Author Adam Rubin on Creativity and Pursuing Your Passion | Did It Make You Better

Ryan reads today’s daily meditation and talks to Adam Rubin about his newest book High Five, taking the leap from being a part time artist to being a full time artist, the magic that is being able to express yourself creatively, following your destiny and inspiring others to do the same, and more. Adam Rubin is a #1 New York Times best selling author of children's books. His books have sold over one million copies. Rubin graduated from Washington University in St. Louis where he studied advertising and worked as an advertising creative director for ten years before leaving his day job to focus on writing books. His new book Gladys the Magic Chicken comes out on October 26th, 2021. Talkspace is an online and mobile therapy company. Talkspace lets you send and receive unlimited messages with your dedicated therapist in the Talkspace platform 24/7. To match with a licensed therapist today, go to Talkspace.com or download the app. Make sure to use the code STOIC to get $100 off of your first month and show your support for the show. KiwiCo believes in the power of kids and that small lessons today can mean big, world-changing ideas tomorrow. KiwiCo is a subscription service that delivers everything your kids will need to make, create and play. Get 30% off your first month plus FREE shipping on ANY crate line with code STOIC at kiwico.com. Ladder makes the process of getting life insurance quick and easy. To apply, you only need a phone or laptop and a few minutes of time. Ladder’s algorithms work quickly and you’ll find out almost immediately if you’re approved. Go to ladderlife.com /stoic to see if you’re instantly approved today. Novo is the #1 Business Banking App - because it’s built from the ground up to be powerfully simple and free business banking that Money Magazine called the Best Business Checking Account of 2021. Novo makes banking easy and secure - you can manage your account in Novo’s customizable web, android, and iOS apps with built in profit first accounting and invoicing. Get your FREE business banking account in just 10 minutes at https://banknovo.com/STOICSign up for the Daily Stoic email: https://DailyStoic.com/signupFollow us: Instagram, Twitter, YouTube, TikTok, FacebookFollow Adam Rubin: Homepage, TwitterSee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info. 📢 Share | ⚙️ Manage Subscription

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

• 0:03Ryan Holiday?

  Welcome to the Daily Stoic Podcast where each weekday we bring you a meditation inspired by the ancient Stoics, a short passage of ancient wisdom designed to help you find strength and insight here in everyday life. And on Wednesdays, we talk to some of our fellow students of ancient philosophy, well-known and obscure, fascinating and powerful. With them, we discuss the strategies and habits that have helped them become who they are, and also to find peace and wisdom in their actual lives.

• 0:39Ryan Holiday?

  Did it make you better? Musonius Rufus was exiled four times. For those of us who just spent a year complaining about pseudo-quarantine and social distancing, can you imagine losing everything, being sent away from home, missing all the things you considered normal, not once, but over and over again? And yet, as I tell in his chapter in Lives of the Stoics, Musonius Rufus never wavered under this pressure. Instead, he was transformed by it each time, just as his heroes like Diogenes had been. He believed that exile was a cure for soft living and luxury, and that by customing a person to live more austereally, it restored

• 1:20Ryan Holiday?

  their health. More impressively, he saw exile as an opportunity to do good. While stuck on an island off the coast of Greece, a freshwater-starved hellhole, he helped local villagers discover an underground spring, which improved life for all who languished there. How did Musonius do this? Well, first, adversity was something he had trained for. While in Rome, he lived on hard mattresses and familiarized himself with hunger and thirst. By training, he said, "The body is strengthened and becomes capable of enduring hardship, sturdy and ready for any task." He also understood that fate visited circumstances on us, whether it was exile or a pandemic, and what mattered was how we responded.

• 2:03Ryan Holiday?

  We could be made better for events or worse. What would it be? That was our call. Now, each of us who had endured this difficult year and who will undoubtedly endure more difficulty at some point in the future, what will it be for you? Will it find you prepared and dug in for assaults? Will you use what happens for good? Can it toughen you up? Let this make you better. It's the only way to find meaning from it. I'm really proud of the chapter about Musonius Rufus in Lives of the Stoics. Musonius is the mentor and philosophy teacher of Epictetus, who in turn influences Marcus Aurelius and was also the philosophy teacher of Rusticus, we think, who was Marcus Aurelius' philosophy teacher.

• 2:48Ryan Holiday?

  All that being said, I really think you'll like the book Lives of the Stoics. It debuted at number one on the National Bestseller List. We've got signed copies of it in the Daily Stoic Store. Pick up a copy at The Painted Porch, my bookstore here in Bastrop, Texas, or anywhere books are sold. Lives of the Stoics: The Art of Living from Xeno to Marcus Aurelius. Check it out. Hey, it's Ryan Holiday. Welcome to another episode of the Daily Stoic Podcast. I don't know if I've told this story before, but when I wrote my first book, Trust Me I'm Lying, which is sort of a marketing media book, I was like, I'm an author. Where do authors live? I moved to New Orleans to write my first book, which is an amazing place to write a book, but didn't feel like necessarily where like an up and coming author should live.

• 3:30Ryan Holiday?

  And my wife and I, not then wife, but then girlfriend, moved to New York. And it was, it was awesome. Didn't end up working out over the long term. New York, still, still with Samantha. But I got to meet all sorts of amazing people and it was this exciting time because my book was new and it had been controversial and I got introduced to these cool people. And I'm going to tell this story a little bit with my guest, but I ended up meeting today's guest roughly 10 years ago, who I didn't realize, although he was a cool guy, we talked, we connected, he sent me a copy of his book. I didn't realize what a big role he would play in my life a decade later.

• 4:11Ryan Holiday?

  Once I had kids, I'm talking about Adam Rubin, of course. But before I get to that, I guess the moral of that story is you don't have to live in New York City as an artist. It was nice to live in New York City for a brief time to be at the center of things. It was fun. I'm glad and thankful for that period in my life, in part because it led me to today's guest, who is one of my favorite writers. He's a writer of children's books. I don't want you to turn this episode off because it is, we touch on children's books tangentially, but we're really talking about creativity, following your sort of destiny or calling in life, how to get good at a craft and a whole bunch of other awesome stuff.

• 4:54Ryan Holiday?

  But Adam is very, very qualified to talk about this. His books have sold millions of copies, multi number one New York Times bestselling author of 10 critically acclaimed children's books, including Those Darned Squirrels, Secret Pizza Party, one of our favorites, Dragons Love Tacos, Dragons Love Tacos 2, his book Robo Sauce, we've read and liked, his book High Five, we really like, just a great guy. We carry them in the painted porch. They're all time favorites. We even have, I remember like a box set that's Dragon Love Tacos and then it's got like stuffed animal dragon with tacos. Just, I love it.

• 5:39Ryan Holiday?

  And I found his, the other day I was reading to my son and we've bought so many copies of this, of Dragons Love Tacos. I, I knew I had a signed copy somewhere, but I pulled it and there was the signed copy that, that Adam had sent to me. And as I talk about in today's episode, we've had kind of this cool journey where he'd written like one book at that time when we met, I'd written one book that came out almost at the exact same time. And then we reconnected, he came to one of my book signings at the Strand, you know, many years later and we both. Left advertising, left marketing, I think left New York City, although he might be back there, and had gone on to have these great careers. And I always love when lives sort of go in separate directions and come back. And so Adam's one of my favorite people.

• 6:24Ryan Holiday?

  Adam was instrumental in influencing, he gave all sorts of great direction and advice when I was coming up with the idea for The Boy Who Would Be King at the beginning of the pandemic. And I'll give you one other funny, quick story about Adam Rubin. I had dinner several years ago with a friend and BJ Novak, the great writer, director, most famously of The Office, but done also two or three great kids books, including the book with no pictures. We were talking about books and kids books, and I mentioned something about Adam. And he was, you know, Adam Rubin? Because Adam is awesome and his work is great. And I think you should check it out. Check out Dragons Love Tacos, check out

• 7:07Ryan Holiday?

  Those Darn Squirrels, check out El Chupacabras, High Five, his other book of stories, The Ice Cream Machine. There is just awesome, great stuff from Adam. Check it out. And here is my interview with the one and only Adam Rubin. You can also follow him on Twitter, at Rubingo. That's R U B I N G O. And you can go to Adam Rubin has a website for all sorts of information about him. And I do hope you check out your books. But mostly, I hope you take from this episode to follow your creative instincts, do something cool, and be like Adam.

