The Daily Stoic - Ask Daily Stoic: Ryan and Niki Papadopoulos Go Inside Writing About Stoicism

Episode Date: September 9, 2020

On today’s Daily Stoic Podcast, Ryan talks with his editor Niki Papadopoulous about their long career together, from the origins of The Obstacle Is the Way and how Ryan became a writer to the development of Ryan’s books on Stoicism, the inner workings of the editing process, and Ryan’s latest book, Lives of the Stoics (now available for preorder).Niki Papadopoulous is the editorial director for the Portfolio imprint at Penguin Random House. She has been Ryan’s editor since The Obstacle Is the Way, and has published several New York Times and Wall Street Journal best sellers. Besides Ryan’s books, Niki has also published works such as Hooked by Nir Eyal, Thinking in Bets by Annie Duke, and The Four by Scott Galloway.This episode is brought to you by Four Sigmatic. Four Sigmatic is a maker of mushroom coffee, lattes, elixirs, and more. Their drinks all taste amazing and they've full of all sorts of all-natural compounds and immunity boosters to help you think clearly and live well. Four Sigmatic has a new exclusive deal for Daily Stoic listeners: get up to 39% off their bestselling Lion’s Mane bundle by visiting foursigmatic.com/stoic.This episode is also brought to you by Trends. Trends is the ultimate online community for entrepreneurs and business aficionados who want to know the latest news about business trends and analysis. It features articles from the most knowledgeable people, interviews with movers and shakers, and a private community of like-minded people with whom you can discuss the latest insights from Trends. Visit trends.co/stoic to start your two-week trial for just one dollar.***If you enjoyed this week’s podcast, we’d love for you to leave a review on Apple Podcasts. It helps with our visibility, and the more people listen to the podcast, the more we can invest into it and make it even better.Sign up for the Daily Stoic email: http://DailyStoic.com/signupFollow @DailyStoic:Twitter: https://twitter.com/dailystoicInstagram: https://www.instagram.com/dailystoic/Facebook: http://facebook.com/dailystoicYouTube: https://www.youtube.com/dailystoicFollow Niki Papadopoulous:  Homepage: http://www.nikipapadopoulos.com/Twitter: https://twitter.com/niki_popSee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Hey, prime members, you can listen to the Daily Stoke Podcast early and add free on Amazon Music. Download the app today. Hi, I'm David Brown, the host of Wondery's podcast business wars. And in our new season, Walmart must fight off target. The new discounter that's both savvy and fashion forward. Listen to business wars on Amazon Music or wherever you get your podcasts. music or wherever you get your podcasts. Welcome to the Daily Stoic. For each day we read a short passage designed to help you cultivate the strength, insight, wisdom necessary for living good life. Each one of these passages is based on

the 2000 year old philosophy that has guided some of history's greatest men and women. For more, you can visit us at dailystoic.com. Raising kids can be one of the greatest rewards of a parent's life. But come on, someday, parenting is unbearable. I love my kid, but is a new parenting podcast from Wondry that shares a refreshingly honest and insightful take on parenting. Hosted by myself, Megan Galey, Chris Garcia, and Kurt Brown-Oller, we will be your resident not-so-expert-experts.

Each week we'll share a parenting story that'll have you laughing, nodding, and thinking. Oh yeah, I have absolutely been there. We'll talk about what went right and wrong. What would we do differently? And the next time you step on yet another stray Lego in the middle of the night, you'll feel less alone. So if you like to laugh with us as we talk about the hardest job in the world,

listen to, I love my kid, but wherever you get your podcasts. You can listen ad-free on the Amazon music or Wondery app. Hey, this is Ryan Holiday. Welcome to another episode of the Daily Stoke Podcast. I tell the story a little bit in the interview, but almost 10 years ago now, I flew to New York City for my first set of publisher meetings for what would be my first set of publisher meetings

for what would be my first book. And I left those meetings. I went into those meetings as a marketing director and I left those meetings and author my first published book would come out I think six or seven months later. And my guest today is the woman who helped make all that possible. Nikki Papadopoulos. She's the editorial director for Portfolio

and imprinted Penguin Random House. And she's been my editor on all my books. I think 10 or 11, who knows at this point, but she, I think I was the second book that she acquired there at Portfolio, Trust Man Mlying, and then she bought the proposal for the obstacle as way. She had the idea for growth hacker marketing. And so, Nicky and I kind of talk not just about

that relationship and we get into some personal stuff about collaborating and some of the conflict we've had even. But we talk about sort of evolution of sort of stillism in publishing, the writing process. And then we delve into sort of something I wanted to tease in this episode, which is my next book, which comes out on September 29th, Lives of the Stoics, the art of living from Xenota,

Marcus Aurelius, I think is the best, most complete sort of exploration of stoicism as a philosophy for living. It's instead of focusing on what these philosophers said historically, I wanted to look at what they did, who they were as people, how they lived these words. As Epictetus said, embody your philosophy. Don't just talk about it. And so, I wouldn't if you would kind of talk about

how that book came to be. And the reason I wanted to talk about that now is just give you a little preview of the book because the book is now available for pre-order. Go to, you can obviously pre-order it anywhere, books are sold, support your local indie retailer if you want, Amazon.com. But if you pre-order it, if you follow the instructions

on our website, dailystoke.com slash pre-order, you'll see we have a whole bunch of awesome bonuses, including three extra chapters that are not in the book. So you can check that out at dailystoic.com slash preorder. But Nikki is one of the best editors in publishing. She's worked on dozen or more New York Times bestsellers, close to two dozen Wall Street Journal bestsellers. She did the four by Scott Galloway,

captivate by Vanessa Van Edwards, thinking in bets by Andy Duke, cooked by near-e-all American Kingpin by Nick B builtin. Previously she was an editor at McGraw Hill, and she worked at Public Affairs Perseus, where she worked on one of my favorite books about the internet, The Net Delusion by Evgeny Morazov. She's a graduate of Brown University, which as a large replica of the Marxist-relations-of-question statue on it, she's got a daughter, and as we are finishing this interview, she was about to go on tourney leave to have her second kid,

and she has a Cavalier King Charles named Ruby Rue. So check out my interview with Nikki Papadopoulos, get it inside peek into how I write, how my books have evolved, maybe some insight into how crazy and insane I am. And of course, don't forget to pre-order lies at the Stoics daily stoke.com slash pre-order. So here we are. I actually don't know what book this is. This is 10 or 11. I think it's 11. You would know better than me. You've had

actually had to write them. Yeah, I just, I, I sometimes I lose track, which is weird, but then I guess I don't know if I should include the journal as a book or not. And then I'm always working on the next one. So it's hard to know if you include only published ones, but another one is officially done. Another one. When did we start this? Writing this book or when did we start working together? Working together. Well, that's actually where I wanted to start too. I think it would have been it would have been October or November, I think it was November of 2011. That sounds like to me.

