You’re Not Lazy: How To Make Discipline Easy - Ryan Holiday
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By the way, in case you haven't heard, my brand new book, Feel Good Productivity, is now out. It is available everywhere books are sold. And it's actually hit the New York Times and also the Sunday Times bestseller list. So thank you to everyone who's already got a copy of the book. If you've read the book already, I would love a review on Amazon. And if you haven't yet checked it out, you may like to check it out. It's available in physical format and also e-book and also audio book everywhere books are sold. So you did it.

We talked three years ago and now it's real. Well, the book is great. I don't think it's going to crush. Fingers crossed, but that's not a thing I can control. So I'm not going to think too hard about it. But it already did crush. The way to think about it is that it already did crush and that

To what extent do you enjoy writing? I enjoy showing up and then I enjoy finishing. At the end of the writing day, I feel good. All of this stuff comes back down to the process. Yes. I said this thing once, maybe you agree with it, but it's like amateurs are obsessed with tools. People go like, what kind of pen do you journal with? Like this fucking matters at all, right? Pick a fucking system and stick with that system. Yeah.

I think it's not quite sufficient to just say trust the process because it's hard to trust a process that you have not been through. There's an expression I like that says painters like painting, writers like having written. Oh, nice. And then you start the next one. So you did it. We talked three years ago and now it's real. We talked three years ago. We talked on the 7th of October, 2023, which was like three years and a week ago.

And I was saying to you in that interview that like, hey, Ryan, you know, I've just started writing my first book. Any tips? You gave some really good advice. Yeah. What did I say? Do you remember? You said so much stuff. You said the importance of structure, the importance of having your materials assembled and kind

kind of knowing what you want to say before you begin to write. Sure. And the analogy you used was like, you're like, well, you know, it would be weird if you decided to settle from New York and try and get to San Francisco. But you were just like, you know what, I'm just going to walk and I'm just going to figure it out along the way. You would, you know, it would be sensible to have a map.

Although even I would say what actually the problem is people don't even know they're trying to head towards San Francisco, right? They just know they're trying to get somewhere and figuring out where you're trying to go as you're doing it. It's a bad idea. That was a big part of my problem in that like the destination changed radically like every year in the three-year process. Sure. Yeah. Well, you do the more the problem is you're trying to figure out when you're working when you're starting a book, you're trying to figure out the end results. Mm-hmm.

But you haven't done all the thinking required to know the end result. Yeah. This is why I think like the proposal was a bit of a scam. Because the proposal, when I look at, compare the proposal to the final result, there's like almost nothing in there that's like the same. But that's how it is in a business plan. Very few businesses resemble the business plan. But,

There's an Eisenhower quote, he says, plans are worthless, but planning is everything. And so I think it's actually similar there in that if you don't do a proposal, this is why actually I think most self-published books don't work. It's that because there's no forcing function required to get approval to start, you're

There's no deadline. There's no constraints as to how long it can be, what it can look like. You can basically do whatever you want, which you would think would be an artistic sort of creative dream, but it's actually like...

potentially a death sentence. So how do you think about this balance? Because like, you've already made it, you can do whatever you want, et cetera, et cetera. And yet you still write books on seemingly on a deadline because they come up fairly frequently. Like how do you balance these? Well, I do balance it. So I sold this four book series on the cardinal virtues. So I've done two and then I finished the third and then I pushed it a year. So it's done. I'm taking more time to do it.

Um, it's, it's now like in, in, in the, the deadlines or the, the releases the summer of next year, but, um, there's a tension. So on discipline, I felt like pushing it and it was actually the right thing to push through and the deadline forced me to get serious about it and do it right. And then on this book, I was actually more or less ahead of schedule and doing great. But then I decided, okay,

for just family and lifestyle reasons to push it a year. So am I pushing it a year because I'm being lazy or am I pushing it because I want more time to do it well, or I want it to fit more in a more balanced way into my life? You know? So I think, uh, I tend, I function well with deadlines. I function well with this sort of day-to-dayness of it. And, um,

I think, again, people think that the perk of success is being able to do whatever you want. And weirdly, you actually find that once you can do whatever you want, you need to self-impose constraints and boundaries if you want to keep doing it well and in a balanced way. Hmm.

Yeah, I found that when the pandemic hit, and that was when I took, you know, took time out of full-time medicine for the first time, suddenly my whole calendar was empty. Yeah. And I immediately realized that, oh, like, I kind of need some constraints here. And so I signed up like art lessons and singing lessons and piano lessons and stuff to give some structure to the day and fit in the YouTube and then some of the latest, some of the writing stuff around that. And I found that that was really nice, but it always felt like a constant battle between kind of,

structuring myself and scheduling things in versus following my energy and like, oh, you know, today I have a lot of energy, therefore I want to film a video today versus I don't really feel like it today, but like, you know, I said I would do it every day, that whole thing. Yeah. It'd be wonderful if inspiration was sufficient, but it usually isn't. And you have to build a structure or a system that

I think it's really important anyway. What does your, like, I guess, daily routine look like? What's the structure you've built around your... I usually try to get up early. I'll give you an example, though. I try to get up early. I try to take my kids for a walk. That's like the beginning of what we do. And this morning, we got up. I got up early. I made their lunches. Just sort of having quiet time in the morning. And then my son got up and...

he got really into Legos and it was also cold. And so I was like, do I want to rip him out of this thing that I'm all, that's also good. That's also, I'm trying to encourage to have a fight over a thing that might spoil him and wanting to do the thing in future times. I'm gonna say no. Uh, so I sort of ripped up the playbook and then I made them breakfast and then I was taking a shower and then, um, Legos,

literally as I'm getting in the shower, they wanted to go on a walk. And so we ended up doing, like, we just sort of, so I guess in the 48 laws of power, the final law, which I think a lot of people miss, is assume formlessness. So there's all these laws about do this, don't do this, do this, don't do this. But the last law is a kind of a strategic flexibility. And so to answer your question earlier about how I think about this stuff, I have found as I've gotten older,

older and more successful that the rigidity that served me well early on has had to give way into a kind of flexibility. Now there's always a tension or a concern is that flexibility actually just complacency or laziness? And I have to question each time, what is my motivation here? But that rigidity has to become

flexibility or one, you suck all the fun out of it. And two, it's not sustainable over a long period of time. And it's not, it's very susceptible to being,

disrupted or blown apart by the complexity of life. So I'm less, I have less of a routine and I have more practices that I try to do consistently and I move them around depending on what's happening. - What are some of those practices? - Well, I try to get up early, I try to walk, I try to do some form of hard exercise every day.

I try to not eat until like, I try to have kind of a fasting window. Um, and then I try to, I try to do writing before I do other things. Okay. So like I am flexible on a lot of stuff, but I don't write at three in the afternoon because that's not conducive to doing it well. So, so just, you kind of know what goes, it's more of a,

an intuition or a gut feel as opposed to when I was younger, it was like, it was almost, it was almost a form of OCD. Like it has to happen at this time. If it doesn't happen at this time, then there is distress and, and that distress, you're almost doing the tasks to avoid the distress, which is not a good way to live. And how did having kids change your relationship with the work? What just blows your whole life up? Yeah.

in a good way but it blows your whole life up i remember this new york times reporter was doing this piece on me right as my son was being born and she she asked me like how do you think you know like having kids is going to change your routine and i said something like i don't think it'll change it at all and which was of course preposterous and uh and uh very naive but uh it's just totally blown it apart but it gives you important stuff that you center your life around so like

I think people are concerned that like having kids or getting married, it'll tie you down. And it does. It objectively does.

but it ties you down to reality. Like it tethers you to the earth. There are school starts at a time and it ends at a time. Like there's nap time, there is eating time, there is activities that happen every week. You know, there's stuff, right? And so it prevents you from making it all about you and it forces you to sort of have

Non-negotiable things. I mean, I guess it doesn't force you You could be a bad parent if you want But if you want your kids to not be a nightmare and you realize that routine is very important structure is very important but then also Rigidity is you know? impossible there's um Lin-manuel Miranda was talking about how he had a kid right as Hamilton blew up and so he would do the play and

and then it's the hottest thing in the world. And so every night, celebrities attend and then they come backstage and they go, "We're going here after, we're going here after." I was getting invited, all this like incredible stuff. And...

He had to say no to all of it because he had to get home. He had to get home not just because he wanted to see his kid, but he knew that his sleep was already a precarious touch and go thing because he has an infant in his house. So if he stays out till like two in the morning and then he gets home and he's woken up five times in the middle of the night or whatever, he's just not gonna be able to perform the night before, the next night.

And so his point was that having a kid actually saved him from spinning off the planet from this kind of stratospheric success that he has. And I have found that for sure, that like, again, we think these things are gonna be baggage. It's more like ballast, like it balances you out in a way that thinking, hey, I'm totally unencumbered. I can do whatever I want. I can fully enjoy all the fruits of all the cool stuff that's happening. You think that's what you want,

But it's kind of a recipe for disaster. Oh, okay. That's so interesting to hear because I guess I've been feeling a bit burnt out from, you know, the whole, like, rush to finish the book and then all of the batch filming podcasts and YouTube videos and the audiobook then and then, like, all of this book promo stuff that it is apparently sensible to do and all this kind of thing. Yeah. And the conclusion I came to a few days ago, like, was, screw it, I just want an empty calendar, a fully empty calendar. Yeah. And I guess...

I'm sure if I experienced that for a few weeks, I'd be like, ah, actually I probably want a bit more structure. I, you want an empty calendar of the stuff that you, you want an empty of the stuff that you don't want to do. So like when I have an empty calendar, that means I have as much time as I want to write and as much time as I want to spend time with my family. What I haven't scheduled is interruptions from those things. Um,

Even if those things are fun or interesting or whatever. By the way, I was reading your bio. It does you no justice. It says 4.5 million YouTube subscribers and it says over 93 million total views. But it's way more than that. Yeah, it's like 4.8, 4.9 now. No, no, no. You've done like hundreds of millions of YouTube views. Have I? Yeah. Oh, I don't even look at that number. You don't? No. Really? I made it a point...

Early in the journey, I think thanks to all the stoicism Kool-Aid that I was drinking to only focus on the things that were within my control. Okay. To the point that I almost never look at analytics. And the only thing I can even vaguely keep track of is like, oh, yeah, I mean, I was watching one of my own videos and it said 4.9 million rather than 4.8 million because it doesn't even give you that. Sure. No, as you get more, the numbers get less precise because you...

