Ask Daily Stoic: Chris Guillebeau

In this super-sized edition of Ask Daily Stoic, Ryan talks about his visit to a mastermind event in Nashville, where he shared ideas and inspiration with other successful authors. Ryan also chats with Chris Guillebeau, author of The Art of Non-Conformity, The $100 Startup, and the upcoming book The Money Tree: A Story About Finding the Fortune in Your Own Backyard. This episode is brought to you by Go Macro. Go Macro is a family-owned maker of some of the finest protein bars around. They're vegan, non-GMO, and they come in a bunch of delicious flavors. Visit http://gomacro.com and use promo code STOIC for 30% off your order plus free shipping. This episode is also 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. Visit http://foursigmatic.com/stoic to get 15% off your order.***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: DailyStoic.com/signupFollow Ryan:Twitter: https://twitter.com/ryanholidayInstagram: https://www.instagram.com/ryanholiday/Facebook: http://facebook.com/ryanholidayYouTube: https://www.youtube.com/dailystoicSee 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.

• 0:05Ryan Holiday?

  Welcome to The Daily Stoic, where each day we read a short passage designed to help you cultivate the strength, insight, wisdom necessary for living a good life. Each one of these passages is based on the 2,000-year-old philosophy that has guided some of history's greatest men and women. For more, you can visit us at dailystoic.com.

• 0:30Speaker 01

  Hey, it's Ryan Holiday. Welcome to another Saturday episode of Daily Stoic. On Saturdays, we explore some stuff. And I just got off a plane yesterday. I landed. I was in Nashville for about a day and a half. Twice a year now, I do these masterminds with authors. Got invited to one a few years ago that James Clear put on. This is another one that James Clear was at. I won't say who's in the groups, somewhat private, but it's been this transformative and actually deeply beneficial experience for me. We fly to a place, usually a central location for everyone, and over a day or a couple

• 1:11Speaker 01

  days, a bunch of people who are in the same industry, but in some ways, you could argue, are competition with each other. We get down and we share ideas and approaches and best practices, and we ask each other questions about what's working and what's not working, and we give each other feedback. It's been this really interesting experience to watch as some of the authors in the group have gone on to sell literally millions and millions of books, to watch as other authors have struggled with stuff. One of the things that I love about being an author, that's a little bit different than I think other professions, is even that idea of competition is a little bit strange, because authors really aren't

• 1:53Speaker 01

  competing with each other. What we're really competing with is getting people to read. And so Seneca has this interesting thing where he talks about like, can you be as happy for other people's success as your own? And watching some of these authors sort of take off in the stratosphere, James being another one, is a sort of both inspiring and challenging thing. How do you, how do you actually do that? How do you, how can you, we did a Daily Stoic email not that long ago about not seeing the world as zero sum. And I think one of the best things I've learned and tried to do in my career is not see it as zero sum. Someone else's success is not come at the expense of my success, just as my success doesn't come at the expense of anyone else's. In fact, as a Stoic said, we're kind of all in this project.

• 2:38Speaker 01

  We're all just supposed to be fulfilling and realizing our potential. And this is what makes the whole project work. But really, why I think the masterminds have been so good for me is that often you get sort of trapped in your own ghetto. So you're, you're focusing on your problems. You're thinking about your stuff. You have, you know, your colleagues, you have your systems. And your own experiences are not diverse or wide enough to really teach you all that you need to know. And so to have a group of other people who are having their own unique experience, then opens you up to learning a whole bunch of things. I have that quote in Ego is the Enemy about how only a fool learns by experience. You want to learn from the experiences of others.

• 3:23Speaker 01

  Every time I go to one of these things, I come back with just like note cards or notepads or emails filled with a whole bunch of stuff that I wasn't even thinking about doing, that I then can apply to my, my own career. I remember I went, Tim Ferriss put on one of these many years ago, almost 10 years ago now. And I remember I spoke in it, but I remember when he put it on, it was $10,000. And I thought like, who, who could possibly, who could and who would pay $10,000 to attend an event like this? And, you know, looking back on that event, I mean, Not only did I meet people like my book agent and other people who ever, you know, done all sorts of business with, but I learned things at that event that I'm still applying

• 4:07Speaker 01

  today that are worth way more than $10,000. And so these two author groups that I'm in, they don't cost anything. We, each person pays, you know, their share of the expenses, but you know, I'm not sure what I would pay, but I would pay a lot of money for it. And so this idea of sort of always investing in and developing your education, building your network, putting yourself in rooms where you're not the most successful person, you're not the most informed person, where there's something for you to learn is really, really important. And it is a deeply stoic idea. Marcus Rilus was famous well into his philosophy career for still attending the lectures of Sextus, for still corresponding

• 4:49Speaker 01

  with his tutors and his teachers. Hadrian traveled the Roman Empire, stopping in at different philosophy classes, having, you know, dinners and meetings with different philosophers. Cato, every night would have dinner with philosophers. Cicero did the same thing. They wanted to be around wise people who made them better. Epictetus talks about how if you brush shoulders with someone covered in mud, you'll get dirty. And I think he's talking about bad influences, but I also think that the same logic holds true for good influences. You know, who are you surrounding yourself with? Who are you exposing yourself to? Who are you rubbing shoulders with? And how is that making you better? Going to these

