The Daily Stoic - Chase Jarvis on Why Embracing Risks is Necessary for Creative Success

Episode Date: October 12, 2024

Risk-taking means diving into the unknown, which is scary because anything could happen, but not taking risks is the only guarantee that nothing will change. That’s what Chase Jarvis is here to talk with Ryan about in today’s episode, as his latest book, Never Play It Safe, is a guide for anyone looking to overcome fear around the unknown, trust their intuition, and become comfortable taking the uncomfortable risks in order to get to where they want to go. Chase talks to Ryan about managing risks when pursuing creative projects, balancing urgency with long-term thinking, the necessity of constraints in fostering creativity, maintaining personal and artistic authenticity, and the role of intuition and wisdom in achieving a well-lived life. Chase is an acclaimed artist, photographer, entrepreneur, podcast host of The Chase Jarvis LIVE Show, and author of Creative Calling and Never Play It Safe. You can follow Chase on Instagram , YouTube, and X @ ChaseJarvis and check out his websiteWatch Ryan’s first appearance on The Chase Jarvis Live Show back in 2012 for Trust Me, I’m Lying: https://www.youtube.com/watch?v=odfH7LZwAQ8Listen to Chase’s podcast: The Chase Jarvis LIVE Show🎟 Ryan Holiday is going on tour! Grab tickets for London, Rotterdam, Dublin, Vancouver, and Toronto at ryanholiday.net/tour✉️ Want Stoic wisdom delivered to your inbox daily? Sign up for the FREE Daily Stoic email at https://dailystoic.com/dailyemail🏛 Get Stoic inspired books, medallions, and prints to remember these lessons at the Daily Stoic Store: https://store.dailystoic.com/📱 Follow us:  Instagram, Twitter, YouTube, TikTok, and FacebookSee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Wondery Plus subscribers can listen to the daily Stoic early and ad free right now. Just join Wondery Plus in the Wondery app or on Apple podcasts. We've got a bit of a commute now with the kids and their new school. And so one of the things we've been doing as a family is listening to audiobooks in the car. Instead of having that be dead time, we want to use it to have a live time. We really want to help their imagination soar. And listening to Audible helps you do precisely that. Whether you listen to short stories,

self-development, fantasy, expert advice, really any genre that you love, maybe you're into stoicism. And there's some books there that I might recommend by this one guy named Ryan. Audible has the best selection of audio books without exception and exclusive Audible originals all in one easy app.

And as an Audible member, you choose one title a month to keep from their entire catalog. By the way, you can grab Right Thing right Now on Audible. You can sign up right now for a free 30-day Audible trial and try your first audiobook for free. You'll get Right Thing Right Now totally for free. Visit audible.ca to sign up. I'm Afua Hirsch. I'm Peter Frankenbaum. And in our podcast Legacy, we explore the lives of some of the biggest characters in history. This season we're exploring the life of Marilyn Monroe. From a tough childhood growing up in foster homes, she became one of the most photographed and famous stars of the 20th century. But off camera the real Marilyn was shrewd, vulnerable, funny and also full of surprises.

I've just come back from Hollywood. I was reminded how omnipresent Marilyn Monroe's image still is. You can barely turn a street without seeing a billboard or an ad imitating her image. It feels like she is still with us in the most visual way imaginable. She is so important as a cultural figure. And Marilyn Monroe is one of those people

who I've seen millions of times, but wish I'd known more about. So I'm really excited to be talking about her life, her times, and her legacy with you, Afua. Follow Legacy Now wherever you get your podcasts. Or binge entire seasons early at ad free on Wondery Plus. Welcome to the weekend edition of The Daily Stoic. Each weekday we bring you a meditation inspired by the ancient Stoics,

something to help you live up to those four Stoic virtues of courage, justice, temperance, and wisdom. And then here on the weekend, we take a deeper dive into those same topics. We interview Stoic philosophers. We explore at length how these stoic ideas can be applied to our actual lives and the challenging issues of our time. Here on the weekend, when you have a little bit more space, when things have slowed down, be sure to take some time to think, to go

for a walk, to sit with your journal, and most importantly, to prepare for what the week ahead may bring. Hey, it's Ryan. Welcome to another episode of The Daily Stoke Podcast. I've been taking you back in time recently because of the 10-year anniversary of the obstacles away. But if I actually take you back further, this would have been in the summer of 2011,

Tim Ferriss put on this conference in Napa. I went, I talked about a bunch of the things I was figuring out, learning about marketing. I sort of gave this talk about how dysfunctional and screwed up the world of media was those days. And I met this guy, I met this guy named Chase Jarvis, who was a very well-known photographer. He won a bunch of awards.

He worked with all these huge brands. We hit it off, we became friends. And so a year later, when my first book came out, trust me, I'm lying, she said, hey, I wanna have you on this show I'm doing. I was like, show? And he's like, yeah, it's a podcast. And I think this may have been one of the first podcasts

that I ever heard of. I'm vaguely remembering like when the term first came out, like pod is from iPod, but like this was like the first real podcast that I'd heard of. And he said, I'll fly out to Seattle, we'll do it. There's a live studio audience. I was like blown away by it.

I went out, it did promptly ruin all podcasts for me because this show that I did was in a studio. They flew me first class. It was like the production value was incredible. You can see videos of it. Like it's still out. I mean, I look like a baby, but I don't think I did another in-person camera podcast

for like seven or eight years. Like it just, he was so far ahead of the game. As Chase often has been, Chase invented an app that lets you, because he's a photographer that lets you take the pictures you're on and put like cool filters on so you don't look like a terrible photographer. He invented this online learning platform

where you, a bunch of people take classes virtually with people at the same time. You know, he didn't create Instagram. He didn't create Coursera or Masterclass. He did all right for himself. Don't get me wrong, but he's always been way ahead of the curve on stuff. And he was way ahead of the curve with this podcast.

And first off, I'm just grateful that he had me on. And we've become friends. I did a bunch of work for Creative Live. He and I had the same book agent. We talk all the time, he's an awesome dude. I've been on his podcast a bunch of times. He's one of my favorite people. He has a great book called Creative Calling

that I've always really liked. You should check that out if you haven't. And he has a new one called Never Play It Safe. He came out to the Daily Stoic podcast studio, which it was really cool to see him. He was joking the cameras that we have mounted in the Daily Stoic studio are actually hung because Braden, the guy that works for me,

hung them, he hung them on hunting mounts. He's like, I've never seen these mounts before. What are they? They're really cool. And I was like, yeah, they seen these mounts before. What are they? They're really cool. And I was like, yeah, they're for deer cameras. Anyways, it's a great book. It's what you do if you're feeling stuck. Chase's photography is incredible.

He's given me great advice over the years. And I'm really excited that we got to have this conversation. You can follow Chase on Instagram and Twitter at Chase Jarvis. You can check out his podcast, The Chase Jarvis Live Show. I'll link to my first appearance way back in 2012

if you wanna listen to that. And if you're not familiar with Chase's work, you absolutely should be great dude, great thinker. And I think my course on marketing, which I did again when I was feel like a baby, you can check that out on CreativeLive also. I have no idea how well it held up, but that's out there too.

So here is me and Chase Jarvis chatting. So I was thinking, I think you were the first podcast that I ever did. I know that. Yeah. And you came to Seattle and we talked to- And your studio. Yes, and we talked about, but trust me, I'm lying, that's right. You were And you came to Seattle and we talked to- And your studio. Yes, and we talked about,

but trust me, I'm lying, that's right. You were a little early to the having a podcast studio thing. Like five years early. Like 15 years or something. That's my problem. That's my problem. Same with online learning, same with podcasts, same with photography.

