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I got an amazing night's sleep last night. One because my 6 year old fell asleep in the car at like 6 o' clock and he transferred him from the car seat to the bed and it stuck, which is just magic. So he's in bed way earlier than normal. But I sleep really well every night because I have a Eight Sleep Pod 5 Ultra which is Eight Sleep's best product. I've used Eight Sleep for many years now and it's just totally transformed how I sleep. Made me sleep better, made my wife sleep better. It's amaz amazing. So basically eight Sleep is this topper that goes over your mattress. It can heat and cool both sides separately. It can raise and lower each side separately so it helps you fall asleep faster, stay asleep and then wake up better. Eight Sleep buzzes me to wake gently every morning as opposed to some loud blaring alarm. And then I can check the app and it tells me my sleep score. It even helps me optimize my day based on how I slept. If you want to survive the holidays pro and just generally sleep better, head over to eightsleep.com dailystoic and use code Daily Stoic to get $350 off your very own Pod 5 Ultra. The best part is you still get 30 days to try it at home and return it if you don't like it. But I know you will. Trust me, your body will thank you for this investment in better sleep shipping to many countries worldwide. See details@eightsleep.com Dailystoic look, if you're listening to this podcast, you've probably heard of HelloFresh, right? They're the number one meal kit in America. They make cooking easier with chef crafted recipes and fresh ingredients delivered straight to your door. This fall, they're serving up even more to love. It's not the hellofresh you remember. It's even better. HelloFresh is bigger. They've doubled their menu. You can choose up to 100 options each week. It's healthier. 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That's hellofresh.com stoic10fm to get 10 free meals plus free breakfast for life. You've probably heard the headlines about all the different cuts to foreign aid and food benefits. This is having a profound impact on the world's poorest people and the world's poorest communities. But you know, just hearing about that, that's not what stoicism is about. Stoicism is to me, what you're going to do about it. And that's where GiveWell comes in. GiveWell is trusted by tens of thousands of donors each year because they provide free and independent research that helps you understand how to have a big impact. GiveWell has spent the last 18 years researching global health and poverty alleviation and they direct funding to the highest impact opportunities. Over 150,000 thousand donors have already trusted GiveWell to give more than two and a half billion dollars over the last several years, and research suggests that these donations will save over 300,000 lives. I myself am one of those donors. I donate to GiveWell every year. It means a lot to me and you can find all their research and recommendations on their site for free. And thanks to the donors that sponsor this research, GiveWell doesn't take a cut from your tax deductible donation to their recommended funds. And if this is your first gift through GiveWell, you can have your donation matched up to $100 before the end of the year or as matching funds. Last to claim your match, go to givewell.org and pick daily Stoic from the dropdown menu under podcast. That's how they know that you heard about GiveWell from the Daily Stoic and you'll get your donation matched. That's givewell.org, code the Daily Stoic to donate or find out more. Welcome to the Daily Stoic Podcast, where each weekday we bring you a meditation inspired by the ancient Stoics, a short passage of ancient wisdom designed to help you find strength and insight here in everyday life. And on Wednesdays we talk to some of our fellow students of ancient philosophy, well known and obscure, fascinating and powerful. With them, we discuss the strategies and habits that have helped them become who they are. And also to find peace and wisdom and in their lives. Hey, it's Ryan. Welcome to another episode of the Daily Stoic podcast. I usually record the podcast during the week, try to keep the weekends free for doing stuff with the family, reading, hanging out, relaxing, whatever. But a couple weeks ago, I came in to do one over the weekend and I got here and there was just like tons of traffic. And I was like, what's going on? And then I could hear all this noise. I barely found a parking spot I'd get in. And we forgot that there was a huge car festival in Bastrop. The whole main street was blocked. There were very loud classic cars up and down the road. There was a snow cone or a lemonade stand in front of the Daily Stokes Studios. Actually, that's something we've been doing. We've been. We took this storefront offline. Used to be a barber shop. John the barber, he passed away. Now it's the studio. And it's sort of like, what do we do with the storefront? We let sort of vendors on the weekends just kind of camp out there and help support, like little small businesses and stuff. So someone from the Painted Porch, not knowing I was doing this podcast, had set up like this lemonade snow cone vendor person. So they were doing their thing and I was like, oh my God, this is. This is not gonna be good for this podcast that I am very excited about. Cause it's gonna be crazy noisy. Thankfully, it was all right. We were able to sort of remove some of the noise. And my guest was very understanding when managed to find his way into the studio. But it was also a nice, you know, like sort of picture of small town life as it had been for many years. It was packed. All the people actually kind of segues. Nice. Imagine it's October 1929. You're walking down Main street in Bastrop. Stock market's at an all time high. Things are going amazing. It's a time of peace and prosperity mostly. And then the music stops. Maybe it takes a couple days for the news to make it this far. Or maybe not, right? Because it was an interconnected world then. But the market