• 5:31Speaker 01

  groups has been deeply educational for me. It's been humbling for me. It's been challenging for me. It's forced me to take my sort of solitary profession, which is sort of writing and these emails and these podcasts and the stuff we do is, is a little bit more solitary by its very nature. It's forced me to think about it more as sort of a cohort or as more of a team sport, or more as the sort of project that we're engaged in together. And so when I find something I really like, it's really been good for me, I want to share it. I want, you know, sort of pass that forward. And so I would urge people to set up something like this in their own career, find meetings like this or opportunities

• 6:14Speaker 01

  to engage with people who are doing the same work as you, people who you are aspiring to be like, people who you are aspiring to be like you are, and sort of engaging in this sort of learning process. Because I think it's just one of the single best things you can do with your time. And I think at the core of it is a deeply philosophical practice.

• 6:34Ryan Holiday?

  Hey, it's Ryan Holiday. Welcome to the Daily Stoic Podcast, the Saturday edition. I was recording the intro you just listened to about my trip to Nashville a couple of weeks ago. And I thought Chris Guillebeau, who's our guest today, was going to be able to fly out after. We're going to do a whole interview about it. We're going to sit in person. We're going to do YouTube. But as the Stoics say, life has a way of just sort of dashing our plans totally to pieces. So we had to make it work. And then on top of that, we had some technical difficulties in between, which we ended up having to record separately and then send each other the files. So if this sounds a little different,

• 7:14Ryan Holiday?

  that's why. But Chris Guillebeau is awesome, super nice guy. Two sort of connections between him and my work. He actually was one of the first and nicest people to blurb The Obstacle is the Way. And I think it had a big impact on the book. So I'm happy to talk about his work because he's been so good and nice to me. And then when I was writing Stillness, I was sort of workshopping some of the ideas. And he had me out to Portland for his World Domination Summit, where I workshopped some of the material. So you can actually see it, a talk of that, if you Google Ryan Holiday, World Domination Summit, you can see my talk there. And you can see how some of the ideas sort of connected into what became

• 7:56Ryan Holiday?

  Stillness is the key. And you can also see sort of some of the ideas that are actually in the in the sort of conclusion of that book, where I'm sort of wrestling with those ideas. All of that is there. And now, actually, there's a third thing. Chris and I have the same editor. Pappadopoulos at Portfolio edited Chris's new book, The Money Tree, A Story About Finding the Fortune in Your Own Backyard, which you can check out on Amazon, Audible, everywhere. Big fan of Chris's stuff. Not only is he a great person and a fan of Stoicism, but he's a great writer. And as we talk about in the interview, this book is interesting because it's sort of a fable. I guess he describes it sort of prescriptive fiction. It sort of teaches how to make the most of adversity

• 8:40Ryan Holiday?

  and then also how to how to sort of control one's own destiny or direct the course of their own life, both entrepreneurially, financially, sort of mindset wise. So Chris is awesome. I'm really glad I got to talk to him. You can listen to the interview now and then I will see you next week. Thanks for everything and I hope everyone is staying safe and most importantly, staying inside your house. Wherever you happen to be in the US or wherever you happen to be in the world, everyone can have a big impact on this pandemic by staying home, not going anywhere. That's why Chris is canceling his book tour, as we talked about, doing interviews. And that's why you, as much as you possibly can, stay inside. Don't see people, be safe and help flatten the curve as they're calling it.

• 9:24Ryan Holiday?

  So I hope you liked the interview. I'll talk to you soon. I'm going to read really fast the April 4th entry in The Daily Stoic. You can get this book on Audible. "Don't let this go to your head. Make sure you're not made emperor. Avoid that imperial stain. It can happen to you. So keep yourself simple, good, pure, saintly, plain, a friend of justice, God-fearing, gracious, affectionate, and strong for your proper work. Fight to remain the person that philosophy wished to make you. Revere the gods and look after each other. Life is short. The fruit of this life is good character and acts for the common good." That's Marcus Aurelius, Meditations 630.

• 10:09Ryan Holiday?

  "It's difficult to even conceive of what life must have been like for Marcus Aurelius. He wasn't born an emperor, nor did he obtain the position deliberately. It was simply thrust upon him. Nevertheless, he was suddenly the richest man in the world, head of the most powerful army on earth, ruling over the largest empire in history, considered a god amongst men. It's no wonder that he wrote little messages like this one to remind himself not to spin off the planet."

