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The Daily Stoic

5 Feb 2026 · 40m · 22 chapters

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BONUS | No One Is Coming to Give You Permission

In short

In this bonus episode of The Daily Stoic, Ryan Holiday and his business partner Brent Underwood discuss the challenges of procrastination, particularly for high achievers. They explore themes around seeking external validation and the difficulty of starting projects without deadlines. The conversation serves as a motivational push for those who may have lost their New Year’s resolutions by emphasizing the importance of self-initiative and prioritization.

Written by AI. May contain mistakes.

Chapters

0:45

The Struggle to Start

Discussion about the challenges of starting projects without external pressure.

“optimistically that I can do whatever I want.”
2:45

Balancing Responsibilities

Exploring the balancing act of personal projects and professional obligations.

“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.”
5:15

The Role of Accountability

How external deadlines and contracts encourage productivity and creativity.

“And that could probably be like accountability partner.”
7:30

Imposter Syndrome and Self-Doubt

Investigating the impact of imposter syndrome on creative endeavors and decision-making.

“But that's how I did Trust Me, I'm Lying.”
10:00

The Importance of Starting

Emphasizing the value of beginning a project regardless of uncertainty about its outcome.

“Every product is independently certified by NSF for sport or informed sport, which means they test it for contaminants, heavy metals, banned substances, and verify for label accuracy.”
12:30

Fear of Success

Discussing the fears associated with success and increased responsibilities.

“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'd be like, actually, I really don't want to do this.”
14:00

Confronting Fitness Fears

Explore the psychological barriers preventing people from starting fitness regimens.

“and he's talked about there's a bunch where like because he really likes working out and he's a fascinated by personal trainers and like saying personal trainers will talk about women.”
15:00

The Reluctance to Start Creative Projects

Discuss why many people hesitate to begin their creative endeavors and the importance of self-motivation.

“And that's not probably going to happen.”
16:00

Balancing Obligations and Interests

Learn how to distinguish between obligations and genuine interests in creative work.

“committed to is like X amount of hours per week.”
17:00

Understanding Procrastination

Examine the different types of procrastination and their implications on decision-making.

“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.”
Show all 22 chapters
18:00

Evaluating Ideas and Opportunities

Discuss the importance of evaluating new ideas and recognizing opportunity costs.

“That I'm more suspicious of my, I guess I'm taking my procrastination as meaning something more there.”
19:00

Sharing Work and Seeking Feedback

Understand the value of sharing drafts for feedback in creative projects.

21:00

Embracing Creative Projects Despite Fear

Explore the fears surrounding creative projects and how to push through them.

“and we were talking about how you have to have it's not ego exactly but you have to have what whatever the thing is that allows you to do your first shitty stuff.”
22:00

Evaluating Past Successes for Future Projects

Learn to leverage past successes to build confidence in new creative endeavors.

“like help me with some of my financial stuff.”
23:00

Identifying Personal Procrastination Triggers

Identify common procrastination triggers and strategies to overcome them.

“So like we talk about this at the daily stoke meetings, I'm like, start the clock, right?”
24:00

Managing Emails and Mental Load

Discuss the challenges of managing emails and how to reduce mental burden.

“No, that's why I'm, I think it's just 90 % of the people out there probably have some creative project that they've thought about and failed to begin for some reason.”
25:00

The Concept of Email Bankruptcy

Introduce the idea of 'email bankruptcy' as a method to declutter one's inbox.

26:00

Procrastination and Low-Stakes Tasks

Explore how procrastination affects the completion of low-stakes tasks and decisions.

“Yeah, because it's them following up about this thing like 10 times, you know, or whatever.”
28:21

Overcoming Procrastination

Exploring the excuses people make to avoid starting tasks.

“that for this this reason like what's a task you've been you've been putting off like what's one thing well i guess like within the stoics like if i had to hold on to something to convince me to do my book.”
30:03

The Myth of Writing Retreats

Why writing retreats can be more about escape than productivity.

“Even, you know, famously when you read like a walk in the woods or like, it's like three different trips.”
33:19

Finding Your Writing Space

Discussion on the best environments to foster writing.

“Like, 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.”
36:22

Writing for Fulfillment

The importance of pursuing writing projects that bring joy and satisfaction.

“It's like he does like the first two hours.”
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Transcript

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0:00Welcome to the Daily Stoic Podcast, designed to help bring those four key Stoic virtues, courage, discipline, justice, and wisdom into the real world. 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 yes why do you think that is it comes i 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.

0:48And 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 i think it's way more than 10 but yeah so we have daily stoic that has many employees that need things every day for me and so it's kind of like a balancing act where 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 to something that has a more urgent commitment to it, then things get reshuffled.

1:36And I guess I get it at some level because sometimes people ask me like, why do you not self-publish? 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 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, uh, document you refused to challenge.

