#11 Ryan Holiday: The Stoic Whisperer

In this episode, I talk with multiple best selling author Ryan Holiday about how he reads, what it means to be a stoic, and how to gracefully deal with freeloaders. *** Go Premium: Members get early access, ad-free episodes, hand-edited transcripts, searchable transcripts, member-only episodes, and more. Sign up at: https://fs.blog/membership/ Every Sunday our newsletter shares timeless insights and ideas that you can use at work and home. Add it to your inbox: https://fs.blog/newsletter/ Follow Shane on Twitter at: https://twitter.com/ShaneAParrish Learn more about your ad choices. Visit megaphone.fm/adchoices

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

• 0:08Shane Parrish?

  Welcome to The Knowledge Project. I'm your host Shane Parrish, curator behind Farnham Street, an online intellectual hub of interestingness that covers topics like human misjudgment, decision-making, strategy, and philosophy. The Knowledge Project allows me to interview amazing people from around the world to deconstruct why they're good at what they do. It's more conversation than prescription. On this episode, I have Ryan Holiday. Since dropping out of college at 19 to apprentice under strategist Robert Greene, the author of The 48 Laws of Power, Ryan has advised many New York Times bestselling authors and musicians. He's a master, and some would say manipulator of the media, as his first book, Trust Me, I'm Lying, outlines. His latest book, The Obstacle is the Way,

• 0:51Shane Parrish?

  reached bestseller status. We explore how he reads, what it means to be a stoic, and his infamous note card system. The conversation is actually cut short. We originally had 90 minutes booked for this interview, but I forgot to turn on the recorder, so we had to re-record the entire interview. Ryan got to practice some of that famous stoicism. With that said, I hope you enjoy the conversation as much as I did.

• 1:17Shane Parrish?

  We'll go quicker. This just, we were just talking for about 20 minutes and just realized that the microphone wasn't on.

• 1:23Speaker 01

  Wouldn't it be funny if I freaked out and knocked over all the mics and was just very un-stoic about it? No, no. So stoicism is a practical philosophy, right? Most people think, when they think philosophy, they think college professor lecturing them. Stoicism is, you know, it's favored by statesmen, politicians, soldiers, artists, et cetera, because it's really, at its core, I think, a series of maxims and exercises for how to live what they would call the good life, or to live virtuously, or with excellence. And, you know, if I was to sort of sum up the central maxim there, it would be, you don't control the world around you, you control how you, you control your thoughts, you control

• 2:06Speaker 01

  how you respond to the world around you. And so the stoics are focused exclusively on that stuff, and that's not just a competitive edge, but it's a recipe for, I think, contentment and fulfillment and stuff like that.

• 2:20Shane Parrish?

  And so what really pulled you into that was, I think, the book recommendation by Dr. Drew.

• 2:25Speaker 01

  Yeah. So I was at a conference, I said, hey, What books would you, I sort of found him afterwards. I said, hey, like, I really love to read. I know you read, what would you recommend that I read? And he told me about Epictetus. I looked up Epictetus on Amazon. Marcus Aurelius was there, who I'd always liked the movie Gladiator. So I was like, oh, I'll get that too. I read Marcus Aurelius and Marcus Aurelius is just, it's just this totally unique historical document in the sense that it is the most powerful, successful man on earth at that time. Literally worshipped as a god. He's deified, writing notes to himself about how to be a better person that were never intended for publication and that survives to us. And so when I picked that up at 19, it was like so radically different than what I'd learned in school,

• 3:10Speaker 01

  radically different than any self-help book I'd ever read, radically different than any of the crap my parents had ever told me. And so I was just like, wow, this is, this is what I want. This is what I want to be. This is how I want to live my life and

• 3:23Shane Parrish?

  Was that the Hayes translation?

• 3:25Speaker 01

  Yeah, the Gregory Hayes translation. So the, one of the mistakes I see people do when they read philosophy is they cheap out. Like, oh, this is free on Project Gutenberg. First off, it's free because according to the copyright system, it's not worth anything, right? Like, that's why it's free. Every generation needs its own translation because a book like Marcus Aurelius, he's writing to himself in colloquial, personal language. So when you see like thou shall not, that's not, he didn't say that. That's what someone in the 17th century would have said. And so you, I, I think you want to read the best translation you can. And right now that's Gregory Hayes.

• 4:04Shane Parrish?

  I remember reading, I first came across that, I think in university and it wasn't the Hayes translation. I read this and I was like, what the is this? And then I found the Hayes translation just randomly in an airport one day and I started reading it going, why didn't I read this before? Like, what was I thinking?

• 4:21Speaker 01

  Who was hiding this for me? This is crazy. Yeah.

• 4:24Shane Parrish?

  So who are your favorites then in terms of the, the Stoics, I guess?

• 4:29Speaker 01

  So Marcus Aurelius is my favorite. Probably Seneca is my second favorite. Seneca was a high sort of profile political advisor. He was also a very famous playwright at the time, famous enough that one of his, as I was saying earlier, I'm trying to remember what I said and didn't say. One of Seneca's lines from his plays is actually a graffitied line on a wall at Pompeii. It's just been preserved for us. So like, he's one of the most famous writers of his time. And his plays are actually great. But I like Seneca a lot. I like Epictetus. Epictetus is a bit preachy for me, but those are the big three. I've read the others. The others are much harder to understand.

• 5:13Shane Parrish?

  Like Chrysphylis or?