I was taking pictures with this thing when it was a 0.3 megapixel camera, and it has served me well. And sometimes it hasn't like the whole, I did the first iPhone app that was a social network that used photography. So I was not the one who made the billion dollars. I was the one who's ass they kicked.

I mean, literally lift and stamp copy of the app that we created. So yeah, I've been early in a lot of stuff. Yeah, but I was trying to think, so that would have been 2012. So like, cause there was a New York Times piece a couple months ago about how there's like an arms race in podcast studios.

Cause like everything's video. And I was just thinking, I think the best podcast studio I've ever been in was in 2012. Yours was in this like whole garage and you had a studio audience. It was insane. It was real.

And we had cameras on cranes, two different cranes flying around and five cameras live switched. We would get about between, you about between 30 and 50,000 people watching live. Because there was just no other things you could do that with. That's right.

Or it was because it was really good, Ryan. Sure, sure. They're like, who is this person? Really good guests. No, and yeah, we did all that stuff super early and I'm proud of that work. It was fun. And it also, it's like, I've been doing it now

since 2009. Wow. So it also, it's like I've been doing it now since 2009. Wow. So it's one of the longest running interview shows, still up, and we used to do one a month, it was really big, fly the guest in, do big dinner the night before, and in-studio audience of 100 people and all that stuff. And now it's a little more of a volume game,

and yet I miss the in-person stuff, I really miss the live broadcast part of it. It added a lot of meat to it. It totally spoiled me. That was my first one. You're like, well, fly you out is this whole thing. And then like the next one and then probably the next like 200 I did were all over Skype. There wasn't even like, there wasn't even like software. Like now that for people who don't know, you're listening to a podcast, there's all this great software that records everything natively

and there's all these tools. And that was not how it was from like 2012 till basically the pandemic. Like the pandemic forced people to invent a bunch of software that would make it somewhat reliable and reasonable and the quality would be good. But I was, I remember doing yours and going like, I could get used to this.

Cause it was nicer than like TV shows that I've done. And then nothing was like that for a decade. It's Saturday night live quality. Like you show up, you got your own, you had your own green room, your own bathroom, the live in studio audience part, we feed you. And the reality is that that actually makes, I think makes for more interesting shows,

the real in-studio audience to be able to ask questions and sign autographs and take pictures, it does feel a little bit more holistic. And it was also crazy expensive. I had 10. I can't imagine. And there weren't even the economics to support a podcast at that point really, right? There were, but I basically pioneered all of that.

So I would go to brands that supported me as a photographer. I go to Nikon or HP, Polaroid underwrote the show and they would essentially sponsor a whole season. So they would write me a significant check. And, you know, the reality is those things were very expensive. Again, 10 people working on it probably for a couple of weeks in order to produce that.

And we had built a lot of the infrastructure. We piggybacked on the back of basically a live streaming software that was originally designed to have overseas soldiers be able to communicate with home. It was called Ustream, and then we hacked Ustream in order to provide a live streaming platform. Because there wasn't, there wasn't, there's no other versions of that.

So we built that as well. Yeah, that's crazy. Crazy. And that's why these dark circles are under my eyes. But I was gonna ask you, who do you think has aged more in the, like if we went to, if we pulled up, we should do this on the video,

we should show side by side of the 2012 thing in your studio. I look like a child. And yes, you were, you, yeah. Side by side of the 2012 thing in your studio. I look like a child. Yes. You were, yeah, so you definitely aged better because you started younger. It's an unfair aging period.

Like 25 to 35 is- Looks a lot better. Don't change that. Yes, that's true. And we won't even say my numbers, but the reality is- Not that I'm 35 either, but- And yet, like I still have Polaroids from, like actually I used to shoot Polaroid pictures

of my guests. Yeah, I remember. I have signed Polaroids of these insane guests like yourself and hundreds of other of our mutual friends over the years. And the archive of the show is, it's actually really fascinating. It's an interesting time capsule. It's crazy like when you do like local news stuff now,

or I did like some morning shows for The Right thing right now, they don't even have camera men's anymore. They're like these robots. And you're just feeling the crew get smaller and smaller. Like if you were like a union cameraman or a gaffer, you're just like, and then there were two and then there were one.

It's just that you're just watching it get lower and lower were one. It's just the years watching it get Slow lower and lower and lower. It's kind of and this here. We are first of all Congratulations. This place is insane. It's amazing and Having created a lot of studios myself and been to a lot of them like this is absolutely world-class It feels really, you know contrast this to morning television now where's like, everything's cold and hard and the floors are run by a robot. Feels like an Airbnb living room that you're sitting in. Yeah, and then, yeah, and then you go on set and it's just like this big hollow cavernous thing with a couple people sitting in a sound booth.

And this is just warm and cozy and comfortable. It was really nice to see Sam. Haven't seen her in a while. Yeah, this is, this has been cool. It sort of started, I don't, you sort of, you start thing. I think that's the interesting thing about playing it safe is like, we often, which is your book, we think that it's often these like

big jumps or risks that you take, but more often it's like you take a thing and then that necessitates another thing and then that necessitates another thing. And so it's like, we decided to do this bookstore and then we were like, we're gonna film in the bookstore. And then the bookstore started doing well and then we were like, we can't film in the bookstore

anymore because people are like knocking on the glass. We're not selling stuff, right? Yeah, actually what happened was we shut the, I was like, okay, look, it's gonna cost like $200 in book sales to just record for two hours. But what happened is someone who sent me an email, they're like, I was flying in at a layover in Austin, I drove all, and you were closed.

I was like, oh, I can't, you can't have a destination that then sporadically closes. So we didn't get to shoot in there. And then this building went for sale during the pandemic and someone else was gonna buy it. And I was like, I just don't want a neighbor. Like, it was like, I wasn't even thinking of this. I was really thinking like, what is the work?

Like I was like, I write in there. What if like a music venue takes us? You know, I was just- A bar. Yeah, I was just thinking like a hassle. You're playing defense. Yeah, but like, you know, you make these decisions and then it's rare that you're jumping off this cliff.

It never actually feels like this. It's like a series of smaller things. Well, this is, I think the punchline of the book is, this is not about some massive betrayal. And I'm very clear in the book. I hate any book that starts off, do perfect thing one, perfect thing two, perfect thing three, and end up with this ideal outcome.

And frankly, a lot of books do that. And that's why I'm always looking for a great, especially about entrepreneur stuff. Like, you know, it's really knowing how hard it is to build anything. And then you see this like polished version of something, you know it's not real. So this book is about the tiny betrayals

that we all go through of ourself. And it's not, so it's not about necessarily avoiding mistakes, it's about recovering it's not about necessarily avoiding mistakes. It's about recovering like 1% more quickly, 1% more kindly faster than before to toward a better realization of who you are and what you really want. And that the best stuff in life is on the other side of risk and not playing it safe. But yeah, we think of entrepreneurs as these like lovers of risk. But like, I forget who said it, but basically, entrepreneurs are mitigators of risk. You're taking sort of one risk and then you're finding ways to,

like the whole point of investors is by definition, a mitigation of risk. Like if you knew it was gonna work, you wouldn't take a- Yeah, it was either Mark Andreessen or Ben Horowitz. First of all, Ben Horowitz, great book, The Hard Thing About Hard Things, one of the best entrepreneur books of all time.

