AJ Jacobs on the Enduring Power of Puzzles and Memento Mori

Ryan talks to A. J. Jacobs about his new book The Puzzler: One Man's Quest to Solve the Most Baffling Puzzles Ever, from Crosswords to Jigsaws to the Meaning of Life, the enduring power of puzzles, the Stoic concept of Memento Mori, and more. A. J. Jacobs is an American journalist, author, and lecturer best known for writing about his lifestyle experiments. He is a self-proclaimed “human guinea pig” and avid nightly crossworder. He has written four New York Times bestsellers that combine memoir, science, humor and a dash of self-help. AJ is also editor at large at Esquire magazine, a commentator on NPR and a columnist for Mental Floss magazine. His first book is called The Know-It-All: One Man’s Humble Quest to Become the Smartest Person in the World (Simon & Schuster, 2004). The memoir — which spent two months on the New York Times bestseller list — chronicles the 18 months Jacobs spent reading the entire Encyclopedia Britannica in a quest to learn everything in the world. MUD WTR is a coffee alternative with 4 adaptogenic mushrooms and ayurvedic herbs with 1/7th the caffeine of a cup of coffee. Go to mudwtr.com/STOIC and use code STOIC to get 15% off your first purchase. InsideTracker provides you with a personalized plan to improve your metabolism, reduce stress, improve sleep, and optimize your health for the long haul. For a limited time, get 20% off the entire InsideTracker store. Just go to insidetracker.com/STOIC to claim this deal. Stamps.com makes it easy to mail and ship right from your computer. Use our promo code STOIC to get a special offer that includes a 4-week trial PLUS free postage and a digital scale. Go to Stamps.com, click on the microphone at the TOP of the homepage and type in STOIC. GiveWell is the best site for figuring out how and where to donate your money to have the greatest impact. Go to Givewell. Org and enter Daily Stoic at checkout so they know we sent you. Sign up for the Daily Stoic email: https://dailystoic.com/dailyemailCheck out the Daily Stoic Store for Stoic inspired products, signed books, and more. Follow us: Instagram, Twitter, YouTube, TikTok, FacebookSee 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.

• 0:07Ryan Holiday?

  Welcome to the Weekend Edition of the Daily Stoic. Each weekday, we bring you a meditation inspired by the ancient Stoics, something to help you live up to those four Stoic virtues of courage, justice, temperance, and wisdom. And then here on the weekend, we take a deeper dive into those same topics. We interview Stoic philosophers. We explore at length how these Stoic ideas can be applied to our actual lives and the challenging issues of our time. Here on the weekend, when you have a little bit more space, when things have slowed down, be sure to take some time to think, to go for a walk, to sit with your journal,

• 0:50Ryan Holiday?

  and most importantly, to prepare for what the week ahead may bring.

• 0:57Ryan Holiday?

  Hey, it's Ryan Holiday. Welcome to another episode of the Daily Stoic Podcast. I think I was in Toronto. This was right as the obstacle is the way it's coming out. I think it might have been Growth Hacker. I was in Toronto, I was giving a talk. This talk called Mastermind Talks that I've been to many times, put on by my friend Jason Gaynor. It was a great event. I was there for the first one, the second one, maybe the third one. I've been to a bunch of them. Anyways, I went up to the hotel gym to work out,

• 1:34Ryan Holiday?

  and I saw this man, today's guest, setting up a treadmill desk in the hotel gym where he then proceeded to write and work for the entire time I was working out and well after I left. And that turned out to be A.J. Jacobs, today's guest. And it makes sense that he had this rather strange work setup because he is a, I wouldn't say a strange man, but he has a unique perspective. On everything. And that's what has made him an incredible writer, whose books have

• 2:16Ryan Holiday?

  sold a bazillion copies, been turned into TV shows. He's a favorite of my friend, Tim Ferriss, a favorite of mine. He's an editor-at-large at Esquire magazine, a commentator on NPR, a columnist for Mental Floss. He's just a fascinating guy. His first book was called The Know-It-All: One Man's Humble Quest to Become the Smartest Person in the World. He did a book called Living Biblically, where he tried to follow the Bible literally for a year. He did a fascinating book that I think I interviewed him for on DailyStoic.com a couple of years ago, where he, it was all about gratitude. And he went to go express

• 2:59Ryan Holiday?

  gratitude and thank every single person involved in making his morning coffee. Like I said, he just think, I mean, who, most of us don't think about that. We don't think about who makes our coffee. We don't think about what it would actually mean to literally follow the Bible. And it makes for fascinating writing and always interesting insights about life. A.J. Jacobs is a self-proclaimed human guinea pig. And that's what goes into the writing. And he writes about what fascinates him. And as it happens, he's also an avid nightly crossworder. And this is what inspired his new book, The Puzzler: One Man's Quest to Solve the Most Baffling Puzzles Ever, From Crosswords to Jigsaws to the Meaning

• 3:42Ryan Holiday?

  of Life. It's a fascinating book. My wife loved it because she's really into crossword puzzles. And as we talk about in today's episode, I happen to not really be that into crossword puzzles. But to each their own, I'm always fascinated. I took a page out of A.J.'s life and tried to really get to the bottom of why he thinks the way he does. And I think this made for an awesome episode. It chronicles his journey to understand the enduring power of puzzles, why we love them, what they do to our brains, how they can improve the world. And as it happens, we end with a fascinating memento mori puzzle that he set up. I think you're really gonna like this. And we do also some riffing on that last part of his subtitle, The Meaning of Life. So you can check out AJ's new book, The Puzzler: One Man's Quest to Solve the Most Baffling Puzzles Ever,

• 4:26Ryan Holiday?

  From Crosswords to Jigsaws to The Meaning of Life. You can check out his book, The Year of Living Biblically, The Know-It-All, Drop Dead Healthy, Thanks A Thousand, It's All Relative, Adventures Up and Down the World's Family Tree, where he looks into genealogy, and a bunch of his articles on Esquire. Enjoy this episode with the one and only AJ Jacobs.

• 4:54Ryan Holiday?

  Well, I feel like I should start you off by saying I don't really like puzzles and I don't like sci-fi. And I feel like those things are related. I feel like that's like a demographic that I'm not. I don't like puzzles of any kind. And I don't like figuring out worlds like in fantasy or fiction or anything like that.