I was curious, maybe we should, what are your recollections of that meeting? I think the first thing is that I don't know if you were actually wearing a hoodie, but you certainly gave the impression of someone who was wearing a hoodie. Okay, what does that mean? Well, you didn't show up in a suit and I thought that that was kind of cool. Like, you were showing up on your own terms, not on the terms of someone who is trying to

make an impression on what they thought a big five publisher would be like. And actually, that's when we were sick because we were on pig wind. So we're not part of random health. Do a lot of people show up in suits at Polish shows? No, not really, but especially I think you were like 23 at the time and it it was like a very, it was like a very marked Zuckerberg kind of move. I'm not sure about that. I think so it was definitely older,

it's definitely older than 23. I think I was 24 maybe 25, but I do, it is funny. It was like sometimes people will cut, like I remember I did this talk with Peter Teal at the Reagan Library. This was like two years ago, this is a very conspiracy and he showed up in a suit and I was more closer to a hoodie than a suit and it was very uncomfortable and then I realized that I don't know if I actually have a suit or I didn't at that time. It's like I feel like

one of the reasons you become a writer is to not have to dress up. And then weirdly you're in these scenarios where people are then appalled or surprised that you are not in the proper attire. It was a good meeting. I mean, I remember being really impressed, although I was really prepared to be impressed. You know, I had reached out to your agent, Steve, Hanselman, when I got to portfolio, which

was in October of 2011. And you know, and just like I'm here and I'm you know really interested in these kinds of books, and I look to hear from you. And and I hadn't really known him very well before that. So it was delightful with his funny circle global for your book. And I remember I was on a plane. And I was reading him, I was like, this is not like anything I have ever read. It's sort of crackling and special

and exciting and a little dangerous. And I feel very original. And so I remember having that feeling of like, oh, like maybe we, maybe this is like, maybe this could really, really work. And I'm having the conversation with my boss, Adrian Zachime. And so we were, we were ready, like we were excited to meet you. We weren't like ready like we were excited to meet you. We weren't like who is the guy. So, and I think the story that opened the proposal was the story of you defacing a billboard somewhere in L.A. And it was just so exciting and naughty. And so we were kind of ready to meet someone who was you know, playing things on their own terms. I do feel like most business books seem to start with, I was delivering the keynote address.

And it's like, or some we, you know, it's always this weird, really lame scene with the author doing something that's not very interesting. It's either that or I gotta tell you if I can just share the one thing that I never want to see ever, ever, ever, ever on a business with the public again, is to quote an engagement survey, like an employee engagement survey and just for the, for the need for the book. It's like, oh, like, you know, it, I would say, like, one out of every four. Like, did you know that, you know, X percentage of people say that they're not engaged at work? And, um, yes, I'm aware at this stage, I'm very aware.

I had this weird memory, maybe because it's always like the, the thing that started a project, but I seem to remember like the moment, it intros of books have always been strange for me. Like, I never sit down and go, this is going to be the intro of the book. It's formally like, it's your sort of hits me from somewhere, which I guess gets into this kind of Steven Pressfield concept of the muses. But like I remember, and we'll talk about obstacle later, but I remember I was on a run in Manhattan along the East River.

And I had the idea for the sort of scene of Mark's to really writing meditations. But I, the trust me, I'm lying one. If my memory serves me correctly, I was eating at quiznos down the street from the American Apparel factory, and some version of that intro of the book hit me, and I jotted it down on a piece of paper,

and that folded up this piece of paper and did not think about it or touch it for like a few years and then obviously when I decided to write a book it sort of unfolded that piece of paper and the intro was all there. So that's funny that that's what resonated with you. Do you still have that piece of paper? I know I have all the note cards still of the books. I'm I may have the folded up piece of the books. I may have folded up piece of paper might not have worked as well for carrying it in the box, but I just found all the note cards

for Trust Me I'm Lying the other day and then I'm gonna close it upstairs in my house. Wow, what was it like to look at them now with the benefit of almost 10 years of hindsight? Yeah, it's weird. I mean, that whole book was strange and it's funny that you were saying that it was sort of crackling.

I mean, for people who don't know, almost all nonfiction books are sold with a proposal. And in that case, I basically sort of half quit my job, moved across the country and wrote. Like two thirds or, you know, most of that book and then went out with it. I think there's a proposal too, but it, I certainly didn't know what I was doing, but I guess the benefit of it was that I didn't know that I didn't quite know what I was doing

because, you know, I worked for Robert, so I had some vague understanding of the process, but I just sort of went out and did it. So there's kind of, I think when I look at the no cards, I'm both sort of impressed and appalled at the same time if that makes sense. I also remember from that meeting, it was a week, so my grandfather had died who I was very close to. And so I'd flown to Sacramento for the funeral. And then I took the red eye that night from Sacramento

to New York. I crashed it in American apparel. I landed it like 7 a.m. or it's 5 a.m. whatever the time difference was and crashed it in American apparel apartment for like three hours. And then I don't remember if your guys' meeting was first or what order they came in, but I remember just mostly running on sort of adrenaline and fumes and not sort of, and then it all kind of got wrapped up very quickly because you guys preempted for people that know like you go to multiple publishers and then sometimes they bid against each other or if you feel like there's a connection, you can, someone can preempt and you guys preempted. So, like, I basically went to New York, not a writer, and then like a few hours later, I remember walking around, I guess, Soho, and it was like, oh, my life has totally changed. not just sort of financially, but as a writer.

