BONUS | No One Is Coming to Give You Permission

If your New Year motivation didn’t make it to February, this episode is for you. Ryan and his business partner and longtime friend, Brent Underwood, talk about how waiting for permission, perfect conditions, or external validation quietly turns into procrastination, even for high performers. They discuss why open-ended ambitions are harder than deadlines, how success can actually make starting new things scarier, and the trap of telling yourself, “I’ll get to it later.”Let’s not write the year off just yet. The Daily Stoic New Year New You challenge is opening back up for a limited time. Learn more and sign up today at dailystoic.com/challenge.👉 Get The Daily Stoic New Year New You & all other Daily Stoic courses for FREE when you join Daily Stoic Life | dailystoic.com/lifeBrent Underwood is the owner of Cerro Gordo, an original boomtown silver mine, established in 1865. Check out Brent's book Ghost Town Living: Mining for Purpose and Chasing Dreams at the Edge of Death Valley at The Painted Porch. Youtube: @GhostTownLivingIG: @BrentWUnderwood🎥 Watch the video episodes on The Daily Stoic YouTube channel: https://www.youtube.com/@DailyStoic/videos✉️ 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 Facebook 📢 Share | ⚙️ Manage Subscription

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

• 0:00Ryan Holiday?

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

• 0:14Ryan Holiday?

  Okay, so I was thinking about you the other day. I'm gonna call you out for a problem you have. You sometimes struggle to start things for which there is not like a contract or a like commitment that you would like get in trouble if you didn't meet.

• 0:31Speaker 01

  Yes.

• 0:31Ryan Holiday?

  Why do you think that is?

• 0:33Speaker 01

  It comes, I've always feel like it's like opportunity cost. Because as we're all very busy, I'm thinking through my every day, there's so many hours in the day. So I think, okay, today I have 12 hours, optimistically, that I can do whatever I want. And a lot of those are going to be eaten up with small tasks. So the bigger tasks, whether they're, I have to, at Cerro Gordo, I have to manage a commercial hotel build. I'm playing general contractor. I am the cameraman and everything else for videos. We have Daily Stoic, which has 10 employees that need things every single day.

• 1:10Ryan Holiday?

  I think it's way more than 10, but sure.

• 1:11Speaker 01

  Yeah, so we have Daily Stoic, there's many employees that need things every day for me. And so it's kind of like a balancing act where I have a lot of things that I would like to do. You know, like for instance, right now, I'm thinking about working on a book, right? And so a book is a thing that is important to me. But when I know that I would be working on it in sacrifice or something that has a more urgent commitment to it, then things get reshuffled.

• 1:36Ryan Holiday?

  And I guess I get it at some level because sometimes people ask me like, why do you not self-publish?

• 1:40Speaker 01

  Yeah.

• 1:41Ryan Holiday?

  And I do feel like the open-ended nature of like, no one is asking for it, no one necessarily wants it. I get to make all the decisions, which means I can always make an excuse. I do find that open-endedness to be less than ideal. So like, there's something to me about like, I've sold like a couple of books in a row. So it's like, I always know what I'm supposed to be doing. But what does, for you, like, what does having a piece of paper change? Because actually, I remember when you worked on your last book, you ended up pushing it like a bunch of, it's not like you actually, you didn't, you didn't breach, you weren't in breach of the contract, but it's not like the contract was like some, some document you refused to challenge.

• 2:22Speaker 01

  Yeah, it's like, why do kids procrastinate on their homework? You know, it's probably a similar thing where it's like, for me,

• 2:28Ryan Holiday?

  But if a kid could be like, actually, I don't have to, I can turn it in whenever I want.

• 2:33Speaker 01

  Yes.

• 2:34Ryan Holiday?

  Which is like effectively what these contracts mean anyway.

• 2:37Speaker 01

  Yeah.

• 2:38Ryan Holiday?

  There's something about it. It's like, I'm just wondering if there's like a little bit of like imposter syndrome in you that's like, you like, you don't think it's real until you've like brought someone else in.

• 2:47Speaker 01

  Probably looking for like a stamp of approval that like, this is worth your time. Also like outsourcing that part of it as well.

• 2:53Ryan Holiday?

  Yeah.

• 2:54Speaker 01

  And so I think that like with videos, as I've gone along, it's gone from like, originally I created them because I really loved creating them. I still love creating them, but then eventually it becomes more of a business where I have like a contract with advertisers that say, hey, you need to produce as many videos per year. And then it's like, I'm a professional videographer at this point, you know? And so there's like that nature of it. And so I think with the book, it's, you are looking for somebody to tell you, this is a good enough idea to spend a lot of time on. And I think that that can come from like, a self motivated place, if you have the bandwidth to like,

• 3:25Ryan Holiday?

  Yeah.

• 3:26Speaker 01

  have that capacity. But I think in a truncated manner, I'm looking for something to say, hey, give this some time when there's a lot of other responsibilities on the horizon.

• 3:36Ryan Holiday?

  The video thing is interesting to me because like, I'm wondering if like having a like a slot, like a sponsor helps you get out of your own head. I'm not like piling on you. I think this is actually a thing a lot of people have, right? You're like, if it has to go out by, by Sunday, it goes out by Sunday, even though it doesn't have to. And you could call the people and be like, hey, I don't have it this week. And they'd be like, fine. But there's something about that thing, just like, just it's slightly enough that it gets you out of your own head in a way that makes you more productive. And by the way, I've never seen anything that you've done. And I thought like, that seemed rushed. He was clearly just doing that to like check a box. That's like the opposite of what your things do. So I'm just wondering what that is.