It matters less. And I can see it in YouTube Studio if I go on and stuff. And I'll occasionally do that just to look at comments and things. But I don't know. I really try it. Like the more I look at the numbers, the less happy I am with the creative output. Well, so tell me why stoicism taught you not to look at how your YouTube videos are doing. That's very interesting to me. I realized that when I would look at how my YouTube videos were doing, in the back of my mind, there would always be that sense of,

You know the whole dichotomy of control thing? A number of views on a YouTube video is sort of in the intersection where it's partly in my control, but partly outside of my control. And I knew that if I... Looking at those, I wasn't able to look at them purely dispassionately, and I would always get a sense of, oh, that one did so well, or that one did, or that one didn't. And I found that

You know, if I keep a general eye on the trend over sort of a period of several months, that gives me all the data I need to be like, oh, that sort of topic is really resonating with the audience. That sort of video got like a thousand comments compared to 300. That helps me figure out, okay, maybe what, like, I should do more of this and less of that. Yeah. But I try not to take it too far because, you know, you get the whole audience capture thing where you become a caricature of

of the person that your audience initially enjoyed. And I very much fell into this trap during the pandemic, actually. So the word productivity in my videos was like really taking off. Any video with the word productivity or productive in it, I was like immediately like doing super well. And so I was thinking, well, you know, this does really well. Let me just say, put productive in everything. My productive day in the life, my productive desk setup, my productive dating habits, my productive sleeping routine and all this kind of stuff.

And after a few videos of it, like people in the comments started to be like, okay, this is getting a bit much. And I started feeling icky about the content because I was putting productive in it to try and get the views. Because videos with the word productive in it were getting more views. I don't know. Whenever I have this sort of weird relationship with numbers versus what's in my control. Well, it's interesting too, because...

It's somewhat in your control as you're making it. But then once it's out, it's done. But that's when we spend the most time refreshing. You've flung it to the public. You've put it out. And now you're like, well, do they like me? Do they like me? Do they like me? How much do they like me? Give me all the likes, right? When...

If there was any time to think about how something was going to do, it maybe could have been as you were making it, right? But now that's over. So now you're really just emoting about what you would like to happen and the ship has sailed. Yeah, man, that's so true. Like the way we do use analytics is in idea generation and titles and thumbnails. Yeah. And that's the thing, thankfully, one of my team members does because I don't get joy out of trying to package up a video with the perfect title and thumbnail to make it

it clickbaity enough, but not so clickbaity that it feels clickbaity. So I come up with the concept that, hey, I'd love to do a video about, I don't know, Ryan's new book. And we were like, okay, cool. We can't call it Discipline is Destiny because that would be a bit weird. Okay, we've got to find an angle of like the one habit that's changing your life, like the discipline expert or like how do we, all that kind of stuff. I outsource that to the team. And then they tell me, okay, we've tested this with the audience. We think the best title is

this book made me more disciplined. And I'm like, great, I can make a video based on that title. Sure. Yeah, and it's also, it's not just...

One of the ways I've found it to be dangerous is actually when it works. So, I don't know, an article comes out about you and it's positive or a video comes out and it's doing well. Your book is out, whatever, you're doing the thing. And then you lose a day or more than a day just kind of basking in it. You're just like refreshing and watching. So it's not even like you're torturing yourself. You feel crappy that nobody likes you.

But it's like your reward for succeeding is a loss in productivity because you're just soaking in this thing that's really not in your control that if it had gone the other way, you would be...

trying to work your mind around not taking it seriously. Do you know what I mean? You'd be like, that's not why I made it. What matters is that I like it. What matters is how it does in the long term. You'd be trying to think through logically why you shouldn't be devastated by this bad news. But then when the positive happens, you don't do any of that. And you just kind of sit there and soak it in. And really the punishment though, is that you're not

spending your energy where it matters or where it makes a difference, which is like making the next thing or just taking the day off. Like if you're going to waste a day, go waste a day. Don't waste a day refreshing your Twitter feed. Mm-hmm.

I think it's that like Zen proverb or something, which is, you know, before enlightenment, after enlightenment. Before enlightenment, chop wood, carry water. After enlightenment, chop wood, carry water. And I often think of that when it comes to videos. And I also suspect with the book, because I think currently I have an unhealthy attachment to the New York Times bestseller list, as a lot of writers do. But I just really try to remind myself of

Whether or not the video does well, you know, learn stuff, write about it, make a video. It's like that's the thing. It's like getting back to the process rather than thinking at all about the outcome. When you asked me about self-publishing earlier, one, I've experienced this unintentionally and intentionally. When The Obstacle is the Way came out, I'd already sold the sequel. And so in one respect, that probably cost me a lot of money because The Obstacle is the Way did sell.

over the next year or two start to do really well. So if I had waited, I probably could have sold what became Ego is the Enemy for a lot of money, a lot more money. And I was, but I'd actually sold like a proposal version of it

while I was still figuring the book out. So I was still doing the work of figuring the book out, but I was under contract. So I really didn't care that the book kind of was doing okay. And then I really didn't care that much when it started to do well. Like that right there is the first time that book hit the bestseller list, which is five years after it came out. Oh, wow. So

I had not only written the next book, but I'd written several more books. Like I, by having contracts for the next projects, I was just focused on doing the next projects, not on how each one did. And then with this four book series, it's kind of in the same thing. Like in 2019, I sold, I basically locked myself in

till 2024, 2025. So basically like the next four or five years of my thing were locked in. So again, the downside is courage came out, it did okay. Discipline came out, it did spectacular. So maybe I could have been selling, I could have sold justice for more, but all of that was irrelevant because I was just in the middle of writing the book. And I think it's better to be chopping wood and carrying water than going,

constantly renegotiating your rate for what you are going to chop wood and carry water for or whatever. You know what I mean? Like to just have the next thing. So, you know, if your thing is I make a video every week, you are already making the next video before one comes out. Yeah. Right? A comedian...

comes up with an hour, records the hour, then there is time before that hour comes out. And it's in that interim period that they're already working on the next hour. So if the special comes out and it's a huge hit,

they're working on the next hour. If the special comes out and it's not a huge hit, they're working on the next special. And you want to be in a rhythm like that because it insulates you from the thing that's not in your control, which is whether other people say you're amazing or whether other people say you suck. Yeah, I feel like all of this stuff comes back down to the process. And a big part of what we talk about in that book is trying to find a way to make the process enjoyable and energizing.

And yeah, I find that when I have that in the front of my mind, when it comes to the videos or even, even writing the book, you know, like there were periods in the book journey where I sort of forgot to enjoy the process because the seriousness of writing a book was like weighing on me. And then I would read like, I don't know, one of your, like your newsletter or one of your books or like,

Drive by Dan Pink and I'm like, oh, it's so good This stuff is so good and I'd be comparing it to my first draft and be like why am I why is my writing? so shit and It would take my editor to remind me that you know I like the whole the whole message of the book is find a way to make it enjoyable and energizing so, you know Well, it's hard if people say trust the process, right? But it's hard to trust a process that you have not been through before and so I

Once you've done it one time, you have a sense of the full scope of the process or what you think is a full scope of the process. And you do it again and again and again, and you start to go, "Oh yeah, this is the part where you start to doubt yourself. This is the part where you get excited." But like in Texas, we have this season, it's called false fall. So it's cool and awesome right here. It'll probably get hot again, right? Like we think the summer's finally broken, but there's actually like several more hot days coming.

Projects are like that too. You think you're over the hump. You think you've done it. And then, oh, wait, no, it's going to get hard again. But you start to get a sense of the rhythms of it. And then you can trust the process. And then you can also enjoy the process because...

you know, it's like the first time you go on a roller coaster, that specific roller coaster, you have no idea. Is this going to be one of the ones where it's like this? Or is it going to be the ones that you, right? But then once you've done it before, then you have some, you can kind of anticipate it and you know when to hold on tight and when you can just go with it. Right. And you can kind of watch the other people that have never been on it before, how much scary it is for them. And so I think it's, it's, it's not quite sufficient to just say, trust the process because it's,

It's hard to trust a process that you have not been through. Yeah, that's so true. I think so. I realized this very sort of tangibly. So, you know, I've made like 700 plus YouTube videos in my time. And

I know that recording it always feels like a total shit show where I'm making so many mistakes and there's so much like crap in it. Sure. But I've done it enough times. I know the final product is going to be good because our editor is amazing. Sure. Chop out all the crap and we'll make it look amazing. But then when beginner YouTubers see the final result and then they see themselves recording and suddenly they're spluttering and swearing all the time. Yeah. You never see that raw uncut version of a YouTuber's first take. You only see the final product. And so...

now that I've been through the process once with the book, knowing how crap the first draft was and then seeing the magic of editing over several months to trim it down and make it good. I'm like, oh, okay. I don't mind so much about having a crappy first draft now. Well, yeah, you have your crappy first draft. I actually have a shirt. There's a Hemingway quote and he says, I have a print of it in my office. I have a shirt too, but he says, you know, the first draft of everything is shit. And

And the conceit is that it's sort of showing how even that sentence probably didn't write it perfectly the first time. But the idea is that every first draft sucks and you want to get comfortable with that. You have to get comfortable with the messiness of the process. But weirdly, as you get better, I do think your first drafts get less shitty or less wasteful, right? So like...

you with your videos, and certainly I've found this with my books, is that there is less and less left over at the end because you start to be able to shoot only what you know you're going to use. Or you write less, you go down less blind alleys as a writer, or you overwrite less. Because again, you know

you know what isn't gonna be possible, what's gonna be extraneous. You have a sense of what you actually need, right? So you're trusting the process, but also you understand the process better. And so, yeah, you tend to be overdoing whatever it is you're doing the first time. And then one of the signs of mastery, or I guess a trait of mastery, is the conservation of energy. Like you know...

Yeah.

I imagine a video three years ago, maybe you shot an hour of footage for a 10-minute video. And hopefully now you could shoot 20 minutes of footage for a 10-minute video. Yeah, it is a little bit tighter now than it was before. But even like, especially on the writing front, initially my worry was I don't have enough material. And then after the first draft, I was like, oh my God, I have way too much material. Yeah. You find...

I think writing becomes a process much more of tightening as you go because you realize you just needed to get it all down. And then you're realizing, oh, I've said this twice now. And actually here covers it over here so I can cancel each other out or I can get rid of one. So it's a process of understanding that.

So I have a question about productivity for you because I feel like people are obsessed with productivity and I'm not always sure why. Like I said this thing once, maybe you agree with it, but it's like that amateurs are obsessed with tools.

Right. Like what's the best software to do this? Yeah. What is the best way? You know, like people go like, what what kind of pen do you journal with? Like this fucking matters at all. Right. What what program do you write with? And if I was to rank the things that contribute the most to what I do, tools are like not even in the top 10.

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This is the thing, like as I've basically tried to read basically every productivity book on the market and then some.

It all fundamentally comes down to really the way to be productive is to figure out where you're trying to go, figure out what habits and what daily slash weekly routines you need to get there, and just sitting down and doing the thing. And then finding a way to make the thing fun so that you don't get distracted with other shit, and then just doing the thing for a long time. And if having a slightly... I mean, I have a really crappy pen that I stole from my brother now because my fountain pen ran out of ink, and it was such a nice fountain pen, but I can write just as well with a crappy ballpoint. The 1% tweaks...