2:22Yeah. It's like, why do kids procrastinate on their homework you know it's probably a similar thing where it's like for me uh but if a kid could be like actually i don't have to i can turn it in whenever i want yes which is like effectively what these contracts mean anyway yeah 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 probably i'm probably looking for like a stamp of approval that like this is worth your time also like outsourcing that part of it as well yeah um 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 this 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, yeah, have that capacity.

3:27But 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. 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 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 that just like, just it's slightly enough that it gets you out of your own head in a way that makes you more productive.

4:06And 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 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 yeah yeah on those books.

4:43I 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. But like, that's what happens. You just get in your own head about it. Well, I think with even going back to my book, like in full transparency, like I pushed the book a numerous times. And I think that it got to a point where basically the publisher is like, if you push again, we will cancel the contract. And so then I got the book done suddenly.

5:12And 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. 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 you're 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.

5:45Yeah. Everybody's individual. Right. And it's like, I've come to learn that a little bit. And I obviously, cause even not, 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. 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 business, built most of what you've done at Cerro Gordo or other projects.

6:14Like 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. And then in other cases, it's like preposterously not an issue for you.

6:47I think I mean, I'm fortunate in the fact that like all these things that we're discussing are things that I want to do. Yeah. So none of them are things I inherently do not want to do. And 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 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. But did you think like, because you'd sent it out and you didn't get all the responses you wanted.

7:12Yeah. If someone had said we're in for$1. Yeah. That would have been totally different than this kind of middling response that you got. And it's like inconsequential distinction. 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 going to write a book, you know, and then it's suddenly just like they're writing a book. But that's how I did Trust Me, I'm Lying. I mean, my whole life changed because I basically quit my job, moved across the country and worked for six months on a book thing that no one was asking for and no one thought would work.

7:48Right. So I wonder if in retrospect, that was delusion. Was that confidence? Was that or maybe I just wasn't thinking about it at all. Was it lack of like, you have a lot more on your plate these days. You know what I mean? That's true. But I remember what somebody said to me, they were like, look, you'll either sell it or you'll self-publish it. So either way, it's going to come out and it's worth you doing. Yeah. 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. Right. But it was just the like, should I or shouldn't I?

8:24That's where you're held up. I think going out as imposter syndrome too, it's like this book that I'm hoping to write is more of like a narrative nonfiction. 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. 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 going to show you that i can do that's definitely part of it i think 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

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12:04Flipping 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 of the brass deck, blah, blah, blah. What do you think I should do? I think you should say like, hey, I'm going to give this a certain amount of time per day or per week. And I'm 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.

12:58You 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'd be like, actually, I really don't want to do this. 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.

13:27Like, 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. You're this close to start. You have most - I've recorded episodes. Yeah. Yeah. yeah so the recorded ups 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 like 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 well no this is something i just saw ramit when i was in uh new york he came to my talk the 90 second street why and he's talked about there's a bunch where like because he really likes working out and he's a fascinated by personal trainers and like saying personal trainers will talk about women.

14:11They 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 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? 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 stoic, which is like, now you have a scaling problem, which you're actually uniquely qualified and practiced at solving.

14:56Yeah, that's true. Well, I think generally, know 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 well seneca 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 some that you're like you're you are working on it yeah yeah 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.

15:32And 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, uh, it's all gotta be self-driven. That's true. No, but so not to put you on a speed, 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. No, 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.

16:17So 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 and that's why we redo the new year new challenge which you can sign up for it dailystoic.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.

16:50But like I try to make a big distinction between like obligations and then like interest 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. 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.

17:32Yeah. Right. I think that's like if it's not a hell yes for something that like sucks. Yeah. That's different than 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. Right. Right. Those are the things you have to like barrel through the procrastination. Right. 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 was like, I've almost signed the paperwork five times. Yeah. That I'm more suspicious of my, I guess I'm taking my procrastination as meaning something more there.

18:08Yeah. 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. Yeah. That procrastination I'm barreling through 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. Right. With the hell yes or hell no, if we're Derek Sivers, you know, he said, things are either hell yes or hell no. I think part of this too is like, as you become more successful, the hell no's are things that you previously would have said hell yes to.

18:40That's a great point. Sure. 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 there but the other areas the trade-off you start doing 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 yeah also i think but it's a genuinely good idea it's like something you would grow for having done yeah and the downside of it is extremely low other than opportunity costs yeah i don't know i'd probably push through i've also one where like i haven't not been working i've been quietly working on it maybe i'm just working out till i get to the point where i feel like oh i've actually been working on it you know yes i have the prologue and the chapter one written already oh um and so there is work behind the scenes and so that i think is like an indication even on myself that i do want to do the thing yeah but it would still be nice to have like a publisher be like you're all right 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.