• 4:17Speaker 01

  It is helpful. I think like, there's like a perfectionist nature to it as anybody that like creates anything I think comes to. So like, I could tinker on a video for a year and still be tinkering on it and tinkering on it. And so I think that like, having that deadline is helpful. And like, I think, looking to you, like, you are like a machine where you have a book every year, which is helpful. And like, we both know authors, some close to us that. Have tinkered on books for a very long time and not made a lot of progress.

• 4:41Ryan Holiday?

  Yeah, yeah.

• 4:42Speaker 01

  On those books.

• 4:43Ryan Holiday?

  I was just reading Camus, The Plague, and this guy's like, he's been working on the first sentence in this book for like 10 years or something. And it's like, you look at all the different iterations of the sentences and they're like, all like solid Bs. By the way, it doesn't matter.

• 4:56Speaker 01

  Yeah.

• 4:56Ryan Holiday?

  But like, that's what happens. You just get in your own head about it.

• 4:59Speaker 01

  I think with even going back to my book, like in full transparency, like I pushed the book numerous times. And I think that it got to a point where basically the publisher was like, if you push again, we will cancel the contract. And so then I got the book done suddenly.

• 5:11Ryan Holiday?

  Yeah.

• 5:12Speaker 01

  So sometimes it does take that person that like, no, you're going to get this done, like that third party. And that could probably be like accountability partner. I know a lot of people have like success having like writing partners in that case.

• 5:22Ryan Holiday?

  There's also, I remember Tim Ferriss told me about this website where you're like, okay, like you have to put, you put like a thousand dollars in escrow. And if you like, don't meet the deadline, it like gives the money to like the KKK or something. And he's just like, you would never want that. And so, so like it just, it forces some like horrifying possibility upon you that if you don't finish or start or whatever it is, it will, um.

• 5:45Speaker 01

  Yeah. Everybody's individual, right? And it's like, I've come to learn that a little bit and I, cause even you know that, like, I need some type of like deadline. Somebody else telling me that this is what I need to be focusing on. Otherwise, like I focus on the other things that somebody else has told me that with.

• 6:00Ryan Holiday?

  But it's funny because like, I don't think anyone would look at you and be like, oh, that's definitely not a self-starter. Like you're, you're perennially self-employed. You've started multiple businesses, built most of what you've done at Cerro Gordo or other projects. Like not only did, did nobody ask you to do it or tell you to do it, but like they told you it would be impossible and it wouldn't work. And like, it was only by self motivation. So that's the other thing is, it's like, usually I guess I would take some solace in it. It's like, most of the people who are high achievers also struggle with like high amounts of procrastination and excuses and paralyzation and perfectionism. But it's interesting that you like, sometimes you struggle with it, or in some cases you clearly struggle with it.

• 6:43Ryan Holiday?

  And then in other cases, it's like preposterously not an issue for you.

• 6:47Speaker 01

  Well, I think, I mean, I'm fortunate in the fact that like, all of these things that we're discussing are things that I want to do.

• 6:52Ryan Holiday?

  Yeah.

• 6:52Speaker 01

  So none of them are things I inherently do not want to do. And so like, it's not that I'm pushing them off because I don't want to do it. It's just, I'm pushing it off because like, I have this checklist of a lot of other things. And I do think. And this is the nature of life, right? Like, if the book sold tomorrow, I would find the time to write it in addition to everything else.

• 7:08Ryan Holiday?

  But did you think, like, because you you'd sent it out and you didn't get all the responses you wanted?

• 7:12Speaker 01

  Yeah.

• 7:12Ryan Holiday?

  If someone had said, we're in.

• 7:15Speaker 01

  Yeah.

• 7:15Ryan Holiday?

  For $1.

• 7:16Speaker 01

  Yeah.

• 7:17Ryan Holiday?

  That would have been totally different than this kind of middling response that you got. And it's like inconsequential distinction.

• 7:23Speaker 01

  I do. I do think a lot of it is imposter syndrome. So like, the idea of just writing a book on spec, right? Just writing a book feels like every person in the world is, I'm gonna write a book, you know? And then it's suddenly just like they're writing a book.

• 7:35Ryan Holiday?

  But that's how I did Trust Me, I'm Lying. I mean, my whole life changed because I I basically quit my job, moved across the country, and worked for six months on a book thing that.

• 7:44Speaker 01

  Yeah.

• 7:44Ryan Holiday?

  No one was asking for, and no one thought it would work, right?

• 7:48Speaker 01

  Yeah.

• 7:49Ryan Holiday?

  So I, yeah, I wonder if in retrospect, that was delusion? Was that confidence? Was that, or maybe I just wasn't thinking about it at all?

• 7:56Speaker 01

  Was it lack of like, you have a lot more on your plate these days? You know what I mean?

• 8:00Ryan Holiday?

  That's true, but I remember somebody, what somebody said to me, they were like, look, you'll either sell it.

• 8:05Speaker 01

  Yeah.

• 8:06Ryan Holiday?

  Or you'll self-publish it. So either way.

• 8:10Speaker 01

  Yeah.

• 8:10Ryan Holiday?

  It's going to come out and it's worth you doing.

• 8:12Speaker 01

  Yeah.

• 8:13Ryan Holiday?

  And I just remember that being very freeing. I was like, okay, I'll just get started, which is like the main thing. It wasn't like two months in, none of this was a problem.

• 8:21Speaker 01

  Right.

• 8:21Ryan Holiday?

  But it was just like, should I or shouldn't I? That's where you're held up.

• 8:26Speaker 01

  I I think going as imposter syndrome too, it's like, this book that I'm hoping to write is more of like a, like a narrative fiction. It's a bigger swing. It's more of a writing book, more than like, less than anything else. And so like, I want a outlet that distinguishes between writers and non-writers to say that you're a writer. You know what I mean? In some way.

• 8:44Ryan Holiday?

