Interview: Ryan Holiday

[0:00:00.5] TG: 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 Grahl 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 Shawn Coyne, who is an editor with over 25 years’ experience.

In this episode, Shawn is 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 which I absolutely loved, devoured it. Other books that I’ve loved of his is Perennial Seller, Ego’s Enemy, The Obstacle Is the Way and he has few others.

He’s a really prolific writer. He’s released about a book a year since he started publishing books. He’s 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. I wanted to talk to him specifically about his editing process, working with this editor and what it looks like going from that first draft to a finished product.

Many times, we hear advice from people talking about how to get your first draft, which is really important. I want to talk about, well okay, how do you go from that first draft to a published work? I really respect Ryan and how he brings himself to the page and to the books that he writes. It’s a really fun interview. I think you’ll get a lot out of it, so let’s jump and get started.


[0:01:37.3] TG: Ryan, when I started thinking 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. What I found both for myself and then as I talk to writers, and like you hear, say like 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 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 non-fiction.

The other reason why I want to talk to you is because you have such a systematic way that you write books. I’ll put links to that in the show notes about how you do note cards and all that stuff too. I just wanted to hear once you have that first draft done, what do you do from there? What do you think through? How do you bring yourself to? Has it been different with the different books? Let’s just start there.

[0:02:57.3] RH: 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. 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.

Then what I like to do is then I’ll review those six chapters. The book is getting stronger, because I’m touching each piece multiple times. I would say the hardest part about writing having now done I think eight books, plus a number of books that I’ve ghost-written is that you are inevitably comparing a first draft against either finished manuscripts that you’ve done, or other books that you’ve read.

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. Know that this is in this weird infancy, and that you can’t compare an infant against 15-year-old, or a 30-year-old. Does that make sense?

[0:04:25.3] TG: Yeah. Let me go back to one of the first things you just said. You’re saying you don’t just write a first draft start to finish?

[0:04:33.2] RH: No. Because to me, a book is like building a house. The idea that you would just build a really shitty house, and I don’t know from [inaudible 0:04:41.0]. The idea that you would just build a house first time and then you go fix everything strikes me as very dangerous, because the errors can pound on each other. If the foundation is slightly crooked, or that you did the framing wrong, 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.

To me, I’m writing an introduction and I’m knowing, okay I’m doing the introduction and I know this is my first pass at the introduction. It gets me enough that I can get to the – let’s say the first chapter. Now I have maybe 3 or 4,000 words. I have 10 or 5% to 10% of a book. Now I can review those and get them a little bit stronger and make sure that I’m not terribly off-base. Then when I’m a little bit more confident than them, then I can build a little bit more and build a little bit more.

In the way that if you’re doing a remodel, or 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 catastrophic mistakes. That’s my process is it’s somewhat iterative. 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.

[0:06:09.1] TG: That’s so interesting, because it’s so opposite most of the advice you hear, which is like don’t edit while you write. It’s all about pushing forward to the finish first draft. I may come back to that, but it remind me –

[0:06:22.6] RH: Well, I’m sort of splitting the difference. 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.

[0:06:42.4] TG: Yeah, it’s interesting because I think that’s – 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.

I want to talk about – most of the entire podcast is me just trying to figure out my own issues with my writings, so that’s pretty much where the questioning is going to go. 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. What’s 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 is coming together, the rest of the book is coming together very quickly. In your experience with your books, and I feel like Conspiracy has a really strong theme as well, like – I feel like you bring – It’s not just recording. You bring in your viewpoint on this and you bring in a lot of history, because you do so much reading on history and stuff.

When did the theme come to you? Did you like, “Okay, I know I want to write a book about ego. I’m going to just get started on that.” I think an ego is the enemy. You have three major things, right? It’s been a while since I read it.

[0:08:05.0] RH: No, no. I’m a theme-first guy. Conspiracy isn’t there to nonfiction, but it’s through – the angle of the book is that it’s – that this was a conspiracy. The book is in some ways also a meditation on conspiracies. I’m telling the singular story as a representation of the act of conspiring. Ego is the same way. It’s a meditation on the perils of ego, The Obstacle is the Way is a meditation on and sort of how we overcome obstacles.

Actually, I got Shawn and Steven’s advice on an obstacle which I’ve now repeated multiple times. This idea of having some three-act structure, or three-part structure that allows you to take the reader on a journey. I’m theme-first. In Obstacle is the Way, okay I was going to write about obstacles. I have a lot of interesting stories about people overcoming obstacles. It’s not and so I sort of settle on the three disciplines of stoicism, which would 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. 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.