• 10:39Speaker 01

  Without them, he might have lost his sense of what was important, falling prey to the lies from all the people who needed things from him. And here we are, whatever we happen to be doing, at risk of spinning off ourselves. When we experience success, we must make sure that it doesn't change us, that we continue to maintain our character despite the temptation not to. Reason must lead the way, no matter what good fortune comes along. I just love this passage from Marcus Aurelius because, you know, we have that idea that absolute power corrupts absolutely, but Marcus is the exception to that. And how did he do it? You know, how did he pull it off? It's just, uh, it's really incredible. You know, his desire,

• 11:22Speaker 01

  as he said, to escape being made emperor, to escape imperialization, the stain of the purple quote. This was not an easy task. He worked at this, just like we have to work, not to let being a parent go to our heads, not to let being an influencer go to our heads, not to let, you know, being a millionaire go to our heads, not to let being, you know, named assistant manager of the McDonald's you work at go to your head. We can't let these things change us. We have to stay who we are. We have to stay good. We have to stay, as Marcus said, good, pure, saintly, plain, a friend of justice, God-fearing, gracious, affectionate, and strong for your proper work. We have to fight to remain the person

• 12:03Speaker 01

  that philosophy wishes us to be. So I hope you guys keep fighting. Thanks for listening. We'll talk soon.

• 12:10Ryan Holiday?

  Hey, Chris, how are you? I'm great, Ryan. How are you? I'm pretty good. I'm pretty good. So I was talking about this in the intro, um, because I recorded the intro a couple of weeks ago, right after we got back from Nashville. And I was talking about how, like, sort of why I like groups like the one we were just in. I guess you can call them sort of a mastermind, but it's like where, you know, a bunch of people get together and they share ideas, even though ostensibly they are competitors. They're, they're sharing and sort of we're all helping each other. But I don't think either of us thought that we would go home and not leave our houses for what's now almost a month. And they were announcing yesterday it might be a month longer. How are you doing?

• 12:54Speaker 02

  You know, that was such a strange, such strange timing, you know, fortuitous in some way, at least for our meeting. But then, of course, going back to that situation, I think I'm doing okay. I still don't know what to think about all of it. But I'm just trying to practice, you know, some of the principles you teach and thinking a lot about, you know, what's within my control, etc. And, you know, how can I spend this time productively? How can I, you know, make something, contribute something that's helpful? Since I can't do anything on the healthcare side of things, you know, all I can do is, you know, try to, try to be safe, keep other people safe. But then also like, okay, what can I make? And how can I find the opportunity in this time of uncertainty?

• 13:32Ryan Holiday?

  Well, that's what I was gonna ask you about, because we're gonna talk about The Money Tree, which is your new book. But first, I thought we could sort of go behind the curtain a little bit and talk about what it's like to put out a book when, you know, sort of weeks before you're about to do that, the entire world basically comes to a complete standstill. So, walk us through what happened. You had a very expensive book tour planned. You had dates all over the country. I'm sure you had tons of media planned. So what happened? And then, how are you, how are you thinking about that?

• 14:05Speaker 02

  Sure. Yeah, yeah. I mean, great timing there. I was hoping to do a 40-city book tour, had just about everything booked, at least probably the first 30 or so, you know, plane tickets, hotels, venues, you know, all that kind of stuff. And then, you know, as it, as it got closer and closer, it just kind of became apparent that the best case scenario would be to do it kind of piecemeal and like, okay, some events are canceled, but some continue, but there's going to be low attendance, etc. And so that didn't make sense. It just, it was just like, we need to just change the whole thing, basically. So I was sad about it, of course, because I really liked the tour. Like, I haven't done a pretty big one in a while, and was looking forward to going to meet readers and listeners. And I try to create a whole, like, community experience at all the events. But, you know, that's, you gotta

• 14:50Speaker 02

  work with what you got, basically. And, and so, after like, you know, like that same day that I started thinking about, you know, what else can I do? And how can I reframe this for myself? You know, what is it within my control? And the thing I started thinking about, you know, on that behind the scenes topic was, well, you know, the tour takes a lot of time. And, you know, if every event is like, three hours or so in the evening, Plus, you know, all the different transit and such, like checking in and out of a different hotel every night. Like even though I'm fairly efficient and I try to like work on the go, that's still a lot of time. What if I spent the same amount of time, you know, basically just, you know, connecting with people and doing live streaming? And otherwise, just doing whatever I can, you know, for the months of April and May. Because I really do want to get the message of this book out to people.

• 15:35Speaker 02

  And so that's how I've kind of reframed it. And, and I actually do see it as kind of an exciting opportunity in that way.

• 15:41Ryan Holiday?

  Yeah, it's, it's interesting. Like, I'm sure you thought about things that could go wrong for the tour. Like, we still have this idea of premeditatio malorum, you know, like sort of meditating on, on, on what can go wrong. And, and, and, and obviously, like, I, I think about that. I think, you know, I thought I had a, a whole bunch of, you know, I had, you know, probably $200,000 worth of, of business scheduled through the

• 16:05Speaker 02

  Yep.

• 16:05Ryan Holiday?

  rest of the year that, you know, evaporated or is, is, it's like every day I'm waking up to have news that more of it has gone away. And, and so I certainly thought about like a scenario in which some of that could happen. But what I think is interesting is that I had no conception that all of it could happen and other, you know, like, it's like we, we can, we plan for a worst case scenario, but, but life sort of humbles us with a worst case scenario that's even worse than the worst case scenario.