  But can't you let the finished product settle that discussion? Like, like, I guess what I'm saying is like, like, uh, why don't you just take the the somewhat ambivalent response that you got and use it as fuel to be like, oh, I'm gonna show you that I can do.

• 8:58Speaker 01

  I definitely, that's definitely part of it. I like, I know the name of every publisher that passed on it, including the editor. And so we'll cut to this when the book's a big bestseller and like, I'll send them a clip, this clip.

• 9:19Speaker 01

  Flipping the table, you know me very well. You've known me for almost 15 years, which is hard to believe. You understand what I'm capable of and also what I struggle with. Given that I have the things that we outlined before, the responsibilities with the Rastech, blah, blah, blah. What do you think I should do?

• 9:35Ryan Holiday?

  I think you should say like, hey, I'm going to give this a certain amount of time per day or per week. And you're going to be like, I'm going to give it one hour a day for, you know, for all of 2025 and just see where it is then. Like, that's what I was telling you is like most of, like, you can either spend a lot of time trying to make it more appealing to get the selection or to get chosen and then still have to be at the exact same starting line. Like, you can either qualify for the marathon or you can just be like, look online and be like, this is the course. I'm going to run the marathon and see if I measure up or not. You know, like, I would just, I would just start by like putting some time in because who knows? Maybe you'll get into it and you'll be like, actually, I really don't want to do this.

• 10:19Ryan Holiday?

  It's really not that satisfying. I think I would just set aside a certain amount of time and put that time into it. And then knowing that, like, if you do that, not only will eventually a book come out of the other side that you'll either sell or self-publish, but if you back up and you see it as a meta project of solving this tendency that you have, that would be good because this isn't the only place you're doing it. Like, again, not to put you on the spot, but you've been talking about this podcast idea, which I think is just as good as the book for like 18 months.

• 10:47Speaker 01

  Yeah.

• 10:48Ryan Holiday?

  You're this close to start. You have most.

• 10:51Speaker 01

  I've recorded episodes, yeah.

• 10:52Ryan Holiday?

  Yeah, yeah.

• 10:53Speaker 01

  So the recorded, it does, I think some of it too is like fear of future bandwidth. Meaning like, I'm afraid as I take these things on, if they are successful, then that's even more I have to do, you know what I mean? And like, I'm not opposed to work. I work very hard, I work very long, but it's like, I don't know. As I'm thinking out loud, that could be something.

• 11:12Ryan Holiday?

  Well, no, this is something I just saw Ramit when I was in New York. He came to my talk, the 92nd Street Y, and he's talked about this a bunch where like, he really likes working out and he's fascinated by personal trainers and like. Saying personal trainers will talk about women. They don't want to hire a personal trainer because they don't want to get too strong. Like they're worried about looking too strong. And it's like, it's like the definition of like cross this bridge when you come to it. It's like, the, the problem is, is that most people sign up and then don't come. The problem is that most people come and get too good of a result too quickly. And then they don't know what to do about it. Right? And so like, I get that where you're like, there's probably some level where subconsciously you're like, I don't want to start this thing because then what if it works?

• 11:56Ryan Holiday?

  And then I'll take, but like you'll cross that bridge the same way. You've crossed every one of those bridges with Daily Stoke, which is like, now you have a, a scaling problem. Which you're actually uniquely qualified and practiced at solving.

• 12:10Speaker 01

  Yeah, that's true. Well, I think generally if we, if we also talk about it, like I'm probably not the only person in the world that has a book idea that's good, that is failing to start because somebody else is saying, yes, what would you say to everybody else out there that has a book idea that hasn't started?

• 12:25Ryan Holiday?

  Well, Seneca will put you on the hot seat here because Seneca says the one thing that all fools have in common is they're always getting ready to start. And that's where it's not like you're like someday, you're like, you're, you are working on it.

• 12:37Speaker 01

  Yeah, yeah.

• 12:38Ryan Holiday?

  Yeah, you're just like, but you're just like waiting for some, like you're waiting for like the, the bell to go off to start. And that's not probably going to happen. Like for, for any of the things, you know, like nobody's hotly anticipating like anything that any of us are doing. Like it's all got to be self driven.

• 13:00Speaker 01

  That's true. No, but so not to put you on the hot seat, don't you ever feel though, that like it becomes an obligation? Meaning like even this podcast, for instance, right? Like you now know that you have to do.

• 13:09Ryan Holiday?

  No, it's like, I go like, hey, like, just like maintenance on the things that I've committed to is like X amount of hours per week. Right? And then like the commute to getting my kids to school is X, there's like increasingly smaller windows, which is definitely a self inflicted, like sort of tighter and tighter pressure cooker that I've put myself in. So I definitely see that, but like, I do try to, I do try to separate like, okay, what is like a work commit? Like, okay, like I'm squeezing in one more. Talk that I'm supposed to do next week. Like, we're recording this before the end of the year. People are probably listening to this at the beginning of the year, which is sort of what we're talking about because we're talking about like, probably already you failed at some of your resolutions.

• 13:54Ryan Holiday?

  And that's why we redo the new year, new year challenge, which you can sign up for it, davisoke.com/challenge. But I'm like squeezing in one more thing before the end of the year. That's like, I probably shouldn't. It's whatever I do that. But like, I try to make a big distinction between like obligations and then like, interests slash creative, like the, the main. So it's like, if I, like, I just had this idea for another book. That's kind of like an in between book. And I pitched it to my publisher on Monday when I was in New York and they were like, like, let's do it, you know? And like, that, to me, like, when I look back, I'm not going to be like, oh, I'm, I'm glad I squeezed in that extra talk. But I am going to be glad that I like, worked on that cool thing I was excited about.

• 14:38Ryan Holiday?

  So like, if it's something that you don't ever actually want to do, and then you're like reticence to start it is probably a good sign.