• 5:14Speaker 01

  That's interesting. Well, I am not a huge sci-fi fan myself, but I will take issue with you saying that you don't like puzzles because I'm not sure you're thinking big enough. Because puzzle, you know, everything's a puzzle. Life is a puzzle. This podcast is a puzzle. Your marriage is a puzzle. And, uh, and within the so-called real puzzles, like you've got a crazy smorgasbord of, you've got word puzzles, logic puzzles, riddles. So there's got, there's a puzzle type for you. I am convinced. It's like dating.

• 5:49Ryan Holiday?

  Well, my, my wife likes crossword puzzles. She's gotten into them somewhat recently. She used to like Sudoku. And the puzzle for me is when she asked me to participate in the crossword. And I could not be less interested. And I have to figure, I have to figure out how hard I can blow this off without getting in an argument instead, you know? So that's, that's, that's the real puzzle for me is like, how can I? How can I not participate in something that bores me and then also avoid getting in an argument?

• 6:18Speaker 01

  Well, you give her the worst possible answers so that she knows never to ask you again. That's one solution.

• 6:24Ryan Holiday?

  Yeah. No, I think, so the reason I think it's related, I mean, there is a big overlap. Like, I feel like, for instance, a lot of sci-fi, they tend to be interested in crypto, not just like crypto, the form of money, but like, like, cryptology, like, the actually figuring out of like weird numeric puzzles and stuff.

• 6:43Speaker 01

  Right.

• 6:44Ryan Holiday?

  But like, what I've always not liked about sci-fi is like, when I want to get like, immersed in a world, I don't want to have to go like, okay, wait, is there gravity here? And like, who are these ghouls or gob, like, I don't like, I feel like reality is interesting enough to me, and I struggle to like, have to like, figure out the rules of a new reality.

• 7:07Speaker 01

  I, you know what, I am, I'm not going to argue that. I prefer the, the history. I love, partly because I love seeing how horrible life was, and it makes me feel a little better, and we've talked about that. But, uh, yeah, I, I don't think you need to love sci-fi to love puzzles, as I say. You know, puzzles are, uh, I, I seriously think that a lot of your life has been a pu, you figured out of the, one of the many solutions to life's puzzle with stoicism. I mean, that, that's a very, that, to me, is the biggest puzzle, is our mind. But that's why I went into it, is just to try to figure out the big puzzle, which is, how do I be less miserable?

• 7:51Ryan Holiday?

  Well, I want to talk about the, I want to talk about the big questions, because the sub, the end of the subtitle of the book is about the, the big question of the meaning of life. So I want to talk about that. But specifically, when we're, when we're using puzzles to refer to like, games, what am I missing by not being interested in games?

• 8:10Speaker 01

  Well, to me, I think there are so many benefits, and I'm not going to force it on you. I believe in consent. But there are many different joys of puzzles. First of all, I was never a big jigsaw puzzle fan, but I became a convert because it's got a meditative quality to it, a mindfulness. It's like very relaxing. I listened to Hugh Jackman on a podcast, our friend Tim Ferriss podcast, and he said that the feeling of putting two jigsaw pieces together is like popping a great zit. So I thought that was a nice metaphor, a little gross, but nice. But that is one of the, for me, the true joy is flexible thinking, that you come to a,

• 8:54Speaker 01

  you come to a puzzle and you're just baffled. You try 100 different ways and then you finally get it. So you've got to embrace the uncertainty. You've got to embrace the experimental mindset. And that's sort of been the theme of my career is experiments. And puzzles are basically just one big experiment.

• 9:14Ryan Holiday?

  Are video games puzzles in your mind?

• 9:16Speaker 01

  Oh, yeah. I mean, first of all, there are video games that are very puzzly. But I think, you know, I am very lenient in my definition of puzzles. I think there was, I quote in the book, this great puzzle maker, Maki Kaji, who is called the godfather of Sudoku. And he says, he breaks puzzles down into three symbols. The question mark, the forward arrow, and the exclamation point. So you get to a situation, you're baffled, like, what do I do? The forward is the trying, the struggle, the testing, and then the exclamation point, the aha moment, the dopamine. But his point was, you've got to start to love that arrow.

• 10:01Speaker 01

  You've got to, you can't be all about the exclamation point. Because you may never get to the exclamation point. So you, it's the, you know, I think it's a more poetic way of saying like, you know, love the journey, not the destination.

• 10:13Ryan Holiday?

  Yeah, my son, uh, my son's obsessed with Minecraft and, uh, which is obviously this sort of weird puzzly sort of world building game. But what I've been, uh, like there's, you know, this sort of instinctive aversion to screen time with kids. And then especially the instinctive screen time to watching videos. And then it occurred to me that like, he's watching videos about how to figure stuff out in Minecraft, which is not bad, right? And then he, he's only six. And so he like, he wants to like, figure out a video to do something, but he doesn't know how to write anything, right? So he has to ask us how to do that. And then it's like, oh, this is also a chance. He's like, you know, I want

• 10:57Ryan Holiday?

  to watch this channel. And it's like, okay, well, you know, what sound does it start with? And then we can work through, you know, like what letters go to spell, you know, that, that thing that he wants to look up. So I guess, uh, I guess if we have this sort of expansive definition as to what is a puzzle, maybe I'm, I'm less averse to it. But I'm also terrible at video games. I kind of feel like one of the gifts my parents gave me is that they didn't let me play video games until it was kind of too late for me. Like, so I probably started playing video games when I was like 12 or 13 and all my friends were like-

• 11:30Speaker 01

  And you don't hold a grudge? You're actually the opposite. I guess you're happy about that.

• 11:34Ryan Holiday?

  Well, it just like, when I see the time that it takes in people's lives, I'm like, oh, I like, that just, I was just never into that. I never, I never figured it out. So I've just, I'm just like, not interested. You know, it's like, it's too late, too late for me. It's a little bittersweet because I'm sure it's fun. But like, I, I feel like, uh, the, I, I had to imagine part of the reason that puzzles are fun is one has some aptitude for it. Like people who are just horrible at them probably are having less fun than people who are good at them.

• 12:08Speaker 01

  Well, yes, a yes and no. Again, I think there are puzzle types for everyone. So I am terrible at spatial reasoning. You know, I am a disaster. I don't, I can barely find my house if I'm three blocks away. So I'm not good at the Rubik's Cube. But I am a bit of a word nerd. So that is closer. But I have to say, stretching the muscles and doing the mechanical puzzles, that was great. I do think there's something about embracing the discomfort and stretching yourself.