Wow. Like that's what I've become. Wow. And then I then I ordered an entire pizza at Lombardies and I ate it all by myself. That's kind of amazing. Yeah, it was a lot of happens since then. I mean, today I've seen so natural to think about talking about a new book What's kind of amazing. Yeah, it was a lot of happens since then. I mean, today I've seen so natural to think about talking about a new book or, you know, talking about the next one. And it's it's funny to think back on that that time. It is, it is. Yeah, it feels like a very long time ago. And, and I think what's weird, so when I wrote Trust Me I'm Lying

because I'd sort of written about philosophy on my blog and stuff. And that was probably what, like, it was weird. I'd sort of kept the marketing side of my life, not a secret, but that wasn't what my sort of online audience was. And then I came out this marketing book and so a bunch of people were like surprised. And they were like I thought you know I think people anticipated maybe something more philosophical for me and then the book was sort of

controversial and weird and then I and then then the audience was very surprised when the next when the when the sort of philosophy books started which it was itself sort of a radical departure. I'm curious, like, what do you, after a trust family I'm like, what do you remember? Because I remember the proposal came very quickly. I can't imagine you were expecting that as my follow-up book. So you were told, when you say that, you mean obstacle,

the book that became the obstacle, it's the way, which I think that was the title that it came in with that I can't know I think the title was turning obstacles upside down. It wasn't quite the phrase. Yeah, it was turn the a conversation with my publisher where we were sort of like, well Ryan is going to write many more fantastic marketing books and we want to keep in so I guess we'll do this pride project for now, which is hilarious because you know I mean and you did write some very good marketing books but but I think that that style of thinking is sort of, you know, the trays, a little bit of what's wrong with, you know, the publishing industry, of always sort of looking at the review in the air, we'd had a success with Trust Me, which is in some ways a marketing book, and we were looking to the future and saying, okay, we're going to have more of this, and not really seeing the potential of this set of ideas in the same way.

Now, I say not seeing the potential, we still knew that we really wanted to give you. And I credit, again, my boss, Adrienne, because he's really good at sticking with writers for the long haul and saying, you know, I might not see, you know, it just far into the future, but, but I believe that this person believes that they can. And I'm willing to stick with them. And so, you know, by the time obstacle was written, I had a lot more of like, oh, I see what this is and I see what Ryan is doing and what his vision is and I think this is going to work. But I remember having that initial conversation and being like, you know, let's like, let's do this. And and then, you know, he'll, he'll come back to the marketing, which is what he really should be doing. So, because I did write another marketing book in between, right? It was weird.

I'm trying to remember the order. It was a growth hack of marketing, which was kind of an experimental publishing thing. That started as, I think that started as what used to be called a Kindle Single, which was a very, very short e-book. And then that took off really, really well, and we ended up expanding it into a book.

But yeah, I'm a little fuzzy on the timing between all of those things. Yeah, because I remember, I remember, so I guess this sort of, it's funny to hear your guys's sort of vision, but what your guys' vision was at the time in mine, because if I remember the timing right, the proposal for obstacle came within a week or two of Trustman line coming out.

Obviously, I've been working on it for a while. I think my intention had always been, I want to get this marketing book out of the way and then write what I want to write about. And you guys are thinking about it the exact opposite order. Well, it worked out. Yes. And, um, and, and I'm glad that it did, you know, and I think that, you know, that's an argument to be made that, you know, when you find a writer that you trust, you really should, you should trust 100% and you can advise them and you can get from feedback and you can share with them what you're seeing in the market or internally, but you really can't be having

a long-term investment with someone and their creative vision. And what I love about portfolio, which is the imprint that I work at, is that we are really good about sticking with people for the long run. And I think something like a quarter or or third of our authors are two, three, four or five book profaters. Nobody's quiet at 10 books in 10 years. So I think you will be record there, but it's unusual and nonfiction, especially to have that kind of long relationship. So that's something really saddled.

So I mean, Seth Dodens had a pretty good run with you guys. He did, he took a break. He took a break. He took a break. He put it mildly. He took a break. He published some books with us, and then he went and did this really interesting start up with Amazon called The Domino Project. And he did some books with them, and then he came back to us,

and then he did some other side projects. And he's come back to us a new book actually, which was coming out as well which I won't plug on your podcast if you're very good. No, it's the I remember two, the decision was not without its risk. I mean obviously you guys were willing to sort of take a book out of left field. But there was this sort of criticism later on from people where it's like,

oh, he's just sort of doing this to make money. And I remember, I find that to be very funny because it certainly wasn't a financial step up to go at a business imprint to go, hey, I know I'm just coming off this book about this controversial marketing book. What do you say we try and obscure school of ancient philosophy next?

Like you guys were not rude, but I don't think you weren't ecstatic about it, if I remember. Well, it wasn't, again, we know, we didn't have a lot of data in the market as it existed, but said there was a huge market for soic philosophy, which that's not the best way to make publishing decisions, but it certainly does influence how you think about things. And it's funny now because if I,

you know, if you could see the number of proposals that come in that use the obstacles away as a comp, as a signal of the strength of the market and the appetite for books of popular philosophy in the sort of business, self-improvement marketplace, I think it would really make you laugh. It's nothing that I was watching with a lot of interest over the years on just thinking, you know,

what if we were so wrong about that, what else are we wrong about today? Hey, it's Ryan. Got a quick message from one of our sponsors, and then we'll get right back to the show. Stay tuned. got a quick message from one of our sponsors and then we'll get right back to the show. Stay tuned. Well, people have this weird impulse, which and I talk about this a little bit in perennial seller, but I think Peter Teal talks about it best in zero to one, which is like

people think that because someone is doing something that's proof of concept and you should copy it, when really you should think about how, when they were the one to do it, no one was doing it. And so, like, I think people see that my books are about stoicism, for instance, and they go, oh, stoicism is a safe, you know, you know, a safe nature, a lucrative nature, you know,