But it's so much more, it's almost like, you know, I'm trying to get into fitness now. And I just love researching, you know, on running shoes, should I get this padding versus that padding? Been for a run maybe once in the last six months. I love the idea of researching running gear because it's great procrastination from actually doing the thing, which is,

put on anything and just go for a run. Yes. Or like just go to the gym and do anything with progressive overload. Yeah, it's like people are optimizing a thing they're not doing. Yes. Which is never going to be the way to get there.

There was a great moment. My girlfriend called me out on this the other day. You know the whole sauna, ice plunge, everyone in Austin seems to be doing it. I was saying to her, hey, what if I join a gym? And it's like, depending on how busy the sauna is, Huberman says four times versus five times and 24-minute protocol versus 12-minute protocol. And she was like, you've been to the sauna once in the last six months. Let's just go to the sauna first and then we can worry about optimizing it later. I was like, yeah. So true.

And I think this obsession with productivity, it often feels productive to be reading productivity books ironically and researching the tools as a distraction from just sitting down and doing the thing. Well, the irony that obsessing about productivity is a form of procrastination, right? It's giving you the sense that you are serious, that your heart's in the right place, that you are trying or making progress, right?

But in fact, you're not. And you're avoiding the hard thing, which is doing the thing. Doing the thing. There is one aspect of productivity that I think is valuable to obsess over. And that is kind of journaling prompts. And just asking yourself serious questions about why you're doing the thing that you think you want to do, where you're actually trying to go.

I spend a lot of time comparatively thinking, is the direction I'm currently going in actually the direction that I want to be going in? And I find that there's almost no amount of too much journaling that can happen there because in an hour of journaling, I might land on one insight, which would, if it nudges my course even 0.1%, that compounds over the long term.

Well, yeah, I would say being intentional about what you're doing and then clear with yourself about why and what you are doing is really important. Whereas like productivity, a lot of productivity advice seems to me is like optimized, optimizing for how you're going to pack your suitcase or what your suitcases is, is, or what brand it is or whatever. And you really haven't questioned, um,

why you're going where you're going or if you should be going there if it's the right time to be going there any of the actually important questions that are going to determine whether this thing is a success or not yeah i think the other unfortunate thing is uh you know we we did a video recently that was something like i read 107 productivity books here's what actually works and all of it was basically like pick some goals figure out the method it was like the basic stuff and

And then we made another video that was like 12 productivity tools I can't live without. And that video did so much better. And I'm like, oh, it's so annoying that like the thing that had the meat versus the thing that had the candy, the candy performs better. Yes. And so writ large, you know, the incentives are there for people who write or make videos or whatever about this stuff is to lean into the tools because the tools are the thing that, you know, is the candy that people want. Well, I don't even know if it's candy. It's just it's concrete, right? So you can go...

here's this sort of ephemeral, you know, metaphysical question about why you're doing it, what success is, you know, why does it matter? You're asking these big picture questions.

And by the time you get to the end of it, there actually isn't an answer because it's about the question. And that's a lot less clear than these are the three best pens. This is the number one bit of software. Or here's a really interesting, complicated system that a successful person can

uses whose work you are a fan of, right? Like one is very concrete and the other is essentially ineffable, right? And so you naturally, especially at the early stages, one's much more digestible and understandable. Do you know what I mean? Like you're also contemplating questions

that someone, if they're an aspiring high school insert, you know, is not even going to understand as a question. Do you know what I mean? Like, like Tom Brady talking about whether, you know, how much is enough or, you know, where to find deep motivation or whatever. That's a lot for someone who's not even competed at an elite level to,

Think about, so it's easier to start with, well, what do you have for breakfast? Right? Or like, what kind of gloves do you wear? Do you know what I mean? Like one is much more relatable and accessible, but ultimately much more inconsequential. Yeah. I do find that there are some tools that...

certainly when I was more of a beginner in the space, helped develop the habit, which was the thing that actually mattered. So for example, reading about how different people do a weekly review is quite helpful. And I downloaded initially the PDF template and then the Google Docs template, and now Notion templates are all the rage. But the point is, the weekly review journaling prompt slash questions helped me actually do a weekly review. And a weekly review is just a very useful habit to figure out like,

How did I do this week? What are my top three things I want to do next week? Great. Let's just do those things. So there are some instances in which a tool helps build the habit, where the habit is the thing that matters. Sure. But it's easy to take it too far. Like I find whenever I rewatch your video about your note card system, I know I'm just procrastinating because the thing you actually do is you write every day. But even in the car on the way here, I was like, you know...

what if I had an analog note card system? And then I'm like, no, but I'm traveling. It's like, oh, well, I get, dang it. Like, let me look at the Zettelkasten system or let me find another app. And

It's so easy for the mind to go in those directions because it's like Ryan Holiday has a notecard system. I also find it's like, you know, people who believe one conspiracy theory tend to believe all the conspiracy theories, right? Even though it actually becomes less likely that they're all true, right? Like it's like if you pick one and that's your thing, maybe you're right, maybe you're wrong. But if you believe all of them simultaneously, well, they contradict each other. So it doesn't really work, right? But it's like I tend to find people who are really into productivity systems, the problem isn't that, you know,

that this system is not as good as this system. It's that they're missing the point that a lot of it is a placebo, which is like pick a fucking system and stick with that system.

That's the hat, like you're supposed to pick a thing and then that's your thing, right? And then you stop thinking about it. The problem is they're like, first they're over here and then they hear this one's a little bit better and then they switch to that. So it's actually, it's not the system that's the problem. It's not the tools that's actually the amateur quality. The amateur quality is the

constantly moving and abandoning, moving and abandoning, because that's what's profoundly inefficient, right? Like you've found the system and it was working for you. Like I know actually at this point, there's probably something better than the no-card system, but is it...

transformatively better? Probably not, right? So am I going to uproot the thing that I'm comfortable with, that works for me, that my old stuff is in for something that's 9% better? Like if I want a 9% productivity increase, that's pretty easy to find. You know what I mean? As opposed to relearning how I do everything.

So back in the day, I used to be a close-up magician, and I would perform at balls and parties at university and stuff. And there was a phrase that was often in the world of magic, the amateur magician is the person who performs 100 tricks to the same audience.

Whereas the professional magician is the one who performs the same tricks to 100 different audiences. Or worse to that effect. And in the world of magic as well, there was this constant thing, constant battle between, you know, on the forums, there are the professionals who are actually doing the thing. And then there are all the amateurs being like, what are the best tricks? And the professionals are like, it doesn't matter. Just pick three to six of them and just do them at nauseam and you will guarantee to be a professional magician. And the amateurs are like...

Oh, but like, I've got $1,000. I want to spend it on like this trick versus that trick versus that trick. It doesn't matter. Just pick a few and just stick with them and do them repeatedly over a long enough time. And that is how you get good at the thing.

but that's a lot less sexy sounding advice, then this one trick will change your life. Yeah, like I've been to conferences that have changed my life, but I'm always interested when I notice people are going to lots of them. Like the chances that every single one is gonna have that same effect is very low, right? And so it's like, you beat the casino, leave.

You know what I mean? Like there's this tendency to sort of chase more and more when you've already gotten most of the gains.

I've got some friends who attended like a sort of $85,000 mastermind week-long retreat type thing. And after day one, they were like, damn, we know what we have to do. We kind of want to leave and just do it. But like we've paid $85,000. So we've got to kind of stay for the next five days, knowing full well that like all of this is going straight over their head because they just know they've got the one thing and they just need to execute on the one thing. And then two years later, maybe the thing number two or three will become relevant. But by then you've forgotten about it and you'll need to go to another event.

So back to procrastination, one of my favorite quotes from Senegazi says, the one thing all fools have in common is that they're always getting ready to start, right? So like they're going to do it tomorrow or they're going to do it later. They're going to do it once they get all the materials or tools that they needed. So I did give you the advice that to start a book, you want to do all your research first, which is true. And yet really the important thing is that at some point you start doing it, right? And because it can go on forever to sort of,

preparing and analyzing and gathering and, you know, I just need this other thing first. I just, but really what you need to be doing is the thing. Yeah. It always just comes down to this. It comes, comes back, back to this. Um, and I've, I don't know if you've played around with this, but I've, I've experimented with so many different ways of doing the thing. Some, you know, when it comes to videos, for example, someday, some, some weeks I'm like, okay,

the way I'm going to keep doing the thing is I'm just going to make a video every single day and then I'll do that for a bit and then I'll be like okay but that's like too rigid and it's like oh more flexibility it's like okay cool Tim Ferriss says batching is good so I'm going to batch it and Thursday's going to be my filming day and it's like I'll do that for a bit and I'll be like oh no but like I missed that Thursday and then I'll be like you know Tim Ferriss said batching is good so why don't I batch in a whole week and film 15 videos in that week and then I can chill for six weeks and then

This was supposed to be a batch filming week in Austin and I felt nothing because I was like, I'm actually not feeling it. So there's almost this constant search, at least in my life, for like this magical, consistent system that will cover me 100% of the time.

um thankfully we have still been publishing like two videos a week for the last six years so it's like it's not hopefully you're not gonna take too much away from actually actually doing the thing but i wonder for you like you've been doing this a lot this sort of stuff a lot longer than i have how how often has your system for doing the thing actually changed um well i do a handful of different things right so like but the main thing and i think it's important you have to know what your main thing is right

We live in a world where there's all these other kind of supporting things. They're necessary. Yeah. Not absolutely necessary, but I think they're important.

But still you have to know what the main driver of everything is. And so for me, that's writing. Like writing the books is the main thing that... The other things are supporting the writing of the books. And the writing of the books is creating the ideas and the platform and the brand and all that make the other things necessary to begin with. So the writing routine is...

essentially unchanged. Um, there's little tweaks here and there, but the main thing is like just sitting down and doing that thing. And it's not a thing that can be outsourced. It's not a thing that can be batched. It's the day-to-dayness of doing it on a consistent basis. To what extent do you enjoy writing? Uh,

Well, there's an expression I like that says painters like painting, writers like having written. So at the end of the writing day, I feel good. Do I feel good the entire time? Not always. Sometimes when it's fucking working, it's nothing better. But if you, that's the only thing that fuels you, you're going to

you're not gonna be in a good spot. 'Cause some days, some of the most important things come one sentence in the midst of two otherwise unproductive pointless hours. So I enjoy showing up and then I enjoy finishing. And sometimes that middle period can be torturous. So I was gonna ask you that when you say feel good productivity, does it actually have to feel good?

Uh, there, there's one school of thought that says it's all about finding the torture that you can tolerate. And it's actually the ability to put up with the grind of it that separates kind of the winners from the losers. Yeah, that's the thing. So I think it, my, my thesis in the book is that it doesn't have to feel good.