• 12:36Ryan Holiday?

  Yeah, it's like, probably like learning languages, like the earlier you do it, the better. But you can do it at any age. I feel like this is one thing, someone was asking me something about like, the city I live in, which is Austin. And I was like, you have to understand, I moved to Austin when I was like, 28, after having lived in a lot of other cities. I have no conception of how this city works or is laid out. Like, like, I moved here well into the Google Maps era, well into the, like, let's figure out where cool new stuff is. So like, I just go where the GPS tells me. I have no conception of where southwest Austin is versus southeast Austin versus, you know, like, I don't get how it works.

• 13:20Speaker 01

  Well, fingers crossed, there's no zombie apocalypse. And the internet stays around, so you can find your way. Yeah, no, I'm the same way. I am terrible. Even though I have lived in New York City all of my life, I still can't find my way.

• 13:34Ryan Holiday?

  But it's a little intuitive, because it's sort of a grid and such, right? You can kind of, but I even feel like when I'm in New York City, I'm like, okay, this is the direction that I should go to go where I'm going. And, or it's like, I can either choose between this way or this way. One of those directions will take me the direction I want to go. I invariably will pick the wrong one. Like, whatever my instincts are, I do the, I've come to go like, I should do the opposite of that, because my compass is all screwed up.

• 14:00Speaker 01

  I know the feeling. Although I do sometimes, I wonder, because we've talked about this, is that, is that just your selective memory? Because I, it's like when I am waiting online at a drugstore,

• 14:15Speaker 01

  And I wait in a line that goes quickly. I like, I have to say to myself out loud, remember this, you idiot. Like, there, there are times when you're on the fast line. Because otherwise, my default is, how do I do it? How do I always pick the slow line? But I don't. It's just the one I remember because it's more annoying.

• 14:35Ryan Holiday?

  Sure, you don't remember the time you hit all green lights. You only imagine the time, you only remember the time when you got hit with traffic or everything went wrong. And you just take for granted all the times that you were good at something or you did it right.

• 14:49Speaker 01

  Right, which is a terrible, yeah, it's a terrible, the negative bias. It's a terrible wiring in our brain. So yeah, fighting against that. So it is possible that you, you half the time choose the right direction.

• 15:02Ryan Holiday?

  Is Jeopardy a puzzle? I guess I like Jeopardy. Like, I like things that are related to, again, I guess, like, reality where it's like, oh, this is the answer to a question that a human would reasonably know the answer to.

• 15:14Speaker 01

  Sure, Jeopardy. And actually, I interviewed Alex Trebek a long time ago for Esquire magazine. And I quote him in this book because he had one of, one of the themes of the book is, it's an ode to curiosity. I think curiosity and gratitude, those are my two favorite human drives. And he had a great quote about curiosity that, on the surface, doesn't make much sense. And yet, I still totally resonate with it. He said to me, when I interviewed him, he said, I'm curious about everything, including those things that don't interest me. And I just thought that was nice, because I am too. And, you know, you take the most stereotypically boring topics, like accounting or something.

• 15:59Speaker 01

  I'm sure that if I scratched the surface, it would be fascinating. Because it's not just about numbers. It's about people and, and their businesses and passion and love. And, you know, it is, everything can be interesting if you can just ramp up your curiosity. So that's a lot of fun.

• 16:18Ryan Holiday?

  And, and also, like, it's interesting that it's interesting to other people. So if it bores you and you're like, I don't get this, this is the dumbest thing in the world. What's interesting, this is kind of also what I think about puzzles, it's like, But why is it interesting to you? Like, that interests me at least, right? Like, why? The puzzle of like, why this thing? That to me is so intrinsically uninteresting, you decided to dedicate your entire life to? Like, being an accountant or whatever?

• 16:47Speaker 01

  Right. Well, I love that. And that is another good puzzle skill, is being able to see the world from another point of view. Like, to solve certain types of logic puzzles, or you have to step inside the mind of the puzzler or the characters in the puzzle. And I love that, because I think that is a skill that we definitely need. And that's like, when I... One of the benefits of this experiment was that, you know, it's been a hard few years in terms of having discussions. Like, I get very angry when someone doesn't see my way. But what this has taught me is sort of the puzzler mindset is about treating a discussion

• 17:32Speaker 01

  with someone on the opposite side of the political spectrum as a puzzle, as a cooperative adventure, a mystery. Why do you believe what you believe? Why do I believe what I believe? Is there any way to change our minds? Any evidence? Is there one... Anything, any way forward? And that is gonna result so much more often in something productive. And I don't get angry, which I hate anger, which is part of why I love Stoicism, is that I am not a fan... I'm angry that we're programmed to have anger. So, this is like, the phrase that I picked up that I love is, "Don't get furious, get curious." So, the puzzling is sort of a way

• 18:17Speaker 01

  to encourage that curiosity.

• 18:22Ryan Holiday?

  Yeah, like, Socrates had this line that "nobody does wrong on purpose." And you could probably extend that to like, "nobody is wrong on purpose either." So, like, almost everything that you see, whether it's someone's belief, or this one is more common, like, you know, you're dealing with something like in a business, you're like, "Why does the grocery store do this?" This this way, it's so stupid. Or why, you know, why is the cable company do it this way? It's so stupid. There's almost always a logic to it. Right, there's a like there. This multi billion dollar company that has thousands of employees is not just utterly ignorant of the fact that the system does something this way. There's usually some sort of industry logic or a constraint.

• 19:08Ryan Holiday?

  You know, there's some reason that it is that way. And I think oftentimes we're so closed minded. We don't want to think about that. We just think about how it affects us as if pleasing us is the only reason is the only logic that a system can operate under. Like, it could just be, hey, it can't operate any other way. They hate it too, but they're stuck with it.

• 19:30Speaker 01

  Right, that is so interesting. I like that. I mean, it relates to one of my favorite themes, which is epistemic humility. Like, don't be so cocky that you know all the right answers. It is possible, and a lot of times institutions do make terrible mistakes and people in them. And and they are not thinking clearly. But yeah, we've got to, first of all, if you do want to change that, then do try. You have to understand their logic before you're able to convince them to change. So yeah, you've got to explore that their their logic. Because they are going to have logic, even if it's if it's crazy logic.

• 20:07Ryan Holiday?