• 7:50Ryan Holiday?

  I was thinking back, do you remember when we met?

• 7:52Speaker 01

  Kind of. I feel like it was on a rooftop, maybe?

• 7:56Ryan Holiday?

  No, it was at a Nets game.

• 7:58Speaker 01

  Oh, that's right. That's right. Through Corey Mintz, is that possible?

• 8:03Ryan Holiday?

  I don't, I'm terrible with names. But it's whoever your boss was at Firstborn.

• 8:08Speaker 01

  Hmm.

• 8:11Speaker 01

  That's right. That was Dan LaCivita. He introduced us.

• 8:14Ryan Holiday?

  Yes, he invited me to a Nets game and you were there. And I remember you were like, oh, I'm a writer too. I write children's books, which is, as I'm sure you've met many people who have said the same thing to you. I was sort of like, oh, sure, sure you are, you know, and you sent it to me and I read it, but I didn't have kids. You sent me Dragon's Love tacos and I read it and I was like, I guess this is a good children's book. I have no idea. And I could have not anticipated that just, you know, six, seven years later, I would have read that book literally hundreds of times to a small human who lives in my house.

• 8:53Speaker 01

  Oh, my, my apologies.

• 8:56Ryan Holiday?

  Well, I was, but I was thinking about that, like, how did you go from advertising to writing? And then I want to talk about the transition from sort of a person wearing two hats to the decision to go full time to one hat. Cause I think that's a, that's a position a lot of people dream of being in and then either don't do, or they do too early. So, so talk to me about how you, how you go about starting the first book.

• 9:27Speaker 01

  Well, I never really looked at advertising as a lifestyle. It was always something I was doing for money. I thought it was a really good way to get paid for being creative, but I never, even when I was looking for jobs straight out of college, I never confused the idea of having a day job with having this identity that's wrapped up in what I did for money. And to that point, I was doing comedy shows at night. I was really invested in the annoyance theater and the people there and the shows that were going on. And I was there almost every night. I lived just down the street.

• 10:06Speaker 01

  So the advertising thing was always kind of the thing I was doing to earn a paycheck and kind of fit into that. Mold of what I thought you were supposed to do after college, or just get a job.

• 10:20Ryan Holiday?

  But I feel like a lot of creative people do that, right? They go like, okay, I need to go get a job to make some money and then I'll go do the thing I really care about. Uh, you're relatively, we don't all make it out alive, I guess what I'm saying.

• 10:37Speaker 01

  Well, yeah, a couple of things can happen. I mean, first of all, they steal your time, right? They, they give you this salary and it seems like you're going to be working a normal amount. And then the next thing you know, you're in there on the weekends and you're traveling last minute and you're, you're there all hours of the night. And some people just get used to eating three meals at the office and that's no good. Like, that's not fair. So, uh, and, and maybe you have to do that at some point in your career to kind of

• 11:03Speaker 01

  get the next promotion or whatever it is. I guess it depends on the culture of the place. But eventually you get to this place where you have a sort of an opposite problem where you don't really have to work that much and they're paying you a whole bunch of money. So it sort of dissuades you and discourages you from pursuing something a little riskier or more exciting. And I think it's sort of like gardening. Projects are concurrent. You try one thing and you're working on that and you, you keep a little space in your head to work on this other thing. So you're never, you're never invested in any one thing to the exclusion of all other endeavors. Uh, just mentally, right? You have a little break and you take it by working on this other thing that interests you. And some of them

• 11:44Speaker 01

  may be more interesting and some of them may be more profitable, but you sort of bounce around between them. This is just how I've approached it. It's just kind of bounce around between these different fun things to do and you stay creatively engaged that way. When I was at the agency and when I was in the agency world, I always had some other stuff going on, whether it was a writing project or something to do with optical illusions or recreational mathematics or magic tricks or comedy. And that just, I feel like being engaged in these different sorts of endeavors.

• 12:18Speaker 01

  Benefits all the others at the same time.

• 12:20Ryan Holiday?

  I, I think it's, it's a tension, right? It's like the starving artist thing is usually not the best way to do it. It doesn't create the best work. People think it's pure, but I'm not sure it does because you can't make, you can't make great creative decisions if you're worried about eating and you, you also don't have any leverage, you know, with publishers or a studio or whatever. If you, you know, you again, don't know where your next dollar is coming from, but then exactly what you said, there's the other side of it, which is you go and you pursue this thing that's supposed to fund or fuel or make the creative work possible. But then it gets so easy, you

• 12:59Ryan Holiday?

  get into a rhythm, sort of a velvet rut, as they call it, where, you know, it's, you're actually disincentivized to go do the hard, risky, creative thing, even though it's less risky to you because your life is so safe.

• 13:15Speaker 01

  It's not just the, the financial risk too. It's the ego risk. Some of these people wind up big muckety mucks at some agency or a design firm or some company somewhere and everybody respects their decision so deeply that nobody questions any of their, their creative impulses. But then if you want to try something new or do something out on your own or collaborate with a different group where you don't have those letters in front of your title, you gotta, you gotta check your ego, which some people can't do after a certain point in their career.

• 13:48Ryan Holiday?

  Yeah, I remember I was reading about Jeff Bezos when he had the idea for Amazon. He was talking to his boss at some like Wall Street firm or some consulting firm. The guy was like, that sounds like a great idea. And he's like, for somebody who doesn't already have a job. So there's also like the, it's not shame, but you have to be willing to, I think ego is a good word for it. We have to be willing to be like, I'm at this level here professionally, and then I have to be comfortable. I imagine when you went to go do comedy and stuff, you were lower on the totem pole than you were on Madison Avenue, right? And you have to be, you have to be comfortable being like lower status in a different world where you're.

• 14:30Ryan Holiday?

  Paying your dues, you know, cutting your chops, whatever. You have to be willing to be like, "Yeah, over here I'm great, but I'm a first time aspiring, you know,

• 14:42Ryan Holiday?

  open mic, you know, insert beginner phrase at this other thing."

• 14:48Speaker 01

  Yeah, that's exactly, that's exactly true. And when you don't have hobbies, I think hobbies are so important to people's mental health. Pastimes and hobbies, just things you do purely for joy that introduce you to different micro communities that have you interact with people that aren't involved in your work life directly because it helps you see yourself outside the identity of whatever your job title is.

• 15:16Ryan Holiday?

  Right. And get comfortable being mediocre as you get good at something.

• 15:24Speaker 01

  Right. And that's okay. You know, I think that's what's one of the great beauties of having a hobby is you don't have to be great at it just to enjoy it.

• 15:33Ryan Holiday?

  Yeah, that's right. I remember I was, because I was in advertising also, marketing and advertising, although in-house, not in an agency. And I remember I went to Adweek like three or four years in a row in New York City, which is sort of a made up, you know, thing that only people in advertising care about. But I remember I went once when I was like 21 and you know, I was like a kid and I'm sitting in this giant room. It was at like the Times Square Sheraton or something. And I'm, I was like one of the only people not in a suit. And then I went the next year and I was one of the only people not in a suit. And then I remember the third year, you know, so now I've done this

• 16:13Ryan Holiday?

  three years in a row. And I remember thinking, if I keep coming to this, I'm gonna be in a suit one day. Like, like the first couple of years, I was like, oh, I'm not the same as these people. I do this stuff on the side, right? Like they're lifers. Like I'm just riding this train. But... It made me realize like if I keep coming to this, I, everyone said that for a while, right? As you said, no one gets into advertising because they're deeply passionate about it. It's usually like you have the skills, but you'd probably rather be doing something else. And I just remember thinking like that if I kept coming, that I would be like them and that, that advertising or the thing you do for money, you can only do for so long before

• 16:56Ryan Holiday?

  it changes who you are. Did you feel that?

• 17:00Speaker 01

  Absolutely. And I kind of felt, I always kind of felt like I had one foot out the door just because I was doing these other things and I was trying to keep in perspective that even though I was on set in my twenties, like, you know, giving input on this huge production for McDonald's or Spiderman swinging in or Jeeps are crashing through the, like, it's easy to think, well, I must know what I'm talking about because

• 17:28Ryan Holiday?

  Sure.

• 17:29Speaker 01

  these people are listening to me, but it's really just a matter of happenstance. And, and it's really important to keep that perspective because otherwise you start to think you're some sort of creative genius just because you have this corporate gig and that can be detrimental to both your mental health and your creative output.

