0:00
Well, the blank page is scary because what's on the page is never as good as what's in your head.
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Yeah, we're all scared of judgment.
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We're all scared of failure.
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The fact that we're all scared is blocking all of us.
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Every project has a trough of despair.
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You are so productive with all the things that you've done.
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The Daily Dad, the Daily Stoic, the podcast. I mean, it's crazy.
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I'm a big believer in writing.
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To think you figure out the idea in the process of writing. Don't lose momentum. Yes.
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The biggest lie in the world is I'm going to do it in the morning.
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You had this dream and it was like 10 9 8 7 6 blastoff and then you woke up and you took that as a sign that it was time to start working on the book.
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I have like a biography project I'm going to do.
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I know what I'm going to do and I know who it's going to be about and Ryan Holidayiday, one of the world's most prolific writers.
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And the volume of his output, it dawned on me as I was prepping for this episode.
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He's published 16 books, written a newsletter every single day for the last eight years. He has 1.
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7 million YouTube subscribers, and then he also ghost writes and runs a creative agency. It's insane.
1:06
So, what's this conversation all about?
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As I was preparing for this episode, I was sleuththing around looking all over the place, and I found this clip that Ryan recorded the week after one of his books came out.
1:16
And I'm about to play the clip for you, but basically some backstory, some context is his editor called him to congratulate Ryan on hitting the number three spot on the New York Times bestseller list.
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And you'll notice in the clip that Ryan, he responds and he's already halfway done with his next book.
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And that is Ryan for you in a nutshell.
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He is a beast of a creator.
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And this episode is all about how he generates momentum. Hey Steve, you made it. I made which one?
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You play two number three. No way. You made it. The New York Times list. You made it. That's fantastic. Congrats.
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It's a great way to kick off the series, I think. That's really clear now.
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That's three books in a row for you at the time. So, yeah. Very exciting, Steve.
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Well, that's amazing news.
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And I'll get back to work. All right, man. Okay. Thanks. Congrats. Bye.
2:08
So, the thing that I want to start off with is my favorite video, okay, of yours is there's this clip where I think that you were working on Discipline is Destiny and you get a call from your editor that Courage is calling was number three on the New York Times list and I'm like, "This guy is so hardcore.
2:25
He's already starting the second part of his next book."
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I should be getting that call today or tomorrow. Nice.
2:31
Um, and I've I've gotten enough of those calls and I would say invariably it's never as good a news as you would like it to be.
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And I just found like the antidote or the insulation from that disappointment is just to be working.
2:48
Like I found so I got I had a weird experience.
2:50
So when the obstacles away came out, it it did okay, but it didn't hit the list.
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It should have and it didn't.
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I found out later it was I think it was like um a categorization error like how they what kind of book they said it was disqualified for some list or whatever.
3:05
But anyways, so Obstacles away came out and did okay. Not amazing.
3:10
But I had already sold the next book.
3:10
I sold what became Ego is the Enemy.
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So I was working on Ego as the Enemy when The Obstacles the way it came out because there's always a big lag like for right thing right now.
3:20
Uh, I mean, I finished the first first draft of it in January of 23 and then and then I spent about a year fiddling with it, but like it's it's been this, you know, for several months because it has to go to the printers and stuff.
3:33
So, um, there's a lot of dead time between projects and I've always found that instead of taking an off season, if you just start on the next project, you're insulated as far as how it how it does.
3:46
So, so anyways, what I noticed is The Obstacle came out, did okay, and then I was working on the next book, so I didn't care.
3:53
And then about a year, year and a half into it, it really started to do well.
3:59
Like it it the New England Patriots had read it and started going through professional sports.
4:03
There was a big article about it and so the book really started to sell.
4:06
Like it sold so many copies it sold out uh on Amazon.
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And also, I didn't care cuz I was writing Ego's Enemy.
4:15
So, and I was like, "Oh, this is I" So, it was this accidental process where it protected me from disappointment and then it also protected me from, ironically, from ego because you're just doing the next thing.
4:29
And so, I try to always start the next project and be not just be in the next project, but I like usually the sales results come in like the Tuesday or the Wednesday subsequent to the launch.
4:43
And so I'm like I better arrange my schedule so like I'm working in that period or you know you are susceptible to good news or bad news and and you the the good news is not any less damaging like you find when something's going really like I' I've found days where like some big press hit happens or something launches and like you spend all a kind of like in an excited days like refreshing or thinking about Yeah.
5:17
And and like what you're not doing is working and so you it ends up costing you like a day for this weird ephemeral mood that's not like doesn't last.
5:31
So I I just try to just always be doing the next thing.
5:33
One of the things that you said that I really resonated with was you were talking about your first book, trust me, I'm lying.
5:38
And you were saying something to the effect of if there were 100 units, you got 90% of the units of satisfaction from how well the book did and 10% 10 units from how hard you worked on it and you want that to flip over the course of your career. Yeah.
5:54
Look, if you derive no satisfaction or enjoyment from it being out and people liking it, why did you do it? You know what I mean?
6:01
like you might as well have just like kept it in a drawer and just said this is totally for me which you know some I guess some creative projects are only for you.
6:10
You like you made choices from putting a cover on it and to writing marketing copy and doing interviews.
6:15
You are like by definition you said you want it to resonate and reach people or you wouldn't have done it.
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But at the same time, the the vast majority of the win should be on terms or conditions of your own making.
6:31
And so, yeah, I I would say it's been a process of flipping.
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And I may be a little too far in the other direction now.
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Like this one, um I probably uh I I think it'll be maybe sell the most or the second most of any of the books.
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And I certainly got the most media.
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Like I was just in New York doing a bunch of stuff and it there was a part of it that felt a little disassociated because I wasn't thinking about like I I was just sort of deliberately not thinking about what any of it meant.
7:06
And there's a part of that that can be kind of a form of ingratitude or disconnection that I don't think is good.
7:12
But largely you want on a creative project because so much of it is outside of your control to define success as much as possible to things that are up to you.
7:24
So like is it the best thing that you wrote?
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Did you leave it all you know in the pages versus whatever?
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Um was it creatively fulfilling?
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Did you like I I've even tried to measure my projects now like how um was this less disruptive in my life than previous projects?
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Like did I just get better at being a normal person while I was doing it as opposed to it like consuming your life?
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So there's just like things like ways that you want to come to define what you're doing that are more and more up to you.
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And then the irony has been like as I've gotten there, the level of success has dwarfed the things that I used to take so much like pride and satisfaction in.
8:14
And I think that's because I'm instead of spending that energy just like sort of hoping or emoting out into the world, I'm spending it like on the thing when it makes a difference, right?
8:31
What had you make the decision to be more of a Bob Dylan prolific quality and quantity type person versus like a Robert Caro I'm going to hunker down and I'm going to publish five or six books in my life?
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Well, I would say a couple things.
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F first off, I would say the economics or the uh possibility of being a Robert Carrow may or may not exist.
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Like I think Robert Green is one of the last sort of big authors, especially in non-fiction, that can spend years working on a book, put it out, and it just like sells to lots of people.
9:04
Like I I in the same way that like they don't make movie stars like they used to.
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Like the reality of what being an author is is different because the number of books that exist is different and our relationship with books is different and our cult like you could be a Robert Caro when they used to have authors on late night television shows.
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Not that he's been on them, but like there there used to be a whole culture in which books and ideas were surfaced and discussed in society and a lot of that's gone away.
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And so I I think the economics of of how you are the industry are different.
9:41
But I don't know I um I I write shorter books and I write books that are appealing to a different kind of audience that that that require a different kind.
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Everyone I talk about in my books is dead for the most part.