crash of 1929 changed everything. Led in many ways to the events of the second World War. It led to, in many ways, that reinvention, the revolution, articulation of the social contract here in America, many market reforms. And also it led to this Fantastic book that I just read, 1929 Inside the Greatest Crash in Wall Street History. How It Shattered a Nation by Andrew Ross Sorkin. He has been on book tour all over the country the last month. And so I was really excited while he was in Texas that he swung by. Really excited to do this in person. And I loved the book. It was a book I was planning to read anyway, but I was gonna wait, I was gonna savor it. It's a big book. And then found out he was coming. I said, all right, can I read this book in a day and a half? And I did and it was fucking great. It is a fantastic, super well researched book. I really enjoyed it. I think you will like it. And in the first part of this episode, Andrew takes us behind the scenes at how it took him eight years to write it and a lot of the lessons that went into writing it and I going to like it. If you don't know who Andrew Ross Sorkin is, you've almost certainly experienced his work over the years. He's a financial columnist for the New York Times. He's the co anchor of CNBC's Squawk Box. He is the founder and editor of DealBook, which is a financial news service published by the Times. He wrote the bestselling book Too Big to Fail, co produced a movie adaptation of it for hbo. He's also the co creator of the Showtime series Billions. And this new book, 1929 Inside the Greatest Crash in Wall Street History and How It Shattered a Nation is a Reid. He signed a bunch of copies of 1929 while he was here. You can follow him on Instagram at Sorkin says or on Twitter. Andrew Rsorkin, I think you're gonna like this episode. Thanks to Andrew for coming out. I wanted to split it up because it was such a great episode. And let's get into it. I feel like the best question to start with is probably one you've never been asked.
B
Please.
A
Which is. So do you think we're in the middle of a bubble right now?
B
You and Lesley Stahl, how many people.
A
Have asked you that? I'm actually more interested in how often you've been asked that question on this book tour than the actual answer.
B
Oh, invariably. Almost every time.
A
Right.
B
So yeah, dozens of times.
A
And people think probably that it's a somewhat original question.
B
I don't know if they think it's original or not. I think that they think it's the question that people want to know even more than they want to know about what actually happened in 1929. They want to know about whether this is going to happen to them Now. I get it. I get it.
A
I don't want to read the book. Just tell me, do I need to be worried?
B
Pretty much, yeah. Give me the Cliff. The Cliff Notes version is, should I sell everything I own?
A
That is the weird part about the book tour part where it's like you're answering the same questions and then you. It almost becomes impossible to give an original answer to a question anymore because you've said it all the ways that it's possible to be said. And then I feel. I don't know about you, but I feel like I feel phony just saying bits.
B
The same thing. Oh, I do too. And I will admit to this now, and maybe I shouldn't admit to this. I did an interview a couple of days ago where I thought to myself, am I repeating myself? Like, did I say earlier in the conversation the exact same thing?
A
Oh, like in that in you. You lost your bearings completely.
B
I was so lost.
A
Yeah.
B
I happened to be in London, so I think the time difference got me. And I was like, did I just say now? Happily, I had not said it prior.
A
Right.
B
I mean, in this particular, I had said it prior or something similar. So, yes, you are right. That's a thing.
A
The other weird one is, like, you have to be somewhat conscious of whether you're just wearing the same things and all the like, oh, clothing. Yes. You're like, outfit tracking yourself because, like, you don't want it to seem like you own one shirt.
B
This is true. I, you know, I wear a lot of suits because.
A
That's true.
B
That's. So I get the different ties. I'm sort of like cognizant of that. That. So like this, by the way, I don't think I've actually worn sneakers casually or anything at all. So this. This for me is. This is actually how I like dress.
A
Up for your stuff.
B
This is like how I like to dress. But, yeah, do I have to dress up? I think people think on that on Squawk Box in the morning that we should be wearing ties.
A
Why? Who cares?
B
Because most of the. Because you're oftentimes interviewing a politician or a CEO who shows up with a tie on. I don't know, it makes us look more official or something.
A
I walked in here the other day, I was interviewing someone and they were like, did you just go for a run? That's what they said.
B
I was like, whoa, you look good. I look good?
A
I look all right.
B
You're always Looking good.
A
Thank you. Okay, so I'm. I am reading this book. Here's what I was. Obviously the book's very interesting, but when the fuck did you write a 600 page book? Do you write, like, in between commercial breaks on squawk walks? Like. No, no, no, no, no.
B
I actually find writing. Okay, couple things, because you. I love watching you and listening to you talk about you, about the craft of writing.
A
Okay.
B
I find writing very hard.
A
Sure.
B
Like, super hard.
A
Yeah.
B
Like, I have visions of people like Michael Lewis playing the computer keyboard like a piano, cackling to himself. I am not cackling to myself. I am in pain as I am typing.
A
Somebody said a writer is someone to whom writing does not come easily. So I think it's a compliment.
B
But to your question about timing, I actually find that I always need to block out at a minimum, two hours.
A
Yeah.
B
And possibly as much more than that, in part because really, for me, the first 30 minutes, even 40 minutes, is almost like a ramp up to get my brain into the right space, to almost reacquaint myself with where I left off last, to sort of reorient, sort of how I'm going to tackle.