But it is generally more energizing when it does. Generally, like positive emotions feel energy, feel creativity, feel like reduced stress, all that fun stuff. And so the question that led to the book in the first place was, you know, when I was trying to juggle working full time as a doctor and also building the YouTube channel and the business on the side.

it just felt like a huge amount of grind in the day job and then a huge amount of grind afterwards to do the videos. And it seemed like, you know, everyone talks about how, you know, journey before destination and

I realized that I wasn't enjoying my day-to-day because of this sort of grind approach. And so I tried to find any tweak that I could to make it feel just a little bit better. And that's not to say that it was fun all the time or that it objectively felt good all the time, but I found a series of strategies that meant that almost anything I could make feel even just a bit better. And if it felt a bit better, it generated more energy and it meant I had more energy at the end of the day to give to my other hobbies and friends and family and stuff.

And it also made me more productive. So I think it's like, you know, when it comes to writing, for example, there are some basic things that I found was, you know, the first chapter in the book is about play and about trying to approach things in the spirit of play. Now, play, you know, a lot of people have talked about how it comes about as a result of, often a result of the stakes being lower. So like Roger Federer probably isn't feeling play when he's in the Wimbledon final because the stakes are too high.

And I found that, for example, with writing the book, when I was thinking about the stakes being high, like this is my first book and it's traditionally published and it's a big deal, that would suck the joy out of it. Whereas when I tried to lower the stakes to be like, that's okay, I'm just writing because I enjoy it. And the goal is for me to write a book I'm proud of. Suddenly it became more enjoyable. So it's the same thing, but like just a different framing that makes it feel good. The problem is you're not in the Wimbledon finals, but you're...

fooling yourself into thinking you are that's where ego comes in and uh anxiety comes in you're just you're just like you're making it much more than it is yeah uh and then you're actually ironically making yourself worse at it yes exactly you know the other big one is um you know the idea of power so we talked about talk about i talked about in chapter two uh play power and people are like the three main energizers that i found um if you

shoehorn a bit. And this idea that we get to choose what we're doing. Like, it's you could be doing the same thing. But if you think of it as I have to do this, versus I choose to do this makes a huge difference to how we personally feel about the thing.

I really found this a lot when I was working in medicine where, you know, there was one day where I'd finished the end of like a 13 hour shift and I was just about to go home to be like, yes, I'm going to go home. And then the nurse was like, hey, Ali, can you put an IV, a cannula in this lady in bay number four or whatever it was? I was like, oh, shit, like this is going to be another half an hour job. It's like the nurse has tried and she couldn't do it. And so this is going to be really hard. I was just about to go home with 13 freaking hours. I haven't eaten.

And then I overheard that some other patient talking about like, oh, it's so nice being in hospital. The doctor's been so nice to me and things. I kind of realized that I'd been falling into that trap of thinking I have to do this thing. And I think Seth Godin has a blog post about this that I remembered at the time, which was you can just reframe that to I get to do the thing. Sure. I was like, huh, I get to do this kind of I get to make this person's morning sickness better so that, you know, her baby's better and that she's better because I was working on OBGYN.

And it was just like this huge wave of relief that came over me purely as a result of a simple mindset shift of like have to becomes get to. Well, also, I think one of the things I add to that is like important things are hard. Right. And so if you are good at something, if you have some sort of calling, you're good.

Like, I feel like each of us has kind of a unique potential or we get sort of certain opportunities. Yeah. And with those opportunities comes a kind of an obligation. So, like...

When I hear about someone who is really talented and really good, and then I get the sense that they're just kind of half-assing it or they're stuck or whatever. It's not that I'm judgmental, but I find it to be sad. You know, like, what do you mean you only wrote one book in 10 years? Like, uh,

you're not Robert Caro. You're not like, you're not, you weren't slaving away on some amazing masterpiece. You were just ill-disciplined and you took the obligations that I think your talent came with. You took, you didn't take them seriously. So I agree. You should mostly be doing what you want to do. But I also think there's something kind of sad and maybe even pathetic about people who are just like,

not unproductive, but maybe only partially fulfill their potential. Yeah, I was going to ask you about this. So you said earlier that, you know, you sometimes ask yourself, am I pushing this book out of laziness for complacency versus like out of a genuine need for balance or something like that? And I was kind of thinking in my mind, like, why does it matter? Like, why does it matter to you if you're being lazy or complacent? You know, you've written like a book a year for the last like 10 years or something like that, like...

Well, I think like you have, I would argue that we sort of have a higher self and a lower self, right? And, you know, the lower self says, just like eat whatever you want, work only when you want. I don't know, say whatever you want. Don't think about consequence. Like there's this sort of immediate gratification, sort of short term gratification.

impulses that we all have, right? That if indulged repeatedly, tend to get us in a place that we actually don't want to be, right? The person, they don't have any friends because they say mean things, right? They're

They feel gross. They look gross. They're not in good health because they don't take good care of themselves. You know, they look back and they go, oh, I wish, you know, I wish that hadn't taken, like if I'd gotten serious about that earlier, I'd have been done sooner. It would have, could have done more, could have helped more people, whatever, right? So there's this kind of tension between like our higher self and the lower self. Steven Pressfield says in between is the resistance, right? And so to me, the question is whether I'm,

Am I doing this because it's the well-adjusted, mature, responsible, you know, right thing to do? Or am I just doing it because the other thing is harder? You know what I mean? The other thing is going to take more out of me and I'm scared or intimidated by that. So it's not like I feel like, oh, I have to write these certain number of books so then I'll be remembered forever. It's just so I just took today off.

But what did I get out? Like, for what reason? Do you know what I mean? Like, so I watched TV all day. I sat around all day. If I decided not to work because I'm going to hang out with my family or I'm going to take a long walk on the beach or I'm going to read or I'm going to take care of myself, that's perfectly fine. That's part of a great life. Doing it because...

I want to watch TV. Yeah, that doesn't, I don't think that gets you where you want to go. Some people might argue that watching TV is self-care. And so it's like, oh, I didn't work today because I felt, I don't know, stressed or burned out and I needed to watch TV. No, I think if you're doing that, because if that's actually what it is, more power to you. But is that it? Or are you lying to yourself?

So for you, when it comes to like writing more books. I'll put it this way. Recovery is important, right? Like if you work out, recovery is important. You have to have a certain number of days where you recover. You let the body rest and recuperate. Yeah. Is that what you're doing or are you just not doing it because it's hard to do?

Hmm. It's always hard to do. Right. So and the whole point is that it's hard to do. It was easy to do. There wouldn't be any benefits to it. Right. So, you know, are you stopping because you're sensitive to an injury or are you stopping because pretending that you're being sensitive to an injury is an excuse to stop?

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So if you're interested in getting completely free access to that keynote, just head over to kajabi.com forward slash Ali. That's kajabi.com forward slash A-L-I. And that'll be linked in the show notes and the video description as well. You just enter your email address and then you will get the recording of that keynote completely for free, whether or not you ever become a Kajabi customer. So thank you so much to Kajabi for sponsoring this episode. Hmm. So I was rereading Bertrand Russell's essay in Praise of Idleness, where...

He's basically talking about how this, you know, this attitude that the modern world inculcates within us, which is that kind of work is inherently meaningful, is like bad and problematic and all that jazz. I'm curious for you, like, you're presumably planning to write more books because you're fairly young in the grand scheme of things. But like, why? What is the, if not like, I want to be remembered, I want a legacy, then what's

What's it all in service of? No, he has a great line. He says, the first sign of an impending nervous collapse is the belief that your work is terribly, terribly important. And I think he's totally right. You know, if you had this sense, like,

I'm building this monument, you know, or the world has to experience my genius. This is going to last for a thousand years. You know, that's not, that's not only delusional, but like it's kind of a miserable place to be. And it usually, and usually feeds on itself and eventually, you know, wears you down. At this point, I write books that I am interested in writing, like that I love.

find myself better for having done. This book that I just did in the Virtue series, so I did Courage, and I did Discipline, and now I'm doing Justice. I'm almost certain this will be the worst selling book in the series, the Justice one, because it's the least...

you talked about certain terms, you know, will perform well. Discipline is good. Yeah. Discipline. Obviously I knew if I did a good job, it would be a home run. Yeah. This one, even if I do the greatest job I possibly can be possibly can do, you know, it probably has a ceiling on it in some way, but like I was better for having done it. If I learned something, I articulated something to myself in writing about it. If,

my kids are the only two people that read it. I try to find standards of success or motivations that have become more self-sufficient as I've gone. So at this point, I write things because creatively I find them interesting and I love the process of being in the middle of it, even

Even when it's really hard. And the same thing is true with running. Like I love and I hate running. Like I...

obviously not doing it is easier than doing it. But when I don't do it, I feel worse. Like I feel not in an addictive way, but I feel when I do it, I feel proud of myself. I feel physically good. My mind gets it. Like it's better that I do it than not do it. And the feeling of being in the middle of a book

Both the momentum of it and the frustratingness of it, it all kind of combines into it just an overall rewarding, immersive experience. That's what a flow state is. So it sounds like for you, writing is the thing that your higher self does most.

and wants to do, and therefore is almost good in its own right, regardless of how the outcome turns out to be. I think so. And so you push yourself to write on days even when you don't feel like it. It's like going for a run, like going to the gym. It's like the thing that you know is good for you, that you know is aligned with your own personal values,

And you don't want to be the sort of guy that's like, you know what, I'm going to skip writing for the next year so I can play more video games kind of vibe. Yeah. One of the Stoics, his name was Mousonis Rufus. He says, when you do something shameful for pleasure, the pleasure passes quickly, but the shame endures. And then he says, but when you do something hard for good.

the effort passes quickly, but the good endures. And I think you find whether it's pushing yourself physically like exercise, that's throwing yourself into a big project, you know, whether it's sacrificing for someone or something, you know, you quickly forget all that it took out of you and all that went into it. And you think about the impact that you had, or you just think about

the plane you temporarily ascended to to get there. And then when you think about, I don't know, the cake that you ate or, you know, the off day that you took or the urge that you submitted to, afterwards there's that period where you go, that's what I did all that for? You know, that five seconds, you know? Or not even the five seconds, right? And that's the higher, lower self.

So you've recently done a bit of a, well, I wouldn't say pivot, like side hustle on the whole daily dad stuff, which is interesting. A lot of, I've been just found, I found myself reading a lot of like parenting advice recently. I'm not even close to becoming a dad, but I was just curious. And I'm part of your daily newsletter on that as well, because it's just interesting. But there seems to be this really common thing of like people working hard

in their career, sometimes at the expense of their family. And you'll hear people say that like, I thought I was doing my kids a favor by working on and doing this thing and like focusing on my career and stuff. But actually what I maybe should have done in hindsight is to spend less time on my career and more time on the kid stuff. How do you think about that balance between like working hard at the thing, but also like being there for the small ones? Well, it's very insidious because you say I'm doing it all for them.