9:58
It's I don't need to spend hundreds of hours researching um you know all the people that grew up with Lyndon Johnson or something. But I don't know.
10:08
Um I I definitely am on this book.
10:12
I slowed like I took an extra year which I don't normally do.
10:14
Um, and there was, I think, some benefits to it, some some downsides to it, but I'm I'm more a believer that quantity is a way to get to quality.
10:28
And I think a lot of people uh there's a there's an expression in football that if you uh don't get out of shape, you don't have to get into shape, you know, like it's easier to stay in shape.
10:37
And and like I think the pauses between books are really hard.
10:42
And I've seen a lot of people I know maybe people we've interviewed where like a book will happen and it'll be a huge success and because they didn't go on to the next thing.
10:52
It becomes harder and harder to start that next thing and and then it becomes harder to get to get and stay in the rhythm to to do it.
10:59
And so like I'm just been a believer of like you just keep doing it and you stay at it.
11:03
I'm I'm just staying in shape for as long as I can stay in shape and then at some point the wheels will come off. Sure.
11:10
You've also spoken about how that it seems like the lows have gotten less low.
11:16
It seems like early on as you were writing there was a real sense of I don't know the success of the book or maybe the success of your writing you'll have better words for it was very tied to your sense of selfworth and that seems to have gone away a little bit. Yeah.
11:37
I just needed to go through hell a few times, learn this on my own to get out through the tunnel.
11:41
I mean, there's really only one way to get confidence and that's to earn it, right?
11:45
I think any any kind of confidence that's not earned is is probably better defined as ego.
11:51
And so um one of the things you you get from having done it is the sense that you can do it.
11:59
Like you know that expression trust the process.
12:01
I think we kind of throw that out.
12:03
Um like trust the process.
12:06
Well, it's very hard to trust a process that you have not been through.
12:10
And so when you have been through the process, you you can trust it because you've felt all the parts of it, right?
12:19
And so, you know, Paul Graham talks about the trough of despair. Yeah.
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Uh, every project has a trough of despair.
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And you you feel it in a book, but the first time you feel it, you're like, "What is this?"
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And then the second time you feel it, you're like, "Oh, is this is it different this time?"
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And then, you know, the third time you feel it, you go, "No, no, no. This is what happens."
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And so, the more you do it, the more the the rhythms of it you have.
12:46
And I think one of the hard parts about writing is that like you're always starting your last project doesn't write your next one.
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So you're starting from nothing.
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So that first time you start your second book or when you're midway through your second book, one of the really hard parts is you're comparing it to your last book because and and you're remembering you're you're comparing a finished product and a halfbaked product.
13:12
But once you've done it a bunch of times, you're just more comfortable being in the middle of a book and you trust your ability to find your way out of it.
13:22
I love that answer, you know.
13:24
Um, and so I I'm just like like I'm working on this one now and like I don't know if it's good or bad right now, but I know it will be good.
13:33
Like I know that I'm very confident in my ability to to make a salvageable publishable book out of this material.
13:41
And I know that I won't quit or be rushed before that happens.
13:44
And so there is a level of chill that I didn't have before because you don't know. Yeah.
13:51
A cool example of this watching one of your vlogs before is you're working on Discipline is Destiny and early on you wanted to orbit it around Queen Elizabeth. Yes.
14:02
And you're thinking about Queen Elizabeth and you're like, I feel like there's going to be something there.
14:04
And you had read some mediocre books about Queen Elizabeth and you have this idea where you're like, I need to just keep the momentum going.
14:10
and you're like, I'm going to put a pin in the Queen Elizabeth stuff and I'm going to keep going.
14:14
I'm going to keep writing.
14:16
And that is a good example, I think, of a kind of place where you had faith in the process.
14:20
You're say, I'm going to put a pin in this.
14:21
It's going to resolve itself and then I'm just going to work on other stuff.
14:23
Well, so I had an experience on discipline is destiny where so and I've been doing them more or less, this is the first year in a while where I would start it on my birthday.
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I would take all my note cards and I'd be like, "Today the project starts."
14:37
And so I'd be like, "These are all the note cards.
14:39
let's see what the book is, right?
14:41
And so you have years of research, but you don't know what it's going to look like, uh, the order things are going to go in.
14:47
You you you just have been throwing stuff in a doom bucket, uh, and saying, I'm going to sift through this later.
14:54
And so, um, when I first started going through discipline, I was just really tired and I'd been doing basically a book a year.
15:03
And I wasn't sure, I didn't have a sense of like who the characters would be.
15:05
I this is well before I I'd even settled on someone like Queen Elizabeth being one of the main characters.
15:11
So I'm going through the cards and I'm like is there a book here?
15:16
Am I going to need to ask for more time and I'm going through the cards and I find this card one day and I still have it in my office and it it was a white index card and I wrote on it with red Sharpie.
15:29
I said when you go through these cards in June um it's going to feel like there's not a book here but there is.
15:35
just keep going through the cards and you'll find it.
15:36
And I don't know why I wrote that and I don't honestly know when I wrote it, but it was like exactly what it was just a reminder. Okay, trust the process.
15:44
Um, so I did I just I'm going to just keep going through these notards and I'm not going to judge it as good or bad or I'm just going to do the thing and I'll let it happen.
15:52
And you know, maybe a couple days later I did think of her or I thought of someone else and and suddenly patterns started to emerge.
16:00
That's the cool part about going through your research is you realize you've been making connections but not realizing you've been making connections.
16:08
So you'd written down 20 things on the same theme but you'd done them months apart.
16:12
So they felt like individual observations when actually what was coalesing was a chapter or a theme.
16:19
And so anyways the book does start to come together and it came together much faster than I thought and ultimately the book was different but better than I thought and and sold better than I thought.
16:28
But what I loved about that was like it was like how did I time travel that way?
16:35
Like how did I send a note to a future version of myself?
16:36
And that's what the process is is just like look, you've been through this before. Don't second guess it.
16:44
Just do the thing that you need to do and and it'll come out of the other side.
16:47
And and I'm a big believer though in momentum.
16:53
And so what was what the reason I hit pause on that chapter is that I knew I just didn't have the material that I needed.
16:59
And so to to try to keep going without the material would have been discouraging.
17:05
But I did have material for these other things over here.
17:07
So why not just do that and then all the while also be reading about this person?
17:12
And I probably for Queen Elizabeth that I mean that's probably like a 5,000word chapter and I probably read 5 to 10,000 pages on her and so that took a while and I had to ask around and I you know there wasn't sometimes there's like a if you want to write about Lyndon Johnson all you have to read is the Robert Carol book.
17:33
Sometimes like someone's got someone like that writing about them.
17:37
Then other times they don't and you have to read a bunch of stuff and you find one thing.
17:40
You'll read a 800page book and you'll find one thing in it.
17:44
Um but eventually I found what I needed for her and uh that that did come together.
17:51
But the forward momentum was more important than chronology.
17:57
How do you feel like your writing is different now in the Stoic Virtue series on the far side of having written the children's books?
18:03
Like I was just playing around with them in the in the bookstore next door and you wrote two of them and they're very very very simple. They're short.
18:11
How did that change your writing process?
18:15
Oo, that's a good question.
18:15
So I wrote those during the pandemic.
18:16
Um I'd had some idea for doing a kid's book about stoicism and then suddenly I just had like a bunch of time and my kids were were younger and so I was like you know what I'll just tell I I just I did it every night.
18:28
I like I I had um actually I used this is funny.
18:32
I use like so when you when you do um signed pages when you do signed books they give you what are called tippins.
18:38
You know what a tipin is? No.
18:39
So a tip in is like a page this is this would be this page in this book.