• 14:46Speaker 01

  Yeah.

• 14:46Ryan Holiday?

  Right? I think that's like, if it's not a hell yes for something that like sucks.

• 14:51Speaker 01

  Yeah.

• 14:52Ryan Holiday?

  That's different than a like, I'm not sure if I should do it or not do it. But like, deep down, you're like, I would love to have done that.

• 14:59Speaker 01

  Right, right.

• 15:00Ryan Holiday?

  Those are the things you have to like barrel through the procrastination.

• 15:03Speaker 01

  Right.

• 15:03Ryan Holiday?

  I'll give you another one. There's like an email in my inbox from this like startup that wants me to invest in it. And like, the guys were really nice and I like, I almost signed the paperwork like five times.

• 15:14Speaker 01

  Yeah.

• 15:15Ryan Holiday?

  That I'm more suspicious of my, I guess I'm taking my procrastination as meaning something more there.

• 15:22Speaker 01

  Yep.

• 15:22Ryan Holiday?

  Than I am when I'm like, I'm in the middle of this project right now. It's really hard and challenging. And I'm like, looking for an excuse not to do it.

• 15:30Speaker 01

  Yeah.

• 15:31Ryan Holiday?

  That procrastination I'm barreling through.

• 15:33Speaker 01

  Right.

• 15:34Ryan Holiday?

  Or resistance I want to see as the enemy versus other resistance that it's like, no, that's like a spooky feeling warning you like you're in dangerous territory.

• 15:43Speaker 01

  Right. Would the hell yes or hell no if we're Derek Sivers? You know, he said, yeah, things are either hell yes or hell no. I think part of this too is like, as you become more successful. The hell knows are things that you previously would have said hell yes to.

• 15:54Ryan Holiday?

  That's a great point. Sure.

• 15:55Speaker 01

  And so like this book idea had come to me five years ago before I had a YouTube channel. I would have been a hundred percent in on that. And as you become more successful in other areas, the trade off, you start doing a little bit more.

• 16:06Ryan Holiday?

  That's where the opportunity cost is. Yeah, for sure. Um, yes. And if you had some competing thing that was like real and concrete and whatever, that would be different. Also, I think, but it's a genuinely good idea. It's like something you would grow for having done.

• 16:23Speaker 01

  Yeah.

• 16:24Ryan Holiday?

  And the downside of it is extremely low, other than opportunity costs.

• 16:28Speaker 01

  Yeah.

• 16:28Ryan Holiday?

  I don't know. I'd probably push through.

• 16:30Speaker 01

  I've also one where like, I haven't not been working. I've been quietly working on it. Maybe I was working out till I get to the point where I feel like, oh, I've actually been working on it, you know?

• 16:37Ryan Holiday?

  Yes.

• 16:37Speaker 01

  I have the prologue and the chapter one written already.

• 16:40Ryan Holiday?

  Oh.

• 16:41Speaker 01

  Um, and so there is work behind the scenes. And so that I think is like an indication even of myself that I do want to do the thing.

• 16:47Ryan Holiday?

  Yeah.

• 16:48Speaker 01

  But it would still be nice to have like a publisher be like, you're all right.

• 16:52Ryan Holiday?

  The book is like this one big thing that you work on for many years and then maybe it works or it doesn't. The podcast is a more, I think illustrative and relatable one because like, you could be 50 episodes into it by now and having like it either, you could have either done it and turned out like your audience isn't interested in it and you're not interested in it. Or you could be 50 stories in, it could be incredible. It could have gotten you whatever cred and security you needed to do the book like.

• 17:25Speaker 01

  Yeah.

• 17:25Ryan Holiday?

  You also just could have been whoever you are on the other side of doing 50 episodes of something.

• 17:30Speaker 01

  That's true.

• 17:30Ryan Holiday?

  So that's like an interesting one because it's closer to what most people are doing, which is like iterative things that they're either starting or not starting the clock on.

• 17:39Speaker 01

  I've done about 10 episodes and the point of that was like, I remember when Tim Ferriss started his podcast, he was like, I'm going to give it 10 or whatever he said. Yeah, do six. And that feel, when you make it a more manageable thing, it is more manageable. You still then have to put them out. But again, that's still like, to me, I'm like, well, if I do six, I'm going to have to do 600, you know what I mean? And then like, uh, it becomes like a growing thing, but.

• 17:59Ryan Holiday?

  Yeah. So, so there is, is that the imposter syndrome of not wanting to launch it? And it doesn't do like, are you, cause that's an interesting thing. You and I talked about this where like, we knew someone who was like, wanted to be a YouTuber, but they just never made any videos.

• 18:14Speaker 01

  Yeah.

• 18:14Ryan Holiday?

  And we were talking about how you have to, it's not ego exactly, but you have to have whatever the thing is that allows you to do your first shitty stuff.

• 18:25Speaker 01

  Yeah.

• 18:25Ryan Holiday?

  That is public, like Hemingway said, oh, the first draft of anything is shit. But like, the problem with a lot of stuff is that, that unlike a manuscript, that draft gets seen by people. And are you struggling then with just not wanting to put something out and getting feedback on it? Like, like you are so good at making videos. Are you, is it more like, you don't know if you're going to be good at this?

• 18:48Speaker 01

  Maybe, yeah, maybe I think that like, I was pretty fortunate where like, my videos have done really well from the very beginning. And so like, I can point to them and look, I'm good at making something. And then if you aren't good at making something else, like, does that?

• 18:58Ryan Holiday?

  But why don't you like, okay, the videos came out, they did well. The email list came out, it did great. Why is your assumption that it won't be a third one in a row?

• 19:10Speaker 01

  I don't know. I don't know.

• 19:12Ryan Holiday?