whatever. And it's like, it wasn't that when I started writing about it. And, you know, if you really read the obstacles the way, I think that's the other thing people miss, is that only kind of retroactively did that book, did that book get sort of fully branded as being about stuacism. Very deliberately, there's an asterisk or a, you know, a footnote in the introduction

of the book that says, although I'm very interested in stoicism, this will not be a book primarily about stoicism because people are not interested in those kinds of books. Or something to that effect. And I wanted it to be sort of a book that's about the ideas inside Stoicism, but not beating anyone over the head with it. And so then, yeah, then people go, oh, I'm going to write this book about this subject, or that subject thinking that it's like, no, this was really a multi-book process of building an audience

and building a style. And then people think that either they can just sort of tap into it or that you can do that without laying the groundwork. I'm glad you brought that up because I think that's something that has always contributed quite a lot to your success. If you have a very authentic connection to your material, and I think people look at you at the success of the books

and they think that it must be engineered in some way, that maybe you look at a set of search terms and work backward to make stylicism the thing. But the reason why the books are successful is because they originate with a very authentic connection between you and these ideas that you're willing to follow no matter where it goes. And even if you're issuing caveats with obstacles,

it's stoicism, but this isn't a stoic philosophy book. I think that your attraction to that set of ideas and your ability to explore it with authenticity and sincerity is what made that book work and also set the stage for a lot of other people to discover and explore the same idea of. I don't know why people struggle with that. It's a weird thing because, so with obstacle, it's like, okay, I was really interested in, and, and remain deeply fascinated by, by stoic philosophy. I mean, like you don't, I, I was running, marketing at a publicly traded fashion company in my early 20s, like if, if, if, to, to leave that for,

you know, writing books about philosophy, writing books about philosophy, you have to actually like it. Otherwise, you're basically committing career suicide. And so you do have to really like it. But then I think this is the thing that people miss. You have to like what you're doing so much, whether it's like a book or a company or starting or some recipe for some new kind of food or whatever. You have to love the things so much and then you have to get to this place where you go, I love this, but nobody else gives a shit. And in fact, not only they not give a shit, they are under the impression that they are infatically not interested in that style or type

or thing or genre or whatever. And then you have to figure out how to translate your fascination and love into something that they would be interested in. And so, I so loved the Stoics when I read them, and then I would read the books about stoicism, and there were a few and they were always like one tenth of as interesting and I found that was because

they were just saying, like Seneca said or Marcus really said or they were just like, you know, it's like the Bible is interesting, people writing about the Bible is not that interesting by definition, it's because it's derivative and so what I wanted to do with obstacle was find a way, like what is the way into the ideas? And it turned out it was sort of illustrating the ideas and stories. But I don't know, I guess people, if you're too self-involved about your love of a thing, you don't do the work that makes it interesting to people who are self-involved in their own things. It's definitely a two-step process.

You make a very good point. I mean, the first thing is the authentic connection. And then the next thing is to be a professional about turning that connection into something that other people can connect with. And you've got to have both, really. I mean, I think a little bit of what I'm really asking to is, I think I see sometimes people trying to very coldly and rationally produce a book that they think would be

commercial based on what they see in the marketplace. And those things, they might be carefully constructed and researched, but they lack an emotional core. And I don't hate the word passion, just as almost as much as you do, but I don't know if anyone hates it as much as you do. But because they are manufactured, readers are smart, they can pick up on that. And I don't think people respond well to that. On the flip side, once you have that authentic

connection and passion, you really do have to work quite hard. And this is where the work of a writer comes in to turn that into something that other people can connect with. And, you know, and to do it in a way that allows for another person's experience and point of view, which is really hard. Yeah, I mean, I've always felt that the way to sort of thread that needle is you have to sort of step back and go, what is the thing that I wished existed earlier on, either in my journey or in my

fandom or whatever. And so, like, you have to make the thing that you would want to exist and you being a representative of hopefully a fairly large underserved audience. Exactly. Yeah. underserved audience. Exactly, yeah. Which was tricky, so if we talk about lies, which is the new one, and it's actually an interesting sort of, there was the tricky part on lives of the Stokes, which is obviously I love Stoicism, somewhat coincidentally, my agent Steve Hanselman and co-author on the book also love stoicism, but I would say we,

it's not that we come at it from different perspectives, but we have very different backgrounds, right? So I'm a college shop out, Steve's a graduate of Harvard Divinity School, Steve can translate Greek and Latin, I can't even pronounce the words. And so I would say like sort of Steve's fascination with the stoic figures. It's not that it's more academic, but it's much more

sort of detailed oriented. And my fascination with the stoics is much, I would, I don't know, I would say I'm much more interested in their essence or in the moral example that they set. And so even as we sort of tried to break down this book, I mean, for instance, one of the early iterations of it was like, do you split it up in chapters or do you split it up in many biographies of each one of the figures? And if you're interested in how they all, you know, like if you're interested in the themes of stoicism throughout history, then you kind of loop them in together

and you have them overlap. If what you're really interested in is what does each one teach you, you're not sort of breaking it up like we did. So it's, it's, it was interesting on this book to have to like, to do what we were just talking about, but then also involve an additional party. They're telling more about that, the process, because by the time I saw the manuscript,

it was very, very big. Like you guys would really solve a lot of, you know, what might have been earlier structural issues or issues of tone and it felt very, very complete. We did have some discussions about whether to include certain details or not or the normal editing conversation you have. But structurally, the book felt like it had been the product of

some very intense thinking. I mean, I feel like that's one of the things I've learned now doing this ten times is like, you have to, the more you do that hard thinking upfront, the better the final product will be, because if you're just sort of like going along, you haven't thought of all these different, contingencies or issues or concerns, what happens is like you and I might get on the phone, you and being the editor,

or you being a random friend or someone reading the book, and then someone goes, Hey, if you thought about doing X, an X might sound perfectly reasonable in the context of that immediate conversation. And so you end up making this change or this change. And then you add enough of those together and you get this sort of weird amalgamation

of small short-term decisions, when really you needed to be like, what is this thing? What's the main goal? What is it accomplishing structurally how is it set up? What's the vision for it? So then you kind of understand how all these little things fit into it.