  Well, and this it's unlikely. I think the epistemic humility is it's unlikely that this thing that I have thought about for seven seconds that is is vastly superior to the people who do this every day and have thought about it all the way through. That's not to say that entrenched players never get it wrong and that the status quo is always right. It's just almost always more complicated than you think it is like that. Yeah, you should it maybe should still be changed. Maybe your solution is better. It's just it's almost never the case that it's as simple as it it seems to you on the surface.

• 20:48Speaker 01

  Right. I mean, that I love that as sort of the. The, the one size fits all answer to almost any big question is, well, it depends. It's complicated and people, it drives people crazy, but it's true. There is, you know, you've got to delve in and look at the nuances on anything. And, and that, you know, again, that comes back to curiosity and not having this black and white picture of the world.

• 21:18Ryan Holiday?

  Well, I was reading an interesting article about this. I'm not sure when this episode will come out, but like people are talking about Elon Musk buying Twitter. And, you know, he's like, well, we gotta do this, we gotta do this. And, and the people who have like really written about this and studied for a long time are like, yeah, you know, Twitter has tried all of those things like they didn't just, they didn't, they're not just where they are sort of unthinkingly. Like it, that's not to say they're doing a good job or that it's perfect because I think Twitter is a cesspool. But like these obvious off the cuff things that you just experienced as a user like, hey, why isn't there an edit button? Or, you know, why isn't this like, there's some of the smartest people in the world have been working at this company for 10 years.

• 22:03Ryan Holiday?

  Like they're, they, they've thought about this. It's, it's like, it's complicated is one answer. The other is like, let me tell you all these other things that you don't know are happening behind the scenes. Like I heard a good, like, I heard that like, when you become president, uh, they must give you like a binder that they're like, let me tell you all the stuff that nobody knows. And then that's why you can't close Guantanamo Bay or whatever. It seems simple, but like, that's because you don't have the full story and that's the puzzle.

• 22:34Speaker 01

  That is a huge puzzle. Yeah. You don't know what you don't know, as, as people say. And, and also, you know, it relates to, who said you don't have to have an opinion? Marcus Aurelius?

• 22:45Ryan Holiday?

  Yes, yes.

• 22:46Speaker 01

  Right. So that like with the Twitter and Elon Musk, I have, I have my gut opinion, but I, I don't want to express it yet because I want to really think about it and, uh, And I love, so that is another part of stoicism I love is, yeah, we don't have to rush into it, just take your time. I even thought, I haven't done this experiment, but I thought instituting this with my family, with my wife, like if we're in an argument, what if we had a 10-second waiting period? So you, I'll say something that might infuriate her. She has to wait for 10 seconds and think about it before she responds. And then, do you think that would make it better? It might make us more frustrated, but maybe it would be an improvement.

• 23:31Ryan Holiday?

  Well, you have to, you have to sit with it, right? Which is uncomfortable. And then you have to, like, the other one I heard is like, people are like, America's falling apart. Like, what we need is, we need more, like, we're too partisan. You know what we need? We need to teach basic civics in school, right? And that sounds like, as a soundbite, that sounds like, of course, of course, we need to teach basic civics. And then I was reading a piece and someone was like, you know, that will just become politicized also, right? Like, there, like, you can't, civics isn't, isn't just this thing that you can teach in a nonpartisan way. It just becomes the new battleground, right? So it's, and the point is not to say, oh, it's complicated, let's do nothing. It's just, there are very rarely simple solutions to complex problems.

• 24:16Ryan Holiday?

  And the arrogance to think, oh, we just need to do X. Why aren't the politicians, why aren't the investors, the CEOs, the elites, so on, doing X, Y, or Z?

• 24:26Speaker 01

  Right. And you have to balance that with sometimes there are out-of-the-box ideas that will revolutionize something. So you need to keep an open mind to both possibilities, I think. And what you brought up about teaching civics, I think, is fascinating because that, I've been thinking about that a lot. Because civics, that is a huge word. That can mean 100 different things.

• 24:48Ryan Holiday?

  Exactly.

• 24:49Speaker 01

  And that is one of, like, I'm trying to convert you to puzzles. One of the things I love about word puzzles, crossword puzzles, is it's all about the different meanings of words. You have to delve in. It's all about wordplay and trickery. And when I researched this, I found out the word run, R U N, has over 600 definitions in the Oxford English Dictionary. That's insane. So this idea of looking at, when I read the news, because I've been trained to look at the meanings of words so closely, I really think it helps me. So, because yeah, like civics, you could fall for that. Or the word freedom. Freedom can mean 100 things.

• 25:32Ryan Holiday?

  Sure.

• 25:32Speaker 01

  You know, I am, I am, you know, pro-capitalism overall, but I think there should be constraints. So if someone says, "Oh, you're messing with the free market." You know, freedom, oh, that's great. That, you know, it has a positive connotation. But it has many other meanings. You know, what about the freedom to choose to shop at not a monopoly? What about the, you know, the freedom to make a wage? So puzzles, word puzzles, I think are good in that they train you to look at the words very carefully. How's that?

• 26:02Ryan Holiday?

  No, no, words, words matter, right? Like, and, and if you're not someone that actually thinks about what's happening, you could very easily be deceived or you fall for sort of empty slogans. Like, again, the Elon Musk thing, like Elon Musk is like, "I'm a believer in free speech." I think, you know, Twitter, he was like, "Twitter should follow the free speech rules of the country that it's in." And I was like, "Oh, yeah, that makes sense." And he's like, "So when I take over Twitter, I'm gonna do that." And he's like, "And I'm gonna get rid of spam and trolls and all these things." And then it's like, but that's not illegal, right? Like, so like, two seconds later, right? You've already contradicted yourself. So I think it's-

• 26:41Speaker 01

  Right, that's Orwellian, yeah.

• 26:42Ryan Holiday?

  Yeah, exactly. And so, in a way, propaganda and understanding what things mean, like slogan, this, this is a puzzle too. Like, what does that mean? What are they really saying? Like, does that even make sense?

• 26:55Speaker 01

  Right. Do you love puzzles? I knew it. I got you.

• 26:59Ryan Holiday?

  Well, writing is a puzzle. Right, like, uh,

• 27:01Speaker 01

  Oh, yeah.

• 27:02Ryan Holiday?

  You know, Mark Twain said, you know, or maybe, maybe he didn't say it, but whatever the quote is, about the right word is the difference between lightning and lightning bug.

• 27:10Speaker 01

  Right.

• 27:11Ryan Holiday?

