Interview: Ryan Holiday

Hello and welcome to the Story Grid podcast. This is a show dedicated to helping you become a better writer. I'm your host, Tim Grall, and I am a struggling writer trying to figure out how to tell a story that works. The creator of Story Grid and the author of the book the Story Grid is Sean Coyne, who is an editor with over 25 years experience.

In this episode.

Sean's not joining us because I interviewed an author that I'm friends with that I really respect by the name of Ryan Holiday. He's the author of many books. The most recent is Conspiracy with I Just Absolutely Love Devoured it, but other.

Books that I've loved of his is.

Perennial seller Ego's the Enemy, the Obstacle Is the Way, and he has a few others. So he's a really prolific writer. He's released about a book a year since he started publishing books, and he's a really just methodical and thoughtful writer. He has written some extensive articles about how he does his writing, and I'm going to put those in the show notes for this episode. But I wanted to talk to him specifically about his editing process, working with his editor, and what it looks like going from that first draft to a finished product. Because so many times we hear advice from people talking about how to get your first draft done, which is really important. But I wanted to talk about, well, okay, how do you go from that first draft to a published work? And I really respect Ryan and how he brings himself to the page and to the books that he writes. And so it's a really fun interview. I think you'll get a lot out of it. So let's jump in and get started.

So, Ryan, when I started thinking through who I wanted to talk to about editing a book, you write the first draft. And there's all this advice out there about how to write the first draft. But what I found both for myself and then as I talk to writers and you hear Anne Lamott say, write a shitty first draft, you hear that, but you don't really believe it, I don't think until you've done it a few times, nobody really talks about a lot, how to go from that first draft to a book that's actually publishable. I wanted to start by talking to you because you've written so many different types of books. You've written marketing books, you've written books about publicity. You've written books on stoic philosophy. And then your most recent one is Conspiracy. That tells. Well, I'll let you say exactly what it is, but it's more of a, I would say narrative nonfiction. Oh. The other reason why I wanted to talk to you is because you have such a systematic way that you write books. And I'll put links to that in the show notes about, like how you do note cards and all that kind of stuff too. But I just wanted to hear, like, once you have that first draft done, like, what do you do from there? Like, what do you think through? How do you bring yourself to. Has it been different with the different books? Let's just start there.

Sure. I think your point about first drafts is a good one because it's confusing for me. I do a first draft, but I do it in parts. I write, let's say, the first few chapters and I accept that they're going to be really terrible. And then I typically review those few chapters before I move on to the next set. I do it in legs where I'm repeating it. I might write three chapters, do a round of editing on those three chapters, and then start the next three chapters. And then what I like to do is then I'll review those six chapters. So the book is getting stronger because I'm touching each piece multiple times. But I would say the hardest part about writing, having now done, I think eight books, plus a number of books that I've ghostwritten, is that you are inevitably comparing a first draft against either finished manuscripts that you've done or other books that you've read. And so there is this. It's almost like the hardest part. The thing that requires the most discipline is being okay with it not being perfect yet and having the confidence to continue on in the process and trust in the process and know that this is in this weird sort of infancy and that you can't compare an infant against 15 year old or 30 year old. Does that make sense?

Yeah. Let me go back to one of the first things you just said. So you're saying you don't just write a first draft start to finish?

No, because to me, a book is sort of like building a house. Right. So the idea that you would just build a really shitty house. Right. And I don't know if I'm allowed to curse, but the idea that you would just build a house a first time and then you go fix everything strikes me as very dangerous. Because the heirs compound on each other. Right. Like if the foundation is slightly crooked or you did the framing wrong and. And then you put the siding on top of the framing, which is on top of the siding or on top of the foundation. Now it's spiraling out of control. This house is going to be unlivable. And so to me, I'm writing an introduction, and I'm knowing, okay, I'm doing the introduction. And I know this is like, my first pass at the introduction, but it gets me enough that I can get to the, let's say, the first chapter. So now I have maybe 3 or 4,000 words. So I have, you know, 10 or 5 to 10% of a book. So now I can review those and get them a little bit stronger and make sure that I'm not sort of terribly off base. And then when I'm a little bit more confident in them, then I can build a little bit more and build a little bit more, but in the way that if you're doing a remodel, you're building something, you're constantly having inspectors come in from the city or agency coming in to check to make sure that you haven't made any, like, catastrophic mistakes. And so that's sort of my process. It's somewhat iterative. Like, I am doing a first draft, and I have lower standards for the first draft. That being said, I am going back and reviewing, and it's getting stronger each time I touch it.