20:04It could have gotten you whatever cred and security you needed to do the book like yeah you also just could have been whoever you are on the other side of doing 50 episodes of something that's true 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 i've done about 10 episodes and the point of that was like i remember when tim ferris started his podcast he was like i'm gonna get 10 or whatever he said yeah i do six and that feel when you make it a more manageable thing it is more manageable um you still then have to put them out but again it's still like to me i'm like well if i do six i'm gonna have to do 600 you know what i mean and then like uh it becomes like a growing thing but yeah so so there is is that the imposter syndrome of not wanting to launch it and it doesn't do like are you because that's an interesting thing you and i talked about this where like we knew someone who's like wanted to be a youtuber but they just never made any videos yeah and we were talking about how you have to have it's not ego exactly but you have to have what whatever the thing is that allows you to do your first shitty stuff.

21:11Yeah. That is public. Like Hemingway said, the first draft of anything is shit. But like the problem with a lot of stuff is that, that on like a manuscript, that draft gets seen by people. And, uh, 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? 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.

21:41And then if you aren't good at making something else, like does that. 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? I don't know. I don't know. I remember I was talking about someone that they were going to like help me with some of my financial stuff. And I was like, I kept being like, you know, because then like this is going to go away and then obviously 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 the 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 biggest one, but he just seen it enough times.

22:40They're like, no, sometimes like you keep going. 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. Yeah. It should transfer a little bit. Like 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 yeah and i was like well i don't want to show them drafts it's like that's the dumbest thing ever because like they're gonna see the final book yeah and it's only gonna be worse because you didn't show anybody drafts and so like i was hiding all the work from everybody including like my closest friends people who can help you make it better yeah instead i was like 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 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.

23:37So like we talk about this at the daily stoke meetings, I'm like, start the clock, right? Like you should start like who you're going to be a year in and two years in and five years in is like obviously much better than who you are at the beginning. So like if you'd started the clock a year ago, you'd be one year in. 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. Totally. No, that's why I'm, I think it's just 90 % of the people out there probably have some creative project that they've thought about and failed to begin for some reason.

24:08And I think it happens. What is that for you? What is the podcast in your version of that world? You know what I mean? 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 i 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 a 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 um 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 yeah 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 stakes stuff yeah 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 yeah projected onto it something i was trying to avoid yeah i don't know like big things i'm procrastinating on i actually don't think that much i'm pretty good at that yeah it's more the little things one of my goals for for 20 26 maybe i'll have already failed at this by the time people are listening but i'm gonna i'm gonna declare email bankruptcy what is that like you're gonna go to mug zero just delete everything that's not delete i'm just gonna mark it all as right and i've been telling myself i've been gonna do it for like where you at right now 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 because 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 yeah it's got like five or six hundred but they're like serious important emails yeah yeah yeah totally and they stretch back two or three years at this point yeah and i'm just gonna like obviously none of them are important or they would have replied again yeah yeah and honestly i bet there's like certain people or certain things that if I just searched that name and marked those as red, it would go - Clear 60 % of it or something.

26:40Yeah, because it's them following up about this thing like 10 times, you know, or whatever. But so it's more like that. There's like things I know I need to do that I'm letting pile up. And I'm like, even the Seneca's thing, right? I'm telling myself I'm going to do it on January 1st. Yes. I could just walk into my office and do it right now. Yes. But on January 1st, it'll be 10 % larger. Yeah. Yeah. You know? Correct. So it'd be better if I did it right now. Yeah. Well, you should do something called the New Year New You. At the New Year New You Challenge.

27:14In 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 that came back from vacation late. or they procrastinated, or 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.

27:54A bunch of great stuff in here. It is not 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 slash challenge and i will see you in there we've got a bunch of awesome stuff i think you're really going to like it so sign up now at dailystoic.com slash challenge i'll see you in there i think we may have built a day around that for this this reason like what's a task you've been you've been putting off like what's one thing well i guess like within the stoics like if i had to hold on to something to convince me to do my book.

28:32Yeah. What am I holding on to? I mean, what I would hold on to is like the whole Sarah Gorda could burn down to the ground again. Like, I mean, you could fall down a fucking mineshaft. Yeah. All these, these are not like extremely unlikely, uh, possibilities. Like one of them is a thing that already happened once. 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 going to be the person who has the freedom that you have now forever. Sure. I agree with that. And like, so this is like the time to do it.

29:10So how, how then, so for a very practical example, this winter I had like three months dedicated and I was either. You already filled up like 50 % of it doing something else. I was either going to write this book full time, full time, meaning in my spare free time or go on a road trip where that is a guaranteed paycheck that's going to guarantee go to the rebuilding the hotel will guarantee advance my goals at cerro gordo sure 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 which i'm excited about but at the same time you know what i mean like well i think two things i don't think your road trip actually needs to take three months.