  Like, the figuring out what the ultimate way to say a thing is to get your point across. I mean, that's the puzzle of writing a book or an article or a tweet is, is like, how do you say the thing most effectively with the fewest or the most or the, the best words? So I like puzzles in that sense.

• 27:29Speaker 01

  And yeah, I definitely, I, I love researching, so I loved researching this book. I am not a fan of the actual sitting alone and writing. I don't know.

• 27:39Ryan Holiday?

  Really?

• 27:39Speaker 01

  Are you? Yeah, I just find it very, um, I don't know, it's solitary and depressing for me. And, and I don't get the feedback. I don't know whether it's resonating. But anyway, the way I got over that for this book was, just like you said, I conceived of the book as a puzzle. So, and it made, it immediately framed it as a more playful thing instead of like a life and death problem. It's a puzzle. I'm going to try to fit these chapters together to tell the most interesting and compelling story. And, uh, and that way I wasn't as miserable. I still prefer the research and talking to people, but, uh, it was better.

• 28:20Ryan Holiday?

  What I love about, right, I, uh, there is that expression, painters like painting, writers like having written, uh, which I, I find to generally be true, but I, I do, like, when I'm, I never write a book until I've cracked the book, if that makes sense. So like, how is it going to be arranged? What is the arc that it's taking? What is the structure, the style? Like, all of those, to me, are puzzles that you solve, that once you solve, then the rest is sort of like following the instructions. Right? Like, you have to figure out, like, okay, is this gonna, is this book gonna be three parts or two parts? Is it gonna have? Fifteen chapters, or is it gonna have six chapters?

• 29:05Ryan Holiday?

  Right? Are they long chapters or short chapters? Like, what does the intro to each chapter look like? And once you crack that, then, then you have like a map to get from, you know, the beginning to the end. But I feel like what a lot of writers do, and why it's harder for them than it needs to be, is they sit down and they, they're just like, well, let's see where this goes. Right? And that's like trying to figure out where you're going by just following the headlights in front of your car. Like, you have to know-

• 29:34Speaker 01

  That's like walking without GPS, right?

• 29:36Ryan Holiday?

  Yes, exactly.

• 29:37Speaker 01

  Well, I am totally with you. I am a huge structureaholic. And I cannot start a book unless I have that structure. Like, for instance, I wanted to write a book about health for many years. I just thought it was an interesting topic, but I didn't know how to do it. And then I said, what if I did it in different body parts? So, you know, I'll do one chapter on the stomach, one on the heart, and one on the eyes. And then, like you said, it was, then the puzzle had been cracked and it was just filling in. By the way, I realized that I did not have, I should have ended with appendix, the appendix.

• 30:13Ryan Holiday?

  Of course, you didn't do that?

• 30:14Speaker 01

  Yeah, I'm embarrassed.

• 30:17Ryan Holiday?

  No, that, that, that is something I, because I, I tend to work pretty fast. And every once in a while, like after a book is done, or it's too late, I go, oh, you know what I should have done? Like, I should have ended with the appendix, or whatever. And then, I wonder, like, if I'd had more time, would I have come up with that? Do you know what I mean? Like, like, did I rush it? And there was this, that, you know, or I go, like, right now, for instance, this is the first time I've ever done this. I'm, I'm doing a four book series. I'm doing one book on each of the four cardinal virtues. So, like, I've written lots of books before, but this is the first time any of the books were related to each other. And so it made it like, not four times more complicated, but like infinitely more complicated.

• 31:01Ryan Holiday?

  Because now I'm thinking, well, okay, this chapter could go in the courage book.

• 31:07Ryan Holiday?

  But is it actually an example of justice or self-discipline? Right? And so, so like having to move things around, but once each book is published, you, you now have fewer options. So it's like, you know, it'd be like doing a crossword puzzle where once you guess, like, you know, it, it's, you're stuck or something, right? Like, once, once you, once you put it down, you can't change, once you make your move, you can't go backwards. And so like, there's a chapter in the courage book that I now very much wish was in the discipline book, which I'm just finishing now. And so the, the having to then be conscious of not just this singular project, but how it fits in

• 31:50Ryan Holiday?

  a larger universe is something I've never, never done before.

• 31:54Speaker 01

  Yeah, that is, that's a good challenge. Well, it's, it's interesting you bring that up because I, I do want to talk a little about regret because yeah, regret is not something that I think is a good emotion. And I'd like to hear what the Stoics have to say about it because I, I too am battling regret. I, I'm spending at least like five minutes a day wasting my time thinking, I think I did the order of the chapters wrong. The jigsaw chapter is really strong. It should have been up first. And, and that is just, it's not helping me. It's not helping the world. So what would the Stoic response to regret be?

• 32:34Ryan Holiday?

  Well, the, the, it's, it's already happened. So it's outside your control. Well, I guess first off, is it outside your control? Could you change it in a paperback or a future edition or whatever? Right? So first off, you have to actually like do the math. Is it, is it, is it done or not? And then if it is done, you have to say, okay, any energy or effort I throw backwards at this is just self-inflicted punishment or whatever.

• 32:58Ryan Holiday?

  The the real thing to take out of it is, well, what factors contributed to me making that wrong decision? I'll give you, I'll give you an example, something I regret. So I have the obstacle is the way tattooed on this arm and ego is the enemy tattooed on this arm. Now, I went to two different tattoo shops and I'm not really, I'm not like a super visual person, so I didn't remember what the font was on the, on the first, first one. So when I went to get the second tattoo, I was like, you know, just match it with this one. And he goes, is this the right font? And I go, yeah, sure, that's the right font. And they don't match. They're not, they're, they're close, but they're definitely not the same font or size, right?

• 33:38Speaker 01

  Right.

• 33:39Ryan Holiday?

  And so every, every day I look at it and I go, God damn it, what was I think, like, you know?

• 33:43Speaker 01

  Right there, you can't escape it. You can't put it in the closet, it's on your skin.

• 33:46Ryan Holiday?

  Like three, you know, basically I rushed a decision. I, it's not that I compromised, but I wasn't enough of a stickler, like detail, I'm not a super detail oriented person on things that I don't care that much about.

• 34:01Speaker 01

  Right.

• 34:02Ryan Holiday?

  And so now when someone's like, hey, can you approve this? And I go like, yeah, sure, that looks good. You know, I try to catch, I try to look at the arms and go, okay, you tend to regret it when you don't take an extra minute to like really think about this thing.

