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The Daily Stoic

12 Oct 2024 · 1h 5m

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Chase Jarvis on Why Embracing Risks is Necessary for Creative Success

In short

In this episode, Ryan Holiday discusses the importance of risk-taking in creative endeavors with Chase Jarvis, a renowned artist, entrepreneur, and author. Jarvis shares insights from his latest book, Never Play It Safe, which addresses overcoming fear of the unknown, trusting intuition, and making calculated risks to achieve success.

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1:41Welcome 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.

2:32Hey, it's Ryan. Welcome to another episode of the Daily Stoic 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.

3:10He'd 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 want to 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 when the term first came out. Pod is from iPod. But this was the first real podcast that I'd heard of. and he said, I'll fly you 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.

3:54They flew me first class. It was like the production value was incredible. You can see videos of it. 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.

4:33He 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 CreativeLive. 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.

5:06And 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 Brayden, 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'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.

5:39You 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 want to listen to that. And if you're not familiar with Chase's work, you absolutely should be. great dude great thinker and i think i have i think my course on marketing which i did again when i was feel like a baby uh you can check that out on creative live also i have no idea how well it held up but that's out there too so here is me and chase jarvis chatting

6:18so i was thinking i think you were the first podcast that i ever did i know that yeah and you came to seattle and you're a studio yes and we can't we talked about 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 that's my problem that's my problem same with online learning same podcast same with you know 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 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.

6:52I was the one whose ass they kicked. I mean, literally lift and stamp copy of, you know, the ad 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 yeah two different cranes flying around and five cameras live switched we would get about between you know 30 and 50 000 people watching live because there was just no other things you could do that right or it was because it was really good ryan sure sure really good guests um 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 and nine.

7:47Wow. 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, we'll fly you out as 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.

8:23Like 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, you know, reasonable and the quality would be good. But I was, I remember doing yours and going like, I could get used to this because it was, it was nicer than like TV shows that I've done. For sure. And then nothing was like that. It's like Saturday, it's Saturday night live quality.

8:58Like you show up, you got your own, you had your own green room, your own bathroom. Yeah. The live in studio audience part, you know, 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 can 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.

9:31I 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, you know, 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 it wasn't, there wasn't, there's no other versions of that.

10:09So we built that as well. Yeah. That's crazy. Crazy. And that's why these dark circles are under my eyes, by the way. I was going to ask you, who do you think is 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, side by side of the, of the 2012 thing in your studio. I look like a child and. Yes. You were, you, yeah, you, so you definitely aged better because you started younger. It's an unfair aging period, like 25 to 35. It looks a lot better. Don't change that. Yeah, that's true. And we won't even say my numbers, but the reality is.

10:43Not that I'm 35 either. And yet, like I still have Polaroids from, like actually I used to shoot Polaroid pictures of my guests. I have signed Polaroids of these insane guests like yourself and, you know, 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 uh the right thing right now they don't even have cameramen's anymore they're like these robots and they're it you're just you're just feeling the the crew get smaller and smaller like if you were like a union cameraman or a gaffer whatever you're just like and then there were two and then there were one it's just you're just watching it get slow lower and lower and lower it's kind of And this, here we are, first of all, congratulations.

11:32This 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 it'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 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 has been cool.

12:04It sort of started, I don't, you sort of, you start thinking, 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 going to film in the bookstore. And then the bookstore started doing well. And we were like, we can't film in the bookstore anymore because people are like knocking on the glass.

12:34We're not selling stuff. Right. Yeah. Actually, what happened was we shut the, I was like, okay, look, it's going to 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 going to buy it. And I was like, I just don't want a neighbor. Like, it was like, I wasn't even thinking of this.

13:06I was really thinking like, what is the word? Like, I was like, I write in there. What if like a music venue takes this? So, you know, I was just thinking like a hassle. You're playing defense. Yeah. But, but like, you know, you, 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. Yeah. 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.

13:43And 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, that's, 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 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, the, the best stuff in life is on the other side of risk and, and not playing it safe.

14:19But 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 going to work, you wouldn't take up. 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.

14:49That'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, you know, 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.