First chapter is like how to fire your friends. Second one is how to tell your investors you lost all their money. Like that's a more realistic book. But I think it was one of those two guys that basically talks about risk and entrepreneurship like an onion. And the goal is to take one at a time,

a layer of risk away from the business. That's one of the reasons you take money, for example, as you just indicated, is that you take away the risk of being able to hire your first four or five high quality employees as an example. And the next one is, oh, we build out an infrastructure so we don't have to rely on someone else's infrastructure. If Facebook decides to change its thing,

then you have your own. So, you know, I think that- And you're also eliminating unnecessary risk that like, this is what like a minimum viable product is. If you're like, I have this brilliant idea It's obviously gonna work I'm gonna spend months and years developing and then we're gonna do this big blowout launch if you're wrong You've just taken this shoot you bet it all on one thing as opposed to a series of smaller more iterative

Bets where you're learning and the costs of being wrong are much lower. This is like the problem with books is like, how long did you work on this? Like three, four years? Yeah, two and a half years. Yeah, and your publisher took it, because you did a two book deal, right? So your publisher took a big swing on you

and it either works or it doesn't work, right? And then they move on very quickly if it doesn't work as opposed to like life is better and safer when you're not sort of taking all or nothing bets. It's just fiction. I mean, Richard Branson invested in my last company, CreativeLive, which has since been acquired by a big public company.

We can cover that journey. But so Richard ended up being a mentor and a friend. And what people think is that he just takes all these big swings. And over lunch, he's always saying, man, you gotta protect the downside. Like that's his mantra. And even starting Virgin Airlines,

the first plane he bought publicly, it looks like a huge swing, he bought a 747. Like who does that? No one's supposed to be able to buy a Cessna and then a little jet. Like who does that? You know, those people buy a Cessna and then a little jet and then in the. As you're building up the thing. Right, so everyone's like, well, look at Richard, he bought a 747 and I'm sitting with him at lunch

and he's saying, you know, actually when I bought that from them, I already, I pre-negotiated the price that I would sell it back to them when it didn't work. Right. Not if it didn't work. He was pretty sure it wasn't going to work. Yeah. And he was really just leasing a plane. He's like borrowing it.

And if it works, there's a lot of upside. If it doesn't work, the downside is not lose all your money. For sure. And in the beginning of Never Play It Safe, I say, look, we're not talking about seat belts and sunscreen. This is not about not protecting the downside or not about emotional or physical safety. All those things are really important.

And to your point, like most people, the story that's about Richard, for example, is that, oh my God, he just takes these big swings. He's got 400. It's like pushing all the chips in, you never go all in. Totally, never, never. And yet, I think it serves so many people poorly to think that that's how it's done. And as you I think it serves so many people poorly

to think that that's how it's done. And as you said, and I talk about a lot in the book, it's just about getting out of your comfort zone on a regular basis, getting comfortable, being uncomfortable is actually the path to the best stuff in life. On the one hand, it makes it all seem glamorous and cooler than it actually is.

So the entrepreneur gets to present themselves as this swashbuckler. Renegade. Yeah, renegade as opposed to this like spreadsheet junkie sort of like, you know, hedger. And then I think the other way it serves us is by making it seem like you have to have enough money to buy a plane outright to start a company. Then you go, then you're able to not do it,

like let yourself off the hook and say that's impossible, then you're able to not do it, like let yourself off the hook, because that's impossible, or you're able to go, oh, I need to get all these things right first, so I'm gonna do it in 10 years, as opposed to taking some tangibles. So you say, oh, I need to buy, to use your metaphor,

I need to buy a jet, so I need to raise $100 million, as opposed to I need $100,000 to buy a Cessna that I'm going to do these small little ferrying flights for and then whatever. So you're able to go, this is a 10 years from now goal instead of what am I going to do today? For sure. Hello, Matt and Alice here, the hosts of Wanderers podcast, British Scandal. Our latest series,

Peru 2, begins on the sandy shores of Ibiza. Michaela McCollum should have been having the summer of her dreams, but it all went wrong when she met the gorgeous Davy in a bar. Think less holiday romance, more recruitment for a drug cartel. She agreed to team up with another young Brit, fly to Spain to collect a drugs package, then head straight back. However, only at 30,000 feet does Michaela realise she's not on the way to Spain, she's heading for Peru. And when they get there, they find out it's not a small drugs package, but 11 kilograms of cocaine. The summer

holiday turns into a spell in a Peruvian prison and a story that becomes an international media sensation. To find out the full story follow British Scandal wherever you listen to podcasts or listen early and ad free on Wondry Plus on Apple podcasts or the Wondry app. podcasts or the Wondry app. I'm Matt Lewis, host of the Echoes of History podcast where every week we'll be delving into the real life history that inspires the locations, characters and storylines of the legendary Assassin's Creed game series. Join us as we explore the streets of a Viking colony, scale sand dunes in the shadow of the Sphinx, witness world-changing revolutions and come face to face with history's most

significant individuals. So whether you love history, games or just a good story, Echoes of History has something for you. Make sure to catch every episode by following Echoes of History, a Ubisoft podcast brought to you by History Hit, wherever you get your podcasts. The second chapter in the book is about time, and I think the time horizons are, have completely destroyed a lot of what we, how we think specifically on two vectors.

One, when you're working on something that you love, time is actually on your side. And just think about this project here. As you said, one thing has unfolded into another. You originally, well, I'm a writer. And then I'm like, ah, it's crazy to buy a bookstore. And then you bought the studio next to it. And then, you know, like that's how time expands. And if you look back, I mean, I look back

and your kids are grown up and you got buildings and you got like, and I don't, it doesn't seem like all that long had passed between the last time I was here. And then, you know, by extension, the alternate version of time is we're taught to believe that there's never enough time. extension, the alternate version of time is where we are taught to believe that there's never enough time.

And what that creates is so much like just bad behavior. You do stupid shit because you think, I mean, and now I'm all for urgency, right? Maybe long-term patients, short-term urgency. Like you need to get up and knock out your listed to-dos. But what have we thought about life being long? What if we could think on 10-year horizons? I have never been disappointed when I've been able to think, when I could afford to think on a long,

I mean, hey, rents do, I get it. But if you can afford to think on a long-term basis, if you can believe that life is long, I can't believe I'm on like my third or fourth, I'm like the cockroach, I'm on like my third or fourth life career. like the cockroach, I'm on like my third or fourth, you know, life career. And I feel like we get that so, so wrong. Yeah, there's a thing called Hofstadter's Law,

and it's basically things always take longer than you expect, even when you take this law into account. So like, I remember with Trust Me I'm Lying, I was like, if this book doesn't come out like right now, it's gonna be like irrelevant. I was like, this is like of the moment. I should have, in retrospect, the idea that you're doing anything that you feel like

you need to rush to get out creatively is a bad sign. Like it means that it's not timeless enough and it's probably not worth doing unless it's like a tweet or something, right? But I remember thinking like, this is very much of this moment, it has to come out. And like ironically, and also terrifyingly, all the ideas in the book are probably more relevant

12 years after it came out than before. And I remember it's like second best week was like the week after Trump got elected. So it had been out for like five years or something. You think like, hey, I need this now. And if it doesn't happen now, it's never gonna happen. But when you give stuff more time and more runway, you just increase your chances of working.