You know, that's so interesting because that's so opposite. Most of the advice you hear, which is like, don't edit while you write. It's all about, like, pushing forward to the finished first draft. So, you know, you're. I may come back to that, but.

It reminded me I'm sort of splitting the difference. Right. I'm not editing while I'm writing. I'm writing, then stopping, then doing some editing and then writing again, if that makes sense. I'm not being bogged down in making everything perfect, but I'm also checking I'm backtracking and checking that I'm on the right course each time so I don't get horribly off track.

Yeah, it's just interesting because I know that's what I've used, and I think that's what a lot of people use as a way to not write, is to keep trying to make previous stuff perfect as a way to not push forward. But I want to talk about most of the entire podcast is me just trying to figure out my own issues with my writing. So that's pretty much where the questioning is going to go. So your two books, Ego is the Enemy and the Obstacle is the Way, have such a strong theme. I mean, that's in the title. And so what I've struggled with my book is it took me a year and a half of struggling with this book to find the theme. Now, as the theme has come together, the rest of the book is coming together very quickly.

Mm.

So in your experience with your books, and I feel like conspiracy has a really strong theme as well. Like, you're. I feel like you bring, you know, it's just not. It's not just reporting. Like, you bring in kind of your viewpoint on this, and you bring in a lot of history, because you do so much reading on history and stuff. And so when did the theme come to you? Did you kind of like, okay, I know I want to write a book about ego. And so I'm going to just get started on that? And then you. I think in Ego is an Enemy, you have three. Three major things, Right. It's been a while since I've read it.

Yeah. No, no, I'm a theme first guy. So conspiracy isn't narrative nonfiction, but it's through the angle of the book is that it's that this was a conspiracy. And so the book is in some ways also a meditation on conspiracies. And I'm telling this singular story as a representation of the act of conspiring. And. And Ego is the same way. It's a meditation on the perils of ego. The Obstacle Is the Way is a meditation on how we overcome obstacles. Actually, I got Sean and Steven's advice on Obstacle, which I've now repeated multiple times. Just the idea of having some sort of three act structure or three part structure that allows you to take the reader on a journey. But I'm theme first. So in Obstacles the Way, okay, I was going to write about obstacles. I have a lot of interesting stories about people overcoming obstacles. But it's not until I sort of settle on this sort of the three disciplines of stoicism, which would be perception, action, and will, that I have an organizational way to attack that thesis. Ego is the Enemy was originally a book about humility. That's what I thought I wanted to write about. And I couldn't find that. I couldn't find the three parts of humility. I found, for instance, that almost all the stories about humility were like, exactly the same. They were really interesting, but they were the same. And that. That wasn't working as a book. And so it wasn't until I pivot towards ego, and then I sort of get the. You know, there's when you're beginning, there's when you're successful, there's when you're dealing with some sort of adversity or difficulty that ego is going to manifest itself differently. And then in conspiracy, it was, you know, I'm reading this chapter in one of Machiavelli's books where he's talking about what it means, how conspiracies work. And he says every conspiracy has the planning phase, the doing phase, and then sort of the after phase or the aftermath. And I was like, oh, boom, there's my three part structure. And so I do all those things. First I might try, like, I might think that I have it and try and then realize I don't. And then I go back. But I just remember. I remember in high school working on essays and, and realizing that when I figured it all out in advance, I wrote really good essays. When I tried to figure it out while I was writing, they tended to be very weak at the beginning. And then by the end I would have nailed it. But if you're writing it on binder paper in a timed setting, you can't go back. And so I really hated that feeling. And I think in a weird way that's carried through to my books, it's like, I want. I want to have it figured out before I start.

So can you tell me, you said you started with the book on humility and then you switched to ego. So those points are really interesting to me. I was up with Steve and Sean in LA back in November, and Sean and I were talking to Steve about my book and how we couldn't figure out what the ending was. So we kind of laid out the introduction and he just pointed out a. Like, he's like, oh, this part in your introduction, that's your ending.

Sure.

And like, it just fixed this huge problem. And like, as soon as I saw it, like, it just fell into place. And what's so hard, what's been so hard for me is like the churning until you see the light. So tell me a little bit about. Just tell me the story of like making that switch to ego. How did you feel when you were realizing humility wasn't working? What kind of prompted you to switch to ego? Like, tell me that story.