A
Right.
B
Things. So that was actually the hardest part. So a lot of times writing at night that. I mean, a lot of times writing at night.
A
Because this is like your fourth job.
B
I got a couple. Yeah, I got a couple. So writing at night. Airplanes without WI fi. Always turn the WI fi off on the airplane. Don't even try to. I mean, it hardly works to begin with, but.
A
Yes.
B
Don't even play that game.
A
Yes.
B
Vacations, though. I know people would think that I. That's not a vacation. My children would say, dad, you're sitting on the beach with a laptop on your lap. What are you doing? And I would say, I'm writing the book and enjoying myself.
A
Yes.
B
And they couldn't contemplate how that could be.
A
No. This is the thing that I don't get to do because of my job.
B
Right.
A
And it's what I actually like to do.
B
For the first couple of years, by the way, it actually did feel like a true hobby because you're just in.
A
This own world, you're.
B
I was just trying to figure it out. I was just trying to figure it out. I wasn't even sure whether I could make it work. I had no real concept or conceit of how it was all going to go.
A
Well, you said. I think you say in the acknowledgments you took a bunch of books about the crash On a vacation.
B
That's. Yeah, that's how it started. I was. Literally went on vacation with my wife, and I had a Kindle. I brought some books, and I remember downloading a couple books, and there's some great books about this period, and they sort of made me obsessed about the period, but also made me think that there was a white space to craft the book that I wanted to write.
A
Right. Yeah. It's the falling in love with a world or a time period that's. That's like. That's the part that's just for you.
B
But the truth was, I was scared.
A
The whole time of writing it.
B
Well, two things. I was scared that I wasn't gonna be able to find the kind of granular detail that I needed to make each character pop in a consistent way.
A
Sure.
B
Because these people aren't alive. So unlike when I wrote Too Big to Fail, I couldn't go back to people or try to, like, find. There wasn't extra material. Either was gonna. Either I was gonna find it in some archive somewhere, or it just doesn't exist.
A
It's a different kind of reporting that you hadn't really done before.
B
Totally. It was completely new to me. I mean, even just learning my way around a library was new to me, to be honest with you. So there was that, and then. I don't know if I should say this, I felt like when I wrote To Make To Fail, it sort of felt like lightning in a bottle had happened in a way that didn't feel real. And I wasn't sure was all really, like, my own doing. Like you say to yourself, it worked like that book worked. But maybe it worked for lots of reasons that I wasn't always sure had to do with me. Meaning, like, the timing of it. There was sort of, like, a crazy interest in what had just happened. And so you get insecure about these things.
A
Yeah.
B
Yeah. Like, about whether you can actually do this for real.
A
So I think it's not intimidating. It probably means you're not doing anything good. Like.
B
But I also think I was so scared because I thought that book worked. I didn't want to do something that didn't work.
A
Yeah.
B
So it's sort of like it was. It felt like there was, like, a different bar that I was trying. I was trying to clear my own bar, but then I was also, like, trying to clear some other bar that I didn't really.
A
The tricky part there is that's a bar that you don't actually control.
B
Right.
A
Like, if you're like, hey, I Want to be better. I want the reporting to be better and the writing to be better and all that, that can be intimidating. But if you're like, well, I just want the vibes to be the same or better. And you're like, you don't control the vibes because you don't control what's happening in the world and you don't control what other people think about what you do.
B
Right. No. So that's scary.
A
Yeah.
B
And I think that weighed on me. I mean, I think that, like, that was like, a little thing in my head the whole time.
A
You worked on it for 10 years?
B
More like 8. Ish. And the truth is, on and off, there were periods of time where I was, like, full pedal to the metal.
A
Yeah.
B
And then there were periods especially. We had the pandemic through things into a bit of a mess and just other periods where I had to, you know, be super intense in my day job.
A
Yeah.
B
So I don't want to say. I mean, I. I have this view that, you know, Caro, when he writes a book, that's all he does. For eight years, I was doing other things.
A
I don't know how that's possible. Like, I mean, I'm a huge Caro fan and, like, obviously you can see it in the book. You're like this. Every sentence was sweated over and truly magnificent and obviously worth it. But I just. I honestly don't know how you could show up and work on something for 15 years every day. I don't understand it in a couple ways. Like, I don't understand, like, cumulatively that many man hours, like, how you wouldn't get done faster. Like, I just. I just can't wrap my head around it. Like, the. The pacing that you. The holding yourself back of it almost is impressive. And then the other thing is, like, how do you have the sense of self and security, financial or otherwise, to be like, I'm going to work on something with no payoff for a decade.
B
Well, that part would be hard for me, but the actual continuing to try to, like, improve it, you know, so even incrementally, all the time.
A
Yeah.
B
So this book is finished.
A
Yeah.