It wasn’t until I pivot towards ego, and then I get the – there is when you’re beginning, there is when you’re successful, there is when you’re dealing with some sort of adversity or difficulty that ego is going to manifest itself differently. Then in conspiracy it was, I’m reading this chapter in one of Machiavelli’s books where he’s talking about what it – how conspiracies work.

He says, every conspiracy has the planning phase, the doing phase and then the after phase, or the aftermath. I was like, “Oh, boom. There is my three-part structure. I do all those things first. I might try. I might think that I have it and try and then realize I don’t, and then I go back. I remember in high school working on essays 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’ve nailed it. If you’re writing it on binder paper in a timed setting, you can’t go back. I really hated that feeling and I think in a weird way that’s carried through to my books. It’s like, I want to have it figured out before I start.

[0:10:50.8] TG: Can you tell me, you said you started with the book on humility and then you switched to ego. Those points are really interesting to me. I was up with Steven, Shawn in LA back in November and Steve and I, or Shawn and I were talking to Steve about my book and how we couldn’t figure out what the ending was.

We laid out the introduction and he just pointed out – he’s like, “Oh, this part in your introduction. That’s your ending.” It just fixed this huge problem. As soon as I saw it, it just fell into place. What’s been so hard for me is the churning until you see the light. Tell me a little bit about – just tell me the story of making that switch to ego, like how did you feel when you’re realizing humility wasn’t working. What prompted you to switch the ego? Tell me that story.

[0:11:46.7] RH: Well, actually it’s funny. I was in LA. I’d actually met with Steven. We’d had breakfast. The book was still this very vague thing in my mind. I was in period where it’s just brewing. To me, like that’s always the hardest part, because that’s where I feel like you’re doing most of the work.

It’s this unsolvable problem that’s just computing in the back of your mind. I remember working on this humility thing. I had this working title of keep your identity small, which was aligned from an essay that Paul Graham had written that I really liked. The point was that everyone is puffing themselves up and trying to make themselves bigger than they are, and really that humility was the antidote to this and that we needed more humility, so on and so forth.

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? I would find out in dinner conversations, I was just having trouble getting – I’d be like, “Oh, I’m writing a book about humility.” People would be like, “Uh-huh.” It wasn’t working.

[0:12:58.5] TG: Talk more about that. What do you mean when things are not working?

[0:13:03.8] RH: That I wasn’t confident in what I was telling people. When I would flusteringly get it out, I wasn’t landing. In the way that a comedian might test out a joke, if it’s not getting a reaction, there’s something not right there.

[0:13:18.9] TG: That’s good. Yeah.

[0:13:20.4] RH: 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. If you don’t solve this problem now, it’s not magically going to resolve itself.

I remember, I was standing in the parking lot of American Apparel and I was on the phone with my editor. 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.

I was like, the opposite of humility is ego. Ego is really the enemy of what we’re trying to do. I remember, I’ve been talking to a football coach who told me that ego 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, which really the cancer of every profession. I mean, there is no profession that’s really good with ego.

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. There wasn’t much on it. I feel like I basically made the phrase up. 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.

It’s like, if you’re just talking about humble people, there is not that many examples that you can use. If you talk about egotistical people, then you can tell lots of stories of failures. You have your Richard Nixon’s or your Howard Hughes, or whatever. You have the story of the – it’s much more compelling to tell ego as this cautionary tale, rather than humility as this somewhat boring, uninspiring example.

Solving that really let me get in to the book very quickly. 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.

[0:15:41.9] TG: Okay. Tell me a little bit about you’ve approached – I want to come back to Conspiracy, because that one to me is an interesting one of what did your first draft of that book look like, or how did you build the first draft of that one? Did you have those three parts when you started writing for Machiavelli already? I know you know every – 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 to that.

[0:16:16.5] RH: 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 and my other books were, because those are just collections of stories to make a general point. This one had to be somewhat chronological. The first thing I did was I ended up reading something like 25,000 pages of legal documents. I did hundreds of pages of interviews.

Then I made a timeline. It was a 55,000-word, 155-page outline of general timeline, simply of the events from 2002 to 2017. That was the first step. I decided to get everything down that happen.