Well, I actually. It's funny, I was in la. I'd actually met with Stephen, we'd had breakfast. I was sort of. The book was still this sort of very vague thing in my mind. I was in period where it's just sort of brewing. And to me, like, that's always the hardest part. Right. Cause that's where I feel like you're doing most of the work. So it's this sort of unsolvable problem that's just like computing in the back of your mind. And I remember sort of working on this humility thing. I had this working title of Keep youp Identity Small, which was a line from an essay that Paul Graham had written that I really liked. And the point was that everyone is sort of puffing themselves up and trying to make themselves bigger than they are. And really that humility was sort of the antidote to this and that we needed more humility, so on and so forth. But it just wasn't working as a book. I had a few stories, but for instance, one test that I have is, can I talk to people about it? And I would find that in dinner conversations I was just having trouble getting, I'd be like, oh, I'm writing a book about humility. And people would be like, uh huh, you know, it wasn't working, so talk more about that.

What do you mean when things not working?

That I wasn't confident in what I was telling people. And when I would flusteringly get it out, I wasn't landing like in the way that a comedian might test out a joke. It's like if it's not getting a reaction, there's something not right there.

Oh, that's good. Yeah.

And this is important because this is representative of the exact kinds of conversations that either you're going to be having when you're pitching the book or that your publicist is going to have when they're pitching the book. Right. And so if you don't solve this problem now, it's not magically going to resolve itself. And I remember I was saying, standing in the parking lot of American Apparel and I was on the phone with my editor and I think this is it. I don't remember the specifics, but I remember being in the parking lot of American Apparel, which was this company that was being destroyed by ego at this very moment. And I was like, the opposite of humility is ego. And ego is really the enemy of what we're trying to do. And I remember I'd been talking to a football coach who told me that ego is, was the cancer of his profession. I remember he said that line. Exactly. I remember thinking, I took that home with me. And I remember thinking, what's really the cancer of every profession? I mean, there's no profession that's really good with ego. And so this idea of ego being the enemy of the thing that ego was really the central issue was huge for me. One, because ego is the enemy came to me as this phrase Which I really liked. And I googled it and there wasn't much on it. I thought. I feel like I basically made the phrase up. But it gave me something that was really valuable in the book, which was being able to argue against something rather than simply for something, allowed me to tell much more interesting stories. So it's like, if you're just talking about humble people, there's not that many examples that you can use. But if you talk about egotistical people, then you can tell lots of stories of failures, right? You have your Richard Nixons or your Howard Hughes or whatever. You have the story of that. It's much more compelling to tell ego as this cautionary tale, rather than humility as this somewhat boring, uninspiring sort of example. And so solving that really let me get into the book very quickly. And so this was all probably in the summer and fall of 2014. And then I started writing in 2015, and I was done by late spring of 2015 with the first real solid draft.

Okay, so tell me a little bit about how you've approached. So I want to come back to Conspiracy, because that one to me is an interesting one of like, what did your first draft of that book look like? Or how did you kind of build the first draft of that one? Did you have those three parts when you started writing for Machiavelli already? And I know you already personally knew most of the people involved, so you probably had a behind the scenes look even before you dug deep for the book. Just tell me a little bit about how you built the first draft of that.

This one was a little different because there was facts. I couldn't choose the order of events in the way that Obstacle or Ego or my other books were, because those are just collections of stories. To make a general point, this one had to be somewhat chronological. So the first thing I did was I ended up reading something like 25,000 pages of legal documents. I did, you know, hundreds of pages of interviews. And so then I made a timeline. It was just a. It was a 55,000 word, 155 page outline or timeline simply of the events from 2002 to 2017. So that was the first step. I just had to get everything down that happened. And then originally I was going to try to map this book on the hero's journey because I felt like in some ways what Peter Thiel had done, even if you disagree with it, was in some ways the hero's journey. There's sort of this inciting incident. Then there's like, what Is it the call to action? And then he refuses the call.

He refuses, accepts the call.