And then also just the idea of compound interest, like that applies to attention, giving stuff time to find its audience and develop. I think too many people quit on stuff too early. There's definitely stuff that people should have quit on a long time ago, like things that are not going anywhere. But I think what a lot of people do with books

or podcasts or any kind of project is they do like one or two and then it doesn't work. And then they go, oh, the idea was bad. And really, audience acquisition is just a long, arduous process. Sometimes the algorithm blesses you and it just happens, but those people are the exceptions to the rule rather than the rule.

And you, the idea that, you know, I'm just doing a 10-year anniversary edition of The Obstacles Away, it comes out next month. It's selling more almost every year than it did when it came out. But if you had asked me how I thought it did the first week or the first month or the first six months, I would have not seen it as a huge success.

In retrospect, I don't like the idea, it's first week of sales is irrelevant because now it has hundreds of weeks of sales into existence and each one of those initial, the unit of measurement becomes larger and larger. I think we get time really wrong in our culture. I really do. And we do so much stuff when we're scurrying around. I mean, just think of the 21 year olds that think they got to figure it out. It's like, I mean, no disrespect. Totally. I'm late to the game. All my friends are, you know, so that's one of the things. And there's also this other fascinating thing

that happens with time is, let's just go back to when we lived in villages. Yeah. We would see, let's just say Gary, learn to ride a bike. Yeah. We see, you know, Gary is our peer, Gary learns to ride a bike. Oh, he's slightly better at riding a bike.

What are these villages? Are these like thousands of years old villages? I'm confused now on the bike. Let's go 10,000. 10,000. Okay. I'm like, what? Good point 10,000. Okay, I'm like what? Good point. I was like, is this the 50s?

Anything, hunting. Gary's a good hunter. We're gonna go 10,000 years back. Gary's a good hunter. And- Where'd he get his bike? I don't know. I'm thinking of Gary the hunter. It's killing me.

But you know, Gary's gifted athlete. And oh, and then he becomes a hunter and he's a really good hunter. But Gary missed a few that he should have. And you basically saw Gary progress in real time. You realized that this took application of effort. Time happened. There were many failures along the way.

There were times where he came back and was dejected because he didn't get the kill that he was supposed to get. And yet, fast forward to today, it's literally, that made sense to our brains. Yeah, sure. Right, now fast forward thousands of years. You just hear about Chappelle Rhone and you're like, she's the biggest performer in the world, came out of nowhere,

but that's not how it happened at all. At all, but we are presented with nothing and then superstar. And the way that it shows up is it just in your feed with this person at Wembley Stadium. And, you know, I've never even heard of this person. How is this possible? And that really screws us up.

Big time. It's depressing and demoralizing and disorienting. Yeah. Disorienting I think is a really good word. You know, so that's one of the reasons. Time is a weird thing to write about. Yeah. And yet it is actually this beautiful thing.

It can be a wind at your back as opposed to time as this conveyor belt that's running in the background and we're always losing it. Yes, it's true. You can say life is short because that may motivate you. But what if you said life is long? What if you didn't scurry around and make stupid decisions

and you actually were thoughtful and invested time and energy because longevity matters, intention matters? To me that's just such a better foundation for not just building a business or a career like we're talking about but a life. You know Seneca's thing is is that life isn't short it's that we make it short because we waste so much of it right so so yeah if you dick around for a huge chunk of your life and then you've belatedly stumbled upon this thing, you're gonna go, oh, I wish I got to this earlier.

That's different than like, hey, I just started playing guitar. Why am I not as good as, you know, the best people in the world? This YouTube hero who started from his garage and oh, it just turns out he's made a thousand YouTube videos about how to do it. And yeah. I think about that too.

I've been trying to give myself a little grace on projects where it's like, this is a thing, hopefully that will last for years. And also I'm gonna be working on it for a year or years. So the idea of kicking myself because I was five minutes late today is silly, right? Or even just measuring how successful I was today, if this isn't a thing whose value

you're gonna measure in days, right? And so, like, obviously every instant matters and not wasting time is important, but you can kind of get in this thing where you're micromanaging in increments that are not reflective of the whole. When you listen to a really great album, you're not like, I'm so glad they rushed this.

You're not like, if this had come out five minutes sooner, or if they'd finished a month earlier, it would be better. You're like, it takes what it takes, right? And just kind of getting to a place where you accept the process is the process, that this isn't a thing measured in individual encounters, but it's a collective cumulative effort over a long period of time.

You can kind of slow it down and really actually treat it with the serious that it deserves. Because yeah, you think you're being like disciplined by holding yourself accountable and going like, I, you know, I can't let my attention drift or whatever. But what you're actually doing this, selling the project short because you're acting as if

like 30 seconds here or there is gonna be reflected in this immensely complicated, enormous thing. Yes, I think there's someone who's listening right now or two ideas, one is like, well, how do you know when, and that's another big topic I take on in the book is your intuition, you actually hone this. This is a thing that will mature if I let it. And you start to be able to pay attention

and listen to the things that are inside you that not just the rational mind that is telling you all the things that we just trotted through of how hard and difficult and wrong this is, it's gonna be laid, blah, blah, blah. And I think that that's a really interesting thing. And I also thought we might actually spar on this time thing because I have one of my favorite gifts

is I have a gift from you that says memento mori coin, which means you're gonna die, right? And that is a sort of a life is short message. And yet I watch you be so deliberate, so patient. I remember the last time we were sitting on back porch eating and you're talking to me about the vision that you had for the building. And now I'm here and it's fully realized.

It doesn't seem like you rushed. Everything is like in its place. It's beautiful and perfect. And so, you know, what's the stoic, are we gonna fight on this or are we clear? I think that was like an important lesson because so I am much more of a like, okay, these are the 10 things we have to do,

let's just knock them out and do them. And Samantha, my wife is much more like, I'm not really feeling it right now. Like I'm gonna think more about it. Just so we're clear, if Samantha was giving me a tour and Ryan's like, we gotta get in here and record. Yeah, I'm much more like, let's just get it done and move it forward and she's not.

And like, I think working on this bookstore together was helpful because, yeah, when I look at each of the individual things, I'm upstairs and I look out over the balcony, I'm not like, see, we could have finished that one thing on Tuesday and instead it was done the following Thursday that like 10 days was an inefficiency. It recedes into the distance.

In the moment it matters, but it recedes in the distance. And the momentum worry thing is, it's easy to get wrong, right? Because look, a lot of people act like they have forever. They are oblivious to the fact that you could go at any moment and that they're really inefficient and wasteful with their time. And I think there's a message where

momentum worry is really important. But the other side of momentum worry, like the part where Mark Struis talks about it, specifically in meditations, I've always been struck by, and it struck me before I had kids and a lot more after he says that, you know, try to do this as you're tucking your kids in at night. He's saying like, say to yourself, like, you could die, they could die, neither of you might make it till the morning. like, say to yourself, like, you could die, they could die, neither of you might make it till the morning.

Now he's not saying both of you could die, so make sure you wrap this up quickly, you know? He's saying the exact opposite, right? He's saying, why are you rushing through this? And so that's- Savor. Yeah, it's like, if you think about what you're actually rushing towards,

you think you're rushing towards the finishing of this project, you know, shipping this thing, going on this trip, getting them to bed. But the other way to think about it, what Estone might say, is what you're rushing towards is death. We're only going one direction in one place.