The originally, I was going to try to map this book on the hero’s journey, because I felt like in some ways what Peter too had done, even if you disagree with it was in some ways the hero’s journey, there is this inciting incident, then there is like what is? The call to action and then he refuses the call.

[0:17:19.9] TG: He refused the call.

[0:17:20.6] RH: Then accepts the call. I’m looking at it across the room. I have all the different phases of the hero’s journey on sort of one sideways piece of paper with lines going through it. Then I’m putting in the main events that are corresponding to this. At first, I had it there, and then I was reading this – Robert Green told me to read this chapter in Machiavelli which I read and then this idea of before, during and after essentially.

I was like, “Oh, wow. I love three-part structures.” Here is essentially a three-part structure, and then I overlaid the three-part structure on top of the hero’s journey. Basically, I’m getting this – so chronologically, it’s the beats that I’m hitting are more or less the beats of Campbell’s hero journey. Then organizationally inside the book, it’s part one, two and three.

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 stroke of the conspiracy itself, that’s part two. Then part three is the unintended consequences and the outcome and the reflection on what happened and then that leads into the last – basically the last section of – the last words of the book are like watching Peter stand on his balcony and thinking about what he might be planning next.

I 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 them lots of stories and other things.

[0:19:12.7] TG: Tell me a little bit about how you work with your editor, as far as like – because your publisher, is it still portfolio?

[0:19:19.7] RH: Yeah. I work with – all my books have been with Penguin Random House. My editor there is Niki Papadopoulos. Then I have an editor/writing partner in the way that Steven and Shawn have worked together for so long. I work with someone named Neils Parker who is my collaborator on – I think he’s worked on every one of my books.

[0:19:40.1] TG: Tell me a little bit about how they play it. Because on the cover of all these books is one name. Tell me a little bit – Actually the other day I was talking to Shawn. I’m like, “Can we put like edited by Shawn Coyne on my book?” Because there is no way this book would ever exist without you. He’s like, “No.”

I’m just fascinated now as I’ve – this is the first book I’ve worked closely with an editor. I’ve been surprised of like, I don’t think not everybody is involved as he is in my projects. Tell me a little bit about how you interact with those people. When do you bring them in, what kind of – you said you were talking to Niki when you had the idea for Ego is the Enemy. Tell me a little bit about how you work with them, when you bring them in, how you take their advice, when you don’t take their advice, just that stuff.

[0:20:33.9] RH: Well, I think that the music in the movie industry have it much better. They have the role of the producer. The editor of a movie is 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.

Neil as I feel is functions in the role of a producer for me and that we talk about a lot of these decisions. It’s like, “Hey, here is 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 is going to care about this media outlet that I’m talking about, or maybe even caring about Peter Teal. How can I make this a bigger story, this idea of making it about conspiracies generally and tracking it on this large – with this larger point.

That required a lot of decisions. Neil is someone who’s seeing pages as they’re written. 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.” That idea we’re talking about earlier is getting some inspections done throughout the process, so you don’t end up horribly, horribly astray or misaligned.

I’m sure it’s actually probably miserable for Neil while I’m writing, because I just – I’ll get stuck and I’ll just call him. I will just be like, “Hey.” By the time he picks up the phone, I’m mid-sentence 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 talkers blocked, why would you get writers blocked?

When I get stuck or when I’m struggling with something, I usually just try to talk it through and get some momentum. I feel like my editor is very instrumental in that role. 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-publish. I’ve tended to find that I want to go to the publish – I’ll talk to the publisher and I’ll talk to Niki early on when I’m’ thinking about things. I want to go to them with the book as well formed as possible.

I don’t mean this to be a knock on them, but publishers think about books and I think of very traditional way. They are traditional publishers. They see lots of books. They tend to try to put things in categories, or limitations. I think I did a better job on Conspiracy than I have on my previous books. By the time it came to Niki, I knew exactly what the book was going to be, and more specifically what it wasn’t going to be.

When I got notes that were not helpful, I was able to ignore them. 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 that I did on this book that I’m going to do on 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. 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. 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.

I tend to find that the worst books are when you split the difference. That’s what happens in the collaborative process. It’s like, here is what I’m trying to do, here is what the publisher wants to publish, let’s do it halfway. Then it’s a book that really no one wants.

[0:24:53.6] TG: That’s interesting, because I think for me I was scared to write the book that Shawn knew I could write. I kept wanting to stop too early. He kept holding my feet to the fire until he thought it was good enough. It’s just interesting. Like you had such a strong idea of the book you are trying to write, and I was very weak on the book I was trying to write. We’ve talked some about the book over a year ago, and that continued – that was a problem then too that’s interesting.