• 17:47Ryan Holiday?

  So you did Dragons Love Tacos while you were in advertising, but then at some point, because that's when I met you, but at some point you said, I'm going all in on this. Walk me through that decision and that sort of what that felt like.

• 18:00Speaker 01

  So my first gig out of college, besides like dressing up like an ear and handing out coupons outside of US Cellular Field was, um, was working at Lea Burnett in Chicago. And it was a great job. I was partnered up with a guy in his 50s named Jim, who taught me so much about the industry and just about the process. And I had some great mentors there that

• 18:24Speaker 01

  Really guided me through and my career in advertising would never have been what it was without that mentorship. But about a year in, I was talking to a friend who introduced me to this guy named Dan Salmieri. And Dan had just graduated from the Philadelphia Institute of the Arts. He wanted to illustrate picture books and his portfolio from his student work was incredible, but he didn't have an idea for a story. So I said, well, I've had this idea for a story for a while, and this is why my friend introduced us. We exchanged some of our work, like some of the ads I had done, some of the comedy sketches I had filmed and written, and we just really hit it off right away, just really shared a similar sensibility. So I wrote this story for him and he had some meetings set up with publishers on the

• 19:09Speaker 01

  strength of his portfolio from college. And just like that, we sold the book. And most people, that's not how they get into publishing and a lot of struggling authors hate that story, but it was really a case of just being in the right place at the right time. And that first book came out, it was called Those Darn Squirrels, came out in 2008, got Borders Regional Voices Award, it got this really great write-up in the New York Times, Pamela Paul was a big fan, and just it got all this attention and praise. So because of that, we got to do a couple more. We did three Those Darn Squirrels books. This is all while I was working in advertising. I would just like write the books in my kitchen at night. And they came out like once a year and then about, I guess after the third book came

• 19:53Speaker 01

  out, I came up with this idea called Dragons Love Tacos and I showed it to Dan, he loved it. But when we tried to sell it to Haun Mifflin, they were like, this is too silly. So Dan had an agent at the time and they shopped it around and Penguin wound up buying it. Now, they didn't, they weren't like, oh, this is gonna be a huge hit, this is gonna be a big seller. They just liked it and put it out. And the initial response was good, but it was, there was no way to know that it was gonna be this juggernaut. So it just kinda kept selling and kept selling and then just, it just caught on and people really liked it and they would buy it for their kids, their friends' kids, when they had kids, they would buy it for kids' birthday parties and like, that was 2012.

• 20:37Speaker 01

  It's 2021 now. It was on the bestseller list last week. It's insane.

• 20:43Ryan Holiday?

  Well, it's a classic. It's a perennial seller, as I would say.

• 20:49Speaker 01

  So that really opened a lot of doors, having a bestseller like that. And did a couple more books, Secret Pizza Party, which was very well received, and Robo Sauce, which was, I think it was a number one bestseller and high five. But after Robo Sauce, I think it hit number one. And that kind of like, at that point, I had, I don't know, three bestsellers or something. And I was kind of thinking, I should probably leave my day job. This is like a pretty smooth transition to step. I'm not risking anything financially or creatively. And it just felt like a natural transition to leave the advertising world. At that time, I was working at Firstborn. That's when you met me. And I don't know if we met before I left. And I was really happy with the job. I liked the people I worked with. I love collaborating with talented people.

• 21:35Speaker 01

  I actually like the thrill of the pitch and like the traveling and all that stuff. But it just opened up a lot of opportunities when I wasn't beholden to some corporate entity for my time each day.

• 21:49Ryan Holiday?

  No, it's funny how similar our journeys were because we met when we'd basically done one book at the same time. And then I also did three books while in sort of in corporate before I moved. And I just looked it up. We met through Michael Furdman at a Nets game. And it was a Nets game in January 2013. So this takes me way back. And I see the email that you're CC'd on. This is hilarious.

• 22:17Ryan Holiday?

  They played the Kings, which I was very excited about. I think that's why Michael picked the game for me.

• 22:24Speaker 01

  Oh, it was Furdman. It wasn't Dan. It was Furdman. It was Michael.

• 22:28Ryan Holiday?

  Right. Yeah, yeah. It was Michael Furdman.

• 22:30Speaker 01

  Right. Gosh.

• 22:30Ryan Holiday?

  Yeah. So but I experienced that too, where you sort of go, you started the book, then you kind of have these two things going on, which is cool. And then I remember it hitting me at some point where I was like, how many people would kill to have written, to be a writer, right? And I would have killed to be a writer. And then how many people would kill to like work in advertising or marketing? Like, much fewer, right? Like, I remember my dad, my dad told me something once. My dad was a police officer and he... He was sort of working his way up through the ranks and he was a detective and then he got promoted to sergeant and like he didn't like being a sergeant as much as he liked being a detective and he was telling me that he was like, he said something once, he was

• 23:13Ryan Holiday?

  like, Ryan, he's like, I realized like, they make movies about detectives, you know, like, like that, that one was like, much cooler for a reason, and yet he'd sort of like, like promoted himself out of the cool part of the job, right? And, and that, that stayed with me where it's like, I meet all these people in advertising, in marketing, in business, they all want to do books, and yet here I am, like, not committing fully to this thing that I have the opportunity to do. And that's, to me, that's when you take the leap, when you're like, the thing, your work is actually holding you back from the thing that you, that so few people get to do. It's almost insulting to continue

• 23:58Ryan Holiday?

  to moonlight.

• 24:01Speaker 01

  There's some, I don't know, there's something romantic about moonlighting, you know, isn't there about leading the double life and, and one has nothing to do with the other, and yet you get to play in both worlds at the same time. For me, I was like, I had, I, for a long time, I had three worlds going on because the comedy world has nothing to do with, and I'm talking specifically about like alt comedy, has nothing to do with the advertising world, or, I guess at some really high level it does, but for me, it was just, and then that kind of really needed to be separate from the picture book world because, you know, nobody wants to, no, no parent buying a book wants to hear me say fucker shit.

• 24:43Ryan Holiday?

  Well, what I think is funny about what you decided to do, I mean, all, all creative people hear this, like, people think they can just do what you do, right? Like, everyone thinks they can write a kids', or everyone thinks they can write a book, right? But like, everyone thinks they can write a children's book. So what I'm fascinated by, about what you do, is that it's something that looks very easy, but is actually quite hard to do at the level that you do it at.

• 25:13Speaker 01

  Uh, yeah, it's, here's what happens is people have different levels of I could do that, right? There's like, it's like, it's like watching UFC. You're like, no, I would have ducked under that punch, right? You know?

• 25:23Ryan Holiday?

  Yeah.

• 25:24Speaker 01

  It seems very simple to like, just avoid getting hit in the face when you're watching it on TV. And I think the same is true of writing a book, or even writing a song. And that kind of helps put it in perspective for people, because there are a lot of picture books, some written by very famous people, where it's like, it seems like they're just looking around their kitchen and being like, there is a refrigerator, there is a clock, there is a door, and then there's an accompanying picture, and that's the whole book. And there are plenty of books like that. I'm sure you have discovered that in your parenthood. But a really good picture book is like a song. And the music is, is the artwork, and the lyrics are the, are the writing, and it just works in this absolutely seamless

• 26:07Speaker 01

  way to create something catchy and moving, and that sticks with you and bears repetition, right? Very few books do people read 10 times.

• 26:17Ryan Holiday?

  Sure.

• 26:17Speaker 01

  And yet, a picture book must stand, a good picture book, or one that's not going to get thrown into the fireplace, must withstand repeated readings, like sometimes multiple times a day.

• 26:28Ryan Holiday?

  Well, there's a, there's a saying from the poet Herakles, that we never step in the same river twice. And I think that's what's interesting about this sort of insane target that you have to hit as a children's book author, but also as a, as a, as a writer of songs, which is, I think is an interesting analogy that you're making, which is like, how do you make something that not only can someone listen to more than one time, but how can you make something that has sustained relevance to them over a relatively long period of time? So like, a song you hear in high school, that still works when you hear it when you're 40 years old. But like, with a kid's book, it's like, I probably read Dragons Love Tacos to my son for the first time when he was a few months old.

• 27:12Ryan Holiday?