• 5:14Speaker 01

  Yeah, if you want to read the others, the best thing to do is Diogenes Laertes, wrote this book that's sort of a biography of all the other, all philosophers. It's like a multi-volume series, but the, one of the volumes is about the Stoics. And so it's like, he's giving a biography, but then also quoting all their best lines. The reason Seneca, Marcus Aurelius, and Epictetus are also the most famous is because their works survive the most completely. So all you really get from the other people are fragments, anyway.

• 5:44Shane Parrish?

  So Seneca is fascinating to me and he led this, this life that's been portrayed in multiple ways. Right. So maybe, we already had this conversation, but maybe you can give me a-

• 5:54Speaker 01

  Sure. Yeah. So, so Seneca's most famous letter, or one of his most famous letters, is to his mother after he'd been exiled. And we don't know whether he deserved to be exiled or not. He supposedly, he had an affair with Claudius, maybe Claudius's, no, Caligula's like sister-in-law. He had an affair with a famous woman and was exiled from Rome. And his mother was of course devastated. He, as a political insider and a powerful person, was of course devastated. This is the end of his professional life. And so he's sent away and so-

• 6:27Shane Parrish?

  He lost all power, all influence, everything.

• 6:30Speaker 01

  Yeah. And so he's not just writing about philosophy in theory. He's writing about it as someone who underwent, you know, who lost everything. It'd be like going bankrupt tomorrow or being impeached from office or something. And so then he's recalled to Rome on the condition that he become Nero's tutor. And he accepts Nero at the time was just a child, right? So no one knew whether he was really good or bad or anything, but- It became increasingly clear that this was a deranged pathological individual, like a true psychopath.

• 7:05Shane Parrish?

  Yeah.

• 7:06Speaker 01

  And he's, and so not only is Seneca his mentor trying to curb these things, but he's also becoming immensely rich. He was one of the richest men in Rome because the emperor is his, you know, he, he's almost more powerful than the emperor.

• 7:21Shane Parrish?

  Right.

• 7:21Speaker 01

  So there's that. And then, you know, he's an artist, which I imagine was stressful and interesting. So it's just some, even in his own time, a lot of people thought he was hypocritical. But at the same time, they loved his writing and they loved his essays. And he was one of the most prominent, considered to be one of the wisest men at the same time. So he's complicated like everyone else. And as someone who's worked for complicated people, and I have a bit of a complicated reputation myself, like I very much related to this idea that there's just a lot more than people see when they hear like rich guy, Nero's tutor, famous writer, stoic. So it's almost impossible to comprehend what this individual must have been like.

• 8:02Shane Parrish?

  I think we're like that with almost everybody, right? We paint them with some sort of brush or label based on a soundbite, a tweet, you know, a headline in a newspaper. And we don't think that we're, you know, we don't think about that person or what's going on in their life or why they make these choices.

• 8:18Speaker 01

  Yeah. In the Eric Rom book, which I know you've recommended, he says, he, he says that the Seneca's critics, and I won't try to pronounce the Greek word, they, what they called him was tyrant teacher. There's actually a Greek word for that. And that was a, considered an epithet, right? And as someone who has represented individuals, many of which are very hated, I've got this, I, I've myself have been accused of enabling these people or encouraging these people or being worse than these people, you know? So like I, and then, you know, I've, my opinion of some of the people that I've worked for has changed over time. And, and I, I read that book about Seneca around the time that American Apparel was

• 9:00Speaker 01

  collapsing and Duff Charny, who was the CEO, sort of went through, you know, did some things I very much disagree with. And so, you know, it was like, uh, there's this great line in one of Seneca's plays where he says, crimes often return upon their teacher. And You know, that that's what happened to Seneca, right? Seneca is ultimately forced to commit suicide by Nero. It's it's a very prescient remark that he would write in one of his plays, something that basically describes the fate that would befall him. And as that was sort of happening to me, and I read that book, I thought like, I I relate on a very small scale to what that person must have been like and what they must have gone through.

• 9:44Shane Parrish?

  You stopped going to school when you were nineteen?

• 9:48Speaker 01

  Yeah.

• 9:49Shane Parrish?

  Can you walk me through that decision and what you did right after that?

• 9:52Speaker 01

  Well, I mean, one of the first things I like to do, if only for my own sake, is I, even though I like, look, I wrote my biography, so I'm responsible for the people who say, like, hey, you know, you dropped out of college at nineteen. But it's interesting how things can become in retrospect more significant than they are. And Nassim Taleb calls this the narrative fallacy. You tell yourself a story about your life. So it's like, my sophomore year of college ended, you know, two weeks before my twentieth birthday, and that's when I stopped going to school. So did I drop out when I was nineteen? Or did I drop out when I was twenty? Is that semantic? Or is that a that's a very significant?

• 10:30Shane Parrish?

  Five percent of your life.

• 10:31Speaker 01

  Right, it's big. So but anyways, I left when I was nineteen or twenty to I was I was at the time, I was a sort of a marketing manager for Tucker Maxx, who had, you know, written these bestselling books and had a sort of a media empire. I was I was working at a talent agency in Hollywood. I signed some of the first YouTube clients to ever become sort of professional actors and content creators. And then I got a tryout to be a research assistant for the author Robert Greene, who wrote The Forty Laws of Power. And so it was just, it was three things that if you told me when I was graduating, that I could choose one of them, I would have said, college was worth it. So to me,

• 11:14Speaker 01

  it was, should I stay in school? Should I turn down these things, stay in school because that's what you're supposed to do, and then hope to get this lucky again? And so I tried

• 11:25Shane Parrish?