So I have like. I'm looking at it across the room. I have like all the different phases of the hero's journey on sort of one sideways piece of paper with lines going through it. And then I'm putting in the main event that are corresponding to this. So at first I had it there and then I was reading this. Robert Greene told me to read this chapter in Machiavelli, which I read. And then this idea of sort of before, during and after, essentially I was like, oh, wow, I love three part structure. So here's essentially a three part structure. And then I overlaid the three part structure on top of the hero's journey. So basically I'm getting sort of this. So chronologically, it's the beats that I'm hitting are more or less the beats of Campbell's Hero's Journey. But then organizationally inside the book, it's part one, two and three. So when does the planning begin? When does the planning end? That's part one. When does the first step of action begin? And when is the last step stroke of the conspiracy itself? That's part two. And then part three is sort of the unintended consequences and the outcome and the sort of reflection on what happened. And then that sort of leads into basically the last section of the last sort of words of the book are like watching Peter sort of stand on his balcony and thinking about what he might be planning next. So that. So I kind of overlaid these two structural devices on top of each other that, since I had a timeline, allowed me to then write the first draft pretty easily. And then I went in and plugged in lots of stories and other things.

So tell me a little bit about how you work with your editor as far as, like, because your publisher, is it still portfolio?

Yeah. So I work with all my books, have been with Penguin Random House. So my editor there is Niki Papadopoulos. And then I have an editor sort of writing partner. And the way that Steven and Sean have worked together for so long, I work with someone named Niels Parker, who is my sort of collaborator on. I think he's worked on every one of my books.

So tell me a little bit about how they play in. Because on the COVID of all these books is one name. So tell me a little bit. Actually, the other day I was talking to Sean. I'm like, can we put edited by Sean Coyne on my book? Because there is no way this book would ever exist without You. He's like, no, but I'm just like, I'm just fascinating, fascinated. Now, as I've. This is the first book I've worked closely with an editor.

Yeah.

And so I've been surprised of, like, I don't think not everybody is involved as he is in my projects. But, you know, tell me a little bit about how you interact with those people. When do you bring them in? What kind of. You said you had. You were talking to Nikki when you had the idea for Ego is the Enemy, you know. So tell me a little bit about how you work with them, when you bring them. Them in, how you take their advice, when you don't take their advice. Just kind of. That kind of stuff.

Well, I think the music and the movie industry have it much better. They have the role of the producer. Right. The editor of a movie is sort of much more of a tactician. But the producers are the ones who are shaping the overall arc and scope of the project and consulting on lots of really important decisions that are made early on in the project. So Nils, I feel, is. Functions in the role of a producer for me in that we talk about a lot of these decisions. It's like, hey, here's how I'm thinking of laying it out. What do you think of this?

The big decision for me on Conspiracy was that I wanted to make the story timeless. I was worried that in five years, no one's going to care about this media outlet that I'm talking about, or maybe even caring about Peter Thiel. So how can I. Of. How can I make this a bigger story? This idea of making it about conspiracies generally and sort of tracking it with this larger point. So that required a lot of decisions. And so Nils is someone who's seeing pages as they're written. So I'm giving him like, hey, look, I'm going to edit these first three chapters. I don't need you to edit them. I just want you to tell me what you like and don't like or what's working and not working or what you think I should be worried about or think about going forward. And that's sort of that idea we were talking about earlier of sort of like, getting some inspections done throughout the process so you don't end up horribly astray or misaligned. And I'm sure it's actually probably miserable for Niels while I'm writing because I just. I'll get stuck and I'll just call him and I'll just be like, hey. And I'll Just like by the time he picks up the phone, like I'm sort of mid sentence, you know, in something that I'm trying to work out, I'm a big. Seth Godin, I think, in the Icarus Deception talked about this idea of writer's block being a myth. He's saying, we never get talker's block. Why would you get writer's block? So when I get stuck or when I'm struggling with something, I usually just try to talk it through and get some momentum. And so I feel like my editor is very instrumental in that role. But to me, it's really important. I don't know what percentage of readers are traditionally published listeners and readers are traditionally published versus self published. But I've tended to find that I want to go to the publisher, I'll talk to the publisher and I'll talk to Nikki early on when I'm thinking about things, but I want to go to them with the book as well formed as possible. And I don't mean this to be a knock on them, but publishers think about books in, I think, a very traditional way. They are traditional publishers. They see lots of books. They tend to try to put things in categories or limitations. And so I think I did a better job on Conspiracy than I have on my previous books. By the time it came to Nikki, I knew exactly what the book was going to be and more specifically what it wasn't going to be. So when I got notes that were not helpful, I was able to ignore them. And by helping by helpful, I mean they were trying to take the book in a direction that I was explicitly not trying to go in. I think one of the things I did on this book that I'm going to do in other books is I really defined what the book was going to be. And I told her this. I said, this is the book that I'm writing and this is what I want your help in getting towards. I'm saying here, this is a very ambitious goal. All the drafts that I send you are going to be short of this goal. But what I need from you is to help me get towards this goal. Not some goal that's in your head about where you think the book should go. That's one of the dangers of publishers, is that they can have a conflicting vision for what they want the book to be for sales purposes or for the purposes of their list or just for their own personal taste. That cannot necessarily be the same as the author. And I tend to find that the worst books are when you split the difference. And that's what happens in the collaborative process. It's like, here's what I'm trying to do, here's what the publisher wants to publish, let's do it halfway. And then it's a book that really no one wants.