  And then we just read it a couple of weeks ago, or your High Five book, we keep it at this place we vacation to every once in a while. So we, it's like, we read it like in six-month intervals, right? And so-

• 27:26Ryan Holiday?

  I mean, for a kid, six months of aging is like, they're an entirely different person. But for the book to be both something familiar and new is a really extraordinarily difficult thing to achieve. You know what I mean?

• 27:42Speaker 01

  Sounds impossible to me. It sounds like an impossible task.

• 27:46Ryan Holiday?

  But somehow you did it.

• 27:47Speaker 01

  And sometimes you don't. Well, the real secret to my process is that I don't think about, I write the book for me. I write a book that I'm gonna like, that me and whoever I'm making the book with like. And I just trust that my sensibilities are appealing enough for a wide audience based on the past. But that's what I was doing in the beginning, too. I just didn't care. I had nothing to lose. I was like, oh, just write something I think is good. And then even if nobody else likes it, at least I'm happy with how it turned out. And the illustrator, too. And so now that I'm doing stuff that has way fewer illustrations,

• 28:29Speaker 01

  it's even more about like, what's bouncing around in my head? Like, you can, I could change the entire universe of this story with a couple of words, and it costs nothing, and it takes no time to make those sorts of changes. So how do you know when to stop? How do you know when it's the way it should be? And I think the only way to tell is when you like it. Of course, it's great to get feedback from other people and then people you respect and opinions that you respect. And sometimes you have to do, or, you know, it's advisable to do something that is maybe slightly against your first instincts, but you have to be happy with it in the end.

• 29:05Ryan Holiday?

  But so obviously, Stoicism is, let's say, a serious philosophy, right? Like, it's, it might not see, it might seem very humorless to people, although the irony is that, and he, he has earned himself a spot on the Wikipedia page for unusual deaths, which is quite, quite a funny page for anyone who hasn't looked at it. But Chrysippus, one of the earlier Stoics, who was a very serious guy, he actually dies as an old man. Over a joke that he makes about this donkey, this donkey walks into his yard and starts eating his figs. And we don't know the joke, but he basically makes this joke and then he starts laughing so hard at his own joke that he, he dies, which to me is a pretty

• 29:48Ryan Holiday?

  good, good way to go. But I'm interested in like,

• 29:51Speaker 01

  Definitely a good way to go.

• 29:52Ryan Holiday?

  When you're at first born, like, obviously you're a serious person. Like, not all your, all your commercials were funny or ridiculous or absurd. They were, you know, like, serious, right? Or, yeah, I'm not saying that, I'm just saying-

• 30:05Speaker 01

  I mean, there was, there was definitely, uh, some projects that were humorless, mostly for brands that were humorless, like American Express or something. They're, I mean, they were funny at some point, but-

• 30:18Ryan Holiday?

  I just mean, you're, you're thinking about it in the adult way of like, okay, we gotta do, the purpose of this commercial is to sell X, Y, or Z. It's not like, let's just, like, let's just do something that's entertaining to me, right? As you were saying with your book-

• 30:32Speaker 01

  That's true.

• 30:32Ryan Holiday?

  I, I'm curious about, like, how do you get to that, like, silly place? Because your books are silly and that's what makes them wonderful. And they're like, like, how do you just get to a, you're like, you know what I, I'm really, like, the itch I really have to scratch today is like dragons and tacos. Do you know what I mean? Like, talk to me about getting to that childlike space, because it seems like that's where your best work comes from.

• 30:59Speaker 01

  Yeah, I love silly things. I love play and wonder. Those are really strong threads in my life. I, I've designed a bunch of optical illusions and impossible objects that are basically sculptural astonishments, like objects that inspire wonder, that you go, what is this magic? What is this? And that magic is, well, you know, right? I, I was a teenage magician. I was doing, I was working at Dave and Buster's on the weekends. And you learn, when you learn magic tricks, you realize, like- Reality is subjective, right? For the person sitting on the other side of the table, something impossible just happened. And for me, I'm like, you know, carefully hiding something behind my hand so they can't see it.

• 31:43Speaker 01

  And as a kid, that was really valuable to me to, to understand because I was the kind of kid that always had this childlike instinct, even when I was like taking AP Calculus and stuff. I'm like, I just was always kind of thinking about silly things or playful things or things that wouldn't be considered appropriate for a serious sort of student. And you can have that kind of beaten out of you and a lot of people do. But somehow I, I kind of hang, hung on to it. And the way I really was able to embrace it and, and develop that sense of play was through improvisation. And it was a really, like a real passion of mine for many years.

• 32:28Speaker 01

  I studied, took a bunch of classes. I performed it on a herald team at, at the Improv Olympic in Chicago for many years. And then when I came to New York, I was teaching improv at the annoyance. And that is a funny, another funny little field, improvisation or comedic improv, just because people get into it because they're, they're excited by the idea of making stuff up and playing around. Like it's, it's, it's very childlike. You're in the backyard as a kid and you go, okay, I'm Batman. You're Superman. The ground is lava. We gotta get across using the swings or something. And you're just playing around and you're having fun. But it's one of those things where like, even though the whole enterprise and the whole architecture of the world is designed to encourage people to play,

• 33:11Speaker 01

  somehow it manages to beat it out of like 90% of the people that engage with this hobby. And by the end of it, they're like, they're not having fun anymore. They're, they're like really judging themselves and the people around them. And it sort of turns into this weird, joyless exercise where everybody on stage is supposed to be having fun, but they're not.

• 33:31Ryan Holiday?

  Well, that's what I love. I love that about Aesop's fables, like as serious as they are and as powerful as the lesson he is trying to impart, like clearly, like, he was a fucking weirdo to make, to teach the lesson, like, in the form of a, like, a talking fox trying to get grapes. Like, clearly, there was, like, a very powerful imagination going on and a sense of the absurd, as well as a strong, sort of, desire to teach.

• 34:04Speaker 01

  I think that that is a wonderful combination. And if you can just give yourself permission to be silly or to play and allow yourself to enjoy whatever weird things happen without judgment, like, that is a powerful ability. That's, that can be really, can, can give you a lot of potential for creative endeavors, just to be able to just give yourself permission to be stupid and silly and fuck around and not be weirded out by whatever happens. A book I'd recommend, if, for anyone that's interested in that sort of, for that sort of thinking, is, is called Improvise by Mick Napier. And he's the founder of the Annoyance

• 34:46Speaker 01

  Theater. And his book Improvise is great. It's got a bunch of exercises you can do just by yourself, for talk, basically talking to yourself, singing, or, or just kind of playing around, little, little mental games you can play with yourself. It also talks about theatrical improv, in a group, for groups to do as a performance. But it's, you can use it for all sorts of, for all sorts of things, to develop, really, anything you're working on, to just put yourself in this mindset where whatever happens is okay for this amount of time, anything goes, and then afterwards, we can look back and see if it was any good or not. But in the moment, you just, you just play.

• 35:28Ryan Holiday?

  I think one of the things kids have going for them is a lack of self-consciousness. And maybe that's

• 35:34Speaker 01

  Oh, absolutely.

• 35:35Ryan Holiday?

  where, what you're talking about. It's, it's not that people don't know how to play, it's that they're too self-conscious to do it in front of other people, or to do it on the page, or whatever.

• 35:45Speaker 01

  Yeah. That's why a lot of people turn to drugs, or alcohol, or these, like, hyper-specific contexts of board games, or karaoke, or something, to give themselves permission to have fun and not judge themselves, as you said, to not be self-conscious. But I see it

• 36:00Speaker 01

  Society basically convinces us we're not good at things because it compares us to all these people that are great at these things. And so then we say, oh, I'm not good at drawing, I'm not good at writing, I'm not good at singing, because look at them, they're so much better. I see it in, I see it visibly reflected in students at elementary schools. Every elementary school when I go and visit, they stuff the gym with every, every kid that's in the school. And they all sit, the kindergarteners in the front, then the first graders, and then in the very back of the auditorium is the sixth grader, the fifth grader, whatever's the oldest grade in that school. And I, I like to ask the kids, I say, who here likes to write? And the first row, every single hand goes up. And the second row, like, most of the hands go up.