18:44
They they cut it around but no they don't paste it in they bind they this just goes in the binding when they when they bind the book. Oh.
18:53
So I I have like some that like that are actually the it's actually this title page.
18:57
Uh they just sent me like 15,000 of these and I signed those. No idea.
19:01
So, anyways, what uh I have just tons of them left over and I use them like to do note cards or I do I I write notes to-do lists on them and whatever.
19:09
I just took a stack of pages and I I would tell the story every night to my son and I would write like a new version of it every night before I told it to him.
19:19
And so, the story was just getting more and more refined.
19:23
And it was I think I think the story is maybe only like 500 words or 800 words or something which is a lot for a kids book but not a lot for a fable.
19:34
Um but uh but I what I found doing it was like the the process of doing it over and over and over again and having a child in the audience and like cutting whenever they got bored and I never produced out loud and iteratively like that.
19:53
So that was really interesting just the process of pairing it down and down and down.
19:56
And I had a similar experience then because then he he asked me to read him one of my books and I think I read him obstacle or ego or just chunks of it.
20:06
And what what struck me about it was how um how much less was in the writing. Like it was just less.
20:17
It was just tighter and uh quicker.
20:20
And I so I had this experience of of noticing, oh, okay, one of the perils of writing more and becoming more successful as a writer is that you can get kind of long- winded and indulgent.
20:37
And so, what's the balance between getting more precise and more uh nuanced, but also not becoming like a windbag?
20:46
And so, that's a great question, you know?
20:49
So, so like I noticed each one of my books was and then I stacked them all up and each one was like longer than the one that came before.
20:54
And in some respects that's better because there were things in the obstacles away like I just read I'm just doing a new anniversary edition and I'm like oh um it's I wouldn't I I don't accept the bluntness of that saying like I would never allow myself to say that.
21:13
Tell me more about this now that you're going through that.
21:14
What are some of the places that you feel like you've gotten way better as a writer where you're looking and you're like capital C cringe, you know? Uh, yes.
21:22
I've And I've had I had that process with Trust Me, I'm Ly, too, because I did the paperback like a year later and then I did a 5-year anniversary edition.
21:30
So, I did that book twice and then I had to read it twice. The audio book. Yes.
21:35
Um, so I think so the the big thing that makes you cringe when you read old things that you wrote is actually less stylistic and and a lot more to do with certainty.
21:50
Certainty does not age well.
21:53
So you are saying things that are a reflection of your experience up until that point.
22:00
Then if you have 10 years more experiences, you go it's a tad more complicated than that.
22:04
And so part of the reason it's just tighter and leaner is that there's nuance that was not there.
22:11
And so um I I I think I I had there's there's changes I wanted to make there.
22:18
There's also um I think I've just uh a decade more reading and learning.
22:26
So there's like I had a stack of note cards of things about how obstacles are the way that I wished I'd known in 2013 when I was writing the book.
22:36
So there was stuff I wanted to put in.
22:37
And then there were other examples which may have been like the best one that I had at the time or I was settling and it just didn't hold up the way that I wanted it to.
22:48
So there was some, you know, stuff I took out and replaced.
22:50
Um the interesting thing was like the acknowledgements like um is the acknowledgements something you update or is it a reflection of like reading the acknowledgements you're like these are all the people I was grateful to at this moment but I think differently about some of the people I think I understand the relationship different and and so but it's also this like product of its it it was pure and authentic in that moment.
23:18
But anyways, it's a it's a weird experience to go back and read your own work, especially work that you've published and lots of people have read. Yeah.
23:28
You were talking earlier about that balance between the precision and the nuance and not being long-winded.
23:34
How have you learned to manage that over time?
23:37
Well, what I So, with Right Thing Right Now, it was it was basically supposed to be the idea was it was going to come out in September of 203.
23:46
So, it was supposed to be more or less it was like turned in in January and then I had some ideas for some other projects I wanted to do like next books and so I sold those to my publisher and then I said I'll sell you these books but I want an extra year on right thing right now because it's just not sustainable for me to do like these other books after.
24:05
And also I think we're just like asking too much of people like let's like let's let the audience catch up a little bit.
24:12
audience catch up a little bit. uh it's just a lot like I I mean I wouldn't even read this many books from one person right and so so I was like let's take an extra year and so which actually I I in discipline I I read this thing about Joyce Carol Oat she like finishes a book and then she puts the she says she puts
24:30
the novel in a drawer for a year before coming back to it and starting the process and I was like what would that be like so I didn't want to do exactly that but but basically I was it it could have been done in January and then gone into production to come out in the fall and instead it's coming out June the follow of the following year, right? Um so I
24:50
Um so I let it sit for a bunch of months.
24:53
I just kept researching and coming up with ideas.
24:56
So I had a stack of things I wanted to do.
24:58
But when I started going through it that summer, um, mostly what I did was cut.
25:03
Like any time two words were there where one could do, then I was making that.
25:10
There was a bunch of chapters that I thought were distinct, but actually became stronger if combined.
25:16
And so it I think I think it was like it was maybe 85,000 words in January.
25:27
and I think I got it down to like 70 or 65 and then back up to 70.
25:33
So, it was this process of like cutting and combining and then making choices and then after I'd done that, going back and reading and then editing that version and adding in all the things that needed to be added to make that version good.
25:52
But mostly it was a process of going, okay, I want it to be leaner and tighter, which means I got to make a lot of cuts and then I have to, you know, you can't just cut and then just leave blank spaces.
26:03
You got to mend all those those incision points back.
26:06
But but it was mostly just a process of cutting.
26:08
So I'm just trying to be much more disciplined about what I leave in.
26:15
There's a piece that you wrote, I think about a decade ago, called How to Write a Great Essay.
26:20
And you have this idea of create that the introduction is the creator of the shape. Yeah.
26:26
The introduction is is the creator of the shape. Tell me about that.
26:29
Well, I think when you're writing an essay, uh your your sort of standard American like five paragraph essay or whatever the the introduction is where where you tell them what this is going to be and you're outlining there.
26:42
And so when I'm thinking about the intro, I'm I'm trying to introduce like the central this is more in a book.
26:50
I'm trying to introduce like the central metaphor of the project.
26:54
I'm trying to introduce the main thoughts that are going to be in there and like this the central conceit of the book.
27:02
So I think it's very hard to figure out shape, structure, form as you go.
27:09
You got to figure that out from the beginning.
27:11
um or else it just becomes unwieldy.
27:14
And so to me that both internally you have to have cracked the whole thing before you get started or most of the thing before you get started and then your intro should be a codification of what that's going to be. Interesting.
27:28
Yeah, there's a few I've been looking a lot at this.
27:30
So in Kanye's Yeus album, the opening sound is super different and like even just in the first like 7 seconds, you're like, "Okay, this is a different kind of Kanye."
27:45
So you see it there and you're getting so much so fast.
27:48
also like the beginning of Lolita where Nbakov is talking about how he sees this young girl.
27:55
You're like, "Okay, what's going on here with the music and the poetry and sort of the but also just the horror of this person sort of juxtaposed with the beauty of the writing." Yeah.
28:03
And then the other thing that I was looking at yesterday was Moringer wrote the book, but it's the Agassy Open biography and both in the prologue and the first chapter, it's setting up Agassi's sort of hatred of tennis and you're like, wait, what is going on here?
28:22
And I just look at those examples of there's so much that you're communicating like in the first 10 seconds of an experience that like you're saying is like the cotification of what's to come. Yes. Yeah.
28:33
And and realizing first off, most people uh are not going to make it all the way to the end.
28:38
So the beginning has to be very powerful.