So why are you trying to get it over quickly? And there's this instinct you have as a parent, where people will say, they'll be walking soon. And you go, I know I can't wait. And then you're like, I can't wait till they start school. I can't wait until they're a little more independent. You're thinking about like all these next steps. And then-

Suddenly you're like, wait a minute. Where did it go? And again, it's only going in one direction for both of you. And so the idea that you now, you're like, I would trade anything for one more minute of each of those phases. And so the idea that you now, you're like, I would trade anything for one more minute of each of those phases and you rushed through them. And so I think what momentum morning can help you speed up

because you don't have forever and why are you showing up every day at this job you hate, you know, telling yourself, I just gotta wait till I can retire. I just gotta wait till things go back to normal. You don't know that you have that. But the other side of it is, why are you rushing around everywhere

a million miles a minute when in reality, this present moment is all that you have and you're rejecting it? This is exactly why I chose to write about the things I chose to write about in this book. There are so many things in our culture that have these, we think it's one way and it's really the other. And when I look at my own life and the mistakes

that I made and the recoveries, and I look at my friends who are the best in the world at so many things, and very, very inspiring, like this just keeps showing itself to be true. And that's one of the reasons that, you know, I write about those are the seven tools in the book. Each one of these things is true. Time, you just laid out,

I thought we would get here to be fair. Like I didn't think we were gonna spar. I knew what Marx release meant. And that it's like people, how can we both like need to, you know, seize the day and be patient? And- Do you know what negative capability is? No.

So Keats, the poet, he said that like, basically that what an artist has to be able to do is sort of hold confusing, contradictory ideas in their head at the same time. Fitzgerald's version of it was that the sign of a first-rate intelligence is to be able to hold two contradictory ideas. I'm familiar with Fitzgerald's. But I think Keats' concept is a little more interesting because it's sort of more vague, but just the idea that it's like, sometimes it's this way and sometimes it's this way, and sometimes it's a combination of all the ways.

Just basically the simplicity of it's complicated. And for your mind to be able to hold that ambiguity and that complication and to sit with it and to find the advice in each particular situation, that is a skill. So many people wanna like reduce it down to these maxims or these rules, always do it this way. But the idea that memento mori could provide

two equally true opposite lessons is kind of the beauty of philosophy and life. It's fucking complicated. Totally, and that's like literally why I was inspired to write the book because there are so many of these things in our culture. I highlighted what I think are the seven most important ones where you think it's one way, it's the other time.

We just sort of talked about, I think attention is another really, really interesting. We are taught, especially in this culture right now, that getting attention is everything. That's how your podcast stands out. And that's, you know, that's, I need to get attention. You know, we've got our mutual friend, Gary, is like, I day trade attention.

And, you know, attention is this buzzword. And also like when a baby comes out, if a baby does not actually get held, it dies. It's not just like it doesn't do well, it can die from not human contact. So a baby's job to coo and be cute is to get attention. So, and yet attention is the most valuable thing, it really defines our entire experience. And if I told you, but that it's actually about paying

and it's about directing it, not about getting it. The irony is that if you are a person who can direct your attention, if you are of the best in the world of this quality, attention will come your way as a downstream effect of you being insanely good at choosing what you pay attention to. So it's not about trying to get it, it's about how to direct-

Yeah, a lot of these things are indirect results of doing the right thing. And to me, there are so many of those that were counterintuitive, and the aggregate of those, I felt like when I look around, it just leads to a bunch of bad behavior counterintuitive and the aggregate of those, I felt like when I look around, it just leads to a bunch of bad behavior

and chaotic outcomes and just not a life well lived, not a rich, meaningful, creative life. And again, that's how I got to those topics in the book. And this reminds me of a little story speaking about time and attention. I was prior to this book being printed, I worked for two and a half years on the wrong book essentially. I don't know if you know this.

I wrote on- Between the creative calling and this one? Yes, I tinkered a lot and then I started writing, I'd say research for about a year and then I started writing and let's just say I'm writing every day for 13 months. Okay, 13 months, eight weeks before my deadline, I throw it all in the trash.

And we have the same agent. I call Steve and you can imagine, right? You can imagine he's a legend. He's just such a great, smart, kind, awesome guy. And you can imagine what he said. And I was like, Steve, this is not the book. And in his own way, he's like, okay, talk to me. He's just closing his eyes and scratching his forehead.

And essentially I said, I think this is gonna be a good book as it is, but it's not the right book. It's not the book that I want to do and I need you to back me here. And this is what needs to happen. And it is actually that process that led to the title of the book because I was reflective of like, wait a minute,

this is actually all of the best things in my life. When I look back at the best decisions, whether those are relationships, businesses, friends, communities that I wanted to build or things that I wanted to leave, things the best decisions, whether those are relationships, businesses, friends, communities that I wanted to build or things that I wanted to leave, things that were toxic. It always felt like a massive risk. And I knew so clearly by listening, developing the muscle that I'm pretty good at as an artist

that developed the muscle of intuition to be able to go away and write the book as it was meant to be written. And I threw away 55,000 of 62,000 words. And when I showed up, both Steve and my publisher were like, oh my God, this is amazing. Like, thank you so much for doing this. This is the book that you needed to do.

And that is one of those bigger risks, but I do believe that there was downside protection in there, right? I do believe that there are safety valves, and yet no one in the room when we're talking about it really wanted to lean into that. Of course, because it's a pain in the ass. Totally, yeah, it's a pain in the ass to be right.

They don't have the benefit of believing in and being artistically inspired by the thing because that's your job. So they're only gonna be looking at it from a paperwork standpoint and a moving standpoint and unpleasant conversation standpoints and then gaps in the schedule standpoint. They're getting only the downside, potentially for the upside of it working. And by the way, they've been in this position a million times.

And what you're saying is also what people who are of weren't working the entire time are also saying, you know what I mean? And so it's, yeah, it can be tough to judge. Yeah, and yet I stand by that as that, to me that's the defining moment of the book. And for so many people in so many ways, as you talked about, like that, if you look back, it is a bunch of deciding that the best stuff

is on the other side of your comfort zone. And what are you going to do to be willing to put yourself there intentionally, willingly? Sometimes you find yourself there accidentally or through no fault of your own. And yet, if you can start to condition yourself, that that's actually a good thing. It's not dissimilar to building a muscle. Yeah. You know, I was thinking of another contradictory one that I think we've talked about before, which is like tools are important, right? Having the right tools, knowing how to use the tools. I'm talking about technology here,

environments, systems, whatever. And then also I find that, who cares a lot about tools is like people who suck. There's like the obsession with like- What camera should I get? Yeah, what's the best gear? What are the greats do? I've memorized all the artistic routines

of all these people. And then I'm like, but what have you ever done? You know? And so there's this, it's this interesting thing where, yeah, you want to come up with an optimized system. And at the same time, like if you've really got the stuff, you could do it in a crayAN and it would still be good. To me, that's beautiful.

And again, the ability to understand that and to know when you are fooling yourself and when that that's real, that's developing that sense of intuition inside of you, which is the, I think the most important thing that we know the least about. Yeah. And if you walk into any sort of science environment,

you talk about intuition, the people who are really studying intuition as a science understand that actually rational thought is pretty slow, pretty clumsy, intuition is super fast. It's a cellular level, your cells have memories, and all of that comes to bear when you're thinking, that's why they call it a gut feeling because it's a body feeling.