And so you are doing something very selfish, but you are cloaking it in selflessness. Like, that's why I'm getting on this airplane. That's why I'm staying this late at the office. That's why I'm, you know, blah, blah, blah, blah. But if you asked your kids, you know, what do they want?

like more money would be nowhere in that list, right? Or if it was on the list, it would be such a preposterously and refreshingly childlike understanding of money, you know, that it would, I think it would humble you. So you're saying you're doing it for them, but you're not, you're doing it for you. You're doing it for you. And the tragedy of, and the irony of I'm doing it for,

I'm doing all this for the people I never see is a very sad, fucked up place that a lot of sort of high-powered, accomplished people find themselves in. And I heard something great when someone said, like, success is your kids wanting to be with you when you're an adult.

And so like how will you measure your life at the end, right? It won't be like the size of the inheritance that you leave them. It will be, are you still in each other's lives now? So how do you invest in, that's not something you can do later. You know what I mean? So you have to make those decisions now. And they're costly and uncertain. And the worst part is you don't even know how much

I mean, this is obviously much scarier and sort of systemically imposed on women, right? So like you're going to take three years out of your, you know, cumulatively three years out of your working life in your 20s and 30s, which has this enormous cumulative compounding effect on the trajectory that you're going to end up.

That's a very scary thing. And it's unfair in a lot of ways, but at the end of your life, it's probably gonna be something you're glad that you did. And so I think a lot of men just sort of unthinkingly don't do it at all, but I've tried to sort of go, yeah, what is,

What is it that you want to do and who do you want to be? There's this great term, an art monster. I forget this female writer, she was saying like, my dream was to be an art monster. Basically just me and my work and a family, no baggage, no impositions, just me. And there are a lot of art monsters and they've written great stuff. But when you read their biographies,

You just sort of go, what? You know, was that worth it? You know, and it kind of taints all of the stuff that they did. It makes it much more bittersweet and not so great. Hmm.

How did you decide to go into the dad stuff rather than stay in your lane as the Stoic guy? I don't know if I really decided it. I mean, so writing The Daily Dad, I mean, the reason I decided to do The Daily Dad was that writing The Daily Stoic made me better as a person. You can't every single day sit down and try to take insights from the wisest people who ever lived and distill them down into a couple hundred words over and over and over again.

and not emerge somewhat bonded to those ideas. It gets in your bloodstream, right? That's what Stoicism is. What Marx is doing in his meditations was writing down things. A lot of it comes from other Stoic texts. He's just writing it down, rephrasing it, and writing it down, and writing it down, and rephrasing it, and looking at it this way. He's having this philosophical discussion with himself. And that's how Marx becomes Marxist. So the

the process of writing the Daily Stoke book and then writing the Daily Stoke every day now for seven years, it's almost a million words that I published for free, uh, to, you know, I think we've done 3000 Daily Stoke emails. It's like seven or eight books worth of content. Um, I have benefited from that. Like it's built a business around it, but like

If I had made precisely $0, that would have been the bargain of a lifetime, right? Like I've gotten so much better from having done that. And so I just decided that I would do the same thing about parenting. And if it helps other people, great. You know, if it sells books, great. But the process of having to intentionally sit down and think about and then write about and then publish, right?

you know, how I want to think about these things has made me better. And that's how you should think about it. I was talking to my wife last night, we were talking about this book that we were reading. And, you know, you get all the way to the end, you're like, oh, that was good. But actually you needed to read it over like six months, like a couple pages a day. Like,

Um, I just read this great book by this parenting expert named Dr. Becky Kennedy. Um, and so I read it, but then because I'm going to write about it for daily dad, I went through it page by page after and took out all the stuff that I liked. Um, and it was the second part was where I got stuff out of it, not the reading at once from cover to cover.

And so there's something about the page a day format that's worked in Daily Stoic and Daily Dad. Like if you're trying to absorb a philosophy or a new way of thinking or transform yourself from here to there, it's not 300 pages that you read, you know, from October 1st to November 17th, you know, that takes you a month and a half to read. It's much better if you're layering it like a page a day for a year, right?

or two years or three years and you're coming back, like the process of that sort of over and over and over and over again, that's where the stuff gets absorbed. What are some of the key, I guess, you know, from here to there, like through the course of writing Daily Dad and kind of being a parent, what are some of the key lessons that have really sort of separated the Ryan today from the Ryan of maybe like three years ago? I think patience,

I think like if I'm thinking like the, the things I've struggled with most as a parent, but that have also made the most difference. Uh, number one, like the greatest thing you can give your gift, your, your, your kids is presence, like not gifts, but presence, like just actually being there, not doing something else. So, you know, in a digital world, that's extremely difficult to do. Um, so I struggled that patience, of course. Um,

you know, it doesn't happen. It doesn't have to happen quickly. It just has to happen, um, to take your time with it, to let them take their time, to not rush things. Um, every time you think you can't go on like this, that's when you get some sort of breakthrough. Every time you think they're never going to figure it out, that's when they figure it out. So I think patience has been a big one. Um, I've, I've read a lot and thought about like, sort of, how do you just like, just root for this person? Like not, not, um,

Attach any conditions, not attach any judgments, not attach any expectations, but just be an unconditional supporter of them and who they are for who they are and what they are.

Um, which I think ties into another idea I've been thinking a lot about, which is like your job is to help your kids become that person, not to make them a person that you want them to be, you know, so to just sort of help them become who they are. That's something I've thought a lot about and worked on a lot. Um, yeah.

And then the one I've been thinking a lot about, which I heard about in Dr. Becky's book, obviously I knew about it, but it made sense. She talks about like, don't try to be a perfect parent. Try to be a parent who's really good at repair, like at fixing it when you mess up, fixing it when things didn't go the way that you wanted them to go, you know, reconnecting when, you know, there is conflict or when people go in separate directions, but, but repair, right?

So I'd say those are sort of the perennial ones that I struggle with and I'm thinking about. That's pretty cool.

Yeah, I, I, um, you know, my YouTube channel is, is essentially an exploration of the stuff I'm interested in. And I've recently started to become interested in, uh, relationships in terms of reading books about how to have a healthier, happier relationship. Uh, and I, I hope that when I become a dad and continue making videos, then I'll be like, yeah, reading all these parenting books and like making a video every, every couple of months to be like, right. I've just read the unconditional parenting. Alfie Koss, good, good shit. You have 10, 10 takeaways, that sort of stuff.

Found I guess similar to you to kind of writing daily stoic through me trying to make a video or two every week for six plus years all personal development adjacent those lessons seep into your Subconscious in a way that like they really would otherwise yeah Yeah, yeah Seneca says we learn as we teach and so if you as a person who writes self-help books or makes YouTube videos or as pockets or whatever if you're thinking I'm really smart and I am Telling you everything that I know

not only is that egotistical, but it actually continues to inflate and puff up the ego, right? But if instead you see it as like, I am trying to figure things out and I am explaining what I am learning as I am learning it, you are learning it and other people are learning it and you're creating this feedback loop in which

You're both learning at the same time. And by having to articulate it and explain it and distill it, you are understanding it better than if you were just learning it for yourself. Yeah. Yeah. There's a book I'm reading at the moment called Notes from a Fellow Traveler by Darren Brown. He's a magician. Yeah. Yeah. He's really into stoicism. Oh, he is. His book Happy is very good. Basically all about stoicism. But I really like the title of that book, Notes from a Fellow Traveler. He's sort of a book written for other magicians. Yeah.

But that framing, like a fellow traveler, I really like that because he's not trying to be a guru. He's not saying I've got the answer. He's just like, hey, I'm in this business just as you are. And here are some notes. And I just love that framing of it. It just takes all the pressure off, reduces the seriousness, makes it feel more like play, all of the good things. Yeah, someone who's just a little bit further along the path in some ways or struggling with their own things. And you're sort of channeling that and trying to make it accessible and practical to other people. Yeah.

what is what are some like i really like this list of the the parenting some things do you have any on relationships in general like uh like the romantic relationship with your wife and things what are some things that you guys do that maybe you've discovered through reading and stuff well i always say that the number one so i've been with my wife now for 17 years we we met when we were in college and um we uh

We met at a college party. We got married almost 10 years ago. Eight years this year, nine years. So it's been a long time. And we've basically been married that whole time in that we always had a very sort of involved, like serious relationship as opposed to just, we've known each other a long time. And so people sometimes ask what the secret to like, you know, lasting that long is. And I usually say that the secret is to not break up.

That's the secret. That's the number one secret is to just not break up. Because I'm joking, but I'm also not joking, right? Like, I think just as a productivity system or a business or a lifestyle, it's about picking a thing and then sticking with that thing, right? Through the ups and downs of...

what life inevitably brings you. And I find, you know, obviously we got together before online dating was really even a thing, but then dating apps and like, I noticed that a lot of my friends struggle because it's easy to break up and it's easy to find another person. Do you know what I mean? Like essentially an unlimited amount of other fish in the sea exists. And if you,

of that, it makes it very hard to do what a relationship requires. You know what I mean? Which is sacrifice, which is struggle, which is putting up with shit, you know? So it's hard. It's like, it's really hard. It's hard. So I profess to have no secrets other than don't quit. I mean, it's amazing how in all these different spheres, like, you know, the stuff you were talking about with kids, presence, patience,

rooting without conditions, judgments, expectations, being repair and not being perfect. All of that stuff applies to every other aspect of life as well, like work too. Well, even the kid stuff applies to yourself, right? Because we all have sort of, we all have this inner child that needs work, right? That's stuck somewhere, not fully developed. And one of the beautiful things about having kids is the way that it allows you to reparent yourself because you suddenly...

fully understand what a six-year-old is going through or a nine-year-old is going through or a nine-month-old is going through. And you can see more clearly now the things that you didn't get that maybe you needed or the ways that how everyone used to do things was insufficient, maybe just for you specifically, or maybe just as a practice it was terrible. And you can kind of see, oh,

Okay, I can't go back in time and fix that, but I can do things differently here. And I can also empathize, connect with an earlier version of myself that needed those things too. And that by giving that thing to someone else, you're also partly healing yourself. That's great stuff.

