's also more of like a performance than a, um.

• 4:32Speaker 01

  Yeah, it's like a show.

• 4:33Ryan Holiday?

  Than a like, like a presentation, you know what I mean? And this is a show.

• 4:38Speaker 01

  Yeah.

• 4:38Ryan Holiday?

  So I like it better. For me, the tour stuff is much more about not being chosen but choosing. If that makes sense.

• 4:46Speaker 01

  Sure.

• 4:46Ryan Holiday?

  Like, there is something weird about, like, why are you going to X, Y, or Z? It's like, well, somebody asked.

• 4:52Speaker 01

  Yeah, somebody asked.

• 4:52Ryan Holiday?

  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.

• 5:05Speaker 01

  Yeah.

• 5:06Ryan Holiday?

  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.

• 5:17Speaker 01

  The real story is Sam wants to do something.

• 5:20Ryan Holiday?

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

• 5:22Speaker 01

  Yeah.

• 5:22Ryan Holiday?

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

• 5:25Speaker 01

  Right.

• 5:25Ryan Holiday?

  And then, um, you know, you actually get to like, talk to real people that chose to be there as opposed to like.

• 5:31Speaker 01

  I work here.

• 5:33Ryan Holiday?

  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're 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.

• 5:48Speaker 01

  Yeah. They're at work.

• 5:50Ryan Holiday?

  Yeah, they're at work.

• 5:50Speaker 01

  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.

• 6:00Ryan Holiday?

  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.

• 6:08Speaker 01

  Yeah, exactly. This is like torture.

• 6:10Ryan Holiday?

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

• 6:13Speaker 01

  Yeah, yeah.

• 6:13Ryan Holiday?

  And so like.

• 6:14Speaker 01

  It's one more thing on their plate.

• 6:15Ryan Holiday?

  Exactly. And so, so anyway. The gigs have been fun and sort of touring around and then trying to like pair it. It's like, oh, I'm already gonna have to be here, so let's do that. So.

• 6:25Speaker 01

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

• 6:28Ryan Holiday?

  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.

• 6:44Speaker 01

  Right.

• 6:45Ryan Holiday?

  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.

• 7:07Speaker 01

  Yeah, it's very like, you know, the Minutemen used to call it jam ekano. You know, it's like you get in the van, they do the show, gigs and flyers, you know?

• 7:16Ryan Holiday?

  Yeah.

• 7:16Speaker 01

  There's a simplicity to it.

• 7:17Ryan Holiday?

  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 P A system and there's no, there's no logistics. There's no crew, there's nothing. And so.

• 7:39Speaker 01

  It's like, do you have an H D M I cable for my laptop? Okay, we're good.

• 7:42Ryan Holiday?

  Actually, and it's talking about like challenging yourself, which I want to talk about. You know, Chris Williamson, he's a podcast, he's modern wisdom, he's busy 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 talked. And I was like, oh, I'll try that.

• 7:58Speaker 01

  Yeah.

• 7:58Ryan Holiday?

  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.

• 8:08Speaker 01

  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.

• 8:16Ryan Holiday?

  And this, 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 behind.

• 8:24Speaker 01

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

• 8:28Ryan Holiday?

  I think I did it first as the challenge. 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 worlds.

• 8:41Speaker 01

  Right.

• 8:41Ryan Holiday?

  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.

• 8:55Speaker 01

  I think it's cool. More of the campfire thing, like we're all.

• 8:58Ryan Holiday?

  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.

• 9:05Speaker 01

  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.

• 9:30Ryan Holiday?

  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 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, they don't need an introduction to what I talk about or they wouldn't be there.

• 9:53Speaker 01

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

• 9:55Ryan Holiday?

  I think by putting yourself in different contexts, you have to sort of rise to meet the occasion.

• 10:00Speaker 01

  Yeah.

• 10:01Ryan Holiday?

  But, and then deciding to do it, it's actually funny, there's a, there's a line in Meditations where Marcus Aurelius talks about.

• 10:07Speaker 01

  How long did that take? 10 minutes? What, where are we at?

• 10:11Ryan Holiday?

  Yeah, let's see.

• 10:11Speaker 01

  It's not the Meditations quote.

• 10:13Ryan Holiday?

  Why don't I see if I can not mention it the rest? That will be my challenge for today.

• 10:17Speaker 01

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

• 10:19Ryan Holiday?

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

• 10:24Speaker 01

  Oh, right.

• 10:25Ryan Holiday?

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

• 10:27Speaker 01

  Exactly.

• 10:28Ryan Holiday?

  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, you know?

• 10:36Speaker 01

  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, right?

• 10:50Ryan Holiday?

  Even with these, this is, I guess, four books, similar size, similar

• 10:54Speaker 01

  Yeah.

• 10:55Ryan Holiday?

  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.

• 11:11Speaker 01

  Right.

• 11:12Ryan Holiday?

  And then sometimes also it's good to be like, okay, I'm going to do something totally different this time.

• 11:17Speaker 01

  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's 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 runs through her face, you know? And then, but like, this book is like, what happens when that just isn't enough anymore, basically?

• 12:00Ryan Holiday?

  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 of years ago, more than a couple of 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, for 40 years. 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 gotta figure out new ways of mixing it up inside there.

• 12:38Speaker 01

  Yeah, I mean, it's kind of the, the, the Carlin versus Seinfeld thing. You know, like Carlin did a new hour every year.

• 12:46Ryan Holiday?

  Right.

• 12:46Speaker 01

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

• 12:51Ryan Holiday?

  Yeah.

• 12:52Speaker 01

  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.

• 13:00Ryan Holiday?

  Yes.

• 13:00Speaker 01

  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.

• 13:15Ryan Holiday?

  Yeah.

• 13:15Speaker 01

  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.

• 13:38Ryan Holiday?

  Yes.

• 13:39Speaker 01

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

• 13:46Ryan Holiday?

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

• 13:49Speaker 01

  Yeah.

• 13:49Ryan Holiday?

  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 gonna do a tour and then they're like, we're gonna 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.

• 14:06Speaker 01

  Yeah.

• 14:07Ryan Holiday?

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

• 14:12Speaker 01

  Yeah.

• 14:12Ryan Holiday?

  But as the cost of filming drop, and then also the value, like, it's this weird thing where it's like the, 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.

• 14:24Speaker 01

  Yeah.

• 14:25Ryan Holiday?

  But the point is, if you do the same thing every night, you can't take advantage of.

• 14:29Speaker 01

  You can't chop it.

• 14:30Ryan Holiday?

  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. 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, I'm then, like, what's the point of the videographer? Right? Like, you know? So I'm gonna, I'm gonna try to tell different stories.