Like, you know, for instance, on this book, the decision to say like, this is about what the Stoics did, not what they wrote or what their theories were. Like that, that solved a lot of problems when we got to someone like Cicero, Cicero being this sort of complicated figure of someone who was like a propagator of the Stoics, and he wrote a lot about what the Stoics wrote about, but then had trouble actually,

like what sort of could never fully commit, sort of like, well, how do you end up portraying that person? If this book is just about Stoicism's evolution through history, you end up with, I think, a really boring chapter there, where you're just like, and then Cicero said this, and then Cicero said this. But to make it, if it's like, no, no, this is a book about philosophies sort of role in the real world, then you end up portraying Cicero

as this sort of tragic figure who, like, knew what he should be doing, but could never quite bring himself to do it. So, yeah, I think you have to, as a writer or as a leader or whatever you're doing, I really do feel like you, if you're not doing that hard thinking, then like, who is doing it? It's a very good question. Yeah, I mean, it's critical. It's absolutely critical. And I think it really helps, as you say, it really helps people write the book. You know, if you, I mean, you can write quite a lot of well polished words without ever figuring out what they're for or what you're trying to do with them.

I think that's probably like the biggest psychological hazard of your profession is not doing that problem solving before the writing process. Because writing is it's not, I mean, I'm an editor I know writing is not magic. It's the tool. It's a tool for achieving a certain outcome in the in the mind of your reader and then by extension in the culture. And so if you don't know what you're trying to achieve, you can dance around without getting a lot done pretty easily. And which is, you know, frustrating to your reader doesn't get, you know, doesn't move your career ahead much. And, you know, it's definitely frustrating for your editors. No, there's a great centric of code. He says, if you don't know what port you're sailing to, no wind is favorable.

And, and I think as a, as a, as a writer, the trickiest thing, it's like when I get notes back from you or when I would get notes back from Steve or from Niels, the other editor I work with, is like, the notes are the notes. And they're not right or wrong, they can, but they have to be evaluated in the context of what are you trying to accomplish, right?

So it's like, I remember here in Brian Coppel I'm talking about in rounders, people kept sort of criticizing that there was all this sort of like dialogue in the movie and it's like, the whole point is that this is like a quotable dialogue driven movie so like your note is taken and politely ignored because that's literally like you think you're criticizing the movie, but you're actually like confirming what we that we did what we said and so

I think if you don't sort of strategically figure out what you're trying to accomplish as a writer, it's very hard to get feedback. And it's weirdly very easy to be led astray by seemingly well-intentioned feedback. That's definitely true. I'm curious. So do you edit a lot of the test of my stoicism was of course, right? Like with with daily stoic, the which I also did was Steve,

the delineation of roles was so much cleaner and clearer, right? It's like, we picked the quotes together, Steve translates them, I sort of write the sections and then Steve's sort of checking the work, so to speak. But I can't imagine that most multi, like I just read another book, portfolio, did the unacceptable about the college admission scandal, and I noticed it was written by two reporters. And I just sort of like, I can't imagine writing a book with another writer often goes well. Well, those two worked a lot quite a bit.

And I think had their relationship figured out before they saw the proposal, which is key. You know, I haven't done a ton of books where you have two equal co-authors. You know, there are definitely books where people have had someone helping them, you know, whether it's on the structure or on the pro-level, but you know, I think it's very difficult as an in your relationship, but especially in a creative relationship, to have two people who are doing the same thing. So, you need to figure out what your comparative advantage is, and be honest with each other about about what that is. And that can be easy for some people and very difficult for other people I imagine.

You know, I thankfully and I'm very grateful to you and to you for this. I did not, you know, you guys presented a very united front. And if there was, if there was drama, but it was it was all the way for my, my eyes, I got a beautiful manuscript on the day I was drawn to it, but it was on the way for my eyes. I got a beautiful manuscript on the day I was promised it, which is rare than a unicorn, by the way, and I was very grateful for that. Hey, it's Ryan.

Got a quick message from one of our sponsors and then we'll get right back to the show. Stay tuned. Hey, it's Ryan Holiday. I am so excited to tell you about my next book, Lives of the Stoics, the Art of Living from Xeno to Mark's Relias, your fan of Stoicism, and you want to know about the people behind the ideas that have been so influential in history that have shaped this philosophy

that's had such a big impact on your life in my life. Well, that's what I wrote this book to do. It's sort of a follow up sequel to the Daily Stoic. It's 26 biographies of the most fascinating Stoic figures in history. Mark Srealis, Zeno, Santa Cate, Santa Cato and so many others. And there's a whole bunch of bonuses. If you pre-order and we even have a limited edition run of signed copies, which you can get from Barnes and Noble. So for the pre-order information, go to dailystowoc.com slash

pre-order, the book is out September 29th, but you've got a pre-order it now that helps me in a big way and gets you the bonus. It's dailystowoc.com slash pre-order. No, there really wasn't any drama. And I do try to, I don't think I've delivered any of my books late. It's a weird, like, I don't think I've delivered any of them late, although it's sort of that thing where it's like, if you've never,

if you've never missed a flight, you spent too much time at the airport. I don't know maybe if I, if I should have delivered some of the books late. Well, you know, it's's it's maddening because it takes away any psychological leverage I have over you. Interesting. What would that do? No I mean you know I think as writers should be they're very you know people people worry about missing their deadlines and I was just kidding but I mean we appreciate it we just kidding, but I mean, we appreciate it. We do appreciate it, but I think there's also a little bit more

understanding in the system than some writers, especially for some writers, give us credit for. If you're writing a book for a major house that has a long investment in your career and your talent, then you know, we wouldn't be making that if we didn't believe in you and believe that you would be able to produce something special. And you know, there are exceptions, of course. I mean, I think there's, you know, if the book is very news driven, and or if it's competing with another book that we know is coming, then the deadline gets very important.