• 36:42Speaker 01

  And then when, by the time you get to the back, to the sixth graders, it's maybe half. And then I say, who likes to draw? And in the front row, in the kindergarten, the first grade, every single hand goes up again. And in the back, by the sixth grader, it's like, very few hands are going up. Because even though drawing is super fun, and painting is like such a pleasing and, and enjoyable kinesthetic experience, somewhere along the line, someone told that kid they're no good at drawing, and now they've, they believe them. And so they don't do it anymore, and they maybe never will again. And that's a tragedy.

• 37:13Ryan Holiday?

  But what I would also say is, maybe they're actually not good, right? Bear with me. They're, they're not good, but that's actually part of it too, right? Like, one of the things that I-

• 37:24Speaker 01

  Because I don't say who's good at writing, I say who likes to write, who likes to draw? And that gets back to what we were talking about hobbies. It, it's like, it's, you got to give yourself permission to not be good at it.

• 37:34Ryan Holiday?

  But that's what I was gonna say about even the creative process, right? One of the best rules I heard for writing is like, just a couple crappy pages a day, right? So like, I think people think that writers, or, or any creators, make sort of perfect first drafts. And so like, you know what I mean? So it's not just like, everyone starts not being good, and you develop skills. But to go back to the idea of self-consciousness, part of it is also like- Understanding that, you know, Hemingway's quote about the first draft of everything is shit. I actually have a print of this on my wall. Like, you, you also have to be comfortable. And I think the better you get, the more comfortable you should get.

• 38:17Ryan Holiday?

  Although it can be hard because you're judging yourself against finished product. But can you get comfortable knowing like, yeah, this doesn't have to be good yet. I'm just figuring it out right now. And my identity isn't tied up in the fact that what I'm putting on the page or, you know, on the screen or whatever it is, that it's not perfect. Like, I'm okay being in process.

• 38:41Speaker 01

  Yeah, and I think that that's, that word process is the key. Because there's nothing writers like to talk about more than their own process. And I think the reason for that is because it's so hard to figure out. Some people just like have it figured out. They, maybe they figured it out at some point and like, this is what I do and they stick with it. For me, from my personal experience, it's kind of evolving as I go, as I take on new projects. But knowing what your own process is, and it's different for everyone, it really is. That is enormously helpful in helping you break through that wall of judgment, that wall of, that writer's block or whatever you choose to call it in that particular day, where you just cannot be productive.

• 39:25Speaker 01

  Like, knowing, okay, I'm going to spend three months on the first draft. I'm going to write the whole thing. Then I'm going to go back once, read the whole thing, fix as much as I can. Then the editor's gonna, gonna read it and give me their notes. And then it comes back and then I do it again. Knowing how the process works is such a relief.

• 39:43Ryan Holiday?

  Yes.

• 39:43Speaker 01

  And so helpful to, to giving you that motivation to keep going. I just finished a book of short stories. It's my second, it's second installment in this, in this series of short stories that I'm writing for, for young readers. And the first one took me like three years because I just didn't know what I was doing. And to be honest, I had to like kind of start over halfway through because I just I fucked the whole thing up. I didn't know what I was doing and and and I kind of did take that that, oh, let me just get the word count. I'm just gonna spit it out, just like get these words. And then when I went back and read everything, I was like, this doesn't make any sense, damn it. So I would highly recommend outlining if you're gonna do fiction or even nonfiction. I think outlining is really, really helpful. At least it was for

• 40:24Speaker 01

  me. But the second one, it took me a year. It was like much and I wasn't grumpy when I was approaching deadlines. And so I'm hoping that the third one is even easier.

• 40:35Ryan Holiday?

  Well, I'm in the middle of this right now because I'm doing a four book series. So I've done one book and I'm I'm about a third of the way through the second book. And and now I'm like on 10 or 11 books. So I have some experience. But I found as I started the book on my birthday on June 16, sitting down with my note cards to sort of find all the stuff. And and you know, the first like three, four weeks, it was not going well. And I was grumpy, as you said, and I was doubting and I wondered if I needed to push the deadline, if it was not going to happen. And then I found a note card that I'd written to myself like months earlier. And I was like, I said something like, when you go through this box of note cards in June, it will be very disorganized, but just keep

• 41:18Ryan Holiday?

  following the process and like, it will come together. Just trust that if you do the stuff, it will come together. And like, three days after I found this note card, it did it magically kind of came together. I've been churning it like

• 41:32Speaker 01

  Thanks, Ryan, from the past.

• 41:34Ryan Holiday?

  Yeah, my brain had been processing it and processing it. And I just couldn't figure out the combination. But I had all the ingredients and then it clicked. And I think as you do hard stuff, whether it's probably the first time you put together an ad campaign, the first time an investor, you know, takes a long position that takes three or four years or seven years or 10 years to pay off, first time you start a company, you know, first time you have a kid, you do a really hard thing, but you have to tell yourself that you're actually figuring out the process. So in the future, there's less uncertainty and you can shut you can kind of just trust that if you follow the steps, it will come together.

• 42:14Speaker 01

  I think about that a lot. I think about time travel because we're doing it right now. Right. We're moving forward.

• 42:19Ryan Holiday?

  Sure.

• 42:20Speaker 01

  The backwards part that's tricky, but I often think about how what I'm doing today. I often think about how what I'm doing today will benefit future Adam.

• 42:29Ryan Holiday?

  And sure.

• 42:30Speaker 01

  How I can make his life easier, you know, and how me screwing around one day when I'm supposed to be writing is going to make future Adam's life a little harder.

• 42:39Ryan Holiday?

  Yeah.

• 42:39Speaker 01

  So there is, there is this kind of bargaining you do and, and I am a master procrastinator. I, like, I have said in the past, I am a professional procrastinator with a writing hobby. Because I, I mean, I wrote a walking tour and produced and performed a walking tour in Brooklyn to avoid writing this book that I'm supposed to be working on, you know what I mean? Like, it's incredible how I'll be so deep into something all of a sudden and realize, wow, I'm doing this so I don't have to do this other thing. And it gets me back to that gardening metaphor where sometimes you, you feel like tending the roses and other times you feel like pruning the bushes or I don't know, I'm not a real

• 43:22Speaker 01

  good gardener, but I hopefully, those broad examples will hold, hold up. If anybody has any rose advice, I do have a bush I'm trying to, trying to keep it alive.

• 43:30Ryan Holiday?

  No, I, have you read, um, this is a book I recommend a lot, but have you read The War of Art by Steven Pressfield?

• 43:36Speaker 01

  No.

• 43:37Ryan Holiday?

  Oh, it's one of the best, but he calls it the resistance. So procrastination, doubt, imposter syndrome, you know, doing other stuff so you don't have to do this thing. He's, it's all about the resistance. We know what we want to do. We know what we need to do. We know what our calling is. But then resistance is what gets between us and that thing. He calls it the resistance, like capital T, capital R. And so I just think he, he's calling it the war of art because instead of the art of war, that it's like, that, that the creative process is the battle against this resistance. And

• 44:10Speaker 01

  Well, I actually, I think that doubt and procrastination are tricky, but I actually think that the imposter syndrome is kind of good.

• 44:18Ryan Holiday?

  Okay, explain.

• 44:20Speaker 01

  Well, if you ever meet somebody that's like, yeah, I did this, I'm great. Aren't I great?

• 44:24Ryan Holiday?

  That's ego.

• 44:25Speaker 01

  You don't want to hang out with that person.

• 44:26Ryan Holiday?

  No, that's ego.

• 44:26Speaker 01

  That sucks, you know. But, I mean, the people I know, and I have some friends that have reached pretty extraordinary levels of success creatively or financially or whatever, they, they look back at their past accomplishments, they go, and they have this kind of like, was that me? Or was it, the work kind of takes on this significance for people that you just can't ascribe to yourself personally, or you start to drive yourself insane.

• 44:52Ryan Holiday?

  Well, that's totally right. And, and, and he actually talks about this in the book. Stephen's a big believer in like the muses. And I think if this connects-

• 45:01Speaker 01

  In Spanish, they have duende.

• 45:04Ryan Holiday?

  Yes.

• 45:04Speaker 01

  It's like a flamenco thing.

• 45:06Ryan Holiday?

  But, but like in sports, like, you know, LeBron James just has this amazing game, so otherworldly experience. He's not like, yeah, I'm fucking LeBron James. He goes like, you know, all glory to God, right? Or he goes like, God was there, this is a team. I think all great people understand very quickly that if you're attributing the success to yourself, not only is it not true, but it's not conducive to future success because it contributes to ego. But I think every artist experiences this most profoundly because you're like, I just found this, I just read the audiobook for my Courageous Calling book, which is the one coming out in the fall. And I, like, there were passages, I was like, who wrote that? You know, like, where did that come from? And the answer is the muses, right?