You're in pretty good shape. What are some of the secrets to staying in good shape as you've been a parent? I profess to have no secrets there either other than I try to run, swim, or bike every day. I just try to do some hard, strenuous physical activity every day. And if there is a health benefit to that,

I consider it a bonus on top of the two real benefits that having an exercise practice gives you. One, you are literally practicing having a practice. Like every day I go for a run, the default is that I do the thing. And every time I do the thing, I am building the muscle of doing the thing and being the kind of person that does the thing.

what I say I'm going to do. Like, it's not fun to do it. It can hurt to do it. But I get up off the couch and I do the thing that I say I'm going to do. And the second benefit of having a physical practice is that it's usually getting the mind moving in some way. And so, you know, there's no screens. There's no multitasking. You're just...

in that headspace. So like I have the flow state every day from the physical activity. And the days when I don't have it, nothing else works as well. Do you do any weight training? Yeah, I try to lift weights like, I don't know, a couple of times a week. I feel like I've seen some B-roll of you in like the backyard. Yeah, I like kettlebells or I have like a squat rack. I do some stuff. In the pandemic, I got more into it than I...

do now the important thing for me is i run swim or bike like i do some form of cardio exercise for a long period of time and if i can get the other stuff in sure changing gears a bit um i was re-listening to the conversation we had three years ago in a car on the way here um and the one of the things you said in that has actually stayed with me for the last three years it was something to the effect of

You know, you've got all these friends who are in real estate and sometimes you're like, huh, maybe I should get into real estate. And then you realize all your friends want to be self-help book writers. And you're like, huh, I've got a pretty good gig. I wonder if you can just sort of like riff on that for a second. Seneca had this word euthymia, which he defines as tranquility. He says tranquility is the sense of the path you were on and not being distracted by the paths that crisscross yours. He says, especially from those who are hopelessly lost.

which I think is very beautiful and true. Sometimes you find like when you're running, you know, someone will pass you and you go, are they faster than me? They could have started eight seconds ago and you could be five miles in or they could be,

stronger than you, they could be doing steroids. The idea that you're comparing yourself to this person when you don't know when they started and you don't know where they're finishing is madness, right? And life is like that. We're all running our own races and you've got to have a sense of the race that you are running and what victory or success in that race is to you. So I think that's the number one life lesson and something I remember learning

I'd run around this track in college and I would sometimes catch myself picking up my pace to keep up with someone else. And then they would stop. And I'm like, I just gassed myself, you know, now I have to cut the run short because I was competing with this person and I have no idea what their goals are, what they're doing. I know nothing about them other than

Someone, competition, you know, and it sucks you in. So I think that's a really important lesson that I've learned from the physical practice over the years. But one of the things about jealousy or envy, that sort of competitive urge that we feel in other parts of our lives, is that we don't spend a lot of time thinking about who that other person is, what their life is like,

and what they want. Marcus Aurelius is like the people whose approval you crave, he says, take a minute to think about who they really are and see what that does to the approval you want from them, right? It's like, you just go, oh, this person has this, I wanna be like them, or I wanna be accepted into that group, I wanna be in this club. And you're not really thinking about who those people are, what they do, whether it's working for them.

And I've had this surreal sort of experience pertaining to that where you meet people and you think they have it all. And then, you know, you're jealous of them. And then it turns out they're jealous of you, right? Like you, jealousy almost always takes for granted what you have because it's, you know, eyeing what someone else has. And there's usually an ignorance of jealousy

would you actually, what is it actually like to be that other person? And I've, yeah, I found it's funny. You meet and meet these billionaires or whatever. And what do they actually want to do? They want to write books. Like they, they have all the money in the world and what are they trying to spend the money on? They're trying to spend it on having the thing that I get to do. And so I, I try to remind myself of that and count myself as lucky to get to do this. Do you feel that sense of comparison or do you slash, did you ever feel that sense of comparison when it comes to

uh, bestseller lists and book sales numbers. And James Clear has got this many five-star reviews on Amazon and I've only got this many, you know, that whole shebang. Well, that's why it's important to understand what race you're running. Right. So, um, I remember I was at a conference in Canada. I don't remember. I was at some conference and James, who was, uh,

Then he had this popular newsletter. I sort of vaguely knew his work. We talked a couple of times. I was doing a panel or a session on publishing and he came and he asked for a bunch of advice, but he was just generally, if I remember correctly, quite skeptical about why anyone would traditionally publish or publish a book at all. He's like, why would I do this? I have this huge email newsletter. Why wouldn't I just write stuff on the internet? And I thought, I said, I'm

Look, people have read books for thousands of years. It's a medium that has a certain cultural significance. And books are actually a great way to deliver ideas, right? But there I was, a person who published, you know, a few successful books at that point. And I'm sort of like condescendingly telling this internet writer why publishing should...

you know, be something that he considers. And then a couple of years later, he puts out a book and that one book has sold more than all of my books combined and then some. So, you know,

And the one reaction to that would just be jealousy, scorn, sin. Like, that could make you feel shitty. And I think there are times in my life when maybe that would have made me feel shitty. But first off, I like James. Second, I think he's a great writer. And I think Atomic Habits is actually a very good book. And third, I don't know how many I'm counting now, but whatever.

There is no universe in which that book selling more or less copies affects my life in any negative or positive way. Right? Like, so that book could sell a hundred million copies. They're not, it's not coming out of my pocket. Right? So more power to them. Right? And so I've tried to remind myself of that. But then what I, you have to do when you realize you're running your own race is you have to go,

James is writing a book about habits, which is for everyone. I am writing about an obscure school of ancient philosophy, which I would like to be for everyone, but by definition is probably going to be for fewer people. And that is a choice that I made willingly. I can write about whatever I want. I could have written about whatever I want. I chose this thing or this thing chose me because I

it's the right thing for me. And you have to be able to go, right, this is where I'm supposed to be. I made a series of choices and for better or for worse, those choices made some outcomes possible and some outcomes not possible. Like I remember I spoke to these high ranking officers in the Navy once a couple of years ago, and I was talking about ego or something. And I said, you know, like

If you got into this for like money and recognition and fame, you fucked up. Like you shouldn't have joined the Navy. Like you joined this because there were certain parts of it that lit you up, that were meaningful to you, that you thought were the right fit for you. You chose classical music, not pop music, right? And by nature of making that choice, some outcomes are possible and some outcomes are not possible, right?

And you have to accept that. And the worst thing you can do is make those choices, which are objective and sort of unbeatable, and then work really hard and expect things that are in contradiction of that choice. Do you know what I mean? Like if you're a classical musician and you go, my goal is to be the best classical musician I can be and to push the boundaries of the blah, blah, blah, blah, blah.

then you can succeed. If you go, I'm putting out this album and I hope it debuts at number one on the billboard charts, you know, you're almost surely going to be severely disappointed because you've chosen something that is a smaller pool. You know, maybe you have a higher floor, but a lower ceiling. That's the nature of the choice that you made. And being honest with yourself about that is really, really important, at least for happiness. Yeah.

Do you ever meet writers who you feel have sort of this unhealthy relationship with comparison? Or are most of the people you hang out with fairly enlightened? No, no. I mean, definitely there's people that are, you know, sort of driven by how much they sell or how much money they make or whatever. But again, if that's why you got into books, you fucked up. You know what I mean? Like if you got into writing books for money and fame and power, you're an idiot. Like there's...

That's not even, that's like, that's probably the worst of all the different genres of entertainment or show business. You pick the worst one. Like for that, if that's what you're optimizing for, you pick the worst one. So to expect, like the Stokes say, don't expect figs in winter. That's like the essence of happiness is to not expect figs in winter. There's a time when you can get figs and it's not winter. So, you know,

You can be successful writing books. You can make a good amount of money. You can make more money than you need. But are you going to rival the fortune of Warren Buffett? No. So to expect otherwise is probably silly. It's not even probably silly. It's stupid. It's stupid. And it's not fair. It's not fair to you or to the people around you, right? Because you are feeling aggrieved

that you didn't get something that it was not possible ever to get. So my book is coming out in, at the end of December. So I'm not sure when this is going to be aired, but end of December, uh, any advice? It's the first one. Um, you've been, been through this a lot. Yeah. Um, so I always tell people when they finish a book that you have completed the first of two marathons and, um,

You finish this first marathon and you think, you know, you stagger across the finish line. And you think they're, someone grabs you by the hand and you think that they're going to take you over to like the medal stand. And instead they're just leading you over to the starting line of the second marathon, which is now marketing and selling the book and talking about it and getting it into people's hands. And so understanding that these are two equally important races is,

I think is really, really important. And not enough people do that. They just write something and they just expect or assume that the world owes them success, which it doesn't. People are busy. People have a lot going on. There's not only all the books that are coming out, but there's literally everything that has ever been published for all of human history up until this point. And a lot of it is very good. And most people haven't even gotten to a fraction of that.

So the idea that your thing is going to jump in front of that line is inherently presumptuous, if not delusional. And so it takes a lot of work to break through. You know, the obstacle is away when it came out. First off, I said to myself, I'm writing a book about ancient philosophy. Most people are not interested in ancient philosophy. So it's already an uphill battle. And then I said to myself, I read a lot.

How many books do I read the week they come out or the month they come out or the year they come out? And I read way more than most people. How many books have I pre-ordered ever in my life? Maybe one or two. So the idea that this thing is going to come out of the gates as a hit is stupid. You know, it's going to take a long time. So first off, you try to make something that doesn't need, doesn't have an expiration date on it. That's number one. Number two,

Seeing it as a marathon and not a sprint is really, really important. So The Obstacle is the Way came out in May of 2014. I'd started writing it in 2012. So it took two years, came out, it sold three, 4,000 copies its first week. It got skunked on the New York Times bestseller list.

Yeah, like it probably sold enough to hit what was then the extended list. There was 20 spots on the advice how to then and it didn't. And it certainly sold enough to hit the Wall Street Journal hardcover business list. And someone at my publisher had decided to list it as a like a different, like it didn't qualify for that list. Like they didn't.

It checked the box, categorized it as something different, didn't hit it. So it did not hit any bestseller list until September of 2019. Wow. Nice. At which point it had sold close to a million copies.

So again, we think of what a bestseller is. We forget that bestseller lists are categorized by the week. So a book that sells 10,000 copies in one week will hit a bestseller list for that week, almost certainly. But a book that sells 1,000 copies a week for a year will sell five times as many copies, but almost certainly not make any bestseller list. And which would you rather have? And so...

It's about setting yourself up to last and it's about not quitting on it. Nice. And the obstacles way sells most years, sells more copies than it did the previous year, which is, you know, pretty rare in publishing. But every single week that comes out it, that it is out, how many copies it sold in its first week becomes less and less important.

Right. And unless you are not successful, that will be true for your project. Right. Like every week, the percentage of how you did at the beginning. It becomes more and more meaningless. It becomes more and more meaningless. But that's very hard to think about when you, when it is 100% of the weeks that you have been out. Right. Um, takes time. And, and realizing that when the thing I've tried to say to myself is, um,

The, to people who have never heard of you, you are new. So I'll probably almost certainly have an email in my inbox when I get done from this from someone and say, I just read your book, The Obstacle is Away, that is approaching its 10 year anniversary. Right? And so to them, it's a brand new book. And it's a brand new book to them because they're

They're a junior in high school, you know, and they were eight when it came out, you know? Um, and so, you know, that's what sort of lasting can do. Um, and to, and to, yeah, to, to sort of be, be patient with it is the main, the main thing.