  I remember I was talking about someone that were, they were going to like, help me with some of my financial stuff. And I was like, I kept being like, you know, cause then like, this is going to go away. And then, and he was like, but what if like, I think it was actually right when I was thinking about the four virtues series, I was like, you know, this is the first time I'm selling four things in a row and the way that money works in publishing, you get like a chunk of it at the front. So I was like, so obviously this is a one time thing and then it's probably done for me, like this is my like, and he was like, but what if it's not like, he was just, he was like, what if the next one is bigger? And like, I couldn't conceive of that. And obviously him having other clients, like he'd worked with a bunch of professional athletes, like they're always like, my first contract is the, the biggest one. But he'd just seen it enough times that like, no, sometimes like, You keep going.

• 19:57Speaker 01

  Yeah.

• 19:57Ryan Holiday?

  And like, that was like, hard for me to conceptualize. I wonder if you're like, the track record says you should be good at this too. Not from an egotistical standpoint, but like, you have an audience. You're good at it.

• 20:10Speaker 01

  Yeah.

• 20:11Ryan Holiday?

  It should transfer a little bit like.

• 20:13Speaker 01

  There's some of that. I mean, I remember even when I was doing my, my book that came out, like, I didn't, I don't think I showed anybody drafts other than you at the very last minute.

• 20:21Ryan Holiday?

  Yeah.

• 20:21Speaker 01

  And I was like, well, I don't want to show them drafts. It's like, that's the dumbest thing ever. Cause like, they're gonna see the final book.

• 20:26Ryan Holiday?

  Yeah.

• 20:27Speaker 01

  And it's only gonna be worse because you didn't show anybody drafts. And so like, I was hiding all of the work from everybody, including like, my closest friends and family.

• 20:34Ryan Holiday?

  Help you make it better.

• 20:35Speaker 01

  Yeah. Instead, I was like, no, no, no, I don't want to show them something that's not good. And instead they saw like, a book that could have been better had I shown people things earlier on.

• 20:43Ryan Holiday?

  That's how you should think about this podcast too, because it's like, only a small percentage of the eventual audience will listen to the early ones. So like, we talk about this at the Daily Stoic meetings. I'm like, start the clock, right? Like, you should start, like, who you're gonna be a year in, and two years in, and five years in, is like, obviously much better than who you are at the beginning.

• 21:02Speaker 01

  Sure.

• 21:03Ryan Holiday?

  So like, if you'd started the clock a year ago, you'd be one year in.

• 21:06Speaker 01

  Yeah. I agree with that. I mean, I think to take the focus off myself a little bit, probably many, many, many people struggle with this exact thing.

• 21:15Ryan Holiday?

  Totally. No, that's why I'm, I think it's just.

• 21:17Speaker 01

  Ninety percent of the people out there probably have some creative project that they've thought about and failed to begin for some reason. And I think it happens. What is that for you? What is the podcast in your version of that world? You know what I mean?

• 21:27Ryan Holiday?

  I don't know. I'd have to think about it like creatively, like, what is that thing? One example, like, I have, I've just noticed it like practically lately, like, there'll be like, an email for some like, like I'm having to handle like some legal paperwork, or I'm having to clean something up, or have to make a decision about something. And I'll see this like email come in and I'll be like, oh, that's gonna be like, uh, that's a high mental load thing. So I'll procrastinate. I won't open it. And then I'm opening it and the person's like, can you send me that thing again? And so it's like, like, actually, it was like, uh, we weren't at the part I was dreading. It was like something leading up to that part, but I just made the whole thing last. Longer by by like making it up in my head, you know?

• 22:10Ryan Holiday?

  Like there was some decision Sam and I have to make on something and I was like, we're like putting it off, putting it off. And then it was like, actually, like the examples that they showed us were like so far from what we could choose between that we had to send it back.

• 22:24Speaker 01

  Yeah.

• 22:24Ryan Holiday?

  And so like, we could have sent it back two weeks ago and then it would be finished faster and whatever. Like, I just find myself doing that a lot, like mostly over like low stake stuff.

• 22:34Speaker 01

  Yeah.

• 22:34Ryan Holiday?

  I'm just like letting stuff sit and pile up and then I feel more and more pressure. And then when I look at them, I'm like, this was a low pressure thing that I

• 22:44Speaker 01

  Yeah.

• 22:44Ryan Holiday?

  projected onto it, something I was trying to avoid.

• 22:48Speaker 01

  Yeah.

• 22:48Ryan Holiday?

  I don't know, like, big things I'm procrastinating on, I actually don't think that much. I'm pretty good at that.

• 22:55Speaker 01

  Yeah.

• 22:55Ryan Holiday?

  It's more the little things. One of my goals for for 2026, maybe I'll have already failed at this by the time people are listening, but I'm gonna, I'm gonna declare email bankruptcy.

• 23:05Speaker 01

  What is that? Like you're gonna go to email like zero, just delete everything that's old?

• 23:08Ryan Holiday?

  I'm just gonna mark it all as red. And I've been telling myself I've been gonna do it for like

• 23:13Speaker 01

  Where are you at right now?

• 23:14Ryan Holiday?

  Two years. Well, okay, so like I have an email, I have like two emails, as you know. I have one email that like newsletters go to and like, hey, we need an email address for this receipt. That could, so that has like 50,000 unread emails. That's like, I never asked for most of those emails, so that doesn't count. But I have like my email.

• 23:32Speaker 01

  Yeah.

• 23:32Ryan Holiday?

  It's got like five or 600, but they're like serious.

• 23:36Speaker 01

  Important emails, yeah.

• 23:38Ryan Holiday?

  And they stretch back two or three years at this point. And I'm just gonna, like, obviously, none of them are important or they would have replied already.

• 23:46Speaker 01

  Again, yeah.

• 23:46Ryan Holiday?