• 16:37Speaker 02

  Yeah, it's a worst case scenario times 10, you know, we, for, for WDS, also like World Domination Summit, the event that I, I produce every summer, which you were very, very kind to speak at either last year or the year before, I believe. For that, we always do a pre-mortem, basically a very similar kind of thing, like a month, month out. We're like, we kind of list, we, like, we get in a conference room and we list everything up on the board and such. And, you know, this is something that we just, I mean, nobody saw this coming. And if we ever think there's about of like a disaster or something, you think of it being local, right? You think of it like, okay, something really bad is going to happen in Portland or in Austin or wherever. But you don't think like the whole world, you know, is going to be on lockdown. So that's why it is, that's why it is, you know, both, both tragic and yet also, you know, whenever there's progress, there are always people that are harmed.

• 17:22Speaker 02

  So that the contrast has to be As well, whenever there's disruption, you know, there also has to be some way to to move forward positively.

• 17:29Ryan Holiday?

  Sure. Yeah, it's it's funny, too, because so Seneca, the one who has this idea of the premeditatio malorum, and we have this quote on the coin that we sell, he says, like, war, torture, shipwreck, like, all the, you know, he says, all the things that could happen should be like on your mind, right? And yet, what he never saw coming was like, basically being executed by the emperor. So like, even the guy writing this is still caught off guard by life. So I think that that's something I've been thinking about. I wonder if you've been thinking about it is like, also just being a little forgiving of myself, you know, like, when I look at my stock market portfolio, or when I look at, you know, decisions I made, I'm like,

• 18:09Ryan Holiday?

  how did I not? And it's like, oh, wait, okay, I saw I'm in a better position than most people because I made those decisions. I didn't have 100% of my eggs in one basket. But like, we still, and Seneca talks about this, too, he says, sort of, fortune acts as she pleases. In a way, we should be sort of humbled by this and go like, okay, even the best laid plans, you're still gonna get some of it wrong, and you've got to be okay with that.

• 18:39Speaker 02

  Right. Because there's no alternative. I mean, the old, normally in these situations, well, not these situations, but normally in any situation, your alternative is to try to fight it, which, you know, doesn't always work out so well. But in this case, like, there's really no no fighting you can do, like, you have to either accept it or just or just kind of be miserable and, you know, keep looking at the news every hour, which is only going to make you more unhappy and such. I think one thing that's interesting is that that we're all in this together. You know what I mean? Like, I think that that is what one thing that is is different. And it's not just like, my own stock portfolio crashed, or, you know, something, it's less like, everybody is kind of experiencing the same sort of things in different and unique ways, of course.

• 19:21Speaker 02

  But there are some commonalities there, and a lot of people that are seeking connection and community. And you've got a whole wave of people that are learning to work remotely that have never done so before, including some that I've heard from that are like, I've been asking my boss for years, you know, if I could work from home, and they've always said, no, right? Like, here's your chance, basically. So I think there's just a lot of shifting that's going to take place, and a lot of lot of a lot of changes coming out of it.

• 19:46Ryan Holiday?

  How have you, because I can imagine one sort of reaction to what you're going through would be sort of frustration, it would be anger, it might be resentment, or just like some depression about it, right? You're like, you've put in all this time, all this work, and then, you know, life just sort of dashed that to pieces. How are you, how are you sort of waking up, keeping yourself going, not, you know what I mean? Like, how are you not just saying fuck it? And how have you worked on that?

• 20:17Speaker 02

  You know, I don't know that it's so much working on this situation now. I think probably for the past two to three years, you know, I've been working on radical acceptance and doing some exposure therapy and just like learning to accept things the way they are, not the way I want them to be. And that has been, that's a scary process, I think, but once you do it, you realize it's actually much better to do it that way than to just, as I said, fight, you know, fight reality, wish that things were different, etc. So I think a lot of it is kind of in the work that I've done leading up to this. And, you know, since there isn't anything we can do about it, for me, like I said, I've been trying to focus on the reframing and, okay, I can't do this, so therefore there's something else. And I think that's probably true for most people. Like, some people might have

• 21:00Speaker 02

  a hard time applying it in the same way. Like, if you're not doing like digital work, if you don't have something like a message you're trying to get out or something. But there has to be some way to flip it. There has to be some way to reframe, or maybe even just lead you into something totally different. And if you don't find that, then I think, or if you don't search for that, let's say, it's not about the finding, it's the searching. If you don't actively search for that, then I think that is a, that's a process that leads to depression.

• 21:25Ryan Holiday?

  Well, I wondered, because you and I have run a couple of times, and I know, I know you're a long distance runner, and I saw that thing you posted on Instagram the other day where you'd sort of, you'd worked out basically every day for 365 days in a row.

• 21:36Speaker 02

  Yeah.

• 21:37Ryan Holiday?