15:18So, 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 going to work. I'm going to spend months and years developing, and then we're going to do this big blowout launch. If you're wrong, you've just taken this, you've 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.

15:53Yeah. 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 fiction. Yeah. I mean, Richard Branson invested in my last company, Creative Live, which has since been acquired by a big public company. We can, you know, 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.

16:30And, you know, over lunch, he's always saying, man, you got to protect the downside. Like that's his, 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. Yeah. Like who does that? Yeah. You know, most people buy a Cessna and then, you know, and then a little jet and then, and they, and yeah. 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.

17:06Not, not if it didn't work, I 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 seatbelts 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.

17:38It's like pushing all the chips in. You never go all in. Totally. Never, never. And yet it, 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. Well, 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 like swashbuckler. Yeah, renegade, as opposed to this like spreadsheet junkie sort of like, you know, hedger.

18:14And 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, then you're able to not do it. Like let yourself off the hook and say that's impossible. Or you're able to go, oh, I need to get all these things right first. So I'm going to do it in 10 years, as opposed to taking some tangible. So, so you say, oh, I need to buy a, to use your metaphor, I need to buy a jet. So I need to, I need to raise a hundred million dollars as opposed to, I need a hundred thousand dollars to buy a Cessna that I'm going to do these small little ferrying flights for and then whatever.

18:53So you're able to go, this is a 10 years from now goal instead of what am I going to do today? For sure.

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22:08The second chapter in the book is about time. And I think the time horizons are, have completely destroyed a lot of what we, you know, 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, oh, 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 has passed between the last time I was here.

22:46And then, you know, by 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 patience, short-term urgency. Like you need to get up and, you know, knock out your list of to-dos. But what if 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, rent's due, I get it.

23:23But 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 a 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 Hofstetter'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 what, trust me, I'm lying. I was like, if this book doesn't come out like right now, it's going to 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.

24:00Like 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 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 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 going to happen. But when you give stuff more time and more runway, you just increase your chances of working.

24:43And then also just the idea of compound interest like that applies to 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 them blesses you and it just happens.

25:20But those people are the exceptions to the rule rather than the rule. And the idea that 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, the its 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.

25:57I think we get time really wrong in our culture. I really do. And we do so much stuff when we're scurrying around things. I mean, just think of the 21 year olds that think they got to figure it out. Yeah. 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 learned to ride a bike. Yeah. We see, you know, Gary was our peer. Gary learns to ride a bike. Oh, he's slightly better at riding a bike.

26:27What are these villages? Are these like thousands of years old? I'm confused now on the bike. Let's go 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 going to go 10 ,000 years back. Gary's a good hunter. Yeah. Where'd he get his bike? I don't No, 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.

27:01Time 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 Rohn 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, you know, nothing and then superstar. And the way that it shows up is it just in your feed with this person, you know, at Wembley Stadium.

27:34Yeah. 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 is this, you know, 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. Yeah. Because that may motivate you. But what if you said life is long?

28:05What 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 that life isn't short, it's that we make it short because we waste so much of it, right? So yeah, if you dick around for a huge chunk of your life and then you've belatedly stumbled upon this thing, you're going to go, oh, I wish I got to this earlier, that's different than like, hey, I just started playing guitar.

28:39Why 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 going to 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 going to measure in days, right?

29:19And so 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.

30:04Because 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 is selling the project short because you're acting as if like 30 seconds here or there is going to 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, you know, 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.

30:40And 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, you know, hard and difficult and wrong this is, it's going to be late, 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's a memento mori coin, which, you know, means you're going to die. Right. And, and that is a sort of a life is short message. And yet I watch you be so deliberate, so patient.

31:15I remember 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 and everything is like in its place. It's beautiful and perfect. And so, you know, what's the stoic, are we going to fight on this? No, no, no. 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 going to think more about it.

31:45Just so we're clear, Samantha was giving me a tour. Yeah. And Ryan's like, we got to 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.

32:18And the memento mori 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 they're really inefficient and wasteful with their time. And I think there's a message where memento mori is really important. But the other side of memento mori, like the part where Mark Sturlus talks about it specifically in meditation, which 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.