• 34:18Speaker 01

  Interesting.

• 34:19Ryan Holiday?

  So the, the regret is not valuable, but using it as a reminder of the flawed decision making process or system or whatever that created the error, like, why did you put the chapters potentially in the wrong order? And then how on a future book do you, do you account and adjust for that?

• 34:37Speaker 01

  So if it can have an effect on the future, then it is worth thinking about a lot. But I will say, I love that story so much. I think that there is another lesson, though, you could have taken out of it, which is... Which is to that it is it is good training in being okay with non perfection.

• 34:56Ryan Holiday?

  Sure.

• 34:57Speaker 01

  That like you you're it trains you to be okay with discomfort because nothing is ever going to be perfect. And actually, one of my favorite stories that I one of my favorite interviews for this book was a guy who he spent the entire pandemic. He bought the a 54,000 piece jigsaw puzzle. It's huge. Like, it takes up your house. And he spent the pandemic doing it. And he got to the 53,999 piece. And the last one was missing. And he just freaked out. You know, he couldn't sleep. He couldn't eat. He tore up his house. He tore up his vacuum cleaner. So my hope was for the end of the story

• 35:37Speaker 01

  that he just left it like that. And as like, here is a like, you know, sort of a tribute to the fact that life is not perfect enclosure is not always you can't always finish. But he didn't, which is understandable. And he got, you know, he called up the company and begged them and they sent him the piece. So he did finish. But I just thought that was a can you imagine, though, like, he spent like, a year getting to that point?

• 36:04Ryan Holiday?

  I think what happens is often the thing that makes you want to do puzzles, or write something, or do like, be great at something, is this is where the stoic virtue of temperance comes in. It's hard to turn it off, right? Like, it's hard to to not be it. It's it's very easy for it to veer into sort of OCD territory, or a compulsion, where you're not able to go like, all right, good enough. You know, like, like, for instance, the Apple Watch, like, is kind of a gamified puzzle. It turns exercise into a puzzle, right? I have a I have a an exercise goal, a standing goal, you

• 36:44Ryan Holiday?

  know, an active calorie goal. And like, I have to sometimes actively decide that, like, I'm in charge and not the watch. You know what I mean? Like, because it'll be like, well, if I don't if I don't get to to break 1000, or whatever the thing is, I

• 37:04Ryan Holiday?

  I'll lose, but then it's like, what am I, what am I winning? I don't get any

• 37:07Speaker 01

  Who's in charge here?

• 37:08Ryan Holiday?

  Yeah, right. Like, they're not going to throw me a parade. This is a made up game, right? And then, and I have to go, I have to go, you know what? 900 out of 1,000 is still an A. You know, like, like, it's not all or nothing. It's, you know, like, I bet to him to not do that, that final piece was the same as not like, as not doing it at all. Do you know what I mean? That it was like undone by missing a piece instead of being 99.9% complete. He saw it as a failure.

• 37:44Speaker 01

  Right. It's like, it's the on off switch versus the dimmer. And I think most of life is a dimmer. And we've got to get used to that. Cause we think in black and white and thinking probabilistically and, you know, in Bayesian terms is so much better. And actually, all right, here's another plug for, for puzzles. I do think puzzles teach you to think probabilistically because you cannot, to be good at crosswords, you cannot be certain that this is the answer. You have to write it in pencil. Like some, some people are like, oh, I do crosswords in pen and that's fine. You know, you're, you're cool, you're macho, but, but actually it's, you know, it's much better.

• 38:26Speaker 01

  I think in life and in puzzles to say, you know, I think 80% chance this is the right answer, but let's, let's keep in mind it's not always the right answer. So yeah, to me, that is, that is the way out of black and white thinking, which is really screwed us up big time.

• 38:44Ryan Holiday?

  And speaking of which, weren't you an answer in the New York Times crossword puzzle?

• 38:49Speaker 01

  I was, and actually I'm interested in the Stoic version of this because here, here's the story. I, I've always been a word nerd, so about five years ago, I was the answer to one down in the New York Times crossword puzzle. And

• 39:04Ryan Holiday?

  Is that better? Is, by the way, is there a status into like where you are is one down? Like, is that

• 39:09Speaker 01

  No.

• 39:09Ryan Holiday?

  Is that considered more prestigious than being like 25 across?

• 39:14Speaker 01

  No, no, that part is random, but, but actually that's a foreshadowing of what's to come. Because I was on a high, so I was like, this is the greatest moment of my life. You know, my kids being born, that was pretty good, but like, I'm in the New York Times crossword puzzle. And then my brother-in-law emailed me, he did congratulate me, so I want to get that out there. But he also pointed out that I was in the Saturday New York Times crossword puzzle. And maybe your wife can tell you, but that is the hardest of the week. It starts out on Monday, super easy, then it gets crazy hard. So on Saturday, all the answers are totally obscure and no one knows what they are. So his point was, this is not a compliment.

• 39:58Speaker 01

  Like, this is proof you are totally, no one knows who you are, that you're obscure.

• 40:02Ryan Holiday?

  Right.

• 40:03Speaker 01

  And he's like, if you get in on Monday or Tuesday.

• 40:05Ryan Holiday?

  It's a statement about your popularity.

• 40:07Speaker 01

  Right. It was proof of my irrelevance is, is his point. And I, so I was, you know, I was devastated. And I, I told that story on a podcast. And it happened that a New York Times crossword maker was listening and decided to save me and put me in a Tuesday puzzle where I don't belong. Like, that's where, you know, Joe Biden or Lady Gaga, those kind of people are in a Tuesday. It's not Monday, but Tuesday is still pretty good. So then he did that, and that was the truly greatest moment of my life. So that was how I started. And, you know, I'm kind of joking, I'm, you know, I'm delighted to be in anything, but, um.

• 40:49Ryan Holiday?

  But I would say even that you were, that when you were just out doing what you do, that your dissatisfaction or your faux hurt with your placement, the fact that that was, that was picked up by an editor of the New York Times is also a state, is, is a more emphatic statement about your place in popular culture than where you appear, you know what I'm saying? It'd be like, if I'm like, Joe Biden's a bum, and then Joe Biden got back to me, he's like, hey, what's that? You know, that's, that's, that's a pretty big statement, right?