We have a Telegram group for our podcast, and we said we were going to interview you, and we had loads of people asking loads of questions. There was one comment from one guy that I felt a bit salty about. He was like, Ryan Holiday says the same stuff on every podcast he's interviewed on. And I was like, hmm. Because I say the same stuff on every podcast I'm interviewed on. It's kind of like a thing you have to do. I found that it was less a comment on you and more like,

I started thinking, fuck, you know, I've made the same video so many times. I've been talking about productivity for like six plus years now. I've basically been saying the same stuff. But each month we get like 100,000 new subscribers. It's clearly new to someone. Yeah, there's some main character energy in people who don't realize that most people are consuming this thing for the first time and hearing about this person for the first time. So, you know,

as a creator, there's a little bit of narcissism in that you go like, everyone's following everything that I do. And in fact, not only is most people not know that you exist, even the people that know you exist and are fans, you're like 500th on their list of priorities. Like I think about my favorite bands, my favorite authors, like how closely am I following their life? Like not at all. I'm in the main character energy of my own life. So realizing that like

That self-consciousness can actually hold you back as a creator because you're like, people will get mad that I just talked about this two videos ago. And actually they didn't see it two videos ago, so you're not. But the other product of this is, the other part I would say to that person that's a little tricky is it's like, dude, it's not my fault. Like I can only answer the questions that I'm being asked.

And I tend to get asked the same questions a lot, right? What is Tesson? So, so, so like, I would love to be, I would love to have a totally new and unique conversation every time. And I do, I definitely feel like there are ones where I'm like, that, that was interesting to me for a change. I didn't feel like I was sort of, you know, giving the same song and dance, but a lot of

People are just asking the same questions because they're introducing you to their audience or they want to get the basics. Do you know what I mean? So it can be weird. Do you ever get bored writing about stoicism? Not really, because one of the ideas from the Greeks is this idea that we don't step in the same river twice because the river changes and you change. And so, I mean, I've been doing the Daily Stoic email every day for seven years, and I've probably...

used some of the same quotes hundreds of times at this point, but it feels new to me every time I do it because what I'm trying to say or the way into the idea is different. And I know the audience is different and I know what's happening in the world is different. So it keeps, it certainly keeps me, it feels fresh to me because life is fresh. But when I am bored, I just write about whatever I want.

You know, like, it isn't the only thing that I do. And so when I feel like writing something, I write that thing. Yeah, because people sometimes ask me that, you know, aren't you bored of talking about productivity? I'm like, honestly, not really. Like, I'm bored of, I guess, making videos that are like top 10 productivity tools. But I do very little of that these days. And I think productivity is...

you know, really just about using our time well, which covers basically everything in personal development. And so even if I'm writing about relationships or making a video about health,

I would count that as productivity. Yeah, but also productivity to you when you were in medical school is different than what productivity is to you now as you are not in medicine. It's different to you when you had one employee. It's different to you when you had 10. What you're going through and where you're applying it is fundamentally different. So even if you're talking about the same ideas, you have...

a larger sense of it you have a larger set of experiences to draw from and so even if it is the same it's it's better and different yeah because it's based on more nice why do you think people are so interested in passive income oh i'm really interested in passive income does it exist i i think it does um

So there's this whole dream. I'm not sure if Tim Ferriss used the phrase in The 4-Hour Workweek or if it was a thing afterwards. But I remember reading that book when I was like 17 and just about to apply to medical school. And my mind just absolutely blew wide open at the thought that I could be making money while I slept. And just that thing was always in the back of my mind.

And now we know it's another one of those things that anytime we make a video on YouTube with the phrase passive income in it, we know it's going to do well because people love the idea of doing a thing and then it making money without needing your additional input. I think kind of like books. Books are a source of passive income. Yeah, well, intellectual property. Exactly, yeah. You know, you wrote The Obstacle is the Way 10 years ago and it's now been making you passive income ever since. I've certainly found in our business...

The stuff that I get so much satisfaction out of seeing like a Stripe notification that someone bought a course I filmed three years ago and I've made $149 from it and way less satisfaction making way more money on a sponsored video.

Because there's something about it being an asset that is spinning off, I guess, free money that is like really nice. And also, I guess it really appeals to other people. Yeah, I guess that makes sense. I was talking to an internet marketer person that I knew and, you know, like, let's say he was saying like the email subject line, like follow a strategy to make $1,000 a month or to make thousands of dollars a month would actually perform worse than say like this strategy helps me make

$1,444.17 per month. He was saying like the specificity of it, even if it was total nonsense, resonated with people more. And I always wondered what, there's something, naive is not the right word, maybe unsophisticated is a nicer way to say it, about the idea that if you just do all this stuff, at some point you won't have to do anything. Do you know what I mean? Yeah.

Because that's not really how life works in my experience. Yeah. No, it's not really how life works. Nor is it how you would actually, nor is it how the life works for most of the people that you admire. Do you know what I mean? Yeah. Like people who do stuff that you're like, that's cool. I want to be like that are not people who own a series of vending machines that passively make money while they sleep. Do you know what I mean? They're people who are actively engaged in what they do.

Yeah, I guess. So I've kind of gone back and forth on this whole passive income thing. We still make videos about passive income. And I always do a whole like 20 minutes of philosophizing at the start to be like, okay, here's how money works. Money is an exchange of value, blah, blah, blah, blah, blah, blah, blah, blah. But I find that...

Like, if I think back to myself, back when I was in medical school, the thought of being able to, if someone gave me a vending machine business and it was making $3,000 a month, I'm like, whoa, I never need to work a day in my life now. Now I can do what I really want to do. Sure. And...

Just that being able to cover the basics through some sort of automated income stream, even if it's not like greatness or anything, even if it's just like, I don't know, automated vending machines selling Coke cans or like a T-shirt business or whatever the thing is. I think that is that is still very appealing because then it's like, cool, the bases are now covered. I can now spend my time doing the things that I actually want to do. I get that. Yeah, I agree.

I thought about it that way earlier in my career. I mean, first off, I had a job as I was becoming a writer, which allowed me to make certain creative decisions that maybe if I was a starving artist, I wouldn't have been able, I wouldn't have had the luxury of being able to turn things down or doing things a certain way or having as much time. But then, yeah, I thought, I was like, I don't have a trust fund, but if I have sort of income streams other than like the creative work that I do,

It's like I gave myself a trust fund. Yeah. And now I have a certain amount of freedom or independence that I wouldn't if I was living and dying by how... Single paycheck. Yes. Or...

until I burned through the book advance or whatever it was. Yeah, honestly, like anytime I make one of these money themed videos, there are always some comments that say, oh, I can't believe you're so obsessed with money. Like stop talking about money all the time. I'm like, oh, this guy's such a greedy and stuff. But I'm always like, no, like having more than one stream of income is genuinely life changing. Like the fact that I had

money coming in from my YouTube channel and my business meant that I could leave my day job or at least go part time on it to focus on the thing that actually brought me joy and fulfillment. Being able to have an extra stream of income is what allows parents to spend more time with their kids. It's like one of the most worthwhile things in the world to have if you care about personal freedom and fulfillment and stuff.

And so I always sort of, I feel a bit distasteful of the phrase passive income, but I almost view it as a bit of a Trojan horse into kind of teaching people that like, hey, you know, the way you actually make money is by creating X amount of value and capturing Y percent of it. Now just figure out a way that you can do that that's not correlated with your time. Generally by creating something that's like media or code or basically those two things. Yeah, or investments. Or money itself, yeah. Yeah, yeah.

Yeah, people talk about like, you know, I want to earn like fuck you money. But really, you could just have enough to be like, eh.

Or like, I don't need to. Or just enough that it can kind of help you swing you one way or another as you're thinking about making a decision. Do you know what I mean? Whereas if your livelihood is dependent on this thing entirely. It's really hard to. I think about like, I mean, obviously you're not American, but in America, the fact that for most people,

their health insurance is tied up. Yeah, that's so unfair. Especially as a country that celebrates entrepreneurialism and risk-taking, it seems like the most basic thing in the world that you would want to separate those two things so people could take bigger risks and bet on themselves. You shouldn't think I could literally die if I leave my job. That's madness to me. But

Being able to go, hey, actually, I'm going to see where this thing takes me. And I know I'm not going to starve. Like, I know that I have...

this thing. Maybe it's not covering my full expenses. Like, you know what I mean? Like I, I have these things that allow me, like when I, when I did The Obstacle is the Way, my publisher offered me about half of what I'd gotten paid for my first book. So if I didn't have my day job, um, I probably, I don't know if I would have said yes. Um, but I, I wasn't

indifferent to money, but I was able to go, I really don't care what the amount is. What I care about is, are you going to publish this book? Because if you are, then I'm going to go all in on this thing. Do you know what I mean? And so having, I do see how that gives you, gives you a certain amount of freedom of movement. Yeah. I think like, even like even in the UK, so obviously like health insurance, your health insurance is not tied to your employment and the national health service is very good. But even then people still

act as if quitting their job means that they're going to die. And I'll often speak to people who, you know, like, you know, back in the day, I was a bit concerned that, oh, if I leave medicine, will people think, oh, fuck you, I don't want to listen to your content anymore. But it's actually kind of the opposite's happened. People are like, oh, man, you got out of the system. You like, I don't know, something about the matrix and stuff. So people keep asking me for advice around quitting their job all the time. They're like, yeah, I really want to leave my job and do this thing. I'm like, great, what's stopping you? They're like, oh, but like, you know, the paycheck. And I'm like, okay.

are you on the poverty line where like this paycheck is actually meaningful there is a difference between survival and not like nope have you got any dependents nope these are all people in their 20s that have a safety net from their parents and yet still the thought i might quote fall behind yeah and like fall behind my friends who are then getting that promotion at mckinsey or whatever the thing might be is preventing people from making a decision

They're just very unlikely to regret. So I try and like nudge that as much as possible. Well, I got so lucky when I dropped out of college because I I've talked about this before. But when I went in there, I was like, I'm here to drop out of college. And they were like, what? You know, they're like, just fill out this form. You take out your you're just taking an indefinite leave of absence. You can come back whenever you want. There were some consequences. Like, I remember I was signing.

I signed something and it was like, your scholarship may not be here when you're back. As an adult now, I realize they probably just would have given it to me again. But like, so it wasn't totally without cost, but there was the idea that like, I thought it was this permanent irrevocable lifestyle decision when in fact it was a pause.

and you think, hey, I'm going to leave this to go do this. I'm going to go give this a try. I'm going to open this coffee shop. You think you can never go back. And of course you can go back. If you were in the hospital for a year, would you be sitting there going, I can never go back to my job? No, you would know...

There's going to, it's going to be an adjustment period. I might have some ketchup I have to, you know, there's, but you just go get another job. Like that's how life works. Right. And, but especially when you're younger and you don't have the experience, it feels like the shift or the transition or the quitting can never be undone. And only the time you realize that the stakes were so much lower than you thought they were.

Yeah, I find the Tim Ferriss fear-setting exercise to be just really helpful. Yeah, what's actually the worst case scenario? Yeah, what's the worst case? And it's like, okay, what does it look like? How could you mitigate against it? Let's say the worst case does happen. What can you do to come back to where you currently are or at least someplace that's good enough?