B
Now, like, it's there in print. And I still think about. I want to make this sentence better. I wish I had added this little thing the other day. Literally, somebody emailed me about something and I was like, shit, you're right. I forgot. And I was even thinking about that at one point. Maybe if I just added one little hint towards that, it would have done something to the reader. In some other way. So I could see a sort of an obsessive nature to it. And frankly, if I didn't have a publisher that was telling me, you know, we would like to publish it this fall, at some point, I think I probably would have taken even more time.
A
No, I, I, I think that's it. You have to become so obsessed by it that you live in a world where, yeah, each one of those, like I, I've got to imagine for someone like Robert caro or David McCullough or whatever, where they, like, they spent three weeks on this sentence or something or like just over and over and over again. And like, that's probably incredibly satisfying and torturous at the same time.
B
So I don't know about you. For me, when I'm writing whatever goes down on the page the first time, I can only really upgrade by one letter grade through editing unless I start over. So it's like an anchoring situation. So if it goes down on the page as a B, I can get it to an A. If it goes down on the page as a C, it will never get better than a B unless I start over. And it's usually because there's something imprecise or wrong conceptually about either the idea or the language. And I sort of trap myself in some way that I'm unhappy about. And I say that only because I know some people who sort of splatter what I call this. They splatter on the page and then they think they're just gonna like, fix, fix, fix, fix, fix, fix, fix. I'm incapable of that. And as a result, it sort of can also hold me back in a way because I'm sometimes like the gears are turning for too long about what I even want to put on the page.
A
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B
I did.
A
So, like, that's a weird. I did. I've done five audiobooks, I think in this room. My publisher hates it because I am like sending significant notes back when it's supposed to be done. Like you do the audiobook like a month before it comes out.
B
Just had the experience you had. I'd never done it Before.
A
Yeah.
B
And I found a whole bunch of things that I was not pleased with myself about. This is nobody else's fault was my own. Yeah, I was able to make a couple of changes, but frankly I couldn't make too many changes because sort of the.
A
They have to redesign the whole thing.
B
Yes. The train was leaving the station.
A
I will say, having done this, a lot of times they always make it seem like it's too far gone. And that's only because it's means work for them.
B
Have you ever. Because I've been thinking about this even recently. Have you ever updated a book just in the Kindle form before or before a second printing?
A
No, like, so what I did, I did the audiobook. And a lot of the things you notice would be like I say the word, I don't know, astonishment three times on the same page. I just never noticed that because, you know, for most of the time I was writing it, it wasn't on this page. The page was bigger or smaller, you know, so you're just seeing things. I remember when I did Daily Dad, I read it and I was like every sports example in the whole book, I'm saying soccer for some reason, like. Cause I wrote it in pieces and then it came together and it's like, I just. I have to like be. I had to write to the editor and be like, look, I don't really care that much, but like, you gotta swap. If there's 50 soccer mentions, like 10 of them have to become basketball and 10 of them have to become baseball. And then let's throw in another couple weird sports and then let's balance this out. There's just things that you wouldn't notice until you've found yourself saying soccer practice a lot over the course of four days. But they usually go like, hey, like we've already printed the first, however many thousands of copies. So this can be in the second edition, but you can go up in the. In the e book right now. So they can definitely do that. But they. I'm sure I do. With when people want me to do stuff. I'm like, ah, that's not possible. You know, because you're really just trying to gauge how adamant they are about wanting it to happen or not. But so. Okay, so I'm just curious about your schedule. Cause you must have to get up incredibly early for.
B
So I wake up at 4:30. Ish.
A
Yeah.
B
By the way. Which is late in morning TV land.
A
Yeah.
B
I usually work on Dealbook, which is this newsletter that I published for the New York Times before then. Before the show starts at 6.
A
Okay.
B
So I'm usually sort of doing last minute little changes and things to it.
A
So you're up at 4:30 and you're on live television by 6?
B
Yes. So it's a race, it's a sprint. I only live about 10 minutes from the studio, so that's not so hard. And I do the makeup as if I'm in a pit stop at the nascar, whatever. And then I do the show till nine in the morning, three hours. But it goes by so quick you don't even know. And it's like having breakfast with some of the most interesting people in the world and basically asking people whatever you want.
A
Yeah.
B
Including people like you, which is fast.
A
Yeah.
B
And then I spend a lot of the day planning and writing and editing and, you know, dealbook. You know, we publish dealbook six days a week.
A
Do you go home and work from home or do you go to an office? What do you do?
B
So the New York Times office is literally just a couple of blocks away.
A
Right.
B
I often go there. Sometimes I go home. If I need to do real writing, I need to go home. The pandemic did something very bad to my brain. I used to be able to sit. We have a big newsroom with, you know, cubicles.
A
Yeah.
B
I used to write just about anything there and fast. Pre pandemic.
A
Yeah.
B
For some reason, working practically from home for, I don't know, six months a year, I don't know if I became spoiled or what. I have a door at home so I can be, you know, I can be in a room that's quiet by myself even when I have my kids around.
A
Sure.
B
By the way, sometimes I even have my daughter who, you know, I think actually sat on the floor while I was writing a lot of this book, you know, in late afternoons. But anyway, so I, as a result, when I have to do like what I call real writing.