  I wondered, part of what running teaches you and the active practice of it, and I think why there is this kind of connection between Stoicism and athletics and running and working out, and philosophy, is that it is training the mind for the other kinds of adversity we find ourselves in, which is like, this This might suck for a month, this might suck for six months, it might suck for six years. But really, the only solution is just like you keep pushing.

• 22:04Speaker 02

  Uh huh. Yeah, I think the endurance factor is is key. I in in December and January, I did a like a running program that ended up being like more miles than I've ever done. It was really good for me. It was like a challenge, but really good. And so I've been off that since then, like I'm still running, but just not as much. And what I noticed was I was worried partly about being bored by running so much. And I kind of got into it after a while and like it was this like long meditative thing. But what's interesting is like coming off it like in the February, March and since it's like. Now I go out to run like three or four miles and and I'm bored. I'm like, is this almost over? And I'm like, wow, you you lose that if you don't actually, you know, keep that practice of endurance.

• 22:46Speaker 02

  It actually goes away. Like, you know, you know, your fitness level is is the thing you have to maintain. But I don't think I realized that this mental part of it was also something that has to be practiced. Or at least has to be experienced on a regular basis. Or else you go back to that that place of kind of pushing or resisting.

• 23:04Ryan Holiday?

  Yeah, and I think that's like an important thing for I I posted something like this on in Daily Stoke Life, which is our member thing. I was like, you know, this is what we train for, like this is the whole point of the philosophy is. When when things go upside down and and and so I feel like that's that's sort of what you're going through more specifically with this launch. But also just what everyone is going through. It's like, uh, this is what living through history is like. Like, it's not always fun and sometimes it's terrifying and sometimes it really sucks.

• 23:35Speaker 02

  The thing is, everyone's going to be able to look back, you know, whenever this is over, as you said, whatever the timing is. And everyone's going to remember it and everyone's going to remember what they did during this time. And I think they're going to have some sharp memories, like a very clear, you know, you have these, you know, different, different things throughout your life. And so some of those memories are obviously influenced by the external events. And for me, my for me, the question is, okay, again, what is within my control? What are the memories that I want to have that I actually create? And I want to be able to look back and just. I mean, obviously, this is just me, but like, I want to look back and say, I had this project I was really excited about. And I had to change all the plans, you know, two weeks out, essentially. But I'm really happy with with what I did.

• 24:18Speaker 02

  And I'm really happy with how I how I made that shift. And it's not so much like what the outcome is. It's not like, oh, and then that that led to it being a huge success or not. It's, you know, was I able to do that? And did I do did I do that to the best of my ability? So I think there's something there that everybody can can apply in their own way. You know, you're going to have those sharp memories just very clear of this time. What are the ones that you want to have?

• 24:41Ryan Holiday?

  No, I think I think that's right. And and one of the reasons I'm, I think I sent this to you, but I'm not that concerned with how The Money Tree is going to be affected by this, which is your new book. It is because I like, and this is one of the things we want to do philosophically is zoom out a little bit. Right? So I remember when I was writing Perennial Seller, Robert Greene was talking to me about how his book, The Art of Seduction, came out like the week after nine 11, you know, and has sold a, let's call it a million copies. Neil Strauss was telling me The Game came out. And he had like the best week of media planned that he'd ever gotten in his career. And then Hurricane Katrina hit. And and there's a Michael Lewis book that came out like right after the tech bubble burst.

• 25:26Ryan Holiday?

  Like, the the reality is like, when you, when you zoom out, you go, oh, hey, I actually don't remember what was happening in the world when most of my favorite books came out. Nobody remembers, you know, where the Great Gatsby hit on the bestseller list. Or in your case, your books are this really interesting fable. You know, I don't even know what year Who Moved My Cheese came out? Or what year The Energy Bus came out? Or, you know, Rich Dad, Poor Dad? They may well have come out in worse, worse periods than this one as far as publishing goes. I think what matters is, as you said, like, do you keep going? Like, do you let that thing determine? Actually, what you could do right now is give up on the book.

• 26:10Ryan Holiday?

  And that would have a large impact on whether it sells or not. Or you could decide, hey, this is going to be sort of a blip on a longer, you know, a longer radar. And and that's weirdly kind of a similar response to how we should be thinking about things like a stock market portfolio, which is that when you zoom out, what matters is the upward trajectory, not what it's doing week to week.

• 26:34Speaker 02

  Right. And what matters is your commitment, like your strategy. Are you in it for the long term? Or are you trying to time it? And I think, you know, I learned a long time ago, like in business and book publishing and whatever else, trying to time things is usually a mistake. You know, like you might get it right once in a while and then you think you're a genius, but the next time you're going to get it wrong. And it's much better to just, you know, the perennial seller is a model that I try to follow. And I want to make something that is going to be helpful to people in a, you know, just a very real emotional and practical way for years to come. So that's the goal, anyway.

• 27:10Ryan Holiday?

  But I do think what's interesting is, as you said, just when things go, uh, go great, some people are doing poorly. And when things go poorly, some people are doing great. Well, the irony here in a cosmic sense is that as much as this book is affected by the short-term shift in what's happening, I gotta feel like there is going to be a rush of people to whom the hundred-dollar startup, the side hustle stuff you've written about in your Side Hustle podcast, both of those things both become, are now almost perfectly timed for where people are, which is stuck in their house, trying to figure out how to use this time, you know, suddenly strapped for resources and trying to make ends meet.