That's interesting because I think for me, I was scared to write the book.

That Sean knew I could write. And so I kept wanting to stop too early and he kept holding my feet to the fire until he thought it was good enough. It's just interesting. You had such a strong idea of the book you were trying to write. And I was very weak on the book I was trying to write. And I think we've talked some about the book over a year ago and that was a problem then too. That's interesting.

I think Sean is unique for two reasons. One, sort of not running a traditional publisher. He is, I think, closer to just like what's the best book? Right. And so he's less concerned with what the sales people. Your editor at a traditional publisher is essentially a conduit for what the marketing team is interested in. And the reactions of the sales staff and the art staff and all this other stuff, they're kind of like this committee. Whereas Sean is at this point in his career, maybe when he was at a publisher might have been different, but at this point his career is much, I think, purer in his sense of what's a good book and what's not a good book. And then also I think Sean is the kind of editor that would demand more of you than you would demand of yourself. That's not always true, especially if you're a first time author at some publisher that gave you a relatively small advance. And maybe they're just trying to get this book out. So it really depends on. That's why I think having an editor of your own is also really important. Just as a check and balance to the financial concerns of publishing.

Was your first book, trust me, I'm lying. Right?

That's your first book. Your most recent one is Conspiracy. You've written a bunch in between. Tell me a little bit about how your writing process has changed over that process or over that time. Then also a little bit about. I always wonder this, like, I think things like, I wonder how close Stephen King is on his first draft to the final version versus of course, you know, somebody just getting started or somebody, you know, these people that have been writing for so long. But you know, his books aren't formulaic. So they're these wide, sweeping things. And so with you having written so many, you know, seven or eight books with your name on them, ghostwriting some. Like, how has your process changed? Do you feel like you're getting not just better at writing, but better at getting closer to that good book on your first try? Just tell me a little bit about, in your view, looking back over, what, the last eight or ten years of writing books, how do you feel like you've grown and changed over that time?

Yeah, I'm interested in that, too. I don't think I'm getting closer on the first drafts like that. The first drafts. I think the first drafts are better. Each one of my first drafts is better than the first draft of the previous book. But I think what I'm trying to do is harder. I'm trying to push myself significantly on each book, and so therefore, it may be a better first draft, but I'm actually falling short more, if that makes sense. I'm trying to beat a better time. So actually, the difference between my first attempt and the last attempt is actually somewhat more gaping. So especially with conspiracy, I mean, I'd literally never written in this style before. My previous books were either memoir or sort of about people who were dead. So this book is basically twice as long as Obstacle and Ego, or it's Obstacle and Ego glued together, essentially. And so it was just very, very different. And so I think every word. I think my first draft was was better written than either book. I think there was a discontinuous leap, like a significant leap in writing quality from the first draft on, but I feel like it was very short of where it ended up. And so I think that's a good thing. I think you should push him yourself. Eventually, I'm going to do a sequel to Obstacle and Ego, but I feel like if I'd gone straight into it, it wouldn't have been as good. So I'm trying to push myself as hard as possible. To me, this might sound weird, but I feel like all the books that I've written are me putting in the practice and the hours for some future book that I haven't even conceived of yet.

Yeah, I can see that. I do jiu jitsu, and I won all of my white belt matches, and then I became a blue belt, so I was significantly better than the first time I ever competed at white belt. And I got put to sleep in my first match as a blue belt.

Put you to sleep? That's crazy.

Yeah, but it was this weird situation where I was better, but I also stepped in an arena where it called Me to be so much better. That's what I was thinking in my head when you were talking about. That is you're taking on these projects that are like the next level. So you can't just bring what you brought to the last book. You have to learn something new. So with that in mind, what do you think? Because you're a young guy, what are you, early 30s?