A
Yeah.
B
I either commander like a conference room at the office or I go home.
A
Okay.
B
And then sometimes, you know, late afternoons I would write the book. Maybe into the night I would write the book. If I went on trips, I'd write on airplanes. You know, obviously I constantly, you know, trying to go to various different libraries all over the country to, you know, sort. Sort through things. I had a researcher very early who really actually taught me how to use a library. She just graduated from Princeton with a Ph.D. in American Studies. And that was super helpful. And then there was a period of time during the pandemic actually where I wasn't sure. The pandemic was ever going to end and I was worried I wasn't going to be able to get on the material because you weren't allowed in a lot of these places.
A
Yeah.
B
So I would befriend, actually with the help of this other researcher, different librarians, find out what kids, students were allowed in the libraries because they had their dissertation due. And then I would literally pay them. I would say, go find. You need to find box 152.
A
Yeah.
B
I need you to take your iPhone and take a picture of every single page in the box.
A
Yeah.
B
Happily I was able to go back to a lot of those libraries afterwards, but I wasn't sure I'd ever. I didn't know what was going to happen, of course.
A
Okay. So as I imagine you both have a. You have a lot of constraints in that you have like the show is this time to this time and you.
B
Can'T really do forcing mechanisms. For me, it's a meaning, I would say to myself, I have two hours and I really. There's no procrastinating. It is two hours. You know, I know some people, you know, use timers and the pomodoro technique and all of these things. This is like my version of that. This is like you have two hours. You have to use all two hours. Having said that, a lot of times the two hours would go by and I wouldn't have a lot of actual writing done, but I would have maybe figured something out in my head.
A
Yeah.
B
Meaning this character is going from here to here. And I wasn't sure how I was getting them there from one place to the other. What was the transition? Or is there something else I was supposed to put in between it? A lot of it was, by the way, still going through research and documents.
A
Getting a document might be the documents, that's a day's work. But it actually is way more valuable than having written 15 pages completely.
B
And sometimes it was even rereading things. So I also scanned. Anytime I'd go to a library, I'd literally use my phone and I would take pictures of, I mean, tens of thousands of pages. And I literally created like a Dropbox system. Unfortunately, AI was too late for me in this project translate them because I didn't really have true ocr, meaning like to be able to like make them.
A
Searchable properly just to. Just to help you with that. It's not because I'm in the middle of doing a very research heavy book right now. It's not really that usable like you think it would be. And then you're like, you know what? I need to have a person do this. Like, you can't trust it. You think you'd be able to trust it, and you can't. That's really the problem. Especially, I can go through a lot of handwritten letters right now.
B
That's what I. A lot of it is handwritten, and.
A
It'S like, I just can't. I can't. It hallucinates 30% of the time. You know what I mean? It's just not good.
B
Interesting.
A
So it's still. It would be wonderful if there was some shortcut that made it magically better. But I don't think.
B
But I found myself even finding stuff three and four years later, meaning documents that I had found in 2018 that I thought I had read and understood. And then two or three years later, because I had gone back to them, because I needed something from one of them, I'd see something and go, oh, shit, yes. That I forgot about that. Or I didn't realize that, or I hadn't connected the dot between something there and some new document that I had found that really explained what these two characters were really doing with each other. And those were the moments where I would have a smile on my face during this project where I felt like, oh, goodness, now this is gonna work.
A
Well, it's almost here. Christmas is just a couple of days away, and maybe you're scrambling. You're like, what should I get my dad? What should I get my mom? I gotta get something to my sister. People love showing off pictures of their kids, and that's where today's sponsor comes in. I've gotten one as a gift. I've given it as a gift, the Aura digital picture frame. It's easy to use. It never gets old. You're constantly updating it with new pictures. Aura digital picture frames are so much better than any digital picture frame I've ever seen. It's got a high resolution. It's got a color calibrated display. You can add video. You can have two pictures come up at the same time. Picture and a video. It'll pair photos together for you, like two pictures of the same person or from the same day. It's really easy to set up. You just download the app, connect the frame, and then you can pick photos and videos right from your phone from anywhere in the world. And there's a reason Oprah added it to her favorite things three different times for a limited time save on the perfect gift by visiting auraframes.com to get $35 off Aura's bestselling Carver Mat frames, named number one by Wirecutter, by using promo code Stoic at checkout. That's a U R A frames.com promo code STOIC. STOIC. This deal is exclusive to listeners, and frames sell out fast, so order yours now to get it in time for the holidays. Support the show by mentioning us at checkout. Terms and conditions apply. Thanks to Toyota Trucks for sponsoring this episode. When I bought my ranch in 2015 out here in Bastrop County, I drove my car about halfway down the dirt road that we live on. Thought, this isn't going to work. Stopped, parked it walked the rest of the way home, borrowed my wife's car, drove into Austin and bought a truck. What I bought was a Toyota Tacoma. And this truck wasn't just transportation getting me to and from my house. It unlocked a whole different style of living for us, not just on the ranch, but in our little Texas towns. There were places I could go now that I couldn't go before, especially out here in the piney forests, through the fields, and on the unpaved