• 27:54Ryan Holiday?

  I think that's the other benefit of having a diverse, you know, sort of portfolio of projects and a portfolio of skills is that you're, when one goes up, the other might go down and vice versa.

• 28:08Speaker 02

  Yeah, I mean, that's, that's my hope as well. And there's a lot of people out there, as you said, that are, you know, navigating difficult decisions, you know, trying to figure out how they can make extra money or trying to figure out how they can make any money at all, you know, for those who are out of work. So, I mean, I certainly want to do whatever I can to support them. And I haven't had the experience of being unemployed. I've never actually really been employed. Like, I've always worked for myself, you know, for better or worse, right? It's not that that's like something to be proud of, but. I do know something about this. I do know something about navigating the sense of creating an income generating project for the first time. And how do you do that on a really practical level without going into debt and by using a skill you already have. And so, you know, the more, the more people that can hear about that, then the better.

• 28:53Ryan Holiday?

  Well, so let's talk about the new book briefly, because this podcast is short like yours. We're not doing a Joe Rogan thing here, but I love a couple of things about this book. One, it's a radically different book than all your other ones. This is fiction, or I guess it's more of a fable or a parable. I love that you challenged yourself as a writer by doing a dramatically different book. Like, I think that people don't do that enough. The other thing I really like about it is that it's a fable and a story, because I think that's often the best way to teach. Like, I think there's a reason that Jesus speaks in parables. I think that most, that there's a reason that Aesop's fables remain true. I think there's a reason that some

• 29:35Ryan Holiday?

  of the other books we're talking about, whether it's John Gordon's stuff, or, or some of the other, a bunch of the bestselling business books of all time are not, here's how to do this. It's, let me impart to you a philosophy through story. So, so why, why did you decide to do that? And then maybe let's, let's sort of talk through the broad strokes of the story and what it offers people.

• 29:58Speaker 02

  Yeah, I think it, it's something that was on my mind for a while. And it was one of those things where, like, I have this belief about, you know, wild ideas or crazy ideas, in the sense that, like, all of us have all sorts of random ideas all the time. And sometimes you have bad ideas. Like, there is such a thing as a bad idea, right? But if you have this idea that keeps coming up, like, over and over, then there is something to it. You know, like, there's some, some reason why that that is there. And, and so, in my case, I kept thinking about, you know, just, just this idea of a story. And I just had the broad, broad strokes of it. And I had never written fiction before, so I didn't know a whole lot about plotting and character development and, and all of that. And so I did some reading and I started outlining, I worked on it for maybe three months of just like outlining, maybe like 30 minutes a day, and

• 30:42Speaker 02

  just thinking through different scenes and such. And then I, Wrote the whole book, or at least the first couple of drafts without, you know, saying anything about it to anybody, to my agent or my editor or anything. Just because I wanted to see if I could do it, you know, to see if I could do something that I actually was proud of. Which is different, as you know, for nonfiction publishing. We usually write like a pitch or proposal essentially, and then you sell the book and you go and write the book. But I wanted to do that. So it's something that, I don't want to say it just came to me because there was a lot of work involved with it. But as, since I knew what I wanted to do after that period of outlying, then it was relatively easy because it was just like, okay, I know what I want to communicate. Then it's a question now of how to communicate it. And I wanted to try to make it, like, it is technically a fable in the sense that it's prescriptive fiction,

• 31:27Speaker 02

  I guess you could call it, but I really wanted to just be a story. Like, I want people to actually read it who don't even care about entrepreneurship. And they can enjoy the story and how the character overcomes obstacles and such, and hopefully go away having learned something, but without necessarily thinking about it all the time. You know, like, I don't have, like, at the end of each chapter, like, hey, here are the three things I told you in the chapter, and I'm gonna tell you them three more times just to make sure you got it. You know, like, the idea is to actually be an engaging story throughout.

• 31:55Ryan Holiday?

  Yeah, it has to be, it has to be subtle. And I think that that's the, that, for instance, that's the genius of something like Aesop's Fables, is that to a kid, these are just weird stories about foxes and bears and lions. And it's only afterwards that you realize, oh, these are teaching lessons. And then those lessons sort of stick in your head in a weird way.

• 32:17Speaker 02

  Yep.

• 32:18Ryan Holiday?

  Like, I've got a three-year-old right now, and we're sort of just going through a lot of those fables. And it's like, he, he wants to talk, for instance, about the fox with no tail. He has no idea what this story is about, but he, the idea of a, so I think, I think that's, that's, it's, it's an interesting medium, and I imagine a very challenging one, given that in your other books, you could just say what you thought. You didn't have to subsume it into events or into what, you know, a character was, you could just be you as Chris saying, here's what I think.