• 41:22Speaker 01

  Oh, I like that spin. I like that. Well, I also think it's, you know, one of, one of the things as a writer I do try to do is to, you know, create a, create a story out of pain. And I know a lot of the times it's a false story, or at least, you know, sort of selective. But, uh, but I do think that it's an important skill as a human to be able to look at a situation and rationalize it. Actually, here were the upsides of, you know, the fact that this person called me the ugliest human they'd ever seen, or whatever. And to be able to turn that into a story

• 42:04Speaker 01

  and take control of it. And I think that, you know, even as long as you're aware that, that you're kind of doing that, and don't delude yourself that that is the ultimate reality. I think it's, it's really good for my mental, mental health, anyway.

• 42:21Ryan Holiday?

  Well, I want to talk about that. One of my claims to fame, and there's some irony in this, is that Ego is the Enemy, my book, was an answer on Jeopardy in one of the last Trebek episodes.

• 42:33Speaker 01

  That's hilarious. Very ironic. That's a tough one. What do you do about that?

• 42:39Ryan Holiday?

  I know. I thought it was pretty cool. Um, no, I, I think what you were just saying, so it's like you're in the New York Times, you could see that as like wonderful, or you could see it as a slight, you know, like, where am I in relation to, like, what day of the week, you know, was I, was I in it? Um, you know, are they, are they implying that I'm well-known or not well-known? So, one of the things you, you talk about is like, the joy of optical illusions, which are another kind of, of, of, of puzzle. I like the one where it's like, am I looking at a duck or a rabbit? You know, am I looking at a woman's legs or a woman's face? You know, like, the, the one where, where you realize, oh, there's two ways of seeing this same image. Like, the image is static,

• 43:23Ryan Holiday?

  but how I look at it from this side or this side, with one eye open or one eye closed, you know, after you've told me what it's supposed to be versus what I instinctively see it as. To me, that's a great illustration of Of Stoicism, Epictetus says that every situation has two handles. You know, you could argue that every image has two or more infinite number of illusions that you can see out of it. And it does kind of humble us that like, oh yeah, what my initial reaction is was wildly off base.

• 43:55Speaker 01

  Yeah, well, that is great. I mean, it's what you say all the time about you can't control what happens to you, but you can control how you react to it. And that's the same, that's, that's all about the framing. So with optical illusions, yeah, it's all about what you have in your mind. Are you thinking about, have you just looked at a bunch of pictures of people? And so this looks like people or is it look like a vase? And you have some control over the frame. And I think about that all the time in life. So if I'm, you know, if I'm feeling jittery before a speech, am I, is that because I'm nervous or excited? I, I just tell myself it's excited and then I'm in a better position.

• 44:36Speaker 01

  I mean, I could look, you could create out of the near random collection of episodes of my life or anyone's life, you know, I could tell a story of that, you know, I'm the biggest loser ever. Cause you could take, you know, all of my failures and weave them into a story. Or you could take, you know, the successes and mix it in with it and, and tell an inspiring story. So framing to me is, is absolute, and I love that the Stoics were behind this idea as well.

• 45:08Ryan Holiday?

  Yeah, the Stoics say, you know, it's not things that upset us. It's our opinion about those things, right? So it's what we, you know, like even to an image, like, is this an, I saw one the other day where it was like, it was this like lovely woman's face or it was like a, an obscene image, right? And so it's like,

• 45:26Speaker 01

  I saw that one, yeah.

• 45:27Ryan Holiday?

  Yeah. So it's like, do you have a dirty mind that, or, or a clean mind? Are you someone who seeks to be offended or you see, or you someone who seeks to see beauty, right? Like you, you make the decision you're, the Stoics also say we're complicit when we get offended. Right? So the idea that like the story we tell ourselves, the, the picture that we see, the, the, what we solve for, that's up to us. That's one of the few things that we control and it's not something that other people are doing to us. It's something we are doing to the objective reality or the, the, the world around us.

• 46:04Speaker 01

  Right, that is so, I mean, that reminds me of why I, you know, I think about words a lot. Partly because I did this book on, you know, word puzzles. But one of the words I've been thinking about is the use of trigger and trigger warning. And I think the word trigger to me is a little problematic because it takes away the agency. It's like you are, you're just a reflex. You hear that word, you have no control and you are immediately, you know, set off into a spiral. So, you know, I am very much against, you know, I think there's a huge problem with vitriol and people using words in terrible ways.

• 46:49Speaker 01

  But, but I don't think that we should call it triggering. We should, we should come up with a more active and empowering way.

• 47:00Speaker 01

  Because to me, the, the, the key is you want to stop people from doing that in the future. And that is where, so by, when you use the word trigger, I'm not, I, I just feel you're taking away some of the power that you could express in trying to stop these things.

• 47:28Ryan Holiday?

  Well, the implication of it is inherently a lack of agency, right? That the thing is doing something to you. You don't have, you are a powerless automaton that does not control whether it upsets you, whether you're hurt, whether you can deal with it or not. I, it is interesting where we are and I think it could be very easy to sort of spiral into like a sort of a right wing, like, you know, sort of anti-woke, whatever, view pretty easily. So I'm not doing that, but I always, I, I find like when people get really upset about microaggressions, like, I understand, you should try to be sensitive. You don't want to try to hurt other people. You want to think about how your actions affect other people.

• 48:12Ryan Holiday?

  But when I hear the word microaggression. I'm like, you know, you're literally describing it as the least amount of aggression possible, right? Like, like you are saying that this is the smallest aggression, the smallest infliction of pain or distress possible. And then you're acting as if it is a regular aggression, right?

• 48:32Speaker 01

  Right.

• 48:33Ryan Holiday?

  And so I think the words we use are illustrative and oftentimes, we use those words with no, almost no sense or awareness of the actual statement we're making, which is to either deprive people of agency, or to overblow something, or whatever. It's kind of strange how people use language.

• 48:53Speaker 01

  Right. Well, I guess to me, I mean, I do want to eliminate speech that hurts people. I think that is a huge, that's, that is, you know, one of the most important things we can do. But I guess to me, there are two strategies, and they are both, they're not incompatible. You should use them both. So the first strategy is to build up your mental armor. Like, you know, I'm in CBT, and I love that, because when I get insulted, I try to use CBT to diminish my feelings. So that's one strategy. And the other strategy is to say to someone, you know, that's not cool. That makes me feel bad. That, you know,

• 49:36Speaker 01

  please don't ever do that again. So you have two strategies that you should use in combination. You know, build up your armor, and then also try to disarm the other person from using that language.

• 49:51Ryan Holiday?

