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

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.

0:14Ryan 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.

0:55Ryan Holiday: 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. It 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.

1:30Ryan Holiday: People who chose to step up when it mattered, whose actions helped inspire 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.

1:57Ryan Holiday: 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.

2:35Ryan Holiday: 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 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.

3:08Ryan Holiday: 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 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.

3:43Ryan Holiday: 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 DailyStoeakLive.com. And of course, grab signed copies of Austin Kleon's new book, Don't Call It Art. the painted porch are at my bookstore here in bastrip texas has a porch on the back and it is painted we actually just repainted it and then we were sort of trying to fix it up a little bit it's been sort of an afterthought but we're trying to make it a little bit nicer and we bought some new outdoor furniture some chairs a rug some string lights you know just some stuff that the employees and uh i myself can hang out on you know this is the best time of year in texas it's cool and nice.

4:36Ryan Holiday: Days are still long, but not so long. Anyways, where did we get all the furniture? We got it from Wayfair. Outdoor seating, grills, major appliances, storage, patio lights, rugs, decor. Wayfair is your one-stop shop for home. Installation and assembly services are available for a truly seamless experience. Wayfair deals with the hard parts so you don't have to. With over 20 million five-star reviews, you can hear from real customers before you buy. Patio season is here and these deals won't last. Head over to Wayfair.com right now to get your outdoor space ready for way less. W-A-Y-F-A-I-R.com.

5:11Wayfair, every style, every home.

5:13Ryan Holiday: 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.

5:50Ryan Holiday: 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 Whatnot. In fact, 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. Sellers are building real thriving businesses on Whatnot. Whatnot buyers spend more than an hour a day on the app, and they're not just browsing, they're bidding and buying and coming back. So you can go live, show off your projects, and turn that into real income.

6:22Ryan Holiday: People selling on Whatnot sell 10 times more than on other major marketplaces, and that's because you're not just listing products you're building real connections with buyers download the whatnot app today and get free shipping on your first order just search whatnot w-h-a-t-n-o-t in the app store to start scoring amazing deals so when's your four stuff uh 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 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 um yeah it's like a show than a like 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 Like there is something weird about like, why are you going to X, Y, or Z?

7:25Ryan Holiday: 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 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?

7:59Ryan Holiday: 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, So 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.

8:33You know, like they're not.

8:34Ryan 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. Yeah. Exactly. This is like torture. You're not only you're the extra meeting. Yeah. And so like one more thing on their plate. 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. So 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?

9:11Ryan Holiday: 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? 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 uh you know the minute man 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 no like you're using a house PA system.

10:08But there's no logistics.

10:11Ryan Holiday: There's no crew. There's nothing. And so - It's like, do you have an HDMI cable for my laptop? Okay, we're good. So actually, and it's talking about like challenging yourself, which I want to talk about. You know, Chris Williamson? Mm-mm. 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 - And I was like, oh, I'll try that. Yeah. 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.

10:42Ryan Holiday: 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 being. 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.

11:15Ryan 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, 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 got to 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.

11:53Like 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.

12:04Ryan 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 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.

12:35Ryan Holiday: Yeah. And then deciding to do it. It's actually funny. There's a line in Meditations where Mark Sturlus talks about. How long did that take? Ten minutes? Where are we at? Yeah, let's see. Why don't I see if I can not mention 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. 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.

13:10It's a new constraint. Like what David's writing, 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?

13:24Ryan Holiday: 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 & 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 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?

14:00Because 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 run through his face you know and then uh but like this book is like what happens when that just isn't enough anymore basically well i want and i want to talk about that but i think

14:36Ryan Holiday: 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 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 speech writer 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 yeah i mean it's kind of the the 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 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 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 uh or in the stand-up 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 yeah And part of the reason they didn't just film every date is because it's expensive.

16:46Ryan Holiday: Yeah. But as the cost 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 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, OK, 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, OK, how am I making sure that each time I'm telling a chunk of new things?

17:23Ryan Holiday: 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, I'm going to try to tell different stories.

18:17We'll see you next time. So yeah, keep playing games. Just maybe get rewarded for it. Download Mistplay today and enter for your chance to win.