But, um, but if it's, you know, if it's the kind of book where you're putting in a ton of research and it really has to be a fantastic read. And, you know, I mean, I'm not going to like cut your legs off for being a weeklaid. No, you can edit part out, right? Yes, no, it is weird though. And I think the sort of stoic virtue of self-discipline moderation being an important one. I do feel like a lot of writers

have created people's struggle with deadlines. You know, they act like it's like, oh, you know, they act that it's sort of inspiration or that what they're doing is very hard or you can't rush magic, whatever. And there's an element of that to it, but I do suspect that a lot of it is just sort of, it's very hard to manage oneself

when you have a lot of freedom. And like writing a book is crazy. I mean, if you think about my first book, it's like I was 24 years old. I'd never published a book before. You guys gave me like a couple hundred thousand dollars. And you were like, please come back with a book soon. You know, like that.

I do see where, I do see where people, sort of, that's almost like the worst punishment you could inflict on someone because no one is actually like making sure you show up for work every day in doing it. And a book is this really hard thing where you're working on it. The finished product, the finished manuscript you're talking about that sort of magically shows up on your desk,

is the result of a whole bunch of sort of average mediocre work days added together, but you have only you, the person doing it can accumulate those, and no one can sort of squeeze them out of you. It's absolutely terrifying. And I think some people use the deadline as almost a way of ducking that gigantic crushing fear that comes with the idea that like, it's only works if I get it right. And I'm here on my own and and people can help me, but really it's my name and giant letters on the covers and nobody else. And that, like you said,

I mean, it's almost a form of punishment. For some people, it's very motivating and it provides a lot of avenues for doing the work that they truly love. But, but as you said, you know, it can also be very lonely, I think. Yeah. It's lonely. And I think the other hard part is like, you, like I was writing, I'm writing today on the next project

that I'm doing, which we don't need to tell people about, but I was writing. It's like, what I did to, I did my workload, but I don't feel like great about it. What I put down, I wasn't like, this is genius, this will obviously work, this will go untouched into the manuscript. It's just sort of like, that's too judgmental. It's more like, you know, meh. You know, like it is, it is, and it exists. And you have to

weirdly be able to manage the like, okay, I can, now that it exists, I can refine and shape it, but you first have to get, be able to get over that hump and deal with the discomfort of mediocrity almost. So how do you deal with that? I think you just do it every day. Well, how do you lie and deal with it? No, that's what I'm saying.

I think I don't really deal with it. I just do it every day. And like, I've been, as I've been working on this one, I have to, especially having done this many books now, I have, weirdly, I remember most of my books as the finished product. And you kind of have to push that out of your mind and remember that all the books were sort of

in that sort of pseudo-Rough, like that you just have to get comfortable with the discomfort of it for extended periods of time. So I just remind myself like it's like pages add up to published work. So I just, I show up every day and I work on it. And then I remember that like when I go for a run or a ride later this evening, probably two or three things will pop in my head that I inserted into earlier pages this morning after I finished doing my actual writing that kind of closed the loop or tightened that,

it was like, it was exactly that missing piece that tied that previously sort of half finished thing altogether. So you just have to have the fortitude to be able to sit with that. I think it's a lot for some people. And it's a muscle that you have to build up every day to like, it's not something you can switch on. No, that's the job.

Yeah, I feel like. And the hardest part too is like, okay, so I've been working on lives for, I don't know, a year and a half or two years or however long it's been. And I find that editors don't talk about this period enough but it's the really hard one, which is like, okay, I did this book, it's now done.

I felt pretty good about it when I finished. I felt pretty good about it when I read the audiobook. And then you go into this kind, so we're recording this, it's mid-August. It won't come out, it comes out in the end of September. And then obviously you don't want to, as stoked, you don't want to be validated by the external results.

But you really don't, it's now just like sitting, this thing is just like sitting there and you don't know, it's like you sent in, speaking of college admissions, it's like you sent in your application, you did your absolute best, but you don't know for several months until the random letter comes in the mail that tells you whether you've been, you know, whether you've whether you've been accepted or rejected or not. So to me, the most existential hard part is not the writing stuff because day in and day out, like I control the writing stuff, the really shitty part is between rap and release. That's to me the most uncertain period. at least, that's to me the most uncertain period.

So you said Ediver's don't talk about that enough. What do you think that Ediver's own publishers could be doing in this period to support their authors? I mean, really, I'm like, you know, oh, books at the printer and being down and distributed like, I don't have to worry about it. Okay. But it's good, you know But it's good to point out that it might be a time of quite a lot of anxiety.

Yeah, I mean, I do think talking about it that sort of, you know, sort of if there was some name for this valley, well, actually in, in Julius Caesar, Shakespeare says like between the decision and the deed, what does he say? It's like a vague illusion or this weird phantasm. It's like when they decide to assassinate Caesar and then the morning they do it,

it's like, that's the roughest period. And so I wish there was some name for that kind of like limbo-y period, but honestly, I mean, I think what writers should do and what publishers should push them to do and my model with you guys a little bit closer to enabling that. But I think what most people should do is start writing the next project, which is what I did. I mean, I started working on ego before obstacle came out and I was already working on daily stoic when ego came out. And I think having just going back into that grind

is actually like maybe the safest place to be. That's interesting. I'm gonna fill out. You should, I mean, I think I stole it from Stephen Pressfield, which is like, you know, you finish one manuscript and the next day you start the next one. That doesn't mean that there's not some pause and that you're not in sort of different stages on stuff, because you obviously do have to go back and work.

But I really feel like, and for, like, when obstacle came out, I mean, it did well. It didn't do poorly at all, but it certainly wasn't, if we're just now here crossing the 1 million mark, it probably sold 100,000 copies in the first two years. Something like that. It certainly didn't come out of the gate. It didn't hit any bestseller list. And it didn't like, it was not clear what it would become,

but the fact that I already had my next book under contract and was working on it was a great place to be. I would love to talk to you more about the content in life. Because, you know, I have, I always have all these questions for authors that, you know, they're not problems to be solved. They're more in curiosity, but, you know, I guess, like, I would love to know about how your feelings towards these characters changed, at all in the process of writing. Because it's like, especially in the biography

and the book did end up being sort of series of many biographies, you hear from writers that you get like these very intense sort of psychological relationships going with your subject. And the book doesn't betray that in any way. It's not clear that any one person is, you know, struck you more than others. But I would just love to hear more about,

as you were writing, like, how are you thinking about these people, and how did you think you changed? It was, it was weird. I mean, I think Marcus really is. I've had the longest relationship with. And that was the kind of most fascinating and weirdest one to write, because it was at the end of a fairly long process that I got to that one. So that one kind of just kind of flowed out and it was really sort of cathartic.