  And so we were talking earlier about being busy and saying no to things and doing three things at once, it sounds like it's a lot. And how have you, you're always doing multiple things at once. You're always trying to do a lot. How do you juggle that?

• 11:41Speaker 01

  Well, it was a lot, but it was also very formative, right? So I was working in, you could argue that what I do now is a combination of all those three things, right? I have my own marketing company, I write books and I, and I, and I advise sort of clients and people on strategy, right? So it's a combination of those three things. And so instead of developing them concurrently, which would have taken a long time, or no consecutively, which would have taken a long time, I did them concurrently. And so it compressed, you know, you want to say your 10,000 hours, if I'm close to that, it compressed it in three years instead of 10, or four, you know, probably closer to four. But I did, I was very overwhelmed and very busy, but by not doing it at a leisurely pace, I got to skip

• 12:23Speaker 01

  ahead in line, so to speak. But it's also been a tendency in my life that I just commit to a lot of stuff. So like, not only was I working for all those people, but I never like stopped working for those people. I would just start doing more things. And so, you know, I probably worked for Robert for like five or six years. And if you called me today, I, oh, what do you need me to do? And so it's very, it's very, it can be very exhausting, but it's also a bit of a compulsion for me. It's hard for me to say no to things.

• 12:55Shane Parrish?

  And you kind of reached a tipping point recently on that, didn't you?

• 12:58Speaker 01

  Yeah, yeah. I mean, around the time of the collapse of the American bear, I was just very overworked. And I, like, I built this life for myself here in Austin where I live. And yet, I was in LA, I was had to show up in an office every day. I was dealing with all sorts of stuff. I tried to cut out of my life because like, someone called me and said, hey, like, we need you, can you come? And I said, I'll be on the next plane. And the idea of stopping and going, what's the opportunity cost of this? Or should I say yes? Is this what I want? What, you know? What am, what is gonna, what's gonna be the problem here? And I didn't ask that until, sometimes you gotta touch the stove to get burned. And so I really got burned and overwhelmed. Um, and I've, I've tried to get better at saying no, but I would say, you know, this is a very first world thing.

• 13:42Speaker 01

  And I get that, but one of the hardest things in the world for people to do is to say no to money. It's extraordinarily difficult.

• 13:50Shane Parrish?

  It almost doesn't matter how much, right? Like if somebody offers you 20 bucks to do something in the next 10 minutes or something.

• 13:57Speaker 01

  I remember like my wife makes fun of me because like a couple of years ago, we were like walking into like a Home Depot or something. And I was like, oh, they're hiring. And she was like, are you looking for a job? But it was like, like somehow like I can't even, I just couldn't turn off that part of my brain. The idea of like, there's an opportunity. Should I consider that like, like, and this is

• 14:17Shane Parrish?

  I have 20 minutes right now.

• 14:18Speaker 01

  Right, right. Like, and so for me, it's, it's, uh, my wife's the same way. It was like, when we see stuff, we think about like, why shouldn't we do it? We don't think like, what is the opportunity cost? We don't think, you know, do we need this? We think, well, they're paying us for it, you know, but, and that, that is not great. That's not a great attitude if you're trying to produce lasting work or to be the ultimate best at what you do.

• 14:43Shane Parrish?

  So how is your framing changed now? In terms of these costs and the, I mean, you must be bombarded all the time with

• 14:49Speaker 01

  I mean, not as much as you think, like, I don't want to make it sound like I'm just drowning in opportunities. Like I'm certainly not there, but, um, one of the things that was formative for me is like, I'd said yes to a bunch of, I said yes. So I said yes to working on this one book. And, um, then for, for some personal reasons, I backed out of it. And then like a week later, um, Tony Robbins called me and wanted me to work on his book for like double the amount. And that book has sold like a million copies since it was like a huge, big life-changing opportunity for me. But I just committed to this other thing, not thinking about like the, it was, you need to have the confidence to be able to go like, things are going to be okay in the future.

• 15:30Shane Parrish?

  Right.

• 15:31Speaker 01

  So you're not, um, you know that, what's that?

• 15:34Shane Parrish?

  You're not driven by that immediate kind of.

• 15:36Speaker 01

  Yeah, there's that fable about, you know, the ant and the cricket about the, you know, the ant's always preparing for winter while the cricket's like playing and then the ants. Well, if you actually read about that story, some of the interpretations, the interpretation of that allegory has changed in different eras. You know, the ant, if the ant is over preparing at a certain point, it's missing out on life that the cricket is experiencing, right? And so I, I think for me, it's this idea of like, okay, this is what enough is, or this is what, this is what my baseline is, and I have to be able to, to say, no, sorry, that's not enough.

• 16:12Shane Parrish?

  And it's also understanding what makes you happy, right? And we're

• 16:15Speaker 01

  Totally.

• 16:16Shane Parrish?

  Yeah.

• 16:16Speaker 01

  Yeah, like, and that, it was like, okay, I'm making great money doing this thing, but I have to show up in an office and my whole life is around, was about not having to show up for an office, right?

• 16:27Speaker 01

  There's that Thoreau line, like, be wary of any enterprise that requires new clothes. It's like, if you don't, if you like, like, if you don't like having to dress up for work, don't, it doesn't matter how good the opportunity is, if they make you dress up for it, you know, like, I, I, you gotta think about what's important to you, and if you don't know, you can end up very far, if you don't know and you don't make those decisions one by one, you will end up very far from where you need to be to be happy.

• 16:54Shane Parrish?