28:40
It's got to sort of grab you by the throat and and make a statement I think is very important.
28:46
Like uh yeah, I just think a lot about that.
28:49
And and so I think this is in some ways why some authors, it's not how I do it, go and write the intro last.
28:56
It's because they wanted to get the you're the intro is like defining the thing like there's this really hard project.
29:03
Book proposals are insane because like you're having to explain a thing that you haven't done yet.
29:08
They still make you do book proposals. No. No.
29:10
But I mean I've done book proposals before and I've helped other people with them.
29:13
But like the idea of a book proposal is insane because you're like you're describing this thing that you haven't done and doing it like you're I'm a big believer in writing to think in the sense that you you figure out the the idea in the process of writing.
29:33
You have your your thesis or your argument, but like if you could do it in any other way, you would just not do it, right?
29:40
like it's it's a there's something that comes out of the other side of a process of spending years with an idea and and tens of thousands of words with it, right?
29:48
And so um you you are being asked to like define this thing that is undefinable at that point.
29:57
And so the intro to me the intro privately is like my sense of it in that moment.
30:04
And then I'm obviously going to go back and make it closer to what the final product ended up being.
30:11
But it's a it's a tough it's a tough thing.
30:14
Um I I try not to be too precious on intros these days.
30:16
Just again the idea of forward momentum.
30:18
Like I'd rather just get most of what I have down and keep going and then come back to it.
30:28
Do you feel like you're working towards something?
30:29
Like Steinbeck always said, East of Eden was like his late life masterpiece.
30:33
Do you feel like you're working towards something like that?
30:36
Like there's something that you want to produce that you just don't have it in you, whether it's skill or knowledge or experience.
30:42
Uh my version of what you're talking about is I I I think Michael Lewis was born to write uh the big short.
30:50
Everything in his life was leading up like his background in finance, all his other books, all his characters, and then the economic history of the United States is leading up to 2008.
30:59
and then the book that explains this thing, right?
31:04
And so that's a person sort of meeting their moment.
31:06
That's, you know, uh decades of experience and writing and all these other amazing books lead like the perfect author and the perfect story intersecting.
31:15
Um I would like to think we all have that or that we should all get lucky enough that those two things would intersect.
31:24
And so I do have some idea of like um I think you want to think your best work is in front of you.
31:31
It would be weird for it to be behind you.
31:33
Um again, this is different than sales, but like I I would like to think that it's all preparation for some project I can't even conceive of yet.
31:45
There's there's this idea in the stoic that Epictitus said that the point of philosophy was to be able to say to like whatever life hands you like this is what I trained for and I would like to think that there's some project that I haven't thought about then you're like this is it this is it but I'm that's not what makes it all worth it.
32:02
It's just that would that's a nice thing to keep you going.
32:09
I want to walk through a specific sentence with you.
32:10
right here at the top and you've spoken about why you like this sentence from Marcus Aurelia.
32:15
So, I want to basically break it down with you. Uh, okay.
32:20
So, he says, "We should remember that even nature's inadvertence has its own charm and its own attractiveness.
32:24
The way loaves of bread split open on top in the oven, the ridges are just the byproduct of baking and yet pleasing somehow.
32:30
They rouse our appetite without knowing why.
32:32
Or how ripe figs begin to burst.
32:34
and olives on the point of falling.
32:37
The shadow of decay gives them a peculiar beauty.
32:41
Stocks of wheat bending under their own weight.
32:43
The furrowed brow of the lion.
32:46
Flexcks of foam on the boar's mouth.
32:48
What I think is to me amazing about these uh this writing is first off you have the most powerful man in the world writing this journal to himself that he's never expecting to be published.
32:59
And I mean we're reading in in English.
33:01
That's the Gregory H translation.
33:01
But he's writing he's he's Roman so he speaks Latin but he's writing in Greek the language of philosophy.
33:08
So he's writing in his he's writing that [ __ ] good in his private diary in his second language.
33:17
Um I just find it spectacular.
33:22
Um and the vividness of it and the beauty of it.
33:25
He he clearly to Marcus there was something similar between the poet's eye and the philosopher's eye.
33:31
He's just walking through the world and he's noticing these little things that are not supposed to be beautiful but are.
33:37
I mean, you could argue the most beautiful scene in the movie Gladiator is when he walks through the field and he's dragging it.
33:43
That's he's evoking that, you know, privately to himself.
33:45
I wonder if that's where the the cinematographer gets the idea for that scene.
33:51
But, um, I I think what's so powerful about it is is just the the beauty of it.
33:56
And there there's this sense that Marcelius is depressed and dark and nihilistic and that meditations is a dark book.
34:04
But like I think when you read things like that, you see that he wasn't.
34:07
He's finding beauty in these I mean what's be if you've ever seen a wild boar.
34:12
Have you gone boore hunting in Texas? Yeah.
34:14
It's it's not a beautiful animal, but he somehow sensed this thing. Like that's cool.
34:18
Um and then to think of like a l like I mean lions are not native to to Europe.
34:23
So, he's looking at this imported lion from Africa and he's just he's just got this sense. He's looking at things. Um, I like that.
34:30
And then I actually, as I've come to think of this passage specifically, how he's talking about how he says bread is uh, you know, the baker puts the bread in the oven, it cracks open in top.
34:44
He says we don't really know why, but he says it's nature's inadvertence.
34:47
nature's inadvertence. like this isn't this isn't what this isn't an aesthetic uh deliberate aesthetic thing but accidentally happens and we love it to me that's kind of even I think you could argue that meditations is itself an
35:02
example of that so you have this guy writing to himself for his own private edification accidentally producing a unprecedented work of literature that lasts for 2,000 years I love that I don't know if this is why you brought up this sentence at all. But that that's I just love that so
35:19
But that that's I just love that so much and I think that has slowly informed like I think stylistically I I've taken as much from Mark's writing or specifically the Haze translation as uh I did philosophically. I love that. Okay.
35:32
So tell me the stylistically how has it sort of bled into your words?
35:38
So you take the the first the the famous first passage not not the the debts and lessons but the the first famous passage.
35:45
He says, "When you wake up in the morning, tell yourself the people I deal with today will be meddling, ungrateful, arrogant, dishonest, jealous, and sirly."
35:51
This is like the powerful sort of meditate in advance.
35:56
Don't be surprised by how awful things can be.
35:57
But he's saying you, but he meant him.
36:01
And so there's something he he's writing specifically to himself, but it somehow becomes universal.
36:07
Like there's something about meditations which on the one hand should be totally unrelatable.
36:14
You have this old white guy from thousands of years ago who lives an utterly unprecedented life.
36:21
Uh should be totally unrelatable speaking in a foreign language speaking about an obscure ancient school of philosophy and somehow it's like timeless and relevant and it feels like it's talking to you directly.
36:33
And to me that's a a reminder that like sometimes the most specific art is actually the most general or the universal.
36:39
So I think I took a lot from that.
36:41
And then you know what's unique about meditations is it doesn't have any kind of formal structure.
36:45
It's just like you dip in and dip out of it and it's these like kind of little little passages that somehow are not related but are related. So I don't know.
36:53
I I just um I just took a I I just took so so much from from how direct it is.
37:03
You know what's a funny thing though?
37:04
So we and I don't remember what page it's on in the Daily Stoke, but like we had to do our own translations for the Daily Stoke cuz we couldn't use this one.
37:11
And it says, you know, um when a a stock of corn bends low under its own weight.
37:16
And the editor um goes, "Guys, this is obviously an incorrect translation because um corn isn't discovered in until the the New World is discovered in the like the first corn we get is like the 1600s maze from the Native Americans."