Aside from the people who study intuition and knowledge and whatnot, everyone else is like, oh God, how do I know when to trust my data, data, data? And data is valuable. And I think of the times where I didn't trust my intuition and I always regret those times. Yeah, or are those just the ones that stand out? You don't remember all the times

that you didn't trust your intuition and it worked out? You know what I mean? It's an interesting thing, right? Because you're like, I didn't want to do this version of the book, so I tore it all down and went on this other one. But I know objectively there are times where I had something.

I remember with the Daily Stoke, I remember I sent a copy of it to my editor. I'd been working on it. First off, Steve was like, this will be your best-selling book. And I was like, what are you talking about? Just from the idea, I was like, this sounds like something an agent would say

that can't possibly be true. Who reads these page-a-day things? It was inconceivable to me because I wasn't familiar with the genre. But then I did it, and because I wasn't as confident with the genre and the approach. I remember thinking I wanted them to tell me it wasn't good enough, and that I needed to go spend a lot more time on it. Like I felt like I was kind of rushing it.

And I felt like I just remember feeling like it wasn't what it was supposed to be. And wanting them to like confirm that. And they didn't, they were like, no, it's actually really good. Here are these things you need to tweak. And then it came out and it did really well, obviously. But that thing of like, I didn't think it was gonna be good and it worked. We forget that feeling a lot, right?

Because that's like when you didn't trust yourself. Like I had a gut feeling and I didn't listen to the gut feeling and it worked out. Well, let me try and do a mind ninja thing with you. You could have stopped the presses. Yeah, sure. But you put it in front of them and they said it was great. And then you said, okay, maybe there is something here.

I am going to trust this process where I am in the, it's really about trusting the process, right? And so to me, just bringing awareness of it, we've talked about like three big topics here, attention and time and intuition, and the murky nature of these things is exactly why I wanted to tackle that stuff in this book. And head nod to Robert Greene,

who helped me think about these things, right? And he's a very, very powerful thinker. And to me, like these, when I look at the array of tools that we have in our toolbox, if I can call those eats, that's how I refer to them in the chapters of the book. Like these are ones that I have had more conversations, more heartfelt, earnest, in-depth, late night conversations with my friends like you that I just don't really see out there in popular culture. And I certainly don't see them assembled into one place as a suite of tools that, man,

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and ad free right now by joining Wondery Plus. It's just the best idea yet early and ad free right now by joining Wondery Plus. It's just the best idea yet. There's just something humbling. I think you experience it in social media where you're putting so much more stuff out. Like you'll do a couple books in your lifetime. You'll do a couple movies in your life. Most big creative projects are so expensive. They take so long. You're not going to get a thousand reps of them. they take so long, you're not gonna get a thousand reps of them. But on social media, you're doing,

it's so much smaller and cheaper, and it's all about how it spreads, that you get more shots at it. And there is this kind of weird experience where you're like, that wasn't very good, I'll have them take it down. And then by the time you get them to take it down, it's like, it's crushed. So you're like, wait, why?

There's this kind of constant feeling of being perplexed about what does well and what doesn't do well. And you sort of go, I think it was William Goldman, the screenwriter said, nobody knows anything about what's gonna work. There is just a randomness to it too. And so you have to have that intuition and then also this kind of humility of like,

if you think you know, you probably don't know. For sure. And I think that's what makes you think hard about things, which is where good stuff comes out of that. I mean, essentially all the Hollywood is a hits-driven machine. And you'd think that if the tens or hundreds of billions of dollars that are spent on movies

cannot figure out what a hit is in advance of putting it out, then nobody can, because there's literally spending hundreds of billions of dollars studying it, creating all sorts of genres and every possible incarnation of it. And yet we still don't know what's gonna be a hit.

And that should tell you the beautiful thing about art, that it really is mysterious and the act of doing it and learning and testing is the only way we get results. Yeah, and you're gonna be surprised and some things are gonna pop right away and some things are gonna take a long time. That's the other part. It's like you're comparing something that popped immediately

with something that's gonna find its audience 10 years from now, but you don gonna find its audience 10 years from now. But you don't know that in 10 years from now, they're gonna be compared to each other very differently. Right, and that's what the last two chapters of the book, one is about failure and the other is about practice. That's essentially what we're talking about, right? We're talking about,

this is the way that you learn these things. You just talked about what social media allows you to do is put so much stuff out there and fail and learn quickly. And then practice is like, this is actually what you do. Yeah. It's not about what you think, it's about what you do. Are you hitting publish? Are you sending this newsletter out?

Are you listening to the response that the market's giving you to your business or to your creative project or whatever? And we believe deeply in good habits and healthy habits. And there's actually a hygiene around how to think and approach all these decisions that we have in life. Creatively, like this is actually a book about creativity. And it's easy to see this hygiene manifest itself in,

go to bed without having had 10 drinks and get up at a decent hour and move your body. And what I advocate for is that there's actually a hygiene to all this stuff that we've been talking about. There's a methodology and it's not rocket science and it's available to anybody. Do you wish sometimes that maybe you'd stay just being an individual creator and not start a company?

I always wondered about it. Well, I do and it's not an accident that right now, so for everyone who's not familiar with my past, I've basically been a lifelong artist and operated pretty successfully in a lot of different in television, in books, in photography, commercial photographers in the world. And sort of accidentally, I was going back to our live streaming the podcast, I also started live streaming some of my photo shoots. It was like, oh my God, 25,000 people are watching me like shoot this album cover for this band.

How random. I bet there's something here. Maybe we could teach some stuff on the internet. And right now this sounds laughable because this was a hundred years ago. But you know, in 2009, that was very innovative. Short story too long already. I started a company that had that as its core ethos. But in 2009, that was very innovative. Short story too long already, I started a company that had that as its core ethos.

It was called CreativeLive. You've taught on that platform, Tim Ferriss, Brene Brown, so many people have appeared there as either a guest or have taught full scale classes. It was basically a precursor to master class that had tens of millions of users, did hundreds of millions in revenue, and it got really big.

And it got really, like all things do, it got really confusing. And at some point I had to segue out of my, hey, I'm an artist and I founded this thing, and I turned it over to the venture capitalists, and basically it wasn't going well, so I had to come back. You had to be a full-time executive, chief executive, instead of being a creative person.

From a venture-backed CEO where $100 million at stake. Not the thing I sign up, wake up and say, I can't wait to do this, but also for any number of reasons I don't have to go into, it was the right thing to do at the right time. Right thing right now. And yet on the other side of that, it was some of the most potent and valuable learnings

that I've had in my entire life. I was connected to so many new people in ways I never could have imagined. And I had insane mentors and learned a lot. And I simultaneously, I'm not going to do that ever again. Just so work crystal clear. The things that I'm working on, books, I got a television show development.

That's not to say I'm not involved with companies because I'm a co-founder in a handful of other companies right now that I'm really excited about. Some at the intersection of AI and creativity and doesn't matter. But one thing's very clear in response to your question is I'm not going to operate any other businesses besides my own personal business.

This is sort of an awareness, know thyself. Let's go back a couple thousand years to that principle, know thyself. That's not where my heart sings and it's not a set of skills. Can I develop those skills? Yeah, I did, I had to. I navigated from founding idea to public company acquisition.

And yet it doesn't make me wanna do it anymore. So I'm going back to basically being, trying to be a polymath artist where I wanna touch a lot of things that interest me and be very, very passionate about the thing that grabs my attention, go all in on that and contribute to a lot of different projects, but just be at my core, an independent artist.