  Right. Oh, I want to come back to working with Robert Greene.

• 16:58Speaker 01

  Yeah.

• 16:59Shane Parrish?

  What did you learn from that?

• 17:02Speaker 01

  I mean, I learned everything, right? Like, he, I would not be a writer if it wasn't for Robert Greene. I would not be able to think the way that I think if it wasn't for Robert Greene. I'd be a much worse person if I never met Robert Greene, which I know is probably funny to people who hear that, you know, he's the author of the Forty Islands of Power. Robert is one of the most generous, patient, wisest people that I've ever met. Um, I, you know, I started for him, I was transcribing interviews for a book that he was writing with 50 Cent, and then he would start to let me read books that he didn't want to read, that he thought there might, you know,

• 17:36Shane Parrish?

  Remote possibility.

• 17:37Speaker 01

  He's like, look, there's a 1% chance this book has some material in it that I might be able to use. Please read it. And most of the time I answered was like, yeah, you're right. There's nothing here. But he would say like, you know, I want, I remember he was saying like, he's like, in the 50 Cent book, he was like, I like to include some stories of like, the great black boxers. He's like, but I've already written about Muhammad Ali in my other books. So let's see what you can find. And so I read biographies of Joe Louis and Jack Johnson and all these other people. And, and so I was like, that was like, one of my first contributions to one of his books. Like, I was like, there's something there about Joe Louis. Like, here's what I would suggest you. That's how that worked. Like, hey, I read this biography of Joe Louis. This is

• 18:20Speaker 01

  something I think you should check out. There might be something there. And then he goes and finds it. I'm not like, contributing in any way there. I'm just, hey, I've eliminated this for you. Check this. But those, like, I never would have read those books if he hadn't assigned me to read them. So in a weird way, it was like, it was sort of like a college-esque experience in that I have an instructor who's assigning me to explore certain things. It was like a work-study

• 18:46Shane Parrish?

  program. I think you refer to it as almost an apprenticeship.

• 18:49Speaker 01

  Yeah, yeah, yeah. I mean, it's not an official apprenticeship and like, we didn't sign like a contract. But yeah, the, the idea is, at a certain point, after I'd gotten a little bit better, he was like, what do you want to do? Because that's how I can make, if you could tell me how I can help you with what you want to do with your life. And this is a conversation I have with people that I work with now. If you, he's like, I'm not going to pay you, like, a ton of money. But if you can tell me what you want to do with your life, I can make sure this is very rewarding for you. And it was like, he, he showed, my note card system, how I research books now is a direct result of the system that he taught me. And how I think about books is a result of, you know, I would go, you know, he'd be like, I want you to do this, I want you to do this, can you do this, can you do this? And I

• 19:34Speaker 01

  And then I'd be like, okay, but I have one question. Like, I remember one time I was like, Robert, like, who makes the indexes for books? Like, how does that happen? And he was like, oh, like, because I thought, like, one of the things that was intimidating to me about writing a book is like, do I have to like, do I have to do that? And he was like, oh, no, that just like happens. A publisher just does that. I was like, oh, okay. Like, so it was just little things. And then when I decided to write my first book, he walked, he was like,

• 19:59Shane Parrish?

  He walked you through the process. That's awesome. Um, let's geek out for a second because the number one question I got when I told people I was interviewing you is, they want to know about this infamous note card system. Can you walk me through, uh, Robert's system and then how you've adapted that to your system now?

• 20:18Speaker 01

  Sure. So Robert does, uh, he's not quite Robert Caro, who writes everything longhand, but Robert, um, I would say probably 80% of his work is in the research and 20% is in the writing. And all the writing is done on these note cards. So you would read a book, he would read a book, go through it and take notes, uh, mark things that he liked, and then he would transfer that knowledge onto note cards. And then if you note it like, so the 48 laws of power might be 48 sections, and then each law is supported by note cards. And so the way that works with a research assistant is like, my job is to find the materials to go in the note cards. So then when he's writing law six in the 50th law or whatever, there's stuff for him to rely on. And, um, so I started using note cards myself.

• 21:02Speaker 01

  And really, I just started, I would write stuff, I would, I would see a quote that I would like, or a word I would like, or a story I would like, I would just write it down on this note card. And I just had a collection of note cards, um, until I had enough note cards that I started organizing them by theme. And then when I wrote my first book, it was, trust me online, it was, I spent a year before I left American Apparel, writing note cards around media. And hey, this is good. I read this book and then I would, you know, all this stuff. And, uh, it became, you know, hundreds and hundreds of note cards. And then what that allows you to do is when you like, my book, uh, The Obstacle is the Way is three parts,

• 21:43Speaker 01

  Ten chapters in each part. So that would be thirty parts plus an intro and a conclusion, right? So that's thirty two sections. You're just filling that up. But let's say I'm writing part two, chapter six. That's all I have to carry with me if I'm going to a library or I'm on the road. You're not carrying the whole book around your head. You're not sitting down and just writing where it leads you. You're focused on that individual section, which makes it all much more manageable.

• 22:12Shane Parrish?

  And how did you pick the themes that you came up with originally?

• 22:16Speaker 01

  For what?

• 22:16Shane Parrish?

  For your note card system.

• 22:18Speaker 01

  Just, it's really just a function of the material, right? Like, you're not like, oh.

• 22:22Shane Parrish?

  Personal categorization of.