37:32
But in England, in English, like in an English translation, corn uh is what the English used to refer to any type of cereal grain.
37:43
and you realize, oh, okay, the translator has so much choice over what they put and how they put it.
37:49
And I just like I feel like one of the formative lucky breaks of my life is that when I went on Amazon in 2006 to buy meditations that I got the Haye translation instead of some other one.
38:02
I had no idea what I was doing or why.
38:06
That's the one that came and that's the one that spoke to me.
38:08
And there's something, I think, poetic and lyrical about that translation that is not in a lot of the other ones. Nice. Yes.
38:15
Hey, quick break from the episode.
38:15
I got to tell you about this project I've been working on.
38:19
It's called writing examples. So, what is it?
38:20
Well, what I've been doing is I've been breaking down and deconstructing the greatest writing in history.
38:26
Sentences, paragraphs, oneliners, poems, whatever you name it.
38:31
And what I've been doing is I've been saying, "What is it that makes this piece of writing work?
38:35
and how can you apply it to your own writing to make it better.
38:39
I publish one every single week.
38:40
So, if you want to get it by email, go to writingexacamples. com.
38:44
Go to the top of the page, enter your email address, and I'll send it to you whenever it goes live.
38:47
All right, back to the episode.
38:51
Why do you have I dreamed a dream on here?
38:53
Because you listen to that a thousand times while you were writing one of your books, right?
38:57
I tend to listen to songs over and over again when I'm writing. Do you do you do that? Yeah.
39:01
You get into a real trance, don't you? Yes.
39:03
and my music tastes are very varied, but I I find there's something there's something about when the music ceases to begin and ends and it's just the loop of the thing and you're kind of just lost in the in the hook of it.
39:19
Um, and you can it gets you to some sort of heightened emotional state I find to to be very conducive to writing.
39:29
And then also there's not any bad songs, right?
39:34
Like if you're just like listening on shuffle, you know, you could be like here and then it could change.
39:37
The mood can like I think there's something stabilizing about writing at a very similar mood.
39:43
And then I think also the uh the the lyrics kind of get burned into your head in the same way that like reading a book hundreds of times gets burned into your head and then there's kind of a a recall that can come from that.
40:00
Are you a someone who would memorize passages and quotes or are you like I'm going to read it and move on?
40:05
No, no, I definitely memor I don't deliberately memorize but like it from my repeated use of stuff it it gets in there and it's like bouncing around.
40:14
One of my favorite metaphors in the English language is that to know something to memorize something is to know it by heart and that it like seeps into your heart.
40:22
I think that there's something profound about that. Yeah.
40:25
Montaigne also said though to to know by heart is not to know.
40:26
Oh, I think he's saying that just just because you memorized it doesn't mean you know it at school, right? Yeah.
40:35
And and so there's something also about like it sort of rattling around in there and then you you get it some at some some level you have to get it more than just knowing it. Of course.
40:49
Let's talk about reading.
40:49
So there was a conversation that you had many years ago. Here's what you say.
40:52
The best piece of advice I've ever got about reading came from a secretive movie producer and talent manager who' sold more than a hundred million albums and done more than a billion dollars in box office returns.
41:02
He said to me one day, "Ryan, it's not enough that you read a lot.
41:05
To do great things, you have to read to lead." Yeah.
41:10
What is it about read to lead that really resonated with you?
41:12
Well, the Truman version of that quote is not all leaders are not all readers are leaders, but all leaders have to be readers, right?
41:19
Um and the idea that you're going to learn things by trial and error I think is very expensive when you are in a position of leadership or responsibility.
41:34
So the the idea is to to learn by trial and error is very expensive and uh to be a leader you have to learn as much as you humanly can from the people that came before you.
41:45
And so I think what he was saying and what I've always taken is that you you have to read the things that challenge you and you have to read about sort of big moments in history and you also have to have a a deep experience.
41:58
Um you you have to borrow all the experiences of that that have cumulatively been in your space.
42:05
General Mattis, have you heard General Mattis's book calls on Chaos? It's very good.
42:09
He said um he said um that you know it's unconscionable for a military leader and speaking of what we're talking about to to to not read about things because when they learn by trial and error they're filling body bags is what he's saying right like the stakes of what they're doing is very high.
42:27
Um, so to have not to have learned something uh that that you could have learned by a book by screwing up is, you know, very costly for someone.
42:39
How's that for a turn of phrase, by the way? It's crazy.
42:41
Body bags like Yeah, it you could say it's costly or you could say it's body bags.
42:47
Yeah, the phrase Well, so and but the phrase he said that I think about a lot, he said, "If you haven't read hundreds of books about what you do, you are functionally illiterate.
42:58
And so, you know, obviously, you know, I can read, but what matters is that you did read, you know, and that there's the Twain thing about I don't think he actually said it, but about there's no difference between someone who can read and someone who doesn't read.
43:11
Um, and so the idea of being functionally illiterate on a topic is really interesting to me.
43:16
Like when I sit down to write about something, obviously I have my experiences, but my experiences are pretty low stakes.
43:24
you know, I if if I want this thing to have weight or to matter or to hold up for a breadth of experiences, I got to make sure it's confirmed at like the real testing point of, you know, the human experience or the laboratory.
43:41
And so it can be easy as a writer to to just like find an example that confirms what you want and to just use it and but to do the work and go, okay, what's what's the full story here?
43:54
what let me look at this from three or four other angles.
43:56
Uh what's something similar?
43:58
And that kind of I think my books have gotten better.
44:00
Um in that and this is maybe also why they're getting longer is that they've just got I've gone deeper and deeper on each thing.
44:09
Whereas I might have been satisfied with an off-handed quote that more or less said what I wanted to say before, you know, now I I enjoy the process so much more that I'm like I'm No, no, I'm like going down this rabbit hole and and I want I want there to be a lot of stuff that I wanted to include that I didn't get to include versus this is all that I had, right?
44:37
There were a few things I noticed from the way that you read that I'm instantly going to apply.
44:41
And the two that stand out was the first one is, and this probably applies more to non-fiction, like if you're talking about that battle, you go to Wikipedia, you look at what happened, you figure it out, you get the narrative arc, and then that way once you're reading, you're just reading to understand, figure out why, what happened here. Yes.
44:58
Rather than trying to say, okay, let's let's go for the adventure.
45:00
And that's a deliberate decision. Yeah.
45:03
And then the other thing is really taking the bibliographies seriously, knowing those well and saying what are the patterns and then I love the idea that you shared of you said trace a subject back to its core.
45:14
Trace a subject back to its core.
45:16
How do you get back and back and back?
45:18
And it's like you can almost think of like the web of links in a bibliography and how do you find the thing that is the most at the core?
45:25
core? Yeah, that's one of the interesting things is when you have a decent uh breadth of of classical knowledge like you've read uh you know most of the sort of core western cannon um you start to see it in other things and I kind of re I got there the other direction which is I would read modern stuff and then I'd go where's this come from what's this come from and then I traced it back but like yeah you realize
45:53
okay all of these things trace back to Aristotle or Plato or whomever uh Herododus Thucidities and um yeah you want to trace the idea back to its core like uh you can read about uh I don't know the rising conflict between China and the US but if you haven't read Thusidities you're not going to understand what the people who are talking about it now are basing all their assumptions on. And so yeah, I try
46:23
And so yeah, I try to I try to go back and I I tend to I I tend to try to find the oldest books on that topic.
46:33
You are so productive with all the things that you've done.
46:38
It's not just the books, but it's Brass Check.
46:40
It is the Daily Dad, the Daily Stoic, the podcast. I mean, it's crazy.
46:44
What is your schedule like this week?