  Yeah. And honestly, I bet there's like certain people or certain things that if I just search that name and mark those as red.

• 23:51Speaker 01

  Yeah.

• 23:52Ryan Holiday?

  It would go

• 23:52Speaker 01

  Clear 60% of it or something.

• 23:54Ryan Holiday?

  Because it's them following up about this thing like 10 times, you know, or whatever. But um, so it's more like that. There's like things I know I need to do that I'm letting pile up. And and I'm like, even the Seneca's thing, right? I'm telling myself I'm gonna do it on January 1st.

• 24:10Speaker 01

  Yes.

• 24:10Ryan Holiday?

  I could just walk into my office and do it right now.

• 24:14Speaker 01

  Yes.

• 24:14Ryan Holiday?

  But on January 1st, it'll be 10% larger.

• 24:17Speaker 01

  Yeah.

• 24:19Ryan Holiday?

  You know?

• 24:19Speaker 01

  Correct.

• 24:20Ryan Holiday?

  So it'd be better if I did it right now.

• 24:21Speaker 01

  Yeah, well, you should do something called the new year, new you.

• 24:24Ryan Holiday?

  After New Year, New John.

• 24:29Ryan Holiday?

  In the spirit of it's never too late, we are breaking with a little bit of tradition over at Daily Stoic and reopening the New Year, New You Challenge. We usually kick off the year with 21 days of Stoic-inspired challenges. And we heard from a bunch of people, they came back from vacation later, they procrastinated, they changed their mind, or they stumbled on their resolution. And, well, we wanted to say it's not too late. You're still working on yourself. You're trying to get better. You want to make changes. And this is all inspired by Stoic wisdom. So I would love to see you in there. Break out of the doom loop, cultivate gratitude, take charge of the year, focus more, develop confidence, find calmness and stillness in a crazy world. A bunch of great stuff in here. It is not

• 25:10Ryan Holiday?

  too late to make 2026 your best year. Stop dreaming and, you know, be that person. Well, you can sign up right now at dailystoic.com/challenge and I will see you in there. We've got a bunch of awesome stuff. I think you're really gonna like it. So sign up now at dailystoic.com/challenge. I'll see you in there.

• 25:33Ryan Holiday?

  I think we may have built a day around that for this reason. Like, what's a task you've been, you've been putting off? Like, what's one thing?

• 25:40Speaker 01

  Well, I guess like, within the Stoics, like, if I had to hold on to something to convince me to do my book.

• 25:46Ryan Holiday?

  Yeah.

• 25:47Speaker 01

  What am I holding on to?

• 25:48Ryan Holiday?

  I mean, what I would hold on to is like, the whole, Sarah Gordon could burn down to the ground again. You know, like, I mean, you could fall down a fucking mind shaft.

• 25:57Speaker 01

  Yeah.

• 25:57Ryan Holiday?

  All these, and these are not like, extremely unlikely possibilities. Like, one of them is a thing that already happened once.

• 26:06Speaker 01

  Yes.

• 26:06Ryan Holiday?

  And another one is a fate you tempt on a regular basis. So, and that's not even getting into other possibilities, which is like, I don't know, you're not gonna be the person who has the freedom that you have now forever.

• 26:20Speaker 01

  Sure. I agree with that.

• 26:21Ryan Holiday?

  And like, so this is like, the time to do it.

• 26:23Speaker 01

  Right. So how, then? So for a very practical example, this winter I had like three months dedicated and I was either

• 26:32Ryan Holiday?

  You already filled up like 50% of it doing something else.

• 26:34Speaker 01

  I was either going to write this book full time.

• 26:36Ryan Holiday?

  Yeah.

• 26:37Speaker 01

  Uh, full time, meaning in my spare free time.

• 26:39Ryan Holiday?

  Yeah.

• 26:40Speaker 01

  Or go on a road trip where that is a guaranteed paycheck.

• 26:45Ryan Holiday?

  Yeah.

• 26:45Speaker 01

  That's gonna guaranteed go to the rebuilding the hotel will guarantee advance my goals at Cerro Gordo.

• 26:51Ryan Holiday?

  Sure.

• 26:51Speaker 01

  And so the proposal didn't get the response I wanted it to. The road trip got an immediate sponsorship for the whole series of it. And so now I'm spending these three months doing a road trip, uh, which I'm excited about, but at the same time, you know what I mean?

• 27:08Ryan Holiday?

  Like, well, I think two things. I don't think your road trip actually needs to take three months.

• 27:11Speaker 01

  Okay.

• 27:11Ryan Holiday?

  And then, and then, uh, and no one actually said that you have to do it all by car.

• 27:17Speaker 01

  That's true.

• 27:17Ryan Holiday?

  Even, you know, famously, when you read like, uh, Walk in the Woods or like, it's like three different trips.

• 27:23Speaker 01

  Compilation.

• 27:24Ryan Holiday?

  You know what I mean?

• 27:24Speaker 01

  Right.

• 27:25Ryan Holiday?

  Like, no one, no one actually needs you to do a contiguous road trip.

• 27:31Speaker 01

  Right.

• 27:31Ryan Holiday?

  Like park your car in an airport and fly home.

• 27:34Speaker 01

  Right.

• 27:34Ryan Holiday?

  And whatever. So I think, I think not needing it to all or nothing is another way that we excuse procrastination.

• 27:41Speaker 01

  Sure.

• 27:41Ryan Holiday?

  I don't, I just don't have the headspace right now, or like, I can't dedicate as much time as I would like to it right now. So I'm just not going to, which is horseshit, right? It's like, and that leads me to the, maybe the thing I was saying earlier, which is like, tell yourself that one is contingent on the other. That accepting this is contingent on you saying, hey, I'm going to wake up at six in the morning every day of the trip. And I'm going to write from six to seven, six, seven.