Like, because obviously I've read this person and interacted with him and having this conversation with him for, you know, going on like 15 years now. But I just, I wasn't aware of all the details, right? I think that was the weirdest part with even Seneca and some of the other figures is like, is you I kind of feel like I always intuitively understood their essence. And then you were kind of going and finding out these figures and scenes and moments that revealed the essence. sense. So, you know, like really, really, like really going into Kato and his death, I found to be sort of haunting and sort of morally vexing. Santa, obviously, to me, as a sort of figure for

our time, you know, this sort of deeply ambitious, deeply talented wise person who ends up, who ends up serving in Nero's administration. And I don't know. I think it's just, it was a moving, weird experience to be sort of biograficizing these people after having spent so much time with them. I don't know if that makes sense. Yeah, definitely. It's interesting about Sena-Fa. He's definitely a very complex character and you can see that it's not much of changed between that and now and some ways. You know, I was just reading this James Rom, PC wrote in the New Yorker and he was like,

Senna could have been the anonymous writer of that, that Trump tell all or the, you know, the person who wrote that op-ed in the New York Times. Like that was what Senna could have thought he was doing. Whether you support Trump or not, that's what Senna could have thought he was doing. He thought he was doing, whether you support Trump or not, that's what Sennaka thought he was doing. He thought he was the sort of adult in the room, and then it really quickly becomes a complicated discussion

about whether you're the adult in the room or whether you're complicit with the bad things that people in the room are doing. And I think Sennaka kind of embodies that. Yeah, definitely. And then I think at the core of all the figures is this sort of courage, especially the ones,

especially the courage of the sort of Roman Stokes. So if you go from like sort of Kato through, Kato through, let's say Musoneus Rufus, there's just this kind of incredible courage with their sort of constantly challenging the powers of B that they're on the razor's edge of losing everything at all times. I mean, Musoneus Rufus is exiled four times, Thrasia and Helvides and Agrippinus all lose their lives,

you know, sort of challenging, Miro. I think that the weird part too was, there was a sadness there for me that now there are senators who, the consequence of being courageous is that you don't get reelected 40 years from now, potentially, and then you go make a ton of money as a lobbyist or a lawyer or a Fox News correspondent and still don't want to do it

because somebody might tweet something mainly at them. Yeah, it really puts some people's behavior and perspective, that's all so about that. Yes, well, I do know portfolio works with some of these figures with these Sentinel imprint, so we won't go too much into it. Thank you. I had one last question. And this might be sort of crazy or inappropriate,

but I thought I'd be interesting to talk about. Sometimes you just don't get opportunities to do this. But I'm curious. So we started it in 2011. I was like a kid. You hadn't had you done any other books at Portfolio, or was I the first author that you signed? I think it was the second book I signed,

but the first one that I signed that came out. Got it. That makes sense. Yeah, yeah, no. And so it's been, yeah, almost 10 years now, we've done at least 10 books, and then we've collaborated in some other projects. I don't know, I feel like,

sometimes I feel like there's more sort of tension and conflict in our relationship than I would like. What do you think? Where do you think we've gone astray as a strong word? What do you think is at the root of that and how do we collaborate better? I think it's true of everybody who has my job that you, that's a lot of masters to please, you know, I, I work as an editor because I love books and I love working with authors, but I don't want for you.

You know, I work for Penguin Random House and, and I represent the interest of my company as I should, as it seems to. And sometimes I think there is tension or conflict over what you want to do or what something you want to try that as a representative of my organization, I can't advocate for it as effectively as I would if, you know, if I was like on your team or as your agent, but, you know, I think that that kind of tension is is probably present in lots of business relationships that are around a creative product. You know, I've never worked in Hollywood, but I've read about it. And it seems like there's a lot of the same kind of thing, you know, where you're balancing, you know, your responsibility to your authors and their work and your responsibility is really the work for us. And also your responsibilities to whoever is funding that work and distributing it. So that's what I would say for the Vosikov.

It's weird too because I think most, like even the other authors that you have that you've worked with for a long time, they don't have as many touch points, right? Like I think the tricky part about doing 10 books in 10 years or whatever is that there's an exponential amount, that creates an exponential amount of things that can go wrong or that need to be managed. And so I think I don't know how to get away from it, but it does feel like, I feel like most of our sort of disputes or arguments or conflict is never about editorial matters.

It's about administrative matters or financial details. Or like, you know what I mean? We end up, it's like, it's like people who are married who also work together, you're arguing over like expense reports or something when and the dishes at the same time. So it's like, I think that's been a tricky part of it. And just the duration of it, normally authors tend to bounce around or whatever, so they're, or the editor leaves

and then you go to a new house or whatever, so they're, or the editor leaves, and then you go to a new house or whatever. And so it's, I think that's a wrinkle in it that we haven't quite figured out how to manage. Yeah, I mean, it is definitely true that there are, I mean, hilariously, like, because you are successful, we have more ICMs assigned to you and more titles and more editions and more reprints. And each one of those has a point for one for fan chance

of having some kind of grew up on it, just because publishing is made up of humans. But if you could only have a published one book with in one edition, you might not have had the full range of everything that can go wrong. So I wonder sometimes I wonder if I should set you up with one of the commercial fiction authors who, you know, were also writing like to, you know,

one or two books a year and who's really had like a long experience. I'm like, Oh, I think that like that actually is probably more your experience than like a typical nonfiction author, because you know, every, I mean, every addition has it has it's wrinkles, wrinkles right whether it's like I'm covering it ebook the audiobook paperback a free of a dream a paperback we did a box set of of three of your books and you know you'd think that like that wouldn't take as much conversation I think work as it did but it did you know like it's it's a it's an ICN and it's a remalor, it's a redesign, we have to try and keep it in stock.