32:54Now, 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 a - 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, shipping this thing, going on this trip, getting them to bed. But the other way to think about it, what a stoic might say, is what you're rushing towards is death. Like, we're only going one direction in one place. So why are you trying to get it over quickly?

33:27And there's this instinct you have as a parent where like, and people will sit there and be like, 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? You know? 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 you rushed through them. And so I think what memento mori can help you speed up because you don't have forever.

34:02And why are you showing up every day at this job you hate, you know, telling yourself, I just got to wait till I can retire. I just got to wait till things go back to normal. You don't know that you have that. But the other side of it is, you know, 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, I mean, very, very inspiring.

34:39Like 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 going to spar. I knew what, you know, what Mark's release meant. And that it's like people, how can we both like need to, you know, seize the day and be patient? And 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.

35:18Fitzgerald's version of it was that, you know, the sign of a first rate intelligence is to be able to hold two contradictory ideas. I'm familiar with Fitzgerald's work. 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 like 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 like the advice in each particular situation, that is a skill.

35:52So many people want to 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.

36:22That'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 it's also toxic. Totally. If I told you, but that it's actually about paying and it's about directing it, not about getting it.

37:03The 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. 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 and chaotic, you know, and chaotic outcomes and just not a life well lived, not a rich, meaningful, creative life.

37:43And, you know, again, that's how I got to those topics in the book. And, you know, this reminds me of a little, a little story speaking about, you know, time and attention. I was prior to, you know, this book being printed, I worked for two and a half years on the wrong book, essentially. Oh, I don't know if you know this. No, I wrote 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. Yeah. Okay. 13 months, eight weeks before my deadline, I throw it all in the trash and we have the same agent.

38:22Yeah. I call, 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, um, this is not the book. Yeah. And he, you know, and in his own way, he's like, you know, okay, talk to me. He's just like, you know, closing his eyes and scratching his forehead. And essentially I said, I think this is going to 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.

39:07When I look back at the best decisions, whether those are, you know, 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 to 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. Thank you so much for doing it.

39:41This 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 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 going to be looking at it from a paperwork standpoint and a moving standpoint and unpleasant conversation standpoints and the gaps in the schedule standpoint.

40:19They'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 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, 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?

40:56Sometimes you find yourself there accidentally or, you know, 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, you know, systems, whatever. And then also I find that, you know, who cares a lot about tools is like people who suck, you know, like there, there's like, like the obsession with like, what's the best gear?

41:33What are the greats do? I've memorized all the artistic routines of all these people. And then I'm, I'm like, but what have you ever done? You know? And, 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 crayon 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's real, that's developing that sense of intuition inside of you, which is I think the most important thing that we know the least about.

42:11And 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 you know it's a cellular level your 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 you know knowledge and whatnot everyone else is like oh god you know how do i know when to trust my data data, data, data, data. And data is valuable.

42:43And 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? Like 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 like I remember with, 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 bestselling book.

43:15And I was like, what are you talking about? Like, 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? Like, it was inconceivable to me because I wasn't like 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.

43:47And 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 like really well, obviously. But that thing of like, I didn't think it was going to 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 on you. You could have stopped the presses. Yeah, sure. But you put it in front of them and they said it was great.

44:23And then you said, okay, maybe there is something here. I am going to trust this process where I am. It's really about trusting the process, right? And so to me, just bringing awareness of it. Look, 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 Green, 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 each, that's how I refer to them in the chapters of the book.

45:05Like 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, if you really learned how to get good with this stuff, then boy, this is a recipe or a blueprint for a life well lived on the other side of your comfort zone.

45:36Thanks to Toyota Trucks for sponsoring this episode. When I bought my ranch in 2015 out here in Baskerville County, I drove my car about halfway down the dirt road that we live on, thought this isn't going to work, stopped, parked it, walked the rest of the way home, borrowed my wife's car, drove into Austin and bought a truck. What I bought was a Toyota Tacoma. And this truck wasn't just transportation getting me to and from my house. It unlocked a whole different style of living for us, not just on the ranch, but in our little Texas towns. There were places I could go now that I couldn't go before, especially out here in the piney forests, through the fields and on the unpaved roads like the one that I lived in.