• 22:24Speaker 01

  Yeah, it's like, look, I read a lot of books about Stoicism, so I have a huge section of note cards that are on Stoicism. But the obstacle is the way, like, you know, I was writing, I read this, this section in Pierre Hadeau's The Inner Citadel, where he talks about this Stoic idea of turning the obstacle upside down, which is how you take a negative thing and turn it into a positive thing. And I wrote that down.

• 22:45Shane Parrish?

  Right.

• 22:46Speaker 01

  And then I would read other examples of people doing that. And I write that down. And I write in the corner, turning the obstacle upside down. So I got to, you know, twenty note cards about that topic. And then I said, hey, when I was thinking about what I wanted to do for my next book, I was like, I think there's something there. And so I wrote a proposal, I sold it. And then I said, okay, I've got twenty note cards, I need a thousand to write a book. Now I have to go read and explore and find things to, to, and to, to build up this database of knowledge, essentially. And then.

• 23:19Shane Parrish?

  And so how do you store these? There must be thousands of them.

• 23:22Speaker 01

  There's thousands of note cards there. I, I use this thing, it's called a cropper hopper, which is just a weird thing they used to make to store, store like.

• 23:31Shane Parrish?

  Photos?

• 23:31Speaker 01

  Photos. Because a four by six photo is the same size as a note card. So I just have bought, I used to buy one at a time, then I started running, they started, stopped making them. So I've got my garage full of them. But each one of my books is one of those boxes. Then I have a, I used to have just one box of general note cards in different categories that have not become books or anything yet. And now that's split into two.

• 23:54Shane Parrish?

  And so do you store these electronically?

• 23:58Speaker 01

  Um, so I store them in my office. I got really scared, like my house got broken into a couple of years ago and I was really scared that like someone stole them, not knowing what they were. They didn't thankfully. And then

• 24:13Shane Parrish?

  But it all would have been gone, like all of that research.

• 24:16Speaker 01

  And then ironically, I came home and knocked the box over and disorganized everything. But Robert, a couple of years ago, found a scanner that can scan note cards. So every couple of weeks I have an assistant go through, scan all of them and then I back them up to Dropbox.

• 24:31Shane Parrish?

  So you don't use Evernote or anything like that?

• 24:33Speaker 01

  Uh, I don't even know how to use Evernote. And a lot of people go like, oh, your system, it sounds just like Evernote. It's not Evernote. It's physical note cards for a reason, like Raymond Chandler has a line, if you take the pain to write it down, you're more likely to remember it and use it. The idea of just quickly being able to copy and paste stuff is antithetical to what I'm doing and why. Like it's the ritual that's important and the act of taking it longhand is very important. Obviously, if it's like a, you know, huge paragraph, I'm gonna type it out, but it's still no copying and pasting. That's sort of the law.

• 25:13Shane Parrish?

  The rule.

• 25:13Speaker 01

  The rule, because it's about taking the knowledge from the book, running it through your body and then putting it in a, in a thing that you can manipulate, but still have tangibly in front of you, right? Like, like my note, I could, I could lay out the box for Obstacles Away and it would be right there and you could see it. And while it was there, I could move stuff around. I could say, actually, this chapter is going to be moved into part three. Or this note card, I thought this note card would work for somewhere in section two, but it didn't. So I'm gonna rework it into section one. I can move stuff around. So I have a

• 25:49Shane Parrish?

  Physically and visually.

• 25:51Speaker 01

  Yes. And I think that's very, very important. I don't want it to be a black hole on my computer.

• 25:57Shane Parrish?

  But it's not searchable, right? Like, how hard is it?

• 26:00Speaker 01

  It's not searchable. If I, look, if I ever couldn't find something, I could have someone go through them for me or I could go through them, which I do all the time. But I've never, one, my memory works as such, like I could tell you what different passages look like in books on my shelf, where that shelf is. I'm a bit like, I don't know, Asperger like that, I guess, but I, I've not found, I think people overestimate, like they're like, oh, I need it to be searchable. It's like, well, what have you ever done with it? Right? Like, I think a lot of people get very nerded out about the system and about having like the perfect optimized thing. When, um, you know, if you told me they'd written 30 books,

• 26:42Speaker 01

  I'd be like, okay, your system's better than mine, but it's certainly not how, I mean,

• 26:47Shane Parrish?

  It's like optimizing for what?

• 26:48Speaker 01

  Yeah, I've written four books in four years. Like, it's, it's, uh, it's not, not having it searchable has not held me back in any way that I can currently tell.

• 26:58Shane Parrish?

  And you wouldn't, you don't envision doing things differently in the future?

• 27:01Speaker 01

  Um, no, I don't think so.

• 27:05Shane Parrish?

  So what's your workflow like for writing a book? Maybe walk me through kind of, okay, I have an idea, uh, not from a publishing perspective, but from a writing perspective. So you go from an idea, what is the structure and the tools that you're using to put that together? So you, you, you have an idea, you do the research, you put them, you get the note cards, you arrange them, are you writing and like, how are you?

• 27:28Speaker 01

  I mean, that's a, that's a more difficult question to, I think when you write your, your book, you will not ask that question because like, it's just different. Like people go like, how long did it take you to write it? And it's like, I don't know, because when did it start? Right? Did it start when I was born? Did it start when I first had the idea? Did it start when you sold it? Um, you know, my, my book that's coming out in June, I started writing it January 1st of 2015. Like I know that, and my first book, I started June 17th, 2011. I know the exact day that I started, but I've been researching them for years, right? Like, so, and I know when I sold it. So it's, it's a little weird, right? But, um, when you, when you have-

• 28:11Speaker 01

  You have the idea, you're researching, it's sort of like you have this general sense of what you're trying to say and what you believe. And then you, you know, you sort of let the confirmation bias do its work, right? Because you're only thinking about this thing, you weirdly just attract all sorts of things that could support that idea, or would be interesting to discuss in that idea. And so one of the, one of the downsides of that is you're paranoid someone's going to steal your idea all the time. But they're not, you're just thinking about your idea all the time.