• 45:50Ryan Holiday?

  Like, it wasn't me, somebody or something or some process gave that to me or created it through me. And if you think about it any other way, it makes you worse.

• 46:04Speaker 01

  Well, see, I kind of think of it like, we are sort of the subconscious result of all of human history. Sure. The people that came before us and all the work that came before us is kind of digested by us. And we're sort of like our ancestors dreaming. Whatever we make is kind of the same, whatever would have come out of

• 46:23Ryan Holiday?

  The shoulders of giants.

• 46:24Speaker 01

  Some synthesis of the things. Exactly, exactly. And conscious or not, like, everything we say and do is informed by the things we've experienced prior. And so much of that is great art that's been created by people that were in a similar position of, of taking in what they saw around them and, and processing it in some personal way and sharing it as much as they can. I think that it, it's a really a great privilege to be able to take what's in your head and share it with someone else. And, and they're not always going to get it exactly the, the way you intended it, or feel the same way that you did, or even maybe they take, they take something totally different from it that you never even imagined was in there.

• 47:07Speaker 01

  But it's still like deeply satisfying to be able to take what's inside of you and kind of bring it outside of yourself.

• 47:17Ryan Holiday?

  No, I think that's right. And, and I have a, a extra relationship with that writing about this ancient philosophy that I didn't come up with. Right? So like when people come and they go like, oh, your books changed my life. Or, oh, I read, you know, the obstacles away every day, or I've read, you know, the Daily Stoic for, you know, five years in a row. I don't want to say it's a defense mechanism, but one of the things I think is part of remaining well adjusted and also being able to create future work is, is when I hear that to go, sure, I played a small part in that, but primarily what's working is the, the reason they're having that reaction is because of the ideas which did not originate in me.

• 47:58Ryan Holiday?

  Right? My, I was a shepherd of them, or I portrayed them a certain way. I put the packaging together, but like, my book is a quotation or a series of quotations. And that we're all, I'm, I'm just, there's that expression like, uh, uh, new wine and old bottles or something like that. I, I sort of see it that way. It's like you're, you're, you're continuing a tradition as opposed to being like some pioneer or trailblazer, creative genius or something.

• 48:31Speaker 01

  That's interesting you say that because especially during the pandemic, when I was stuck inside, I got really interested in collective mythology, in these stories that stand the test of time and just keep getting repeated and repeated in different ways.

• 48:44Ryan Holiday?

  Like the Joseph Campbell stuff?

• 48:46Speaker 01

  Yeah, I was reading a lot of Joseph Campbell and Carl Jung, and there was even, there's this great book by a guy named Goodson, who, it's called Magic, A History, and it's not about theatrical magic at all, it's about what he calls the triple helix of religion, science, and magic, as he describes it, or as he defines it. It's a fascinating book, and it just talks about all these things that are kind of tied into what Jung talks about, these rituals and the idea of picking up rocks from an important place and keeping them or collecting them because they have some sort of emotional significance to people is something that has been found all over the world. So there's this, there's something inside of us as humans that like attracts us to certain kinds of stories and behaviors,

• 49:30Speaker 01

  and that to me is fascinating. The book that I wrote during that period was a classic hero's journey, just that big circle of going out into the world and discovering new things and changing and beating, you know, overcoming obstacles and then coming right back to where you started, a little bit different than when you began. And to me, it's really funny that you can kind of take that story and pull it, put it on to almost, almost anything, almost any epic adventure. Vonnegut has this famous lecture where he says there are six shapes of stories that there's, and if you think about this as like on an X Y axis,

• 50:11Speaker 01

  you got a line that goes from the bottom left to the top right, that's the rise, right? That's the rags to riches story. The opposite of that is the fall, that's like, you know, the descent of, you know. A tragedy, basically. Then you've got like a little hill, which is a sort of an Icarus story, right? You start at the bottom, you get too close to the sun, you fall back down to where you started again. And the opposite of that is like a rabbit in a hole is one way people have described it where you got to solve a problem. You know, you get into this position, you got to figure your way out, you get out of it, it's sort of like a diehard. That's how I like to think about it. And then there's the S ones. The S ones are fun because the S is a Cinderella story, which he says is the most popular story shape in the world, where you start at the bottom, you rise, you get, you rise

• 50:56Speaker 01

  to the top, you're at the ball, but then it strikes midnight, you're back down to the bottom again. The prince doesn't know who you are, but he's got that glass slipper and he finds you eventually and you live happily ever after and then goes back up again like a sideways S. And the inverse of that is like Twilight Zone or a Black Mirror kind of twist ending, where you start sort of, you start kind of at the top, you fall down into this hole, you think you've solved the problem and you go back up, but then uh-oh, like everybody's face is messed up, or you sit on your glasses and now you can't read any of those books and you wind up in a, in a, in a tragedy at the end.

• 51:31Ryan Holiday?

  Well, I, I think what's interesting about all of that, it ties into something, as we were sitting here, I pulled up my email and I guess this would have been in March or April of 2020, when I was working on my kid's book, The Boy Who Would Be King, I sent you like a really early draft of it and you gave me a bunch of amazing notes, but I was going through the notes and I, you were so nice, you sent me like a handful of them, or you, you looked at it a handful of times. But as I'm looking at what your notes are saying, I see two themes. One, you kept telling me to like simplify, just like pare it down. You're like, does this character even need to be in here? Right? Like, what about, you know, what is, you kept simplifying. And then the other thing you kept sort of looking at is like, what is the arc of the characters, right?

• 52:15Ryan Holiday?

  Like what, they're going from here to here and you, you sort of boiled The Boy Who Would Be King down to the central conflict of like the world and Julius Rusticus want Marcus Aurelius to be great and he wants to be a kid and that that's like the conflict, right? And so I, I was just thinking that, that yeah, the core, it boils down to like, what is the story and arc and is it really, really simple? Even if there's a lot built on top of it, it has to be very simple.

• 52:46Speaker 01

  I was doing these writing workshops during quarantine where I would meet with these kids like three times over the course of three weeks and we would talk, we would write a story. They would write a story. I would just kind of guide them along. And I learned a lot about my own process and just how to articulate certain things that I felt instinctively but wasn't sure how to intellectualize or explain. And I realized kind of halfway through it from talking to these kids that a really good place to start if you want to write a story is to have a char- is with a character that we like as a reader. They could be bad. They could be evil, but we repeat, they're appealing in some way. And we just, that whole story is them trying to get something

• 53:30Speaker 01

  they want. And that is a, is a pretty good place to start.

• 53:33Ryan Holiday?

  Right.

• 53:34Speaker 01

  Is a character we like trying to get something they want. And they don't even have to get it. We just, you know, like they don't even have to succeed in the end. It depends how you want to end the story. If you want it, which shape of that, which shape, which are those shapes? You want a tragedy or comedy or a twist ending or what? But that's a really a good place to start.

• 53:51Ryan Holiday?

  Yeah. Like what do these characters want? I feel like that's a pretty common artistic question, particularly in Hollywood or like on a TV show where you're like sketching out the arc of someone. It's like, what does this person want?

• 54:04Speaker 01

  Yeah. It's, it's a, it's a, it's an easy thing to articulate. And then when you sit down to write the character and write the story, you can often forget it. But they got it. They can't, they can't just want something. They got to try to get it in some way. It could be a small way.

• 54:22Ryan Holiday?

  I feel like actually it's not bad life advice too. Like when, whenever I talk to like authors or people who are doing stuff or asking me for career advice, the question I always ask is like, what does success look like to you? And I'm always amazed at like how rarely people have a good answer. Cause it's like, it's either stuff they've stolen from other people. They haven't thought about it. Or it's like 50 different things. And it can't be 50 different things. It has to be like, what are you, where are you trying to get? What do you want? Um, feels like a very clarifying question to me.

• 54:55Speaker 01

  What's your, what's, what's your definition of success?

• 54:59Ryan Holiday?