46:21We got to go deep into the hill country's wild beauty. We've driven all the way out to East Texas. We've driven across the country. and by we I mean not just my wife but both my kids who I drove home from the hospital in that truck. Toyota trucks are built for those who understand that the best adventures happen when you're willing to veer off course because you never know when you'll end up on a Toyota adventure detour. And of course this is stoicism too because every detour, every obstacle is an opportunity. But it's helpful if you can handle the difficulty inherent in that. If you've got the resilience and the right companion to make it wherever the road takes you.

47:01Discover your uncharted territory. Learn more at toyota.com slash trucks slash adventure dash detours. This message comes from Capital One. The Capital One Venture X business card has no preset spending limit, so the card's purchasing power can adapt to meet business needs. Plus, the card earns unlimited double miles on every purchase, so the more a business spends, the more miles earned. And when traveling, the VentureX Business Card grants access to over a thousand airport lounges. The VentureX Business Card. What's in your wallet? Terms and conditions apply. Find out more at CapitalOne.com slash VentureXBusiness.

47:43There'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. But in social media, you're doing it so much smaller and cheaper. And it's all about, you know, 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.

48:13You're just like, so you're like, wait, why? You know, like 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 like, 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.

48:48and 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 every all sorts of genres and every possible incarnation of it and yet we still don't know what's going to be a hit right and that should tell you the beautiful thing about art right yeah 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 going to be surprised and some things are going to pop right away and some things are going to take a long time.

49:28That's the other part. It's like you're comparing something that popped immediately with something that's going to find its audience 10 years from now, but you don't know that in 10 years from now, they're going to be compared to each other very differently. And that's why 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 you know sending this newsletter out are you listening to the response that the mark is giving you to your business or to your creative project or whatever.

50:13And, uh, 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 there's, it's easy to see this hygiene manifest itself in, you know, go to bed, you know, 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 started a company?

50:51I 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, go 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.

51:26And right Right now, this sounds laughable because this was 100 years ago, but in 2009, it 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 masterclass that had tens of millions of users, did hundreds 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 that basically it wasn't going well.

52:09So I had to come back. Yeah. You had to be a full-time executive, chief executive instead of being a creative person. From a venture backed, you know, a venture backed CEO where hundreds of millions of dollars at stake, not my, not the thing I sign a wake, wake up and say, I can't wait to do this. But also, you know, 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, I've had in my entire life. I was connected to so many new people in ways I never could have imagined.

52:47And, you know, I had insane mentors and learned a lot. And I simultaneously, I'm not going to do that ever again. Like 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 summit, you know, at the intersection of AI and creativity and it doesn't matter. But one thing is 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.

53:21Know thyself. Let's go back a couple thousand years to that principle, right? Know thyself. That's not where, you know, 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 want to do it anymore. So I'm going back to, you know, basically being, trying to be a polymath artist where I want to 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, uh, an independent artist.

53:57Well, 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'm, I, I've done this. And then he'd raise like a bunch of money. And then now it was like very big, like a hundred employees big. And there was part of me that was like, oh, this is the playbook, you know? And then I just, I was like, wait a minute. I don't think Chase had that much fun. And that's literally what I was thinking of. If this thought enters your mind, fuck, call me. Yeah. No, that's what I was like.

54:30Literally, I was like, oh, I'm so glad Chase is coming. Because 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 CreativeLive for a life-changing amount of money, 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. That was a failure.

55:01To 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. Yeah. 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, but we were educating tens of millions of people on the internet for free, teaching real skills that were transforming lives all over the world.

55:50We had thousands of transformation stories that were coming in from every corner of the globe, a hundred, you know, classes that were being watched by 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, you know, keep doing it. And yet, and, 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.

56:22And there's a lot of basically 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, 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?

57:14What gets us bigger? What gets me more famous? What gets me more followers? Cause you don't actually know if that's what you want. I'm telling you, man, that, so I, 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. You know, constraints actually create and cultivate and can direct creativity. It's a very powerful act. You know, if you ask Edward De Bono, who's got a really famous lateral thinking theory about how to, you know, basically cultivate creative thinking, We don't have to go into it.