46:46
like really just to brass tax like how are you organizing it and constructing a life that allows you to do this?
46:55
This week's a little weird cuz uh it's it's I'm just coming off the book tour and uh my my kids just started summer school, but like I took uh I got up early with the kids um sort of did breakfast, made school lunches, took one of them to school, my wife took the other and then because of where he was going, I ran this.
47:14
So, I ran after I dropped him off at school instead of like either before or uh later this afternoon.
47:21
So, I got a run in and then I I wrote for like an hour before I did this with you.
47:26
And then I've got a bunch of stuff to catch up on.
47:31
Uh I just had COVID so I was like isolating so I I managed to get caught up on like a ton of note cards that I had to do.
47:38
So, I have like a big I just have a big stack of like notes that I have to integrate into the manuscript that I'm working on right now.
47:46
And those are like So, explain that.
47:46
So, it's there's three steps.
47:48
So, you read the book, you have the stickies, then you take a few weeks away, then you only transfer the stuff that's really worthy. Yes.
47:55
And then now what you're saying is you have certain notes that you want in the book on wisdom.
47:59
And now you're trying to take the notes and put them into the book.
48:03
So, I I went through all the books, got the stack of note cards.
48:04
Some of these are for wisdom.
48:06
Some of them are I I uh I made some notes like on uh books I've already written like like that if I ever go back I'll put that in there.
48:14
Then I have some for future part.
48:15
So I just have this big stack of cards.
48:17
So like today I will go and I will file those cards where they belong.
48:21
So some of them are for chapters I haven't written in the new book.
48:25
So that'll go like in there.
48:28
Some of them will go in uh chapters that I have already written.
48:33
So, I'll sort of stick those I'll flag those so I know I'm just like they're basically like pickups and then other ones will just go kind of in the more general box to hopefully find a home at some point in the future.
48:45
Like I don't I don't know what that I just struck by something.
48:49
I don't know what it's for.
48:51
Um but but hopefully it's for something.
48:55
So that's kind of the that's kind of the process.
48:57
So like today isn't going to be a super productive day because I'm still, you know, putting out this book.
49:02
But um like I got I don't know 50ish minutes of like focus on this chapter that I was writing and I was actually doing something from the Eric Larson thing that I was just telling you about.
49:12
Um and so my kind of rule I just think about it as like did I make like a positive contribution today?
49:17
So like would it be nice to make several hours of positive contribution? Sure.
49:23
But like I re basically I I'd already written the chapter but the way I there's no I restructured it and reoriented and I'm adding this new stuff and so like some version of that will end up in the final product.
49:39
So like I feel I feel good about the contribution that I made today.
49:42
How much are you reading for style as opposed to content? What does that mean?
49:47
Like for example, I've spoken to a lot of authors who as speaking for myself, I would like to get better at describing things.
49:55
So what I'll do is I'll read David Foster Wallace. Sure.
49:59
And as I'm working on a piece, I'll go through David Foster Wallace and the content of the way that he describes the sink on the cruise ship is fine.
50:07
I mean, it's beautiful, but that's not really what I'm going for.
50:10
I'm like, but what is he doing?
50:12
What is the rhythm of the sentences, the word choice?
50:14
How is he bringing style into his writing?
50:16
And then what can I bring into my own? I would say none then.
50:20
I I don't really I have I don't really think that way that much.
50:24
I mean, there's definitely people I read and I go, "This is like amazing, but I don't think I'm I'm deliberately I don't think I'm deliberately seeking out style."
50:34
Now, um when I did, for instance, when I did Conspiracy, that was like the first time I'd ever done something in a very different genre.
50:40
So, uh, I I definitely read more in that genre and was thinking and taking notes about like sort of interesting devices or things that I might want to try.
50:52
And then I'm going to do a I have like a biography project I'm going to do in not maybe the next book. I'm not sure.
50:58
Um, but so I might read more like I I haven't I know what I'm going to do and I know who it's going to be about, but I haven't I haven't settled on what kind of biography it's going to be.
51:10
Is it going to be this thick?
51:12
Is it going to be this thick?
51:12
Is it going to be, you know, like a Rich Cohen style biography?
51:17
Or is it going to be Yeah.
51:20
a Doris Karns Goodwin style biography?
51:22
What are the differences?
51:23
Well, have you ever read Rich Cohen? I haven't read that.
51:25
He wrote like uh Tough Jews.
51:25
He wrote um he did that book uh you'll know I'm uh when I'm when I stop talking, you'll know I'm dead.
51:33
Uh and then but his his I think his best biography wrote this book called The Fish That Ate the Whale. Oh, yeah.
51:39
I saw that in the book store. I I love that.
51:41
It's a but it's a weird biography.
51:43
It's it's like it's it's kind of this like Gonzo style biography which I've always really liked.
51:48
Um so maybe I could do that or maybe I could do something that is much more you know your sort of established like big thick important biography. I haven't decided yet.
52:00
Um so I might that I'm not even there yet but I I might read I might be thinking more stylistically closer to starting that project.
52:10
What makes for a good biography?
52:13
Well, um I think the greatest biographer of all time is Plutarch.
52:16
Uh probably the longest lasting biographer.
52:18
And you know, his point was that you often discover more about a subject in an off-handed remark or a gesture or an encounter than you do exactly how many people were at this battle or exactly where it took place or exactly what time it was.
52:39
And I think the problem is that most biographers don't understand the essence of the person.
52:47
They only understand them as a series of facts and figures.
52:51
And they think that you just instruct a reader by assembling these and throwing them at them one person after another.
53:02
and they they they didn't quite understand what made them great or what made them terrible or why they we should love them or why we should hate them.
53:13
And so I'm I I tend to find that older biographies were very rarely do I read a new biography and I go, "This is worthy of being up there with those other ones."
53:26
And I I think it's because the the they're too scholarly and they don't understand why we read biographies, which is to understand people, places, moments, and then also ourselves.
53:42
I think that final one is crucial, of course. Yeah.
53:45
How do you balance vision and criticism in your books?
53:49
Well, it's interesting, right?
53:49
You It's It's harder to find negative criticism and then also there's more of it. It's tricky.
53:55
Like so the daily stoic email goes out to a million people every day.
53:58
If I wanted to just mainline positive and negative uh criticism, I could just open that every day, right?
54:05
And like I could just open the email address that those replies go to and probably break my brain.
54:13
So I try I try not to um I try not to get much of it at all.
54:20
Um, I yeah, I think I I have a sense of what I'm trying to do on projects and that's what I'm thinking most about.
54:30
But I I've had a I've had a weird experience with my books, too.
54:32
So, you you get edited less the more you sell because they just let you do what you want, you know?
54:42
And so I'm thinking about that on this one.
54:45
How I I haven't quite figured out how I want to do it, but like how how do you stay coachable and how do you seek out coaching?
54:55
To me, that's very different than feedback, right?
54:57
Like like what what you know what reviews say doesn't mean that much to me or you know what random people say it doesn't mean that much to me.
55:08
I in an environment where you could arrange it so everything is rubber stamped.
55:15
How do you not allow that for yourself?
55:18
If did you watch Enthusiasm? I love that show. Yeah. Okay.
55:22
I think last season he uh he's like selling a show to Netflix or whatever and he's like just don't give me any notes. And they're like haha.
55:28
And he's like just don't give me any [ __ ] notes. Right.
55:31
Like he's like I'm not joking. I don't take notes.
55:33
like there's a tension because like you know what you're doing and most people don't know what you're doing and you want to create an environment where you're creatively unencumbered.
55:43
Um and yet that's also a recipe for self-indulgence and laziness and I've always I I believe my my this is a huge digression but I think curb your enthusiasm is funnier than Seinfeld but also unfunnier than Seinfeld.