[0:25:26.0] RH: I think Shawn is unique for two reasons; one, sort of not running a traditional publisher. He is I think closer to just what’s the best book. He’s less concerned what the sales – like your editor at a traditional publisher is essentially a conduit for what the marketing team is interested in and the reaction of the sale staff and the art staff and all these other stuff.

They’re like this committee. Whereas, Shawn is at this point in his career, maybe when he was at a publisher might have been different. At this point in his career is much I think pure in his sense of what’s a good book and what’s not a good book. Then also, I think Shawn 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. Maybe they’re just trying to get this book out. 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.

[0:26:45.6] TG: Was your first book Trust me I’m Lying right?

[0:26:48.6] RH: (Affirmative) Mm-hmm.

[0:26:50.5] TG: 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 process has changed over that process, or over that time, and then also a little bit about – I always wondered this like – I think things, like I wonder how close Stephen King is on his first draft to the final version, verse of course, somebody just getting started, or somebody – these people that have been writing for so long, but his books aren’t formulaic, so they’re these wide-sweeping things.

With you having written so many – some of the right books with your name on and it goes writing some – 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 with the last eight or 10 years of writing books. How do you feel like you’ve grown and changed over that time.

[0:27:51.9] RH: Yeah. I’m interested in that too. I don’t think I’m getting closer on the first drafts, like 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. I think what I’m trying to do is harder. I’m trying to push myself on significantly on each book.

Therefore, I may – 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. Especially with Conspiracy. I mean, I literally never written in this style before. My previous books were either a memoire, or about people who were dead.

This book is basically twice as long as obstacle and ego. Or it’s obstacle and ego glued together essentially. It was just very, very different. I think every word – I think my first draft was better written in either book. I think there was a discontinuous leap, like a significant leap in writing quality, but from the first draft on. I feel like it was very short of where it ended up.

I think that’s a good thing. I think you should question yourself. Eventually, I’m going to do a sequel to obstacle and ego, but I feel like if I’ve gone straight into it, it wouldn’t have been as good. 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 like me putting in the practice and the hours for some future book that I haven’t even conceived of yet.

[0:29:41.0] TG: 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. I was significantly better than the first time I ever competed at white belt. I got put to sleep in my first match as a blue. It was like –

[0:30:01.4] RH: It actually put you to sleep? That’s crazy.

[0:30:04.7] TG: Yeah. 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’re talking about that as 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. With that in mind, what do you think – because you’re a young guy. What are you, early 30s?

[0:30:36.6] RH: Yeah. I turned 31 this year.

[0:30:38.9] TG: Okay. 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?

[0:30:54.6] RH: 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. I mean, my first book came out in 2012, so let’s say it rode in 2011. I’ve done eight books and seven this years.

One, that’s not sustainable just like on a pure human level. I also think that’s not necessarily the recipe for really great books. To me, the next mountain is what if I took two or three years on my next book and I just really – What does happen if I slow way down, or I put way more into one specific project?

I feel like I’m getting more confident. Maybe early in my career I would’ve 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? I do feel like I’ve got a little bit more time and I’ve got – it’s weird, like I’ll hear from readers now. They’re like, “Look, I just read ego.” I’m like, “You’re like three books behind at this point.”

[0:32:15.8] TG: It was funny, because you came out with perennial bestseller last summer, which is another just great one. I recommend it all the time. A buddy of mine who’s a writer as well, because we’re both on your e-mail list and he texted me, he was like, “Ryan came out with another fucking book. How did he do that?”

Actually, I wanted to stop and ask – that reminds me, I want to ask that question. Was there overlap in writing – were you writing two books at one time at one point?

[0:32:45.0] RH: Yeah. Sort of. Traditional publishing has this huge – huge amounts of dead time, which I’m very much opposed to. Even Conspiracy which was the fastest of all my books, we didn’t do [inaudible 0:33:00.8], it was totally embargoed, we’ve 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.

It those three months, I was writing and I wrote and sold the proposal for my next book. In previous books, I’ve just been already writing or working on the book that I had sold in between. I’m just never one for leaving those gaps. I realize that that means there is catch-up that the readers are having to play, but I mean, I don’t really care.

The books don’t have an expiration date on them, so it’s not as important. I feel like I’m just 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.