57:41But the ironic twist is that I've, 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 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, you know, famously was the...

58:16From Entourage? Yeah, the Entourage. He had literally had two cell phones up to his head and he was Ladies Gaga's agent. We're, you know, backstage. She's in the meat dress period. So she's like literally the most famous... Biggest person in the world. The biggest person in the world. And I've just gotten off stage making this big announcement. Creative Live and just, you know, 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?

58:45Yeah. Like this sucks. Yeah. How, like, what are you doing? How much, how much is enough? Yeah. 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, you know, that is very much about how I, if that was a betrayal of myself, then this moment here on the backside of having Creative Live acquired, and you're asking me, do you want to, you know, to go blow it out again in our sermon company i'm actually no i have i have actually learned i've wisened 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 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 is 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?

1:00:07And 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 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.

1:00:48That's 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, like, I don't want to do this. Cause I'm not, I'm not sleeping at home in my house with my kids. Yeah. And how many nights are you away? And very shortly after this, we were sitting down intimate dinner, you know, 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.

1:01:23Huge, huge fan, lifelong fan. And then you're like, what has happened? Yeah. And this is, we're talking like a fraction of a fraction of actual Hollywood celebrity status. And it was like, this makes me 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, 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.

1:01:59It's, it's, you have to go that, that is insanity. Yeah. And this is, again, go back to the book. Like this is, 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. No, constraints are super important. One of the Stoics, Cleanthes, was saying, that's like the beauty of poetry, he says, is the fetters.

1:02:34He'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.

1:03:14here'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, I don't think there's a lot of those North Stars for us culturally, you know, to me, that's, that was when I threw it all in the trash, it was really that North star that I was like, no, I, we, I need, these are the things, these are the things that I struggle with.

1:03:54And if you can't write a book about something you're struggling with, what, what kind of book are you writing? This is not a book about how to, you know, again, do perfect thing, ABC. 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, you know, 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.

1:04:25So 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. It could constrain. 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 want to 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.

1:05:04Yeah. But, 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, interested spirit discussion about it. and yet you decided, because this is what I mean, this is 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.

1:05:39And 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, I'm vibing. And then lo and behold, it's this massive success. So 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, you know, it doesn't mean that we're trying to, you know, only fix the things we suck at, you know, I, 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.

1:06:25And when you're paying attention to something, you know, time fundamentally changes, right? If you're, if you're walking in the woods for five days, it can feel like five weeks. Time dilation is real. This is so you, 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.

1:06:58But 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 um 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 you're how the hours in your day were much more yours and you were you found that you loved baking or you loved uh like binging on these shows that you never heard of you went down all these rabbit holes.

1:07:51That's why book sales went way up. It was 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 because it's so unfamiliar to not have all of that, like basically bullshit construct. You know, 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.

1:08:26Like, 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 a as a corporate executive, you weren't Chase Jarvis photographer artist at all. And it was very, very awakening. So in a roundabout way, very grateful for that sort of this destabilizing element for myself. And, you know, to me, that's what this is right at the end. I forget who developed the series Mad Men. Matthew Weiner. Yeah. 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.

1:09:10I 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. It's not lazy. I'm just, I guess, savvy. I just go, I'm just going to 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 advanced 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.

1:09:48I don't know his name. I just know what it looks like. And it's just a bunch of freaking bells. Mihaly is what I told myself it was. I have no idea. That guy. His first name is in his last name, right? Like it's like. Mihaly. Chick sent me high. Yeah. But he's going to set and all his brilliance. He circles us and says, you know, you have to read this. And I'm like, okay, noted. Yeah. 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.

1:10:26So I don't humiliate myself. Although we just did it on Right Thing 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? 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 know. Well, I want to show you some books. Yeah. Thanks again, bud. I appreciate it.

1:10:53Thanks so much for listening. If you could rate this podcast and leave a review on iTunes, That would mean so much to us and it would really help the show. We appreciate it. And I'll see you next episode.

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From the publisher

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 website


Watch 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=odfH7LZwAQ8


Listen 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


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