Yeah, I turned 31 this year.

Okay, so 31. You have a lot of writing left. What are you thinking when you start thinking about how you want to push yourself in the future? Do you have ideas of projects or directions you're hoping to go?

Well, I feel like Conspiracy was a book that maybe I was planning to write in the future, but the timeline got sped up because it was a once in a lifetime opportunity. I feel like I've done a lot of books in a relatively short amount of time. My first book came out in 2012, so let's say I wrote it in 2011. I've done eight books in.

7Ish years. Right. That's not one that's not sustainable. Just like on a pure human level. Right. But I also think that's not necessarily the recipe for really great books. And so to me, the next sort of mountain is like, what if I took two or three years on my next book and I just really now I want. What does happen if I slow way down or I put way more into one specific project? And I feel like I'm getting more confident. And so maybe early in my career I would have actually been too insecure to take that long. What if everyone forgets about me? What if I drop off?

What if that's a huge mistake? And so I do feel like I've got a little bit more time and I've got. It's weird. I'll hear from readers now. They're like, look, I just read Ego and I'm like, you're like three books behind at this point.

Yeah, well, it was funny because you came out with perennial bestseller last summer, which is another just great one. I recommend it all the time. And a buddy of mine who's a writer as well, because we're both on your email list, he texted me. He was like, brian came out with another fucking book. How did he do that?

Actually, I wanted to stop and ask. That reminds me, I wanted to ask that question, was there overlap in writing? Were you writing two books at one time? At one point?

Yeah, sort of. So traditional publishing has these huge, sort of huge amounts of dead time, which I'm Very much opposed to. So, like even Conspiracy, which was the fastest of all my books, you know, we didn't do galleys. It was totally embargoed. We cut out huge chunks of the process. I mean, that book, I think the last copy edit on that book was in late November and it came out in the last day of February. So in those three months I was writing and I wrote and sold the proposal for my next book. And in previous books I've just been already writing or working on the book that I'd sold in between. And so I'm just never one for leaving those gaps. And I realize that that means there's catch up that the readers are having to play. But I mean, I don't really care. The books aren't have an expiration date on them, so it's not as important. So I feel like I'm just sort of accumulating a back catalog or a library. And then if readers are three or four books behind, that's not the worst thing in the world.

So how do you pick your next projects? Because I know just from knowing you, and then we're in a couple, well, one Facebook group together and you talk about your writing and I read your articles. And so like, you kind of have this attitude of like, I'm always writing. Like you said, I'm already working on the next proposal. I'm already working on the next book. In the dead time. You write articles for lots of different outlets. How do you approach finding your next book? Is it one of these where you always have eight ideas and it's picking one, or are you just kind of waiting for something to speak to you when you finally decide, okay, this is my next one. How do you come to that decision?

Yeah, to me, writing is like a job, and you always want to have the job. Even if you're a freelancer, you're an independent contractor, you always want to have a job. It's like when you're wrapping up one job, let's say you're a construction worker. To continue this analogy, you're almost done on this remodel that you just did. Well, maybe one day a week, on the final three or four weeks of the job, you're taking appointments to put in bids on your next job. That's my thinking is as I'm wrapping up conspiracy, it's no longer occupying as much space in my brain. It's not as all consuming. I can see the light at the end of the tunnel, so on and so forth. So now I'm like, okay, what am I going to do next? I want to line that up. And that was really huge for me. On Obstacle, for instance, I sold what became Ego as the Enemy before the Obstacles the Way came out. And when Obstacles the Way came out, it sold maybe three or 4,000 copies its first week, and then probably 1,500 copies the second week. And then, I don't know, 1,000 the third week. Then it was just there. It just sort of dribbled out from there. It wasn't the success that it became out the gate. It took several months for it to really start to pick up. If I hadn't been already working on the next book, I'm not sure I would have done the next book.

I might not have done the next book. And then when it did succeed, I think it would have had a more outsized impact on my life than I would have wanted it to.

I'll go back. Yeah. So you're saying you wouldn't have done the next book. Why? Because you were discouraged at how it was selling?

Well, I would have either been discouraged or I would have been too encouraged when it came out. Like Mark Manson. In some ways, a book like the Subtle Art of Not Giving a Fuck, blowing up the level that it did, makes it really hard to start thinking about your next book. Because now the standard is so high that you're not thinking necessarily about just what book do I want to write next. You're also having to think, what is just as good as this? And does it have the same sales potential?