29:57And then, and then, uh, and no one actually said that you have to do it all by car. That's true. Even, you know, famously when you read like a walk in the woods or like, it's like three different trips. You know what I mean? Like no one, no one actually needs you to do a contiguous road trip, like park your car in an airport and fly home and whatever. So I think not needing it, all or nothing is another way that we excuse procrastination. Like, 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?

30:37And that leads me to 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. Yeah. That's what I, it's probably by the time this is people are like, what are you talking about? That's 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.

31:12Right. 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. I like that. Cause 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. You know, 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 gonna go off in the woods and that's where they, that's what they need to finish their book.

31:47Why do you hate writers' retreats? I mean, I hate writing retreats because it's basically an expensive form of procrastination. 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 when I go to this glamorous cabin in the woods. and like you're just looking for an escape from the day-to-dayness 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.

32:28It's a marathon, right? It's a long extended endurance sport. 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, 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 boyfriends and he would, whoever you are here, you're going to be where you're going. You're just paying for it. And it's a slightly more glamorous setting.

33:02And 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 shop, sit in your car, do it on your phone. Like, 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. But don't you ever have the fantasies for me? Like, right, my fantasy this winter was a publisher. This was going to be a writer's retreat. You're coming here. Yeah. Yeah. So like publisher gives you an advance. I come to somewhere where no one's bothering me. Better weather.

33:39Better 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 seep in Hemingway. I'll have everything I need. You know, I like the aura of the place will get to me. And like, but having at some point in your career, you've fallen victim at all of like wanting to live the lifestyle of what we perceive to be a writer. Well, first off, how's the writing retreat going for you? you're leaving in two days to drive thousands of miles over the country to not do the thing that you specifically said you're going to do. I mean, yeah, sure. Yeah. And look, sometimes it is nice to be in a cool spot.

34:12Like, 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 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. That's how I would. That said, you've lived in what many would consider writing hotspots.

34:50You lived in New York City. You lived in LA. You lived in New Orleans. You lived in Austin. You've lived in Florida. And so what is the best place to write? 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 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.

35:29There 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. And if there was a magical solution, someone would have figured it out already. Yeah. So none of those cities do it for you. I mean, no more than any other place. No more than any other place. Because it's not about the one thing they all have in common is you. And as they say, like, wherever you go, there you are. Isn't there this narrative that, like, you go to Gertrude Stein's apartment in Paris and you suddenly become a great writer?

36:06So, like, scene, right? But you're 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 that's all very silly. Like James Clear talked to me about it. 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 how I do it. Like most of us are not Robert Caro or Robert Green or whatever, where you're working like for 12 hours a day on this insane project for 10 years. And by the way, most of what we're trying to do does not demand that.

36:37Like 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 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.

37:13Just 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 were like, no, no, no, I want it. 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 got to do both. And so it just comes down to just like fucking do it. You know what I mean? Like just say to yourself, you're going to do it.

37:49I 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 do it. And then, all right, so how about this? I'll go back and mark unread on all those emails. Yes. And you will schedule the first episode. Everything. Deal. Subscribe to the below. 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 consume them. 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.

38:30And 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. What I wonder to 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 the 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 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.

39:31There'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. I think so. I think that the idea of like, because with that seemingly comes more responsibility because then you're responsible for another person and then another person. And you're like, we have two of the things. It's partially that. But it's like, it's weird too, because 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 well that's what he's saying it's like what do I have to be or what do I want and then you're like yeah then you got to do what you you know you you know what you have to do and so you just have to do that thing 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.

40:30It's further from home. I can vary. I mean, what do you think my book was just like, let's do a philosophy book to follow up this marketing hit. And so like when you feel like you did a good job within the space, but then the response to your next idea is like tepid, you know, it's like a little loop warm. The Conspiracy is my worst selling book. It's one of, if not my favorite book of yours. That's what I'm saying. And I can say that very confidently. Like I'm in many respects proudest of it. Yeah. And like the book that I'm working on now, if it works, it will probably also be one of my worst selling books.

41:02Like success is like a foregone conclusion. Sure. Not as good as the other ones. But so you got to know where different things fit. Yeah. But then also like what I know is that day to day, I'm fucking loving doing it because like I, it's what I wanted to do. It's what I'm interested in and I'm learning. 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. Yeah. which I guess at some point, if you're like advance and then the advances here and then like the expenses of research and time or whatever, at some point it does become a money losing proposition.

41:38Thankfully, we're nowhere close to that. But like, I'd be like, okay, because like I'm making withdrawals too. And then I'm like liking what I'm doing every day. 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.

From the publisher

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/life


Brent 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: @GhostTownLiving

IG: @BrentWUnderwood


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