I think I've done that like three or four times in my life at the sort of crux of making a big decision. And I've always been like, oh, this is really helpful. Yeah. The worst case is never as bad as we think it is. And recovering from the worst case is also never as hard as we initially think it's going to be. Yeah. I remember when I was thinking of dropping out, I was talking to this person and he was telling me I should do it. And I go, you know, what happens if it doesn't work out? You know? And he was like, when I was in college, he's like, I got mono or something. He got something and he spent a year recovering. Yeah. And he's like,

Do you know how many times this has come up in my life that it took me five years to graduate from college? Zero times. Nobody knows. Nobody even does the math. You started college at this date. You got your first, like nobody knows. It just, as more time goes by, it just all, like you spent your time in college, now you're not in college. No one's like, oh, but what about that year between your sophomore and your junior year? What was that about? It never comes up. And his point was like,

If I take this risk and it doesn't work out, I just go back and it takes you four years to graduate, five years to graduate, whatever. It's a rounding error in the big scheme of things. There's a good, I think it's the thing that Jeff Bezos says, which is like,

You know, he's talking about the kind of the game of entrepreneurship and he's sort of likening it to a baseball match. And he's like, normally in a baseball match, you can either hit one to four runs or whatever the number is. I don't know anything about baseball, but he's like in entrepreneurship, you can take a swing, but like the upside of the swing is infinite. Yes. And so if you take enough swings, you can actually get an outcome that way outperforms what you could have done if you were doing the job thing, for example. And I think the

Now, I wish more people would appreciate the asymmetry of the upside that you get from taking a risk and doing your own thing potentially. Right. So you understand and you articulate the downside, which is less than you think. And then it's hard to wrap your head around the fact that the upside could literally be incomprehensible. Like when Jeff Bezos starts Amazon, he has some idea that it could be successful. Yeah.

But it would have been literally impossible to conceive of what it became because it didn't exist yet. And when I left, I had this sense that I wanted to be a writer. And I knew that I thought leaving got me closer, a better chance of being that writer than staying. And maybe it's true, maybe it's not. But like the writing that I ended up doing and the level at which I ended up doing it

Would have been, if I thought that's what I was doing, I should have been certified. Do you know what I mean? Like, I would have been a sign of a mental illness. Like, any sense that...

this is how it was going to go. You know what I mean? So you're just taking it step by step. Yeah. I think the other big thing that I found really helpful was, you know, back in Jeff's day, where there were very few examples of what does entrepreneurship look like. Like these days, people don't have that excuse anymore. Like if someone is even entertaining the thought of being a writer, there are a zillion interviews with professional writers out there. Sure. Someone wants to be an entrepreneur, there are a zillion interviews with entrepreneurs where they're literally talking about how much money they're making. Yeah. Similarly for YouTube and stuff.

And so,

I think an information diet is a really important part of this. Like even just watching videos, reading books and listening to podcasts from people who are doing the thing that you think you want to do helps you realize that, oh, that's fairly normal. They've just been doing it for a while and that's what the outcome could look like. Yeah, like look, if you're, no one goes, it must be impossible to be an accountant. How does someone become an accountant? Right? Because accountants are everywhere, right? Although, you know, if you grew up in the inner city and your parents

parents didn't work and you never had it might actually seem utterly unattainable and impossible to become that thing and the reality is it's not people do it every fucking day and i said say it's easy but it is possible it's very possible and if you steep yourself

in how possible it is and surround yourself, not physically, but intellectually with people who have done it, you figure out how it can be done. And we talk a lot these days about like nepo babies and nepotism. I think so much of that is if your mom was a famous actress, sure, that gives you advantages and introductions and you're in this sort of milieu that's beneficial. But also that doesn't seem...

impossible or impractical because your mom is doing it. She's not that great. Do you know what I mean? She's like, you know, you're just like, people do this. It is a job. You see how it works. It's deconstructed and demystified for you in a way that allows you to go, to give yourself that self-assignment. Like I could do that.

Yeah, it was the same for me with the medicine stuff. Like, I didn't have any official advantage getting into medical school. But both my parents are doctors. All of my friends' parents are doctors. Basically, everyone I knew growing up was a doctor. And so, like, it doesn't seem that hard. People become doctors. People become doctors. And then, you know, it was only when I started applying to med school and stuff where some people, oh, my God, you're applying to med school. Wow, that's so hard. Is it? Like, everyone I know is a doctor. It's not that big a deal. Yeah.

I think it's that same concept applied to anything. So people will probably be listening to this towards the end of the year when they start thinking of habits and resolutions. If someone's like, I want to be more productive next year, what would you tell them? If someone wants to be more productive next year, all right, I've got three things. Number one is actually just figure out

or at least make a rough first draft of where do you actually want to go? Like, sure, you can be more productive by cranking out more words per day or whatever, but like, if you're not trying to be a writer... Don't have a vague sense of what... Productivity is not a goal. Exactly. Yes. Productivity is like a sort of an effectiveness measurement en route to a particular goal. And if you don't have that goal, then optimizing for productivity is completely pointless. Yeah. So I think step one is to figure out what the goal is. You know...

Some people don't like the word goal. The most helpful exercise I've ever found for this is something called the Odyssey Plan from the book Designing Your Life by Bill Burnett and this other guy who's like some Stanford professors. And basically the idea is that you imagine your life three to five years in the future if you continued down your current path and you write out what it would look like. Then you go back to day one, back to today, and you imagine your life three to five years from now if you had to take a completely different path

And then you go back and then you imagine your life three to five years from now if you had to take a completely different path, but money was no object and you didn't care about what people thought of you. And that just gives you sort of this divergent thinking that most people just never do.

And I personally enjoy like doing that exercise every year and then converting it into a, okay, what does my 12 month celebration look like? 12 months from now, what would I like to be celebrating in the different realms of life, health, work, relationships, joy? Those are the four that I like personally. And now I've got some goals written down. And there's so much evidence that says that people who write down goals, people who have goals are way more productive than people who don't. And people who write them down are even way more productive than people who don't write them down. So step one,

figure out what your goals are and just write them down. Step two, I find it super helpful to just convert all of those goals into what is the action I have to take each week. So if you're, for example, trying to write a book, it might be a daily action of writing for two hours a day or a thousand words or whatever the thing might be. In my case, I'm trying to get fit. And so weight training three times, three times a week is the habit or the system I'm trying to develop. And then number three is putting all those things in the calendar. And then

If they're in the calendar and you can turn and you can make yourself the sort of person that does what's in the calendar. Honestly, that is like 95% of all of all of the world's productivity advice condensed into three things. Figure out where you want to go, turn it into and figure out how you're going to get there and then just put it in the calendar and do the thing when it comes around. With a fresh year coming, what would you recommend people stop doing? Like what's a what's like a destructive habit that you would say to get rid of?

A really big one that holds everyone back is overthinking. So much research from this book around procrastination was realizing that procrastination is primarily an emotional problem. There is some sort of kind of fear of looking bad, fear of failure, self-doubt. The mind starts to weave all these stories about how we're not good enough to do this particular thing. And

I've interviewed a couple of professors in procrastination who've done all the research about this, and their whole thing is like, you've just got to find a way to cut through the bullshit that the mind will present to you and just make a start on the thing.

And often procrastination is a problem with getting started because once we get started, the inertia means that we'll just continue going. It's way harder to... Objects in motion tend to continue. Exactly. Newton's first law. You know, we talk about that in chapter four of the book. So recognizing that has really helped me recognize that when the mind is getting in the way, the best thing I can do is just get started with the thing. And then the mind has a habit of just sort of getting out of the way.

But if people can stop overthinking and stop letting this fear of self-doubt and failure and stuff get in the way, getting in the way of living their best life, I would love that. I would love for that to happen. All right. Last question. What's something you feel like the Stoics can teach a person who wants feel good productivity? Yeah, I think the main one I always come back to is the dichotomy of control. Epictetus is it? Yeah. You know, there are some things that are within our control and there are other things that are not within our control. And any amount of

worrying about the things that are not within our control is usually worried that it's wasted. And I think a big part of feel-good productivity is find a way to control the things that you can control. You know, a huge part of what drives intrinsic motivation is the sense of autonomy, sense of control, the sense that we have power over what we're doing.

And some people are like, well, you know, I don't have any control over what my boss tells me to do. Okay, you might not have control over the specific thing you have to do, but you might have control over how you choose to approach it. You have control over the process. Can you find a way to make it more interesting? Can you find a way to speed it up? Can you find a way to slow it down? Can you find a way to add music in the background to make it more interesting? There is always control that we can take.

in basically every situation, even in situations where we feel like we have none. And there's that quote from Viktor Frankl where he's in Auschwitz and is sort of surrounded by the German concentration camps and everything. And even in that scenario where he and his fellow inmates have no control over anything at all, at least they retain control over their own mind and over how they choose to approach the situation. So even in the most extreme of situations,

We can find the things that we can control and we can focus on controlling those. And I think that's such a nice idea from Stoicism that I always come back to. No, that's very well said. My productivity advice from the Stoics would be a question. Mark Stoics says you have to ask yourself every moment, is this essential? He says, because most of what we do and say is not essential. And he says, when you eliminate the inessential, you get the double benefit of doing the essential things better.

And so when I think about how I'm able to do what I do, it's there's the things that I don't do that I've stopped doing or that I have delegated someone to do or that I have brought on a team to scale being able to do. And when you get rid of the wasted movements or the wasted thoughts or you stop chasing the things that don't matter or move the needle, you

You find that actually, I mean, it takes a lot of energy to be great at something, but it's less than people think. You know what I mean? Like, I think maybe someone would assume that like a writer writes 10 hours a day, but it's like two. You know what I mean? You think that, you know, an athlete is practicing and lifting weights and training all the time, but

You know, they're also taking long naps during the day and, you know, and they, and they built a lifestyle where someone's cooking for them and the team takes them from place to like, they've also eliminated so much of what is inessential that just concentrated bursts of the essential thing allows them to be best in the world at what they do. Absolutely.

And yeah, I just wanted to say thank you so much for all your advice and tips and stuff over the last three plus years of this book coming together. Well, the book is great. I don't think it's going to crush. Fingers crossed, but that's not a thing I can control. So I'm not going to think too hard about it. But it already did crush. The way to think about it is that it already did crush and that it exists. It exists. And I'm proud of it. That would be more satisfying if this was the actual book. The hardback. This is the advanced reader copy that we've sent away. They're deliberately very flaccid, unfortunately. But...

It doesn't have the satisfying crud or thud of a hardcover, but it exists. And so literally every person that reads it, even if that's seven people and three of them are related to you, it's all extra. It's all extra. Sweet, man. Well, thanks. Thank you.

All right, so that's it for this week's episode of Deep Dive. Thank you so much for watching or listening. All the links and resources that we mentioned in the podcast are gonna be linked down in the video description or in the show notes, depending on where you're watching or listening to this. If you're listening to this on a podcast platform, then do please leave us a review on the iTunes store. It really helps other people discover the podcast. Or if you're watching this in full HD or 4K on YouTube, then you can leave a comment down below and ask any questions or any insights or any thoughts about the episode. That would be awesome. And if you enjoyed this episode, you might like to check out this episode here as well, which links in with some of the stuff that we talked about in the episode. So thanks for watching.

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