So, yeah, I think it's similarly, it's important to preserve that purity, I think, of the conversation about the creators, about the title, about the cover, about the main script, and to try to keep the administrative stuff on a sideline. But it is hard because, you know, and I am keenly aware of this, like, you know, this is a direct, like, all of the things that happen on your books have a really direct effect on you and your life and your family and in a major way. And like that, you know, that fact has not escaped me.

Yeah, no, it's, yeah, we do it in that sense. We kind of exist in different universes. I remember when we had that issue with the pirated copies or something and we won't get into the details, but you said something like, oh, so-and-so doesn't care about the little guy, and you're referring to their relationship with Penguin Random House. And I was like, Penguin Random House is not the little guy. Penguin Random House is a multi-billion dollar company. I'm the little guy, right? And so it's, yeah, it's like you have a job

and the things affect me differently than they affect the, like you have a job and you have, there's a bureaucracy as part of the job and expectations and relationships and I exist over here in this kind of fantasy world of just me answering only to myself and whatever I wrote. And so, yeah, I figure, I feel like that we have to do a better job of keeping church and state separate too

in the sense of the editorial sort of content relationship and then the the business administrative execution side of the relationship where it seems like the majority of the tension ends up actually being. Well, let me flip the question on you since we're doing a sort of sold-of-fold moment. OK. Like, you know, you're a man of many options,

and yet you've stuck by us. You know, can I assume that the value we provide is greater than the sum of our reprint mishap? In some respects, yes, of course. No, and certainly, the equation was very different 10 years ago, and it's a weird situation, too, where the calculations made 10 years ago are precise and the collaboration in the some of the parts are.

You know very are what have contributed to the increase in options you know now so that's like a weird thing to consider but. Yeah, I don't I do I love. I love working with portfolio. I love the reach of it, of course. But doing this leather-bound edition of Daily Stoke has been an interesting experience, too. It's been a lot of work and it's like getting things shipped by boat from Europe has been a nightmare and gave me a little bit of insight into what you guys are dealing with every day. But it's also looking at the sort of retail environment.

It's the pandemic has been interesting because Amazon was dominant before. And now it's like, who's even going inside bookstores? Who can go inside bookstores? So it's been weird to think about where the future of the business is going. Yeah, I'd be lying if I said that that didn't keep me up at night, but it's an interesting point that you make. I think that I've had many authors who either

prefer self-publishing or have tried self-publishing and have decided that that's not how they want to spend their time. And I have total respect for both ways of looking at it, right? I mean, if you are the kind of person who, you know, if you're doing a project where it's more important to you than anything else to have total control over the creative, over the cover, over the timing, over everything. Then, yeah, you probably don't want to partner up with a general corporation. Like that, you know, if you were a business, like you probably wouldn't want to take a huge loan from JP Morgan either.

You know, like that, and so, you know, thinking about it in terms of like, sort of sending the business decision with the creative decision, and like, is this partnership gonna be something that adds value to my project, or is it gonna, you know, am I sort of finding up for this kind of wish fulfillment of like, oh, I'll, you know, I'll take this investment

and then everything we look out. I think that's really important for writers to think about. And a lot of people, I'm gonna be happy to say, I do think we add a lot of value because people do come back to us. And maybe it's because we handle a lot of those and we ask them to help, like the slowboat from,

from Belarus or wherever, you know, and in, in a way that is efficient for them. But, you know, I'm hopeful that also, you know, we add some kind of, uh, some kind of value on the, on the creative and on the editorial as well. The thing about doing yourself is that you can do anything you want, which is both great and also an upgrade, you know, and you've written a lot before about the value of having someone push back on you when you don't want to be pushed back on creatively. And it do think that there's something to that. I mean, here I'm just talking to General, but.

No, I think those constraints are helpful creatively. I just think it'll be interesting for publishers going forward as the distribution side of things becomes much and much less important. And it's sort of like, yeah, we put your book up on Amazon for you or whatever, or we put it on Audible for you. Like this last one, I recorded the audio book for Liza the Stoke.

I recorded Liza the Stokes in my, the annex to my office. And so it becomes the sort of technical side of it becomes less important, I think, and it will have to be, does the publisher help a person realize something that they would have trouble realizing on their own, or does the publisher help get creatively more out of the author than they might be able to get on their own. In addition to handling, you know, pesky details, I think that's going to be, I think that's going to be important because yeah, you we used to have lots of big marketing discussions about how many, you know, copies this account was ordering or that account and is not that that doesn't exist anymore, but it is a smaller percentage of the pie. I mean, we're not even talking about airport distribution

on lives of the Stokes, because who's spending time in airports, right? And so it's a weird change that everyone has to adapt to, I guess. Yeah, I mean, hopefully this is temporary. Yes. Yeah, I mean, hopefully this is temporary. The Hentenine Play lasted for 15 years, Nikki. Thank you.

Thank you. I'll keep that in mind. No, no, I think it makes sense. Well, here's to many more books and we can tease two people that we are already set to be in business together for several more books. And so all the discussion we're having is moot anyway because we're hitched for a few more and people can stay tuned for those.

Awesome. Well Ryan, I'm so pleased for you and excited about this one that's coming out in September. It's called Life in the Stoic. If you're interested, don't know about that yet. You know, I think it's going to be really cool. It's got a lot of fun stuff, Sam. Well, thank you. And yeah, thanks for taking the meeting 10 years ago.

And more importantly, thanks for taking the meeting 10 years ago and more importantly, thanks for for, I guess, reluctantly purchasing the obstacles the way. So I would get it out of my system and write other marketing books. And because without that, we wouldn't be here right now. Amazing. All right. Thanks. If you're liking this podcast, we would love for you to subscribe. Please leave us a review

on iTunes or any of your favorite podcasts, listening apps. It really helps and tell a friend. Hey, Prime Members. You can listen to the Daily Stoic early and ad-free on Amazon Music, download the Amazon Music app today, or you can listen early and ad-free with Wondery Plus in Apple Podcasts.