• 28:08Speaker 01

  Yeah.

• 28:10Ryan Holiday?

  So that's what I, it's probably by the time this is.

• 28:16Ryan Holiday?

  This is how you know I have a nine year old and a six year old. That's what I would do. I would make, you know, like, I will allow myself this, which is important and responsible for like adult business reasons.

• 28:26Speaker 01

  Right.

• 28:27Ryan Holiday?

  But I'm only going to accept that if I use it to support what I've committed to do for like creative fulfillment, meaning purposes.

• 28:36Speaker 01

  Like that because I think it's very easy for everybody to fill available space with anything, right? And especially like we said, like as you have success, you can fill with, they're both very cool things to do. They're not like, one's not undesirable to do. And so I have no problem filling my days with plenty of things that are really cool, which is a very fortunate position to be in. A lot of people have this fantasy that they're going to go off in the woods and that's where they, that's what they need to finish their book. Why do you hate writers' retreats?

• 29:04Ryan Holiday?

  I mean, I hate writing retreats because it's, it's basically an expensive form of procrastination. It's a, it's a fantasy camp. You are saying, I could be writing right now. I could have written this morning, I could write tomorrow morning, but actually I need to save it up for like three weeks when I go to this expensive place in upstate New York or, or when I go to this glamorous cabin in the woods. And like, you're just looking for an escape from the day to day-ness that is doing the thing. The idea that you're gonna get a book done in two weeks or in a month, in a sprint, it's like, the whole thing was never a sprint to begin with. It's a marathon, right? It's a long extended endurance sport.

• 29:48Ryan Holiday?

  And there might be punctuated moments of intensity, sure, but like, that's probably not what's gonna happen. And in fact, you're not doing it day to day because you're saving it up for this period when you're really going to be ready. I'm like, I'm like, you know, Baldwin was obsessed with these writing retreats and then he would go and mostly drink and talk on the phone. He would call his, his boyfriends and he would, whoever you are here, you're going to be where you're going. It's just, you're just paying for it and it's a slightly more glamorous setting and you're going to be telling yourself that this is contributive and it's not. And so I think mostly it's dumb and mostly it's like, go to your office, go to a coffee

• 30:28Ryan Holiday?

  shop, sit in your car on, do it on your phone, like just, just do it and do it a couple crappy pages a day and eventually you have a manuscript that can be turned into not crap.

• 30:41Speaker 01

  But don't you ever have the fantasies for me like, right? My fantasy this winter was a publisher.

• 30:46Ryan Holiday?

  This was going to be your writer's retreat. You're coming here.

• 30:48Speaker 01

  Yeah. Yeah. So like publisher gives you an advance. I come to somewhere where no one's bothering me.

• 30:53Ryan Holiday?

  Better weather.

• 30:53Speaker 01

  Better weather. Or I was like, you know, if I want to get crazy, I'll rent a cabin in Key West. You know, I'll, I'll seep in Hemingway.

• 31:02Ryan Holiday?

  I need.

• 31:02Speaker 01

  You know, I like the aura of the place will get to me and like, but having at some point in your career, you have fallen victim at all of like wanting to live the lifestyle of what we perceive to be a writer.

• 31:12Ryan Holiday?

  Well, first off, how's the writing retreat going for you? You're, you're, you're leaving in two days to drive thousands of miles over the country to not do the thing that you specifically said you were going to do. I mean, yeah, sure. Yeah. And look, sometimes it is nice to be in a cool spot like, and I like taking my stuff with me when I'm already going somewhere and I'll get a little bit here or there. It can be fun sometimes, but it's mostly a day to day thing and there's no escape. There's no hack there. I would almost count on the destination, writing, fostering creativity. I would, I would say like, you're actually paying for it to be worse. It's like, they say like, when you take your kids on vacation, you're paying to not have childcare. That's like what you're doing. So like, it's actually much less relaxing.

• 31:56Ryan Holiday?

  That's how I would.

• 31:58Speaker 01

  That said, you've lived in what many would consider writing hotspots. You lived in New York City, you lived in LA, you lived in New Orleans, you lived in Austin, you've lived in Florida. Sure. And so what is the best place to write?

• 32:13Ryan Holiday?

  My friend Chase Jarvis says the best camera is the one that you have on you. Like the best place to write is wherever you are, whenever you have time. I would say the best, the best place to write is like early in the morning or late at night, wherever the fuck you happen to be. And everything else is window dressing and fantasy and pretending and nonsense. But sure, like there's a reason I live outside Austin as opposed to, you know, wherever. And there's a reason I have an office instead of at a coffee shop. There are ways you're turning the dials a little bit, but there's not a button you can press or a ticket you can buy or a fellowship you can give that's going to make you do this hard thing that is mostly only yours to do.

• 32:57Ryan Holiday?

  And if there was a magical solution, someone would figure it out already.

• 32:59Speaker 01

  Yeah. So none of those cities do it for you?

• 33:02Ryan Holiday?

  I mean, no more than any other place. I, I, no more than any other place because it's not about the, the, the one thing they all have in common is you. And as they say, like wherever you go, there you are.

• 33:15Speaker 01

  Isn't there this narrative that like you go to Gertrude Stein's apartment in Paris and you suddenly become a great writer? So like scene, right?

• 33:21Ryan Holiday?