roads like the one that I lived in. We got to go deep into the hill country's wild beauty. We've driven all the way out to East Texas. We've driven it across the country. And by we, I mean not just my wife, but both my kids, who I drove home from the hospital in that truck. Toyota trucks are built for those who understand that the best adventures happen when you're willing to veer off course, because you never know when you'll end up on a Toyota Adventure detour. And of course, this is stoicism, too, because every detour, every obstacle is an opportunity. But it's helpful if you can handle the difficulty inherent in that, if you've got the resilience and the right companion to make it wherever the road takes you, discover your uncharted territory. Learn more at toyota.com trucks adventure-detours. There's a philosophical paradox, like, I think Plato was talking about this, where it's like. Like, how can you be looking for something if you don't know what it is? Like, how are you knowing that you found it if you've never seen it before, right? It's like this paradox of you're searching for something you don't know, and yet you're like, I found it, right? Like, I'm struggling with this myself. Because you're going through the documents trying to learn about this thing, and then it's not until you've Gone through all the documents that you know which of the documents you needed. Right, right. So you're like. Or there's just allusions and references in the letter, like, Y. You're like, oh, this person was. They were talking about this thing, and These letters are 16 years apart or whatever. And you're reading it and you're like, this one's not interesting. This one's not interesting. This one's not interesting. And then months later, you're like, oh, they mentioned this most interesting thing the whole book is pivoting around in this letter that I put in the don't need pile.
B
Exactly that. So that happens a lot.
A
Yeah.
B
And I think even just trying to understand the characters, it took me years to really feel like I understood them. So there's this guy, Charlie Mitchell, who's the main character for a very long time. I don't think I understood what really motivated him. Like, what was the hole that he was trying to fill? What was that insecurity thing that he, you know, was. What was he trying to prove to himself or to somebody else?
A
Yeah.
B
And I think I was looking for. I was looking for those things in all the characters, but I. So some of those things did not reveal themselves to me for a very long time. And it wasn't until I sort of had some of those breakthroughs where then I felt like I could then set the character up in a way so that when they did things later on, as the reader, you could understand where it was coming from. Even if you thought that they were wrong or seemed completely irrational. When you understand sort of them as people, all of a sudden, things. Well, they may not be right. They no longer seem as completely irrational.
A
It's consistent and logical to them.
B
To them. Yeah, exactly.
A
That must be what takes Robert Caro so long. Right. Like, he's. Most of it is just figuring the person out and the different people out over the course of all those years. Like always.
B
I mean, at least for me, I'm always. I do this, and I think in my reporting today with people who are alive, but in this case, people who were alive 100 years ago, trying to put myself in their shoes and trying to think through, okay, you know, why did they think what they think? By the way, certain things that they were doing then today would be completely illegal, you would think, clearly immoral. We would, you know, be very judgmental about those things. And I would try to think, okay, well, is there some level of empathy that I can have for them also, sort of, given the distance of today and Then try to think, how did they rationalize and justify these things to themselves? Because invariably they would have had to somehow.
A
Yeah. Like, the complicated contradictoriness of the. Like, the senator who's both. Like, the guy who's like, the banking system is rigged and it's fucking over the little guy.
B
Right.
A
Is also, like, fucking over the little guy if they have a different skin color. So, like, how do you wrap your head around this sort of. Of moral kind of compass and commitment with this, you know, this sort of worldview that's so impossible to wrap your head around that. That complicatedness of people is hard.
B
And I think by the way, you're talking about Carter Glass, who was a senator in Virginia, who's sort of responsible for, to some degree, the creation of the Federal Reserve and then later breaking up the banks, who was a racist. I mean, a true racist.
A
Segregationist. And not like, oh, it's the old ways, but it's like, no, no, I wanna steal. I wanna disenfranchise black people. My main reason for being a politician.
B
Completely.
A
Yeah.
B
And yet, by the way, today he's sort of held up by probably, you know, the most progressive left as some kind of, you know, great bastion of, you know, regulating the banks.
A
Because his name is on. We don't know him, we just know the name on the bills.
B
Exactly.
A
Yeah.
B
But I think back then he divided his brain. I don't think he thought of these things in the same context.
A
Yeah. When you realize the time it takes to, like, actually get into someone's brain and the logic of why they're doing it. There's something about that that journalism is just fundamentally incapable of doing because of the rapidness of it. It's like the first draft. It's like, by nature of it being a first draft of events, it's not, considering most of the things that make for an amazing book.
B
Yeah. But I do think, or at least I tell myself this. I like to believe that having now reported on this world of sort of business and policy leaders for so long and then also in the context of the crisis of 2008, that I tell myself that it sort of, like, keyed me in to the way people like this think and the different kinds of emotional reactions that they were having and, like, the way they approached certain moments and. And that that sort of educated me in terms of then how I at least approached or thought about the reporting about these other people. Meaning what kind of material did I need to go find? Oh, they likely would have been doing X. I need to Go find out. Were they doing X?