• 28:39Shane Parrish?

  So you feel almost a pressure to get it out there really quickly, so nobody...

• 28:44Speaker 01

  So what I do is, um, when I sit down to write, let's say, I'm, I've broken it up into pieces. That's part of what the note card system does. So it's like, today I'm writing the intro. Like on, when I say-

• 28:55Shane Parrish?

  So you've chunked it.

• 28:56Speaker 01

  On January 1st, I started, I was writing the intro. And now that intro is radically different now than it was, but I was writing that. And then I got to a point where I could say like, the, in, the rough draft of the intro is done. Then, now I'm writing, you know, part one, chapter one. And I'm writing these discrete pieces because writing a book is very demoralizing. Um, like, think about it, let's say a book is 60,000 words, and you're writing 500 words, 500 usable words a day, let's say, which is, you know, people write two or 3,000, but you're not getting rid of them, right? So, um, you, you could work for eight hours on something, or three hours, you could work a day's work of writing, and make no visible, perceivable progress towards your goal. So, there's no, you only

• 29:41Speaker 01

  get to the light at the end of the tunnel, like, three or four months in. Or, you know, think about someone like Robert Caro, who's been, he wrote, um, you know, he's been writing about Lyndon Johnson for like 40 years. He's, Lyndon Johnson's like 60 in the book, right? And so he's like, and that's only to get him to volume four. So, um, you, you have to break it up into discrete tasks. Um, at least I think, when you break it into discrete tasks, then, like, even Robert Caro, he knows the last sentence and the first sentence of the book, and then everything else is filling it in. But what you don't do, what I think is the most dangerous thing for writers to do, is to just, maybe it works when you're writing fiction, I don't know, but sitting down and just writing.

• 30:26Speaker 01

  Like you can't hit a target that you didn't aim for.

• 30:28Shane Parrish?

  Oh, but that's like the whole notion that people sell, isn't it about being an author? Oh, you just go to the coffee shop, you sit down, the words magically spew out of your mouth.

• 30:36Speaker 01

  And I mean, there's the, there's this Hemingway quote where he says, writing is easy. It's just sitting down and writing, sitting down at a typewriter and opening a vein or something. Right. And that would be great, except for he didn't write that way. Like, if you look at a farewell to arms, there are eight, no, 27 handwritten different endings to that book. So he was not sitting down and bleeding unless he was bleeding to death. Right. Like, he was meticulously editing and rewriting and getting closer to something like, so writing, I think when you break it up into tasks, you're like, okay, all I have to do is get these 2,000 words right. That's much easier to wrap my head around. And then later you're linking all these pieces together.

• 31:21Speaker 01

  But I write, I write in, this is another weird thing with that. So I write those, those chunks in Google Docs, like in separate Google documents. So I'm not doing like a day to day word count. It's like, hey, today I'm writing part two, chapter four. And then only when I've gotten to the end, do I then combine all the things and then begin to look at the book as a whole. So it's a big, then I switched to, and this is all personal, but then I switched to Microsoft Word. So I'm taking it off the internet and now it's a, now it's a distinct manuscript. And now I'm thinking about the project as a whole. I think editing while you write the whole thing is hard, but if you're just doing these pieces, then I'm able to sort of be a bit recursive about these smaller sections.

• 32:06Shane Parrish?

  And do you mop it out in that like today I'm going to do this section tomorrow? I'm going to do this section. Are you doing anything else where you're doing this?

• 32:14Speaker 01

  It's not scheduled like on Tuesday, I'm doing this and Wednesday I'm doing this. It's more like. You have to go from A to Z and so you're starting in A and then when you're done with A then you move on to B. But like I don't write full time like I could, but I have a company and I I try to write one or two articles a week. I have my own site. I do a lot of consulting for the first three books. I was also working in American Apparel. So I tend to, I don't know how someone writes for an entire day. So I write, I usually get up early. I love your stuff about, you know, if you want to be more productive, wake up early. I wake up around seven. I try to start writing by like eight and I write usually like at like 11, 11:30 like I'm done.

• 32:59Speaker 01

  There's it's, it's hard.

• 33:01Shane Parrish?

  It's draining.

• 33:02Speaker 01

  It's very draining and you just hit diminishing returns, right? So then I stop and then I, I don't give myself a break for the rest of the day. I'm not going to work for three hours. I, I work on my other stuff. So I just schedule everything after I start.

• 33:17Shane Parrish?

  But you're matching your energy and intensity to the work in some way, right?

• 33:22Speaker 01

  Yeah, yeah. Like you're writing to, you're writing till you stop and then you're moving on to these other things. And then usually throughout the course of the day, other things occur to you that would be valuable to the writing. And you're either taking notes and doing them tomorrow or you're, I'm sending an email to myself or whatever. Like for instance, I like to exercise in the middle of the day, not in the middle of the day, in the mid afternoon.

• 33:44Shane Parrish?

  Okay.