56:00
So Seinfeld is a much more disciplined show.
56:05
So basically everything in it is uh there's no bad moments in it whereas like Curb has plenty of moments where you're just like this could have come together better.
56:16
They started all these things that they then forgot about.
56:19
There's like a there's a a haphazardness to curb your enthusiasm which creates higher highs but lower lows.
56:24
Whereas like um Seinfeld is basically just like tight and perfect.
56:32
And so, um, I I don't know, you probably want some balance between the two extremes.
56:40
I think there's also a time for self-indulgence, which I would say is probably earlier in the creative process.
56:46
Like, you ever watch Get Back, the Beatles documentary?
56:49
So, when they're playing or when any musician is going, you're not like, "What is the audience going to like?
56:53
What are they going to like?"
56:53
It's no, you're just riffing.
56:55
You're like, "Yes, I'm feeling this right now."
56:56
I'm feeling this right now." M and then later on after that initial construction is done that's a time for notes hey is the compression right here whatever I don't know the words for music but I think it's also important to almost break down the process and say
57:11
this is when I'm receptive to feedback and also this is when I'm not so what I have learned is um you have to you have to do the hard work of figuring out what you are trying to do and to be able to articulate that to the people you are asking for notes from. So, if you just say,
57:27
So, if you just say, "Here's my book. What do you think?"
57:31
Um, or even even with your editor, you're just like, "Here's the book."
57:35
They're going to give you a bunch of notes.
57:36
And where I've had uh conflict with editors and where I've come to sort of assert certain power that I have is is knowing, okay, this is the book that I'm trying to write.
57:46
So, give me notes that help me do that.
57:49
Anything else is is of no consequence to me.
57:53
And so like on conspiracy which I'm very proud of I I went some rounds with my editor because I was very this is where I figured out I had to do that work.
58:04
I was like this is the kind of book that I am writing.
58:06
It's going to be different than most books in this genre.
58:09
I'm not I'm not interested in doing this.
58:12
I am interested in doing this. This is the book.
58:14
You cannot publish that book but this is the book that I'm interested in writing.
58:18
And so when I was getting notes that were not right or wrong, but had did not get me closer to that, now I can I can actually say like these notes are not good because you're trying to help me write a book that I'm not trying to write.
58:40
And I think the job of an editor, what a great editor does is figure like they say like the the parenting strategy to figure out what your kids want to do and help them do it.
58:48
Um, if you can figure out what the author or the creative is trying to do and help them do that, then you can be an important part of the journey.
58:59
If you think your job is to help them make the book that you're trying to publish or the song that you think they should write, now you're in in conflict.
59:08
And so, I think having having a strong sense of what you want to do is really really helpful.
59:15
and then it makes all the other decisions and disagreements and whatever better.
59:19
It's like again there's no such thing as a good or bad cover, but there's a right and wrong cover for the book you are writing, you know.
59:28
Um if you're trying to make a a type of thing, there's things that are not that type and but but then you get these just general notes or you realize you you see this in advice too, right?
59:42
People are giving you advice for what they would do in your situation, but you're you have a different set of values.
59:49
So, but it has to line up with what you're trying to do.
59:54
I thought this was interesting when you were writing I think it was ego is the enemy. You had a dream. Oh.
1:00:00
before and you had been prepping and you had this dream and it was like 10 9 8 7 6 and then you hit one blastoff and then you woke up and you took that as a sign that it was time to start working on the book. Yeah.
1:00:14
I basically don't have a lot of dreams and I'm not like a big believer in the sort of unconscious subconscious like I I don't know.
1:00:21
It's just never been there for me.
1:00:22
But I yeah, I was working on that project and I I didn't so I'm only I guess it's my third book really.
1:00:30
Um and so I I didn't know when I was going to start it.
1:00:35
I didn't know if I was I there's always this when are you ready, you know, and you don't know when you're ready.
1:00:41
And I think um I probably was ready, but I wasn't able to give myself permission to start.
1:00:48
And I had this dream and I had a dream. I was an astronaut.
1:00:53
I was basically being loaded into this spaceship and the countdown's happening and then it it takes off.
1:00:57
And yeah, I just took that as like, okay, this is this is a sign like this thing you've been putting off, it's time to just get started. And yeah, I did.
1:01:07
Um that's I think that's the only time that's ever happened to me.
1:01:10
But the idea of like you waited too long to just start the thing is a very common problem cuz you never you never really feel like you're ready.
1:01:20
Um, and a lot of times you aren't ready, but at some point you have to just do the thing. Yeah, it was striking.
1:01:27
I was at a dinner last week and it was a bunch of writers and we're talking about some things we're struggling with and we' all got around the circle and I was just like, you know what the problem is? Everyone's just scared. Everyone is scared.
1:01:40
We're all scared of judgment.
1:01:42
We're all scared of failure.
1:01:43
The fact that we're all scared is blocking all of us.
1:01:45
And we just at least need to acknowledge how much fear there is at this table that is stopping us from doing the work that we're trying to do.
1:01:54
Well, the blank page is scary because it sucks, you know, like like your finished stuff, whatever it is, it's done and it's as good as it could be.
1:02:02
So that's, you know, it exists and uh the blank page is is scary.
1:02:09
And I think there's also something humbling and awful about what's on the page is never as good as what's in your head.
1:02:17
And so if you keep it in your head, it's safe and good.
1:02:23
And you're not going through this awful uncomfortable middle period, like this teenage growth spurt adolescence, you know, awkwardness.
1:02:36
And it's easier just to keep it there.
1:02:38
And I think this is why people hang on to projects uh or write and rewrite them and they they're just there's every part of the process is scary and you find one and you can kind of develop almost like a phobia and there's a real ugliness to the early creative process.
1:02:54
So, if you go to Florence and you see the statue of David, what I didn't realize is the statue is beautiful, but there's a I think it's called the Hall of Prisoners and you see these uncompleted statues by Michelangelo and they look demented. Yes. They are so ugly. Yeah.
1:03:10
And they're like almost a person, but they're definitely not a person still.
1:03:15
And to see the difference between the statue of David and these ugly statues that are still under construction that never got finished really is a telling tale of you have to get through that ugliness before you get that statue at the end.
1:03:31
Well, if I remember correctly, they gave him this like enormous block of marble, right, that like was incredibly valuable and like different sculptors had like vied for it and couldn't figure it.
1:03:41
It's like it's it's like a huge block that he's given, right?
1:03:46
And and and I think it was like somewhat flawed or something like he had to be creative with how he used it.
1:03:51
You can imagine for him the sort of uh both imposttor syndrome and procrastination that would come in from like knowing like hey um you [ __ ] up a lot in the process and as long as it's this unformed untouched thing it's it's perfect in one sense and that the the perfection that I'm trying to get on the other side.
1:04:13
The risk is when you start because you could [ __ ] it up and and I you could imagine coming up with endless delays and reasons for not doing it because you want to get it right.
1:04:27
There's a Senica thing he says the one thing all fools have in common is that they're always getting ready to start.
1:04:34
And so there's always something some reason why you're like, "Okay, I'm going to start on, you know what, it would be weird to start it like the holidays are coming up and you know, family's going to be here, so I'll start it like on January 1st."
1:04:50
And then January 1, you're like, "Well, I'm hung over."
1:04:53
You know, like you're you're you always can come up with reasons.
1:04:57
I I got to read one more thing.
1:04:59
I got to research one more thing.
1:05:00
I got to take one more trip. I got to do this.
1:05:02
you you just come up with reasons to not start and then that procrastination or perfectionism kind of becomes a paralysis. There's a great Nike ad. The copyy's so good.