[0:33:53.7] TG: 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. You 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 waiting for something to speak to you? When you finally decide like, “Okay this is my next one,” how do you come to that decision?

[0:34:35.5] RH: Yeah. To me, writing is like a job and you always want to have the – 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 and the final three or 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. Now I’m like, “Okay, what am I going to do next? I want to line that up.” That was really huge for me on obstacle, for instance. I saw what became Ego is the Enemy before The Obstacle is the Way came out.

When Obstacle is the Way came out, it sold maybe 3 or 4,000 copies in its first week and then probably 1,500 copies the second week. Then I don’t know, a 1,000 the third week. Then it was just – it 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’ve done the next book. I might not have done the next book.  Then when it did succeed, I think it would’ve had a more outsized impact on my life than I would’ve wanted it to.

[0:36:12.2] TG: I’ll go back. Yes. You’re saying you wouldn’t have done the next book. Why? Because you’re discouraged at how it was selling?

[0:36:18.1] RH: Well, I would’ve either been discouraged or I would’ve been encouraged when it came – like Mark Manson, in some ways like 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 like what is just as good as this? Does it have the same sales potential? It was a bit of pressure.

[0:36:54.1] TG: 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.

[0:37:09.2] RH: Yeah. Obstacle wasn’t that successful, or that unsuccessful. I’m talking about a smaller version of the same problem. It’s like, I sold ego for the low six figures. It was like, “Look, I’ve got a job. I have middle-class income for the next year and a half. I got to get to work.” Then I got to think of the next one.

I tend to think more like a journeymen writer, rather than a professional athlete that signs some life-changing contract. I’m just like, I’m working every day. You and I have talked about this. I like to see myself as a middle-class writer. 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 how I think about it. I always want to have that project and I’m just always working.

[0:38:09.8] TG: Yeah. I remember, wasn’t it a Saturday night live thing you told me about, where about an actor.

[0:38:15.0] RH: Yeah. I think Jane Morris has it. Jane Morris said he is in the showbiz middle-class. Yeah.

[0:38:22.2] TG: I mean, there is a lot of people that would kill to be there.

[0:38:25.6] RH: Of course.

[0:38:26.5] TG: Yeah. It’s interesting that – I guess, we’ll talk about that a little bit. Tell me just a little bit and 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. That’s where publishers are run everything very project-based. You view yourself as like a 9 to 5er typewriter. How do you growing 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?

[0:39:01.6] RH: I mean, 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 like someone who can just sit and just think. I feel like I have to be moving towards something. That impulse is what drives me. I always 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, like this could all go away tomorrow. Do I want to be – do I want to go like, “I’m so glad I took three months off in 2016.” Those were the last three months that my books were selling. I don’t know. That’s sort of part of it for me.

I’m also on the mind that quantity is how you get to the 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. To me, I feel like all my writing is 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.

I feel like I’m just collecting and making material and then some of that material is going in the albums down the road. I’m just always working and I think it’s one, it’s a productivity tool. But two, I also think it’s a natural ego suppressant, because I’m not sitting around 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 then go to my head is like, “I have a delivery. I have a contractual obligation to deliver a manuscript by a certain day.”

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.” That’s not going to be fun.


[0:41:22.4] TG: Thanks for listening to this episode of the Story Grid Podcast. I want to thank Ryan for coming on the show and submitting to all of my weird and in-depth questions. Make sure you go to our show notes at 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 e-mail list. Every month, he sends out book recommendations and other things. It’s one of the few e-mail newsletters that I actually look forward to every month.

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. When we do, you know it’s from a place. Again, Conspiracy was just a great book. I just ran-write through it. It was really compelling. Perennial Seller, I think every person doing any creative work should read as a way to just thinking about how they’re creating and marketing their work. Then of course his books on Stoic philosophy, Ego is the Enemy and The Obstacle is the Way are both fantastic. Check out all his work at ryanholiday.net.

As always, you can find us at storygriid.com. You can reach out to us on Twitter @StoryGrid. If you want to support the show, you can do that by telling another author about the show and by visiting us on Apple Podcast 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.



The Book

Is this your first crack at writing and finishing your book? Are you lost on how to tackle this project? This is the place to start.

First Time Writer

Is this your first crack at writing and finishing your book? Are you lost on how to tackle this project? This is the place to start.


Is this your first crack at writing and finishing your book? Are you lost on how to tackle this project? This is the place to start.