A
Yeah.
B
Were they thinking that? Were they not thinking that? I gotta. I gotta go see how. How similar or different they are. And the truth is, I guess one of the big lessons for me is we're all the same.
A
But I mean, in the present moment, the reporter's like, so and so said this, this happened. They're not like, let me think about their childhood and let me, you know, like, it's. It's this sort of snapshot and it's not the sort of all the factors swirling around. And it's just. It's weirdly. It's like the books. Like when you read history, it's like you actually know what's gonna happen. So you'd think it could be more black and white, but actually great. History is gray, and it shows you. Like David McCullough talks about how the one thing you can never forget when you're writing history is that they didn't know.
B
They didn't know. It is always gray. It's never black and white. But I do think there are some reporters I was thinking of, Peter Baker at the New York Times or Maggie Haberman, who I think actually write daily journalism, that because they're so steeped in it and have covered these people as long as they have, there's sometimes these little hints and things in certain sentences contextually that sort of. Of get you to understand why some of these things may be happening. Even when you think the whole thing is crazy.
A
But even that, it's not that they're the exception that proves the rule, but that is what happens when you have 20, 30, 40 years on a beast.
B
Exactly.
A
And, and so they're churning out breaking news, but it's like the tip of the ice, or it's the, you know, the inverted iceberg thing or whatever that Hemingway was talking about. And we don't necessarily celebrate that as the virtue or set people up to be in that position.
B
Right.
A
They're almost remnants of the old system.
B
Well, look, I've been covering the same thing for now, 30 years. Peter and Maggie have probably similarly. But you're right, for whatever reason, in journalism, most people go from beat to beat to beat. They sort of do two or three or four years in one beat, and then they jump to another thing and another thing and another thing. And arguably they come maybe a lot more well rounded than I am, for example.
A
Yeah.
B
But it's harder to be super deep as a result.
A
And what I meant about your schedule. So on the one hand, you have a lot of Constraints like the show takes this long and then you have this to get out and whatever. But then you also probably have a lot of freedom in that you sort of can decide how you want to do things. Are you just like winging it day to day? You're like, you know, today I want to go work from home, or today I want to go work for the New York Times. Or do you have like a rhythm?
B
I map it out. Meaning. Because also I'm traveling oftentimes for work. I would, would sit with a calendar and I can usually tell you for, you know, a given couple of weeks at a shot, maybe even longer. Like this is what, like this afternoon I'm probably going to work from home.
A
Yeah.
B
This morning I have meetings at the office. This day I'm doing this. This day I have to be so. And you know, this weekend I would even write on the weekends. My calendar is like, there's a phrase productivity hackers use. Blocking time.
A
Blocking time.
B
Blocking.
A
Yeah.
B
I'm a big time blocker.
A
Okay.
B
So if you were to look at my, my calendar for many years, there would be a lot of 1929 in orange.
A
Yeah.
B
In boxes.
A
Okay.
B
And those were my boxes. And so I knew Saturday afternoon I was, you know, from 1 to 5, 1929.
A
Wow.
B
That's what it's going to be. But it would also say morning, you know, taking my daughter here and you know, lunch with my kids or, or my other son plays tennis. We gotta go. By the way, I would take him to play tennis and he might be taking a lesson and I'd be sitting there with my laptop.
A
Yeah.
B
Working on 1929.
A
Yeah. Are you reading documents? Yeah. So theoretically you could go back to your calendar and add up the hours.
B
I've thought about doing that. I, I'm too scared to put my calendar into ChatGPT, but I actually thought that it would do a better. It would make it a lot easier to actually map it all out. But I have it for years. So yes, I could, I could see it would clearly be thousands of hours, but I don't know what it ultimately.
A
Yeah. I wonder if you would be proud of the number or you'd be like, oh, I thought I worked on this more.
B
Yeah. I don't know. I think my wife would say that I probably did it super inefficiently and she's probably right because there were days where even though I told myself, gotta do it, gotta do it.
A
Yeah.
B
That I would have these moments where I'm doing the reporting or the research and I Couldn't find the thing. Oh, by the way, that would happen all the time. I thought of something that I knew that I needed. I thought I even saw it, like, two years earlier. Yeah. Yes. It would take me two or three days to find it.
A
And as research assistants, you need to have a second person who can be like, we have something like that. Right. You need to have a document fetcher.
B
Yes. For about a year, I had a researcher who I worked with who was super helpful. But as the project continued and just obviously metastasized, I was sort of on my own.
A
That's the tough part. It would be wonderful if everything was neatly organized. But you can't do that because you're doing other things in your life.
B
Right.
A
Do you feel like that's the thing you get lit up by doing and all the other things are distractions, or do you think they all kind of feed into.