Well, cause I was listening to this podcast the other day and this guy, he'd started a blog and then he'd started doing some products. And then he built like a YouTube following. And I was like, oh, I've done this. And then he'd raised like a bunch of money. And then now it was like very big, like a hundred employees big. And there was part was like very big, like a hundred employees big.

And there was part of me that was like, oh, this is the playbook. And then I just, I was like, I don't think Chase had that much fun. And that's literally what I was thinking of. If this thought enters your mind, call me. Yeah, no, that's what I was like. I'm so glad Chase is coming.

Cause I just, I was like, Chase didn't have that much fun. And I remember you telling me something too. There's something that I think people get attracted to the idea of scale and they get attracted to these big numbers. And I remember you telling me that early on, someone had tried to acquire creative life

for a life-changing amount of money. For sure, yeah. But because that was a life-changing amount of money to you as a person and you as an artist, but to the VC companies that had given you money, that was not a life-changing amount of money to you as a person and you as an artist, but to the VC companies that have given you money, that was not a life-changing amount of money, that was a failure.

To me, part of being a creative or a lot of what attracts someone to be a creative is not only not having to be the boss, but not having a boss. And you think that scale is empowering you and actually it's disempowering you because somebody else is ultimately the decision maker of whether you accept this deal or that deal,

grow this rate or this rate, and now you have somebody else calling the shots. Yeah, and that is a very, it's a very interesting thing that happens in your mind. And at the beginning it's, wow, this is, it's working. This is so great. Who wouldn't, especially if it has a virtuous sort of underpinning, I mean, we were educating tens

of millions of people on the internet for free, teaching real skills that were transforming lives all over the world. We had thousands of transformation stories that were coming in from every corner of the globe, 100 classes that were being watched, about 150,000 people in real time. So there's this narrative that is easy to cook up

for oneself, which is like, good for everybody, let's just keep doing it. And yet, and I do still feel like the path that we took was the right path. Looking backwards, I can connect the dots. And yet to someone who, a friend of mine, who might be asking, should I do this? I would just list the things, are you sure?

Because here's what you get with that. And there's a lot of basically a personal, a very, very high personal cost that you will pay for that. I think what I took from your experience and you can take from the experiences of some other people is that sometimes staying small or boutique or bespoke, not going as big as you can go is actually the riskier, more courageous thing. And they're just kind of defaulting towards growth,

defaulting towards the traditional playbook for building a business is the less risky, brave thing. Like the bookstore is working and people go, have you thought about opening another one? And I go, brave thing. Like the bookstore is working and people go, have you thought about opening another one? And I go, absolutely not. Because I have, and Robert Greene talks about this a lot, about not going past the mark that you aimed for and having some version of success

or having some version of your life that you're optimizing for and making sure that you're not just always making the decision like, what makes us more money? What gets us bigger? What gets me more money, what gets us bigger, what gets me more famous, what gets me more followers, because you don't actually know if that's what you want. I'm telling you, man, that's why I hate to be that dude who's on in the interview talking

about his book, but that is there's a whole chapter about that. It's the constraints chapter. Constraints actually create and cultivate and can direct creativity. It's a very powerful. Sure. If you ask Edward de Bono, who's got a really famous lateral thinking theory about how to basically cultivate creative thinking, we don't have to go into it.

But the ironic twist is that I've told a story in the constraints chapter, which is the opposite of constraints. Constraints are great, and oh, here's what happens if you don't. And I use my own personal example. And essentially I was at a hotel room in Las Vegas, you know, it was a brand new hotel.

We were in the suite. I'd just gotten out. I'm, you know, I'm showering to go catch, you know, probably a private flight. And I'd just gotten off stage with Lady Gaga. We had announced that she and I were relaunching the Polaroid brand. Ari Emanuel, the agent who's famously was the-

From Entourage? Yeah, the Entourage. He had literally had two cell phones up to his head and he was ladies Gaga's agent. We're backstage, it's a meat dress period. So she's like literally the most famous- Biggest person in the world, yeah. The biggest person in the world.

And I've just gotten off stage making this big announcement. Creative Live, people are trying to buy Creative Live. I've got millions of people barking up, just got back from an overnight trip to Shanghai. It couldn't have been better. And I get out of the shower thinking, I'm pretty sweet, and my wife, and she said, what are you doing?

Yeah, this sucks. Yeah, what are you doing? How much is enough? And it was exactly the same response that you would think. I was like so confused because literally this is like the dream on steroids. Doesn't everyone want this?

This is the dream on steroids. And she made me like our partners in life often do. She made me just, just stopped me dead in my tracks. And I said, what do you mean? And then I thought about it and I knew exactly what she meant without having to say anything more. And that is very much about how I, if that was a betrayal of myself,

then this moment here on the backside of having CreativeLive acquired, and you're asking me, do you wanna do that? Do you wanna go blow it out again in the dark? So I'm like, I'm actually, no, I have actually learned, I've wisen up. You got to go kind of right up, maybe even a little bit after over the edge.

And then you're like pulling, you know, you got to figure it out. I've had that with Samantha too. She's pointed out, I think rightly, it's like, look, it wasn't, it's not like it was easy for you to do it. It was hard and it required sacrifices, but like you're also getting the upside. Oh, for sure.

And she's like, you know, like, this isn't the rest of our dream. Like, you know, like this was your dream. So as hard as it is for you, it's hard for us, but without the benefit of being the person who's doing it. Right? And real, sometimes seeing it from another person's perspective,

like your wife's coming on all the travel or whatever. She's like, this is a grind. Actually, these people are awful, actually, you know, blah, blah, blah, blah, blah. And you're like, oh yeah, you see it, you see it just slightly from the side and you go, this isn't healthy, this isn't natural, this isn't good for you.

And by the way, I haven't taken pictures in a year or I have no time to write or I actually hate the material that I'm doing. And you go, oh, so wait, the reward for me, for all my success is that I don't get to be creative anymore or creative in the way that I like to be creative. What kind of success is that? Totally.

And that's exactly the kind of stuff that I feel like we don't talk a lot about and it's real. I mean, we talk about it and sometimes like, oh my gosh, like, I don't wanna do this cause I'm not sleeping at home in my house with my kids. Yeah, how many nights are you away? Yeah. And very shortly after this,

we were sitting down, intimate dinner, table for two in the corner, having a very heartfelt, earnest conversation about family stuff, and we're having this really intimate conversation, and I get up to leave, and the person who's sitting two and a half feet away from me, huge, huge fan, lifelong fan,

and then you're like, what has happened? And we're talking like a fraction of a fraction of actual Hollywood celebrity status. And it was- No, but you're like, this makes you uncomfortable. And yet what I'm doing is trying to get more of it. That's a contradiction that you do have to resolve. You go, this thing that I have isn't making me happy. It's not working.