Yeah, like.

Her TED Talk when she talked about trying to write after Eat, Pray, Love and knowing that her most successful work is probably behind her. I think her line was, it makes you want to start drinking gin at 10 in the morning.

And look, Obstacle wasn't that successful or that unsuccessful. So I'm talking about a smaller version of the same problem. But it's like I sold Ego for the low six figures. So it was like, look, I've got a job, I have middle class income for the next year and a half, I gotta get to work and then I gotta think of the next one. So I tend to think more like a journeyman writer rather than a professional athlete that signs some sort of life changing contract. So I'm just like, I'm working every day. And you and I have talked about this. I like to see myself as sort of a middle class writer. And it's a job. I'm very lucky. I'm lucky not to be in the bottom half. But I also feel I'm lucky not to be in the top 1%.

I get to do this for a living, but it is a living. That's kind of how I think about it. So I always want to have that project.

And I'm just always working.

Yeah, I remember. Wasn't it a Saturday Night Live thing you told me about where.

Yeah, I think.

Jay Moore said he's in the showbiz middle class and.

Yeah, but that's. I mean, there's a lot of people that would kill to be there. So it's just. Yeah, so it's interesting that. So I guess we'll talk about that a little bit. So tell me just a little bit, expound on that a little more about how you see your job as a writer. Because I think a lot of people think very project based like we've talked about and I know, and that's where publishers are kind of run everything very project based. But you view yourself as a nine to fiver type writer. How do you bring yourself to that kind of thinking? Why do you think that's better than these project based one off things? How do you approach writing in that way?

Some of it might just be my personality and my working style. I don't know what some of these people do all day.

I'm not someone who can just sit and, and just think. I feel like I have to be moving towards something. And so that impulse is kind of what drives me. I always want to be writing something, whether it's a book or an article, or it's an article to support a book or it's marketing for a book. I want to be moving forward. I think part of that is driven by an insecurity. This could all go away tomorrow. Do I want to be. Do I want to go like, oh, I'm so GLAD I took three months off in 2016 and those were the last three months that my books were selling. I don't know. That's sort of part of it for me. But I'm also of the mind that quantity is how you get to quality, that you have to go to the original point about crappy first drafts. If you're not putting stuff on the page, it can't get better. You can't edit writing that doesn't exist. And so to me, I feel like all my writing is sort of part of this big project. I'm writing articles and then when those articles are doing well or I come up with a story that really seems to resonate, I might use that again somewhere else. So I feel like I'm just sort of collecting and making material and then some of that material is going in the albums down the road. So I'm just always working. And and I think one, it's a productivity tool, but two, I also think it's sort of a natural ego suppressant because I'm not sitting around sort of like marveling at what I've accomplished or how the sales have been. Because like with ego, it's like part of the reason that the success of Obstacle didn't go to my head is like I have a delivery date. I have a contractual obligation to deliver a manuscript by a certain date date. That's what I'm thinking about. I'm not tallying up the sales figures and then getting my royalty rate out from there and then shopping for a vacation house. I'm like, if I don't deliver this, they're going to ask for the advance back and that's not going to be.

Fun thanks for listening to this episode of the StoryGrid podcast. I want to thank Ryan for coming on the show and submitting to all all of my weird and in depth questions. So make sure you go to our show notes@storygrid.com podcast to check out the articles that I mentioned that I think you're really going to want to see that he's written. Also go to ryanholiday.net and sign up.

For his email list.

Every month he sends out book recommendations and other things. It's one of the few email newsletters that I actually look forward to every month. Also, also check out his books. As you know, we don't recommend a lot of books. We obviously don't interview a lot of people on this show and so when we do, you know, it's from a good place. Again, Conspiracy was just a great book. I just ran right through it. It was really compelling. Perennial seller. I think every person doing any kind of creative work should read as a way to just think about how they're creating and marketing their work. And then of course, his books on stoic philosophy, Ego is the Enemy and the Obstacle Is the Way, are both fantastic. So check out all his work@ryanholiday.net and as always, you can find us@storygrid.com you can reach out to us on Twitter ToryGrid. And if you want to support the show, you can do that by telling another author about the show and by visiting us on Apple Podcasts and leaving a rating and review. Thanks for subscribing and being a part.

Of our work here at Story grid. We will see you next week.