B
Oh, the truth is they all feed each other. So Squawk box in the morning feeds the way I think about my reporting all day. Yeah, a lot of the reporting all day feeds what I do on television. Working on all of those things. I think fed a lot of what ultimately ends up in the book. I mean, a lot of all of the nonfiction work I've done helped me when I was involved in things like Billions and Other Things to think about sort of worlds. So, yeah, it probably looks or feels like I'm doing a lot of things, but to me, they're all sort of in the same vein.
A
Yes.
B
Maybe you'll think I'm ADHD because of the jumping around. It actually keeps me engaged and excited in all of them.
A
But is your phone just going off all the time? I feel like the hardest thing about the large blocks of uninterrupted concentration that a book like this would require would be sort of at odds with the sort of plugged in the plug in.
B
There's no question that you're texting people back, back and forth. I have reporters that work on my team. I gotta call them back. I'm editing their work. They're giving me tips. I'm giving them tips, for sure. And that was the thing that probably, you know, would throw me the most. I did occasionally try to use. There's now the do not Disturb function on the phone. That only works to a degree. That's why weekends are great.
A
Yes, well, the do not disturb prevents other people from disturbing you, but it doesn't prevent you from disturbing yourself by looking for.
B
By looking for it. Yes, I. Yes, I. I fully cop to that problem.
A
No, that. That's the. I'm like, don't. Don't call me. And then I'm like, I'm not using this two hour block. I'm using 30% of it because I dicked around for a large chunk of it. Thanks so much for listening. If you could rate this podcast and leave a review on itunes, that would mean so much to us and it would really help the show. We appreciate it. And I'll see you next episode.
B
You hear that? That's not just a Toyota truck. That's the sound of no crowds, no alerts, no distractions, and no telling what you'll find next. You know, like a detour. So why would you ever take a tour when you could take a detour? Toyota Trucks.
C
My family owns a 2023 Toyota 4Runner, and honestly, it's my favorite vehicle that I've ever owned around town. It's smooth and reliable, but where it really shines is on our trips into the backcountry. We've taken it on backpacking adventures to Colorado and New Mexico, loaded up with gear and never had to think twice about whether it could handle the terrain.
A
Terrain.
C
That's what Toyota Trucks are built for. Off road confidence, rugged durability, and the freedom to explore. Toyota has a long history with the outdoor community, and they're committed to helping more people get out there and experience what nature has to offer. From remote trails to scenic byways, Toyota Trucks empowers you to take the detour, roam freely, and discover places that still feel wild and untouched. And they're not just making great trucks. They're working to expand access to adventure so more people can connect with the outdoors and pass that passion on to the next generation. Discover your uncharted territory. Learn more at toyota.com trucks adventure-detours that's toyota.com trucks adventure detours.
Episode Title: Why Andrew Ross Sorkin Spent 8 Years Chasing One Story
Host: Ryan Holiday
Guest: Andrew Ross Sorkin (financial journalist, author of 1929: Inside the Greatest Crash in Wall Street History and How It Shattered a Nation)
Date: December 3, 2025
This episode features a rich conversation between host Ryan Holiday and renowned journalist/author Andrew Ross Sorkin. The focus is Sorkin's new book, 1929, a sweeping and deeply researched account of the infamous stock market crash. Sorkin discusses his eight-year journey crafting the book, the painstaking process of historical storytelling, and the personal and professional challenges involved in writing such a weighty narrative. The discussion also veers into themes of motivation, the complexity of human nature, and the mechanics of deep journalistic and historical research—all viewed through a Stoic lens.
On Book Tours & Interviews:
On Writing Pain:
On Falling in Love with History:
On Fear and Legacy:
On Obsession:
On Historical Empathy:
On Motivation:
On Routine:
On Frustrations in Research:
| Segment | Key Topic | Timestamps | |-----------------------------------------|---------------------------------------------------------------|--------------| | Book Tours & Bubble Questions | The repetitive nature of interviews and present parallels | 09:30–10:16 | | Writing Challenges & Process | Pain, routine, blocks, obsession | 12:23–14:38 | | Falling In Love & Fear | Obsession with period, fear of failure | 14:38–16:48 | | Perfectionism & Continuous Revision | Obsessive editing, not letting go | 17:18–21:04 | | Research Methods & Audiobook Lessons | Tools, assistants, pandemic, tech limits | 22:45–30:48 | | Routine & Deep Work | Morning schedule, blocked time for writing | 25:56–29:32; 42:01–43:40 | | Research Serendipity | Uncovering key evidence over time | 29:46–31:37 | | Motivation & Empathy for Historical Figures | Understanding “characters,” shades of morality | 35:29–38:48 | | Limitations of Journalism | News vs. deep history, narrative depth | 38:48–41:12 | | Experience, Specialization, Depth | Journalistic expertise, longevity | 41:12–42:04 | | Productivity, Distraction, Focus | Managing interruptions, mental strategies | 45:32–46:30 |
This episode is a tour de force on historical research, the taxing nature of creative work, and the motivations behind digging deep into a pivotal moment in financial history. Sorkin's candor on fear, obsession, and productivity offers rare insight for writers, historians, and anyone wrestling with a long-term project.