• 33:45Speaker 01

  So it's like I write till, let's say hypothetical schedules, I write into 11. From 11 to three, I'm doing calls or working on client stuff or I'm editing stuff for other people, whatever I'm doing. And then at three, I'm going to go for like an hour run. And on that run, wherever I was stuck in the writing, some of that's going to come loose in my head and I'm going to be like, oh, that's a great phrase. And I'll email it to myself or I'll, God, I remember this when I come home. And then I'm like bursting in like some, the amount of times I've burst into my house and said to my wife, like, don't say anything to me. Like until I get this down on paper and then I'm just writing, you know, in shorthand, like little notes and, and then it's like,

• 34:26Speaker 01

  and that, then I can go back to being a normal person. So I either run or swim, but that breaks it up for me.

• 34:31Shane Parrish?

  And what's your night like?

• 34:33Speaker 01

  Um, I usually am done by like five or six and then I just sort of dick around. We watch, we eat dinner, we'll watch TV, play with our animals. Sometimes I'll check email. I I'm checking email throughout this time. I'm not not working at all, but.

• 34:49Shane Parrish?

  So you are one of the quickest responders that I know for a busy person on email. Can you? How do you do that?

• 34:57Speaker 01

  I mean, my job is to communicate the like, so I don't do much phone. So I'm sitting there working on stuff and part of what I'm working on is email. I mean.

• 35:06Shane Parrish?

  I'm amazed. I get responses from you. Sometimes I've like barely hit send and gone to like a new message and it's like a response.

• 35:12Speaker 01

  So I'm like inbox zero. So like I'm, I pride myself on having gotten to a point that I can deal with stu- new stuff as they come in. But one of my tricks is like, if you send me something and it's worth responding to, I'm responding. If someone is sending me something like, you know, I'll get a letter from someone who read one of my books. It's really nice. But I, you may have written about this, the Eisenhower stuff, urgent, not important or whatever. Um, I save a lot of stuff until like, like, like to you, I'm this is so maybe this doesn't work, but to you, I'm responding in two minutes. But then I have people I owe emails to from three weeks ago that I probably won't do until the next time I'm on a flight or I'm stuck without wifi and I'm just getting caught up on old stuff.

• 35:56Shane Parrish?

  I'm notoriously bad for email and I struggle with something that maybe you struggle with as well, which is I get a lot of unsolicited email that I feel in some ways that people are burdening my time and they're not necessarily thinking about it. Like the requests, can you read this 20 page document? I got one last week. Can you do it? Is, you know, well worded, but it was basically like, can you do my homework assignment for me?

• 36:19Speaker 01

  Yeah. So one, I, Ramit Sethi talks about this a lot where it's like, you can just not respond, like just pretend you didn't get it.

• 36:26Shane Parrish?

  I have personally, I struggle like I've adapted over the last year. I would say I've come leaps and bounds, but at first I had to respond to everything.

• 36:34Speaker 01

  Sure. So I find like on stuff like that, responding is what they want, right? You don't actually have to do the request. You can say like, hey, I can't read this, but here's a thought. Or like I'll go like, hey, one, one of the things I think about for the articles I write is what do I get the most email about? Can I write an article about that? Cause now I, now the first I know that at least one person is interested in this idea.

• 37:01Shane Parrish?

  Oh, that's a really good idea.

• 37:02Speaker 01

  And then now in the future, all emails I get about this thing, like, how do I find a book agent? Boom. Here's all, I don't even link them to the post. I just go like, I wrote an article about this. Google my name and book agent and then it'll come up. And so I'm, it's sort of treating it like a frequently asked questions thing.

• 37:21Shane Parrish?

  Oh, that's a good idea.

• 37:21Speaker 01

  That's a sign that somebody, you know, like, what does a politician go like one calls a thousand constituents or whatever? It's probably similar on email. Most people don't email.

• 37:31Shane Parrish?

  I've, I've, I've started adding a little bit of friction to it. I like your idea of you always have some sort of caveat. Like if you email me, think about it beforehand and.

• 37:40Speaker 01

  Yeah. And my reading newsletter, where I recommend books, I was just tired of people going like, they would just email me their thoughts, which is great, but like, it's like, what do you want me to do with this? So, um, but the reality is like, I don't think it actually deters anyone.

• 37:58Shane Parrish?

  So one thing I've done, uh, that I find interesting, and I don't know where I got this. I didn't come up with it myself, which was, when people are sending me 20 page, 30 page documents, proposals.

• 38:07Speaker 01

  Yeah.

• 38:08Shane Parrish?

  I'll just reply saying, hey, my, uh, you know, can you print this out and mail it to me? And so what I've done is now I've added some sort of, and if they do, and they mail it to me, I will read it. But if it's not worth their time to print it out and mail it, cause it's so easy to send email. And a lot of them are, I don't want to say form emails, but you know, it's very easy to insert, you know, switch Ryan and Shane and send the exact same email.

• 38:30Speaker 01

  So one of the things that I realized with my company, which is like a consulting and, and sort of strategy, we call it creative advisory, but. I I realized I was spending a lot of time talking to people who may or may not have become my clients.

• 38:44Shane Parrish?

  Right.

• 38:45Speaker 01

  Right. And that was very inefficient for me. So it was like, wait, did I just like I first I'd go meet with someone, which meant I couldn't be writing. Then we would talk and I'd have to give them a ton of ideas on the spot. Then they'd be like, well, send me a proposal. Then I'd have to make a proposal and then we'd have to negotiate a rate and blah, blah, blah.

• 39:01Shane Parrish?

  Totally suboptimal.

• 39:02Speaker 01

  Yeah. So especially because I'm trying to run a lifestyle business, not trying to create a scaled major company.

• 39:10Shane Parrish?