  Um, in a word, autonomy. I like to be in control of my life, not, not like control of every little thing. What I mean is like, I want to be deciding what I'm doing, when I'm doing it, how I'm doing it, as opposed to like, like, for instance, being a senator doesn't have any appeal to me because I know a handful of them. And I'm like, oh, your day is like mostly meetings and phone calls and a certain amount of fundraiser. Like you're, you have a lot of power, but also

• 55:31Speaker 01

  You're a civil servant.

• 55:32Ryan Holiday?

  The, yeah, the profession has a lot of power over you. What I like about being a writer is like, I own my life.

• 55:40Speaker 01

  Yeah. It's pretty incredible to be able to change the setting. I have friends that work in TV. And if they want there to be, you know, if they want a lion to walk out of a refrigerator, that's the second time I've represented a refrigerator, if you can't tell where I'm sitting right now.

• 55:57Ryan Holiday?

  Okay.

• 55:58Speaker 01

  If they want, if they want a lion to walk out of a refrigerator, there's all these meetings that have to be done. Props need to be built. A lion has to be casted, the animal trainer and the hours and all this stuff. But for me or for you, you just write it down. And then later you decide it's going to be hippopotamus, very easy to change. And that is like, that is, is pretty extreme power in that little universe that you've created.

• 56:22Ryan Holiday?

  Well, I would add something else to that. So my book Conspiracy, um, which is about Peter Thiel and Hulk Hogan and Gawker, it got optioned to be a movie and Charles Randolph, like one of the great screenwriters of our time, he wrote The Big Short and he wrote Bombshell. He like did a, an adaptation of my book. It's like incredible honor, surreal experience. Like they've cast like some really cool people in the movie, except for, that movie got optioned, or that, that That book got optioned in the summer of 2016, right?

• 56:55Speaker 01

  Right.

• 56:56Ryan Holiday?

  And it is 0% closer, as I understand it, to ever actually being real. I've written like five books since then. So the other thing is just also like, like as far as your emotional, you know, state, as far as your like rhythms as a person, as far as like what you like and how you operate, like also just understanding like where, what kind of system do you function well in? And so like I've mostly been resistant to sort of television or movie projects for that reason. It's like, I don't like not being able to make what I want into reality. I hate the idea of like, let's get on another conference call and then we'll talk about this and then six months later we'll talk again. And it's like, yes, so we're just starting to take action on what we talked about six months ago, right?

• 57:41Ryan Holiday?

  Like also just knowing like, what kind of creative environment do you, or what kind of environment period do you thrive in? And ideally not picking a profession that is the opposite of that environment. But a lot of people do.

• 57:53Speaker 01

  Yeah, yeah, they do, they do. Cause it's sexy and it's exciting and there's beautiful people involved. But it is hard, it is hard to do a project with so many people. That's why I think a lot of corporations become unwieldy because it's just hard to organize a large group of people. And so that's one of the reasons when you find a good collaborator, someone you share a sensibility with, that you can work with effectively and enjoyably, like you gotta hang on to them, you know? Do another project with them. That is so, so precious.

• 58:30Ryan Holiday?

  No, I think, I think that's great advice. And, and yeah, it's like, look, there are some people whose temperament is like, yeah, I can do one project every four years. Or, you know, like I can work on this project for 10 years. 70% of that being like pre-production work. And then there's other people who, like me, who that sounds like a specifically designed form of torture. But like, still, if somebody came and said, hey, Ryan, I want you to work on this film project. The ego part of you, or the attractive part of the money can, can, can suck you away from what you know is right. So like you, you have to have a certain amount of discipline too, to sort of like know what you're good at, know what you like,

• 59:15Ryan Holiday?

  know where you have the most autonomy and stick to it.

• 59:19Speaker 01

  Yeah, and I think that the the flip side of autonomy is responsibility, which is that if it sucks, there's no one to blame but yourself.

• 59:28Ryan Holiday?

  True, true.

• 59:30Speaker 01

  That may be part of the appeal for people that like to work in a group environment is that if it sucks, they're not going to get fired.

• 59:37Ryan Holiday?

  Yes, and that's true with publishers also, like, and that was something I was going to ask you, because like, so for instance, I was going back through this email chain where you're giving me advice. Now, I took some of the advice and some of the advice you had was was it was perfectly fine advice, but I knew it was not, it was the opposite of what I was trying to do. Like, for instance, you said, like, I gave you this long text and you're like, Ryan, the average children's book is 32 pages. This isn't possibly going to work, which was perfectly correct.

• 1:00:09Speaker 01

  Yeah, I'm sure I told you that some of my books are are over are around 50 pages. But if I remember correctly, that draft was somewhere closer to 70 pages.

• 1:00:19Ryan Holiday?

  Right. And the the finished book is like 115 pages. It's a different style of book. But the point is, and I think this is something that we should kick around. And this is why you have to know what you're trying to do. If you don't know what you're trying to do, like, if I was like, I'm just generally doing a kid's book, you your advice would have been helpful, or or I would have taken it because there's conventional wisdom behind you. But I had a strong sense of, in this specific instance, I want to do something that's not conventional. So I think, like, I remember Brian Koppelman has talked about this. He was saying that when they did the first, when they went out with the screenplay of Rounders, people were like, there's too much dialogue. They're like, this whole movie is just dialogue. And he was like,

• 1:01:03Speaker 01

  Right.

• 1:01:04Ryan Holiday?

  But that's, we want to make like, a movie that's just dialogue that people quote to their friends. He was like, that was very specifically what we wanted to try to do. So I guess what I'm saying is

• 1:01:13Speaker 01

  It helps. It really does help to have a vision.

• 1:01:16Ryan Holiday?

  Yes.

• 1:01:16Speaker 01

  Then you know. And and that goes back to what I was saying earlier about make shit that you like, because it's the it's the guiding star to know when you're making the right decision or not. Otherwise, you can get really confused because you get conflicting advice from different people, but people that you respect. And one tells you one thing, and the other tells you the other. And how do you know what to choose? Well, if you just do what you like, what you think is good, that's a good, a good way to to.

• 1:01:43Ryan Holiday?

  And you're getting advice from committees. I remember I went to my publisher with The Boy Who Would Be King and they, they talk about conflicting advice. You were like, Ryan, this has to be way shorter. This has to be like 30 pages or 50 pages or whatever. My publisher was like, we would love to turn this into a book, but we want it to be 10,000 words, which is 10 times longer than it was. Also, the opposite of what I was trying to do. So you have to know what your vision is.

• 1:02:09Speaker 01

  You have to know, you have to know. And, and you have to also consider your audience often. You can be pure and just be like, it's just for me. Truth be told, I don't do that. I think, okay, this is for kids. I can't say certain words, you know, and I need to explain things like if I'm going to reference insurance, I need to explain that in a way that a kid knows what it is because the average kid has no idea what the hell insurance is. And I want them to understand the story or the reference, unless I don't. There's certainly, there's certainly references in many of my books that aren't for the kids. They're for the parents that are reading them to get a laugh too. But the length thing is something that is brought up pretty often.

• 1:02:50Speaker 01

  I have some books like High Five, for example. I think it's like, I don't know, you would know better than me. You've read it more recently, but I think it's like 60 pages.

• 1:02:57Ryan Holiday?

  Yes.

• 1:02:58Speaker 01

  And I hear from parents, they're like, we love High Five, but it's too long. And I think about, I'm like, it's not, it's not like it's very, it's because they're reading it every night. And so when the kid is ready to go to bed, and I'm sure you can relate to this, the kid is ready to go to bed. They get to pick maybe one book, two books.

• 1:03:16Ryan Holiday?

  Right.

• 1:03:16Speaker 01

  And in that case, they want to, they want to be done with that, get out of that bed, have that kid go to bed. And in a more broad sense, it's hard to keep a kid's attention, especially if they can't read the words yet. They're going to be poring over those pictures and there has to be something to keep them engaged. Now that could be, and often is, just straight up the enthusiasm of the parents. If the parent loves biology, they could take the kid through Darwin's Origin of the Species. And a seven-year-old kid is going to be fascinated by that.

• 1:03:48Ryan Holiday?

  Sure.

• 1:03:48Speaker 01

  If the kid, if the parent decides they're not into The Stinky Cheese Man, one of the greatest picture books ever written, then, you know, the kid's not going to be into it either.

• 1:03:59Ryan Holiday?