1:05:14
Yesterday you said tomorrow just do it. Yes.
1:05:19
The big the biggest lie in the world is I'm going to do it in the morning. Right. And you won't.
1:05:25
Tell me about storytelling and how you've learned to tell better stories over time.
1:05:29
And maybe this will be a fun place to begin.
1:05:32
How is storytelling different on the page versus in the spoken word like we're doing right now?
1:05:39
Oh, I think a couple things I'm looking for in a story.
1:05:41
Ideally, something that someone hasn't heard before or something surprising, but I it's often about someone that they have heard about before. Oh, interesting. Um, those are powerful.
1:05:52
I think when you're doing stories that are very obscure um or about obscure people, there's at least for the kinds of lessons that I'm trying to teach, there's something that is not quite powerful enough about them.
1:06:12
You want someone that either they have a strong opinion, positive or negative, about, and then a story that shows something about them or what made them great or not great that they they wouldn't know.
1:06:22
And the other thing I'm looking for in stories is that this can't be an aberration.
1:06:27
This has to often be a a theme.
1:06:29
Like this story is similar to this story which is similar to this story.
1:06:35
And I can layer them on top of each other to kind of make the point that this is this is a an observable demonstrable fact or trend or reality of existence.
1:06:47
So, I'm I'm I'm just kind of looking for for those things often.
1:06:52
Um, how do you judge the pacing?
1:06:54
Like, when you're editing, how are you judging the cadence of what's going on?
1:07:00
Um, there's a story about uh Raymond Chandler, who's like one of the great greatest writers of all time, and he would write uh on these like little sheets of paper.
1:07:12
He would put this like t like a sheet of paper like this big in his typewriter.
1:07:16
and his his thing was that like uh something had to happen on every page.
1:07:20
And so, you know, one of the things that can happen is if you're writing a book, you your pacing can all be [ __ ] up because you're thinking of this big huge thing.
1:07:28
You're not being uh urgent enough.
1:07:33
So, I everyone like so this book is say it's three parts, 10 chapters.
1:07:38
I don't write a manuscript draft.
1:07:42
I I have 30 or 40 individual drafts.
1:07:46
So each one of the chapters is its own thing.
1:07:49
Is that like its own Google doc?
1:07:51
It's own I I So I write everything in individual Google Docs first. Huh.
1:07:55
So I'm thinking about it more as a like a small blog post or a story.
1:07:59
Like it's it's a thousandword chunk that I'm writing.
1:08:05
And this helps me with the momentum dayto-day because I'm working on this this one section.
1:08:08
But it also is helping me with the pacing because I'm I'm thinking each thousand words or 1500 words has to be self-contained, has its own pacing and work by itself.
1:08:25
And then there's some point where like I'm I'm I'm about 2/ird of the way through the wisdom book.
1:08:31
Um, so but but maybe a maybe two months from now there'll be a process where all those come together and then I'll see for the first time how many words the whole book is and then I'll have to start adjusting the pacing as how the stories all intersect with each other.
1:08:50
But I'm writing in these these self-contained pieces.
1:08:52
And the story has to be interesting and self-justifying and um exciting in and of itself.
1:08:58
There can't be lots of callbacks and connections.
1:09:05
Oh, we were talking about this earlier. No, no, no.
1:09:06
It has to be like this is the first time you're hearing of this person and uh it has to work by itself.
1:09:14
then it can become interwoven later, but I want to do it as a self-contained story by itself first.
1:09:21
What do you think in the realm of storytelling that you've gotten better at since your Ryan Green days?
1:09:24
I mean, I I promise I'm not just blowing smoke.
1:09:29
Like, when I was reading Discipline is Destiny and you were telling those Lou Garri stories, I was just like, where did this guy learn to tell stories?
1:09:37
Uh, I would say 80% of it is I just got much better at researching.
1:09:41
Like I just So for Lug Garrick, again, there's not there's not one good biography of Lug Garrick.
1:09:48
I probably read eight and and then I read obituaries and articles and, you know, ESPN pieces.
1:09:54
I just read a ton about him and um I think it's largely the I I would say it's the vast majority of it is the material.
1:10:04
I just found better material.
1:10:07
better material. And then I think one of the things I have gotten better at though is okay I think in obstacle for instance I would just I'd be like here's a story um this person is this thing I'm telling I think I've gotten better I think stillness is the first time I really was able to do it well where like
1:10:25
I talked a lot I talked um in Stillness the the the first main character is is Kennedy and I talk about Kennedy and the missile crisis but in part two of the book I I tell a bunch of negative stories about Kennedy and that was the first time that I was I I had a full enough sense of the person that I was able to show the the the the greatness and the weakness. And so the rounding
1:10:44
And so the rounding the person out was has been a big part of it.
1:10:51
And that I think comes back to research.
1:10:53
But how the like starting threads and then picking them back up and not leaving anything hanging.
1:10:58
I think I've gotten better at that.
1:11:00
Um or I mean like as an example my understanding of Luger and in discipline who I loved is in partly informed though by my understanding and I would say disappointment in Babe Ruth.
1:11:15
So like, so I'm not just I'm not just understanding Lug Gareric, but I'm now I have this contrast.
1:11:23
And so I'm able to explain the person and also explain someone else in relation to them.
1:11:30
And I think the reason that story works is that it's the contrast between L, these two guys on the same team, two all-time greats, both leave something on the table, one more tragically than the other.
1:11:43
and and uh yeah, I think that was that was maybe why that worked. Let's close with this.
1:11:50
I want to just take this conversation and just throw out some lessons that I think I want to bring to my own writing that really stand out from how you write.
1:11:59
The one big one is don't lose momentum. Yes.
1:12:03
So many people lose momentum and it really stuck with me what you said about people finish their f first book and they just stop. That's a big one.
1:12:10
Another thing is trust the process. Yes.
1:12:15
And there's an element of you just have to trust the process and you need to know that intellectually, but a lot of that confidence is going to come through the reps. Yes.
1:12:22
I think people don't have enough reps, period.
1:12:25
So like standup comedy is a it's very easy to get reps in that thing.
1:12:30
thing. writing it is hard to get reps because I mean even 16 books which is an absurd amount uh in in sort of modern publishing that's not that many reps compared to how many shows a musician would do right um it's just it's really
1:12:48
books take a long time they're expensive um you know it's hard being a screenwriter would be even tougher right and or a movie director would be like impossible you might get to do it twice in your whole life so like how do you find other ways of getting reps for what you do. And I would say one of the
1:13:02
And I would say one of the things I accidentally chanced upon, speaking of stories, is because I started the Daily Stoke.
1:13:10
So the the book The Daily Stoke is 366 stories.
1:13:12
So just like that's a lot of stories and then every day for 8 years I've put out this email and that's like a very set uh structured format that's short and tight with a pretty uh not unforgiving but but like an audience, right?
1:13:36
So I'm not doing it like just in my bedroom or something.
1:13:37
So like to to put on a show for that many people that's probably eight books that I've done at least of practice.
1:13:45
So I just I just re I think if anything made me a better storyteller it's that I do that every day.
1:13:52
Well and to that point I looked it up.
1:13:53
You wrote 44 blog posts in 2007 and 2008.
1:13:56
So your career just started with volume. Yes. Yeah.
1:13:59
I was always just writing lots of stuff and they weren't always long but you you write and then you get used to hearing from people and not hearing from people and Yeah.
1:14:06
just the the whole soup to nuts process of like doing the thing.
1:14:12
You got to find ways to get reps. Thanks, Ryan.
1:14:17
Yeah, thanks for having me. That was a blast. Thanks,