• 32:52Speaker 02

  I think there are a lot of different directions you can go with it. This is something that my agent talked to me about. Once I was in the midst of it, he's like, with fiction, there are so many different ways you could do the same thing. Like, you have a goal, there's a lot of different ways to accomplish it. Whereas with nonfiction, it's a lot more straightforward. I mean, it's not that there's no creativity in writing a how-to book, because there is, but there is kind of a path that you follow when you're writing the nonfiction. And with fiction, you can go this direction, you can go this one. So there's a lot more choice involved. And there's not one necessarily right way to do it. But hopefully, when you actually do it, then you come to one way that is right. You know, one way that is right, a good way that is right, something that you feel kind of wraps things up in a believable way

• 33:36Speaker 02

  and just leaves the reader feeling something. I think that's always the goal. It's like, I want the reader to feel something after having read the book or even part of the book.

• 33:44Ryan Holiday?

  Yeah, I'm curious too, as someone who has taken risks in your career, and I think this one was probably a risk, or it felt like a risk.

• 33:52Speaker 02

  Sure.

• 33:53Ryan Holiday?

  There's sort of this tension, right? Like, it's crazy to think that you could write a book, and both of us at one point or another had not done a book before. So when we decided that we... There's like, kind of an insanity, but there's also, like, if it really is insane, like, there's some ego, I guess, in saying like, "I can write a novel," or "I can write a story," or "I can write a book." And yet, because you've never done it before, but yet, if there's too much ego, or if you truly are doing it out of ego, you won't do what you were talking about doing with this book, which is painstakingly go through the drafts, take advice. You know, sort of like, it's almost like you have to ignore the call several times,

• 34:38Ryan Holiday?

  and then only when it's persistent, really listen and then do it right. I'm just sort of curious, how did you walk yourself through this process, which must have been scary, and your compass must have been a little screwed up? Like, how did you get to the finished book?

• 34:54Speaker 02

  Well, Ryan, it was, part of it was scary, but a lot of it was exciting. A lot of it was fun, I have to say.

• 34:58Ryan Holiday?

  Okay.

• 34:59Speaker 02

  Once I, once I kind of knew more or less what I was doing, and then it was about the development of it and such, I actually really looked forward to, to working on it. Now, I will say as well, like you're correct about the editing and the drafts and such. I mean, that's where the majority of the work is, right? So for this book, I think I did six or seven full drafts, which I don't normally do. Normally I'm like three or four, maybe. And I did have, you know, have various critique I took from my agent and from my editors, the same as your editor now. And, but it was fun. I don't know, I really enjoyed it. So it was like, it was scary, but also exciting. And I think that's the combination you need to look for in a creative project. You know, you want, you need to be intimidated by something in a good way, in a way that like, whoa, that's, that's big. You know, whatever that is for you.

• 35:44Speaker 02

  But it's the kind of thing that you're drawn to. And you can imagine, okay, if I can get over the, whatever is holding me back from this, you know, whether it's fear ego or something else, and if I can actually dive into it, you know, how will it feel to come to the other side? Or even how will, how will it feel to immerse myself in it? And I'm really glad I did. It is a risk, like you said, it's a creative risk in some ways, a business risk. But honestly, I can say truly, like apart from whatever the outcome is, you know, if it, if it sells a lot of copies, that's wonderful. If it doesn't, you know, I'll be disappointed in that, but I'm still glad that I've done it. Like I'm still proud of the, of the work itself.

• 36:18Ryan Holiday?

  Sure. Right. And, and that is, to me, the most, the, the thing the Stoics can teach us most about projects is like, all we controlled is what went in it and the, the joy of it and the work of it and the challenge of it. And then we have to somewhat detach from the results for precisely the, the situation that, that you're in right now, which is that a global pandemic can melt down society like days before it comes out. And you, you have to be able to, to sort of go, hey, I've, I've won most of what there is to win on this project. By nature, the fact that like it physically exists. And then the, how many copies it sells, how many people it reaches, the impact that it has.

• 37:03Ryan Holiday?

  It's not that that doesn't matter, but it can't be everything because it is the part you control the least.

• 37:09Speaker 02

  Yeah, and I have to say that I've come a long way in this. Like, I just want to be clear that I wasn't, I didn't always have this perspective. I mean, there are things that you know intellectually and then, but you don't have the emotional connection with it. And so probably, you know, from my first book, I was saying things like, oh, it doesn't matter, you know, what happens, et cetera. But I was, I was actually really attached, you know, to the outcome, you know, I really was attached. I mean, there's like, I think it was like my third book that, you know, for whatever reason, I really was like, I want this to be, you know, a bestseller and bigger than the last one. And it wasn't, and I felt just really, really disappointed. And that was a good lesson for me, basically, in going forward and like, well, you know, there are lots of elements that you can't control.

• 37:47Speaker 02

  And, and was I proud of the book as a book itself? Or was I just proud of the book as like, this is my marketing tool to help me achieve this goal of my platform? Or, you know, something else that is really disconnected from the creative process. So it's something that I've had to, to evolve in.

• 38:02Ryan Holiday?