  Well, what I think about the High Five book too, just to push back if anyone's not read it, it's not that it's too long. It's that's not a good bedtime book. That's a get your kids excited. You know what I mean? Like you're literally, they're supposed to be hitting the book as hard as they can, right? Like that's a, that's a, that's a, let's read this like, instead of watch TV book, right? So I think that is an important thing that a lot of people don't think about, not just with creative projects, but anything like an app or a company or whatever, is like, where does this fit in the life of the person making it? Like, so obviously, what is your vision? What are you making it? But like, what is the target that you're trying to hit? Not just as far as the audience, but

• 1:04:42Ryan Holiday?

  like, what is, what does this do? My editor said that to me once. She said, it's not what a book is, it's what a book does, right? Like, what does it do for the reader? And knowing that is really important, and people don't think enough about it.

• 1:04:55Speaker 01

  So that's what inspired me to write these short stories, these collections of short stories, because for the past 10 years, I've been the guy that stands up in front of the kids in the gymnasium and says, hey, reading is fun, and I can prove it, because I'm gonna read you this book I wrote, and we're gonna all gonna have a blast. You're gonna laugh, and it's gonna be great. But as the kids get older, I want to tell them the things you're, you're telling your audience, the things that we're talking about now, which is that writing is, is the best part of the whole thing. Like, to be able to take what's inside of you and share it with somebody else, to be able to express your inner world is, is a, is a kind of magic. And so, all these short stories, though I get to write

• 1:05:36Speaker 01

  whatever I want, what they, what do, what do they do is that, in my, in my hope, is that they inspire kids to try it themselves, to try writing their own story. And in that way, what the book does is directly connected to what the book is, but in a strange way, doesn't limit what the book can be or what the story is can be about.

• 1:06:04Ryan Holiday?

  All right. So I have two last questions for you. One, my wife told me that there is a weird QAnon story or conspiracy about one of your books. Do you know about this?

• 1:06:14Speaker 01

  Yeah, it's not just one of my books. I mean, it's just every, anything for kids. Like you could, if you do QAnon in any beloved children's entertainment, you will find, you'll go down a rabbit hole of just very strange conspiracies of people just basically entertaining themselves, I think. But, you know, you can find it for like, for SpongeBob and just any, any beloved children's entertainment was tainted by QAnon at some point or another.

• 1:06:44Ryan Holiday?

  And wasn't one of your books a little politically incorrect as, I forget which one it was, but I remember liking it. And then you telling me, like, I couldn't even conceive of how someone would not love it. But you were telling me something about that.

• 1:06:58Speaker 01

  Well, so I wrote a book in Spanish, or it's a bilingual book. It's simultaneously in English and Spanish. It's called El Chupacabra, and it was awarded the Texas Blue Bonded Award in 2020, which is voted by Texas public school students. Or maybe it's private and public, but either way, it's voted by the students of Texas. And it was like this huge honor. And I was so happy because when the book came out, even before it came out, there was some people on Twitter that were like, this book is racist. This guy can't be, look at him. He can't be writing a book in Spanish. And it hadn't even come out yet. You know, like, they hadn't read it. So it was just this weird, just internet vitriol. And people started piling on and like, making pictures of the book with an X through it. And the publisher got freaked

• 1:07:43Speaker 01

  out. So they like, made me put my grandmother, which is true, my grandmother grew up in Cuba, on the dust jacket of the book to like, try to assuage any, I was living in Spain when I wrote it. Like, it's just so, the whole thing was really, really weird. And I didn't want to offend anybody. They had a sensitivity reader, who somebody basically they hired to tell you what's racist in the book.

• 1:08:04Ryan Holiday?

  I've done that.

• 1:08:06Speaker 01

  Yeah, very rarely do they come back and they're like, well, you paid me all this money, but there's nothing racist.

• 1:08:10Ryan Holiday?

  Yeah.

• 1:08:11Speaker 01

  It's like, it's like humor, right? You can find it in almost anything, if you have the right mindset. But

• 1:08:18Speaker 01

  You know, we came back, we came through it and everybody was happy with the story. And it's incredible artwork. Uh, but when it came out, there was, there was no tour, there was no marketing, there was no nothing. And I had had many bestselling books before that, but it was just, they were, they were terrified that there would be a negative response. And so it just kind of went out totally under the radar. And so it was really vindicating when the students and teachers of Texas who have it, many of them are bilingual or speak both Spanish and English. They, they really responded to the book in a positive way. And that made me feel vindication.

• 1:08:55Ryan Holiday?

  No, no, it's, it's a great book and it goes to what we were talking about earlier, which is like, you gotta do it because you care about it and you have to have some ability to tune that stuff out.

• 1:09:05Speaker 01

  Yeah, and it, it really bummed me out. It really made me sad because I was trying to do the complete opposite thing, which is force English speakers to confront the second language. Because living in, in Spain taught me how unremarkable it is to be bilingual, trilingual, quadrilingual. Like, there are so many polyglots and they just treat it like it's, it's no big deal. Here in America, if you speak even a little bit of another language, it's like telling somebody you can do a standing backflip. It's, it's enormously impressive. Like, how did you even, how is that possible? But if we make it more accessible to kids from a young age and force Americans to confront the idea that the word that they're saying doesn't mean the exact same thing to everybody

• 1:09:50Speaker 01

  on the planet, I think it engenders empathy and, and that's really good for society and for, for civilization.

• 1:09:58Ryan Holiday?

  Well, last question, and this might be sensitive, so we can cut if you don't want to answer, but is, is it unusual that you're a children's book author who doesn't have kids? Are you, are you ever going to have kids? Is that, or are you just such a kid that you don't want to have kids?

• 1:10:12Speaker 01

  Yeah, I mean, there's plenty of people with kids that don't understand kids at all and can't relate to kids. And so I don't think having kids of your own is the, is the deciding factor of whether you can write for kids or relate to kids. I don't have kids.

• 1:10:34Speaker 01

  I may never have kids. I like kids. I don't necessarily... You know, the nice thing about not having kids and being a children's author is you get to see the best side of the kids. You don't get the temper tantrums.

• 1:10:47Ryan Holiday?

  You're like an aunt or an uncle.

• 1:10:49Speaker 01

  Exactly. I'm like the uncle that comes in. We have a great time. They start to get cranky or they crap in their pants. And I'm like, alright, see you later. I'm gonna go get a beer.

• 1:11:00Speaker 01

  And it's really the best of all sides for me.

• 1:11:03Ryan Holiday?

  I love that. That's funny. Well, dude, I'm so glad we're here talking 10 years after we met. And I can't wait for many more books. And my youngest is now right around the age of being able to discover your books for the first time, so...

• 1:11:20Speaker 01

  Well, that's so cool. And I want to tell... I mean, I gotta plug the new book, which comes out in October.

• 1:11:25Ryan Holiday?

  Yes.

• 1:11:26Speaker 01

  It's called Gladys the Magic Chicken. And I'm sure it's available from a particular bookstore in Texas, at least.

• 1:11:34Ryan Holiday?

  It will be, yes.

• 1:11:35Speaker 01

  I believe, in October. And it should be available from your local bookstore. And if you give them a ring or send them an email, I'm sure they'll be happy to preorder it for you. It is an epic adventure. It's an epic swords and sandals adventure where the hero is a dancing chicken that is totally oblivious to her status as a legend.

• 1:11:58Ryan Holiday?

  I love it. It sounds awesome. I can't wait. We have all your books at the Painted Portrait now, so we'll add it to the stack.

• 1:12:06Speaker 01

  Well, I really hope I get to travel around and see some faces in person and sign some books in October. But I'm not sure if it's gonna happen or not. I really would love to.

• 1:12:16Ryan Holiday?

  Alright, man. This was amazing.

• 1:12:18Speaker 01

  Thanks so much for having me. It's great to chat with you, as always. I always love putting life through the lens of the Stoics. It's always interesting and enlightening.

• 1:12:29Ryan Holiday?

  My newest book, Courage is Calling: Fortune Favors the Brave, is now available for preorder. We've got a bunch of amazing bonuses. You can get signed copies, of course. I'm so proud of this book. General Jim Mattis has called it "a superb handbook for crafting a purposeful life." Matthew McConaughey called it "an urgent call to arms to each and all of us." I do hope you check it out. It's my first in the Four Virtues series, courage, temperance, justice, wisdom. Courage is calling, fortune favors the brave. If you want to preorder it, I'd really appreciate your support. Go to dailystoic.com/preorder.