  Right.

• 39:10Speaker 01

  So like, cause otherwise the whole that that's why you hire people, but I was trying not to do that. So one of the things that I realized, and this has been a huge, not only source of growth for my company, but it's been a huge relief. I go like, look, when unless it's like a kid asking me for advice about life, my job is to give companies advice on how to grow, how authors, how to write books, people how to, you know, think about stuff, um, you know, how to market things. So if you'd asked me that, I'm not going to respond to that email. So what I and and I'm not going to get together to pitch you on why you should pay me to tell you how to do that. So what I've come up with is

• 39:46Shane Parrish?

  By giving you the answers that you're looking for to begin with.

• 39:48Speaker 01

  I'm not going to give you, you know, some of my answers and then try to hold some stuff back.

• 39:54Shane Parrish?

  Right.

• 39:54Speaker 01

  You know, it's, it's just ridiculous. So what I came up with is all my clients, even ones I know I want to work with, I start with a paid strategy session.

• 40:02Shane Parrish?

  Right.

• 40:02Speaker 01

  So I charge like 1500 bucks an hour. Um, and we get on the phone and like you can send me a little bit of stuff, but almost no prep. And then we get on the phone and then I will, I will not shoot the shit with you. I will give you my best work for an hour.

• 40:21Shane Parrish?

  Right away.

• 40:21Speaker 01

  About that idea, what you need to know, what I would think, what I would do if you hired me.

• 40:25Shane Parrish?

  Yeah.

• 40:25Speaker 01

  Like I'll give all my ideas away. And then, um, cause the, the people think like the execution is the hard part.

• 40:32Shane Parrish?

  Right.

• 40:33Speaker 01

  Um, but to me, the thinking is the hard part. So I'm not going to think for free and then get paid to execute.

• 40:37Shane Parrish?

  Right.

• 40:37Speaker 01

  I would rather get paid to think and then maybe get paid a little bit more to execute.

• 40:41Shane Parrish?

  Right.

• 40:42Speaker 01

  If you want to hire someone else to execute, that's fine. So, so then I do these sessions, which is on the one hand, it qualifies. All leads because the people who are never going to hire me or just milking me for free advice. They go away right away. Um, the people who can afford whatever I am going to charge are like, you know, they don't balk at the fee. So we work, we do, we then we map out exactly what they should do. And then if they hire me or they hire my company, which is called Brass Check, that fee just counts again. So it's like, you know, let's say we end up working for twenty or thirty thousand dollars. It's like, they paid a deposit essentially.

• 41:15Shane Parrish?

  That's a brilliant idea because I'm struggling. Like I'm overwhelmed with this, these people asking for advice. Which I love, right? Because it's a sign that you're doing something and people are valuing what you're doing. But on the same token, you're trying to make a living and you can't just give away, you know, ninety percent of your day.

• 41:30Speaker 01

  Well, um, a, a couple of things. So one, uh, I hate the phrase pick your brain. Like my brain is how I make my living. And I say that to people. I go like, I would, look, if I could, I would do all of this for free because I love it. But my wife would kill me. Uh, I wouldn't be able to eat. And more importantly, I have other clients who have paid me and it's not fair for me to do for, do for free for you what they pay me for.

• 41:58Shane Parrish?

  Right.

• 41:58Speaker 01

  So I ha- I can't do it for free. I'm sorry. If that, like, I totally understand if that pisses you off. And like, let's not work together. And so, um, there's that. And then the other thing is you have to value your time. Like Neil Strauss. He, he has a thing. He's like, look, I can buy my own coffee. You taking me out to coffee or like there's if, if a consulting session for me for an hour is worth fifteen hundred dollars. And like, you might think that that's too high, but plenty of people pay for it and almost all of them say it was worth it or worth many times that. There's not a dinner in the world that you could pay, that you could pick up the tab for that would cost fifteen hundred dollars. Right? So, um,

• 42:40Speaker 01

  and that means I have to drive somewhere. I have to block like for this. It's like what I do. It not only the other hack is I go for a walk when I do these calls. So I get an hour walk in and I talk to people and I'm stimulated and it challenges me and it works out my chops and then they leave with either a, in most cases, a plan they can totally execute themselves at a fraction of what it would have cost to pay to have me do it for them. Or we, it's the start of a really good relationship. And so that obviously worked out only by trial and error, but it's, it's been a huge relief for me because. I have a way, I can just pass these things to a coordinator. He negotiates it and then I either get to talk to someone and we do awesome work together.

• 43:24Speaker 01

  Or, you know, nobody, no, I don't feel like I'm giving a piece of my life away. There's a quote from Seneca, where he's like, let no man take a day of my life without, you know, giving me something worthwhile in return. And like, we sell our time for money, that's what we do. Don't give it away. And, you know, that's just how I think about it.

• 43:50Shane Parrish?

  I think that's the perfect way to end this. Listen, this has been a fascinating conversation, even the second take. But I really appreciate you taking the time and we'll have to do this again sometime.

• 44:02Speaker 01

  For sure.

• 44:06Shane Parrish?

  Hey guys, this is Shane again. Just a few more things before we wrap up. You can find show notes at farnamstreetblog.com/podcast. That's F A R N A M S T R E E T B L O G dot com slash podcast. You can also find information there on how to get it transcribed. And if you'd like to receive a weekly email from me filled with all sorts of brain food, go to farnamstreetblog.com/newsletter. This is all the good stuff I've found on the web that week that I've read and shared with close friends, books I'm reading and so much more. Thank you for listening.