  Yeah, I think from my first book, I was saying the same things and I was probably 10% focused on the process, 90% on the results. And, and I'd like to think I got to a place on stillness where that's closer to being reversed. I'm not sure it totally is there. And, and I'm not sure from a business perspective, how close you actually want to get. Like, do you want to be like, you know, you can't be completely indifferent to the results because that you won't get to publish anymore if you don't. But you want to get closer. So, so to wrap up, walk us through why this book was so important and to you to do. And what do you feel like, what, what are you hoping to teach people through it? Or I guess, what can people learn?

• 38:47Ryan Holiday?

  And, and why is that? To me, it seems like a message well suited. The subtitle is a story about finding the fortune in your own backyard, given that a lot of people can't do anything but look around their own backyard right now. You know, sort of, why should they, why should they pick up this book?

• 39:06Speaker 02

  Yeah, I should have like a different addition, Finding the Fortune in Your Studio Apartment, you know, for New York or whatever.

• 39:12Ryan Holiday?

  Totally.

• 39:14Speaker 02

  So I started with the character. I started with like this, this idea in my mind of this guy named Jake and he's a millennial and he has a good job, but even though he has a good job, he also has a lot of debt. He has a lot of student loan debt, which of course is very common. And these debt payments are starting to come due and it really affects, you know, every part of his life. It affects his professional life. It affects his relationship. And he realizes that, you know, to get out of this problem, he can't just work harder. You know, he's already got the, you know, good or decent job.

• 39:44Ryan Holiday?

  Sure.

• 39:45Speaker 02

  He, he can't just, you know, drive for Uber and Lyft. Like, that's not really going to help. And so, you know, at first he's feeling kind of, kind of down about it. And he ends up going to this group called The Third Way, which consists of people who are creating these, you know, new income streams and side hustles and so on. And they're all doing it on a budget without going into debt. And so he kind of meets a figure there who, you know, ends up talking with him, giving him a challenge to make a thousand dollars in the next week. And at first he's like, well, how do I do that? If I knew how to do that, I wouldn't be in this problem. You know, but he, you know, kind of figures it out from there. And then, you know, essentially the, the book is his journey of, you know, how do I go from this situation of despair to one of hope? And, you know, inevitably it's, it's filled with, you know, setbacks and advances and, and all that kind of stuff.

• 40:30Speaker 02

  But my hope is that a reader can, can identify, you know, with, with him and other characters in the book. There's also like a whole second thread, a whole second story within the book about like a ridiculous startup. And so I'm trying to contrast like different business models. Like here is a model of a, of a startup that has a lot of investor money. And here is Jake who doesn't have any money, doesn't have investors, but he's, you know, just kind of scrappily moving forward and trying to figure something out for himself. So my hope is that readers will be like, you know, I can do that too. Or if he was able to do that, then maybe there's something I can do. And here's the idea that I'm going to take based on, you know, this particular chapter or scene or experience.

• 41:10Ryan Holiday?

  I love it. Well, um, so for, for people who like Chris's stuff, I strongly recommend the new book, The Money Tree, but I also love Side Hustle, The $100 Startup, The Happiness of Pursuit, Born for This, The Art of Nonconformity. So how many books have you done? Is this seven?

• 41:27Speaker 02

  Yeah, this is number seven. So I was gonna say, I'm trying to catch up to you, but that'll probably never happen.

• 41:33Ryan Holiday?

  Yeah, I actually have, sometimes people ask me and I have trouble. I have to like count exactly how many have been released versus how many are done. But, but no, you have quite, you have quite a catalog. And then every, for people who listen to this, who like daily podcasts, who listen to everything every day, you have Side Hustle School, which is a daily podcast about a lot of the same themes in the book, which is basically like, how do you sort of control your own destiny? How do you start small, build something and, and sort of create that autonomy? You don't have to, you don't have to raise hundreds of millions of venture capital and start the next Facebook to be an entrepreneur. There are plenty of people who are doing this on a, a sort of a small scale and you

• 42:15Ryan Holiday?

  can grow and build something and then, and get closer to the life you want.

• 42:20Speaker 02

  Yeah, small but meaningful, you know, small but meaningful. Not everything has to scale. You know, the Side Hustle School podcast, as you said, it's like this daily, daily case study model where for three years, I'm now doing question and answer with it, but for the first three years, every day it was a different story, different story of somebody out there. And this is like a true story. So somebody who has a job, lots of responsibilities, but finds a way, you know, to create this additional source of income. So just kind of deconstructing it and like, how do they do it? And what went wrong and what worked? And how did it affect their life in the end?

• 42:49Ryan Holiday?

  Well, awesome. It was, it was a pleasure to chat. I wish we could have done it in person. We'll do it in person when you finally do get your book tour back on track and I'll see you soon.

• 42:59Speaker 02

  Thank you. I look forward to it. Cheers, man.

• 43:01Ryan Holiday?

  All right, thanks, man. Don't forget to subscribe to this podcast on iTunes or your favorite podcast app. And if you don't get the Daily Stoic email, go to dailystoic.com/email.