  Sitting at Joan Didion's table, is it doing anything for you? I literally sit in Joan Didion's chair every day. It's pretty uncomfortable to be perfectly honest. And, uh, that's all, that's all very silly. Like James Clear talked to me about, he's like, two magical hours. That's all he asked for himself. It's like, he does like the first two hours. And that's, that's how I do it. Like, most of us are not Robert Caro or Robert Greene or whatever. Where you're working like for 12 hours a day on this insane project for 10 years. Like, and by the way, most of what we're trying to do does not demand that. Like, we're not trying to solve complex theoretical physics either. So we don't need to do what Richard Feynman is doing. So I think like just the decision to go like, hey, I'm going to spend this amount of time on a day

• 34:03Ryan Holiday?

  in and day out basis. Like, if you can do that, you'll eventually get where you want to go. And in this case, because you don't have a contract, you don't have a time. Like, it doesn't have to be done by any time. And it's not like anyone's going to scoop you on this idea. And it's not like it's becoming any more or less relevant. It's a timeless idea about a thing that you have a monopoly on. And you're one of the only people in the world that even knows about, like, just do it, just chip away at it. The funny thing is like, the thing that you think will give you permission or make it easier, doesn't actually solve that logistical problem at all. Because like, let's say actually one of the people who went out to got back late and they're like, no, no, I want it.

• 34:48Ryan Holiday?

  And it's a great art. You still have this other thing and you probably still would have had this other thing anyway. And you'd be like, well, what order should I do them in? And you'd be like, I gotta do both. And so it just comes down to just like fucking do it. You know what I mean? Like this, this is, say to yourself, you're going to do it. I think Epictetus, I think I actually have this as the epigraph to the Daily Dad. This is Epictetus's, first say to yourself what you would be and then do what you have to do. Like, what's the thing that you want to do? And then you, you do it. And then, all right, so how about this? I'll go back and mark unread on all those emails.

• 35:23Speaker 01

  Yes.

• 35:24Ryan Holiday?

  And you will schedule the first episode of your thing.

• 35:27Speaker 01

  Deal. Subscribe below.

• 35:31Ryan Holiday?

  I'm only nagging you about these two things too, because I want you to do both of them. Like, I think they're both really good ideas and I would like to

• 35:37Speaker 01

  Yeah.

• 35:38Ryan Holiday?

  consume them.

• 35:39Speaker 01

  I'm very excited about both of them, even though I'm not, well, I am pursuing both of them in like my own timid way. And I do think that also though, like the road trip will feed into both in some way, maybe. So I think that it'll be end up pretty good.

• 35:52Ryan Holiday?

  What I wonder too, like if I'm like psychoanalyzing you, I think it's less like you're worried about like the commitment in the future. Like if you do this thing, then it's like you have this thing. I think you kind of have a good, not a good setup, but you have a, you have a perfectly unscalable setup now. It's mostly you, there's a handful of people, it all runs through you. There's no hierarchy, organization, structure. It's just like you waking up and what am I going to do today? And there's probably some level where like operationalizing it, the way that ironically, that's been your role with Daily Stoic is like, I have ideas and then you help me operationalize them into,

• 36:35Ryan Holiday?

  like I was like, hey, we're doing the email, it's going well, but like, what if we did a podcast version? Like for people don't know, Brent's the one that like makes the things real for the most part. There's probably some level where you are either afraid to do that for yourself, or you are intimidated by the idea of having to get someone to help you do that.

• 36:58Speaker 01

  I think so. I think that the idea of like, cause with that seemingly comes more responsibility. Cause then you're responsible for another person and then another person and

• 37:07Ryan Holiday?

  And you're like, wait, I have two of the things?

• 37:10Speaker 01

  Yeah, so there's part, it's partially that, but it's like, it's weird too, cause like, I think a lot of people resonate with this too. Like I want the things, you know, I want the podcast to be doing well, I want the book to be under development. It's just something about like,

• 37:23Ryan Holiday?

  Well, that's what he's saying. He's like, what do I have to be or what do I want? And then you're like, yeah, then you gotta do what you, you know, you, you know what you have to do. And so you just have to do that thing.

• 37:33Speaker 01

  Yeah. What's it, it's also like, and probably you could speak to this as well, especially to the authors. Like my first book did well. The next book that I want to do is not in the same genre of the first book. It's further from home.

• 37:45Ryan Holiday?

  I can vary, I mean, what do you think my book was? It was like, uh, let's do a philosophy book to follow up this marketing hit.

• 37:51Speaker 01

  And so like, when you feel like you did a good job within a space, but then the response to your next idea is like tepid. You know, it's like a little

• 38:00Ryan Holiday?

  But conspiracy is my worst selling book.

• 38:02Speaker 01

  It's one of, if not my favorite book of yours.

• 38:04Ryan Holiday?

  That's what I'm saying. But I, but I, and I can say that very confidently. Like I'm in, in many respects, proudest of it.

• 38:10Speaker 01

  Yeah.

• 38:10Ryan Holiday?

  And like the book that I'm working on now, if it works.

• 38:13Speaker 01

  Right.

• 38:14Ryan Holiday?

  It will probably also be one of my worst selling books. Like success is like a foregone conclusion.

• 38:21Speaker 01

  Sure.

• 38:21Ryan Holiday?

  Not as good as the other ones, but you gotta know where different things fit.

• 38:25Speaker 01

  Yeah.

• 38:25Ryan Holiday?

  But then also like what I know is that day to day, I'm fucking loving doing it. Cause like I, it's what I wanted to do. It's what I'm interested in and I'm learning and growing. So I'm like, oh, it's like, it's success. Even if I was doing it for, even if it was a money losing project.

• 38:39Speaker 01

  Yeah.

• 38:40Ryan Holiday?

  Which I guess at some point, if you're like advanced and then the cost, the advances here. And then like the, the expenses of research and time or whatever, at some point it does become a, a money losing proposition. Thankfully we're nowhere close to that, but like, I'd be like, okay. Because like I'm, I'm making withdrawals too. And then I'm like liking what I'm doing every day.

• 39:03Ryan Holiday?

  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 it would really help the show. We appreciate it and I'll see you next episode.