And yet I'm spending all of my waking hours trying to get more of it because everyone else seems to think that it's great. And the economic logic is very clear that if I keep doing this, I'll get more. You have to go that, that is insanity. Yeah. And this is, again, go back to the book. We have a compass inside us, we have values, and navigating like, am I doing the right thing and is this right for me and right now? And those are some of the hardest discussions

and decisions that we have on this planet, especially the world's getting more complex, not less. So we need more tools for this, right? And that's why I think that the book is well timed. You know, constraints are super important. One of the Stoics, Cleanthes, was saying, that's like the beauty of poetry, he says, is the fetters. He's saying that like the rhyming structure,

the size, the length, there is such a thing as free verse poetry and some of it's beautiful, but the best poems are not that, right? They're not just blah, because it doesn't mean anything. Because you can do anything and everything, it kind of means nothing. It's the rhyming structure or the system, the haiku being like the most

constrained of it, it forces creativity by nature of eliminating some of the creative options. And if you think about that with life too, like here are the things I'm not willing to do. Here's the time I'm allotting to it. Here's how long I'm willing to do something. Here's what's actually important to me. Here's my number that I'm retiring after, you know, whatever it is, it can create a system where it actually makes you think that it's weighing you down. And it is, it's just like weighing you down in a good way. It's like connecting you to reality

instead of drifting off into fantasy land or self-absorption or narcissism or worse. Yeah. And there are just not a lot of those. of drifting off into fantasy land or self-absorption or narcissism or worse. Yeah. And there are just not a lot of those. I don't think there's a lot of those North stars for us culturally. To me, that was when I threw it all in the trash. It was really that North star that I was like, no, I need, these are the things that I struggle with. And if you can't write a book about something you're struggling with,

what kind of book are you writing? This is not a book about how to, again, do perfect thing A, B, C, so get great result D. This is like, what are the, and I know this about, we have a lot of mutual friends who struggle with this stuff and we've talked a lot about it, over dinners and meals. And to me, this is why it's interesting,

is that I know where my challenges are and where my blind spots are. And I look, where have I made the most mistakes? Oh my gosh, what is it? The universe teaches you the same lesson over and over and over until you get it. So I just looked back, it was really easy. I looked back and it's like,

where have I totally blown it the most? Those are my chapters. Well, that's a good artistic rule, by the way, a good constraint. It's like, that's a good artistic rule, by the way, a good constraint. It's like, if it feels good to do, in the sense that like, it's not dangerous, you're not afraid, it's not making you vulnerable in some way,

it's probably like, claptrap, you know? If it's not, do I really wanna put this out there? It's probably somebody else could do it. The idea of it being scary and weird and uncomfortable and challenging to you as a person, that's a sign, not always, because it could be also delusions. Yeah, but it could be that kind of thing.

Like, hey, you could have kept that to yourself. No one was asking for that, but it should be not safe. What are you delivering, you know, if you're just, if you feel comfortable and safe with it? Let's go back to daily stoic. Okay. You felt uncomfortable.

It was scary, sure. Delivering it, and this is sort of what I mean. Like we just had this, I think, an interested spirit discussion about it, and yet you decided, because this is what I mean, your intuition actually was working for you. You're like, oh, I don't know. It's like, oh, it's not gonna be the thing.

And then it's not just you. It's like, you got a bunch of people around you. There's other inputs to the system. You're like, okay, yeah, and by then, and then lo and behold, it's this massive success. So, you know, this is why this is the things that are uncomfortable. This is a great place to look for interesting stuff in life.

And the people who I feel like that I know are the most connected and heartfelt, earnest people, like they actually, this is their sort of master muscle. Like they're good at looking at these places. And it doesn't mean that we're trying to only fix the things we suck at. And I don't mean to say that as I look back at my life, but these are to me a suite, there's a suite of tools

that when together they can combine in really interesting and useful ways. Just think of the idea of attention. And when you're paying attention to something, time fundamentally changes, right? If you're walking in the woods for five days, it can feel like five weeks. Time dilation is real.

This is how, say, attention, that tool, and the understanding of time can go together. One of my rules is like, or one of my sort of observations about life is if you don't regularly forget what day it is, you're not doing interesting enough work. You know, you should be lost in what you're doing on a regular basis.

It doesn't just have to be work, you could just be lost because you're having a great time with your family, you have great hobbies, but if you're not regularly just losing track of time, if you're regularly thinking, how much time do I have left on this? That's probably a sign that you're caught up too much in the day-to-day minutiae or the obligations

for just doing what everyone else is doing. The experience for people during the pandemic where they're like, what day is it? What month is it? That's something that I don't think was due to artists. Artists, they're like, that's awesome. You're experiencing that because your life isn't being dictated by a commute, by your boss, by stupid meetings.

You know, you are in, you have a certain amount of autonomy in your life for a change, even though actually you've lost a whole bunch of autonomy, you can't leave your house, but the hours in your day were much more yours. And you found that you loved baking or you loved like binging on these shows that you never heard of.

You went down all these rabbit holes. That's why book sales went way up. It's like people were getting lost in things for a change. And like, that's obviously, that's not sustainable, but you have to have, if you don't have some version of that in your life, it strikes as probably an empty life. And let's talk about how disorienting that was. And the reason it's disorienting is

cause it's so unfamiliar to not have all of that, like basically bullshit construct. You knew it's Monday because you hate Monday. Because you had a stupid calendar on your desk that you had to, you know, I genuinely felt disoriented in that universe. And to me, that was another good thing. Like that's a sign, like, why am I disoriented?

Oh man, it's because, you know, I'm too tied. And that was when I was, you know, peak executive. I mean, if- You had spent every day as, peak executive. I mean, if you had spent every day as a, as a corporate executive, you weren't Chase Jarvis photographer artists at all. And it was very, very awakening. So in a, in a roundabout way, very grateful for that sort of this, I don't know, destabilizing element for myself. And, you know, to me that's what this is, right? And I forget who developed the series Mad Men.

Oh, Matthew Weiner? Yeah. Matthew Weiner? Yeah, yeah, actually we had to look that up when I was doing the audio book. I'm doing an audio book in this chair later today. I was doing it yesterday. And you go, I'm not sure I know how to read, you know?

And all of a sudden I find myself, I'm just doing it now. I'm, it's not lazy. I'm just, I guess savvy. I just go, I'm just gonna use a different word here for the audio book. The written one is who I would like to be as a person and the audio book is my actual reading comprehension and vocabulary.

Seth Godin, mutual friend, lovely human. I sent him an advance copy. He's like the most generous person. Sent me about this great feedback. And there's one of the original authors of the concept of flow is Mihaly Csikszentmihalyi. I don't know his name. I just know what it looks like.

And it's just a bunch of fricking vowels. Mihaly is what I told myself it was. I have no idea. This is gonna be blah, blah, blah, that guy. His first name is in his last name, right? Like it's like- Mihai, Jake sent Mihai. Yeah, yeah.

But he's gonna set and is all has the brilliance. He circles this and says, you know, you have to read this. And I'm like, okay, noted, noted. I'll do like Latin sayings in my books. And then I'll be like, as the Latin saying says, and then I'll just say it in English. I'm like, I, noted, noted. I'll do like Latin sayings in my books. And then I'll be like, as the Latin saying says, and then I'll just say it in English. I'm like, I'm not fucking embarrassing myself. Although this is one of the nice things about AI

is it can be like, do this in my voice so I don't humiliate myself. Although we just did it on writing right now, the ethnic pronunciations were too good. It was like, I sounded like someone who was like, I just went to Barcelona. you know, as I think perfect. Yeah, it was like it was like cringe, how good it was. It was like, can you make it sound worse? Like a regular person doesn't. Well, I want to show you some books. Yeah, thanks again, but I appreciate it.

Thanks so much for listening. If you could rate this podcast and leave a review on iTunes, that would mean so much to us and would really help the show. We appreciate it. I'll see you next episode. If you like The Daily Stoic and thanks for listening, you can listen early and ad free right now by joining Wondery Plus in the Wondery app or on Apple podcasts. Prime members can listen ad free on Amazon Music. And before you go, would you tell us about yourself by filling out a short survey on wondery.com slash survey.