  I think that's right. I think that's right. I was thinking about the big question of the book, which is the sort of question about the meaning of life. But I mentioned Socrates earlier. What I think is interesting about Socrates is he seemed to be interested in Going around, to him, the ultimate puzzle was like, why do people think what they think? And he seemed to be very interested in figuring it out in a very judgment, non judgment, non judgmental way, right? Like, isn't that the Socratic method? Like, why? Why? Well, what about this? Why? What about this? What about this? Right? Like, to me, that

• 50:29Ryan Holiday?

  philosophy is, in that sense, the ultimate form of puzzling. But, I mean, look, I do have some objections to how easily philosophy can descend into, you know, how do we know we're not living in a computer simulation? Right? Like, I guess we don't know, but what am I supposed to do with this information? Right? Like, you're taking, you're, you're almost getting bogged down in puzzles instead of asking questions that actually matter. But I do feel like philosophy is like, how do I know what I know? Right? Or how do I know that that's true or not? What about this? There, there is inherently in philosophy the pursuit of answers to life's most difficult puzzles.

• 51:11Speaker 01

  Absolutely. Yeah, I love that. And, and that's like what I was saying when I talked to someone who's on the other side of the spec, political spectrum. The puzzle is, why do I believe what I believe? And why do they believe what they believe? That, yeah, that is the ultimate puzzle, to approach it with curiosity, like Socrates did, to be asking questions. And, yeah, I mean, I don't want to spoil it, but I might not have figured out the final meaning of life at the end. But, but part of my answer is, the meaning of life is partly in the search for meaning of life. It's partly in the curiosity, the asking of questions, and, and in the process. So that, that I totally agree with. And philosophy

• 51:54Speaker 01

  and puzzles, they're very, they're very similar.

• 51:57Ryan Holiday?

  Well, Seneca says that the ultimate puzzle in life, he says, if you put all the great minds of philosophy together, they wouldn't be able to answer. Why do we protect our property and money much more rigorously and vigorously than our time when one resource is much more precious than the other?

• 52:21Speaker 01

  Hmm, I love that. I'm gonna have to think about that. I don't have an opinion like where Chris really is right now, but I'm gonna think about it because that is, yeah, it's true. I mean, I think, you know, we're built with a lot of biases and the, one of the, one of our huge blind spots is just how fast time goes and how, you know, life can be over in a flash. And that's why we've talked about this. I love memento mori. I'm a huge memento mori. And, and actually, as part of this puzzle book, I kind of created a memento mori in puzzle form because I teamed up with this designer, a Dutch puzzle designer. He's

• 53:05Speaker 01

  crazy and he makes these, they're mechanical puzzles, like where you twist things and Rubik's Cube. He and I designed what's called the Jacob's Tower, which is this tower, you can see it in the back. It's this wooden tower with 55 pegs. And you've got to move the pegs in a certain order and to get out the, this metal rod that's in the middle. But you have to turn the pegs a lot of times. You have to turn them exactly 1.3 decillion times. So that's one with 33 zeros. So it's just a mind bogglingly big number. If you turn one every second, the universe will run out of energy before you finish. And I just love

• 53:47Speaker 01

  this because to me, it's, it's what's called a generation puzzle. So you're passing it down from you to your kids to their, their kids, and no one's gonna be able to solve it. But it's just a reminder that, you know, we're here for a short time. There is a long future ahead of us. And so we should A, think about people in the future and try to make the world better for them. But B, the memento mori, you know, we're only here for a little bit. Let's try to make the most of it.

• 54:17Ryan Holiday?

  Yeah, it's that you can spend your whole life furrowing your brow at this puzzle, but it will outlive you and all of your descendants many times over. There's a humility in that.

• 54:32Speaker 01

  Right, yes, it is very humbling. And I think that's a good thing that puzzles sometimes do is humble you.

• 54:38Ryan Holiday?

  We just did one for Daily Stoic that's, which is another thing I love from Seneca. Seneca goes like, "The problem is that we think about death as something in the future that we're moving slowly towards, right? That's our perception of time, right? We go from zero to 80 and you're moving towards it." But he says, "Actually, death is happening right now. The time that passes belongs to death." So we made a print and it has 4,000 weeks on it, which is roughly 80 years. But the idea is that every week that you live, you have to exit out, right? So it's not how long do you have left, but how much have you already died?

• 55:18Speaker 01

  Oh, I love that. Because actually, that is another thing I talk about in the book is seeing the world from the complete opposite point of view. And that is a perfect example that I think I am going to use. I'll give you credit, or the Stoics credit. All right, I'll give Seneca credit.

• 55:36Ryan Holiday?

  And to me, that's kind of the solution to that, the riddle that he posed, which is why do we value money and resources more than time? It's because we fundamentally misunderstand time, right? We think we have more time in the future as opposed to seeing time as something that's escaping us constantly, that we're spending time, right? Like, we think about what we get paid per hour, but we don't think about us spending an hour to get paid, right? Like fundamentally, you brought up capitalism. Capitalism is paying with your labor, with your life for money.

• 56:19Ryan Holiday?

  But we don't think, we think about the exchange going often only in one direction. Like, I get paid $20 an hour, or I get paid $200 an hour. We don't think about... I just gave one of the 4,000 weeks that I have in my life to this job that I hate.

• 56:37Speaker 01

  Hmm, yeah, that is great.

• 56:39Ryan Holiday?

  Or to this thing that I regret. Like you were talking, like you said, five minutes. Five minutes doesn't seem like a lot, but cumulatively, it is a lot. And it's five minutes you never get back.

• 56:49Speaker 01

  Absolutely, yeah. I mean, uh, it's funny, one, the first, the, the reason I met, uh, Tim Ferriss was our mutual friend, was that I wrote an article called "My Outsourced Life", and one, I tried to outsource everything. So I outsourced my phone calls, my emails. But one of the other things I did, you know, I hired these, this lovely woman in Bangalore, India. And one of the things I asked her to do for me was, can you worry for five minutes a day on my behalf? And, uh, cause I had a deadline. I'm like, I'm worrying about it and it's eating away at me. But if I know that someone else is worrying, if, and, and I said, I'll, I'll even worry about something

• 57:31Speaker 01

  in your life for you, cause then it doesn't have the emotional heft. So outsourcing your worry, uh, I think is, believe it or not, that was one of the most effective things in that, in that experiment, was outsourcing my worry, having someone else worry for me. And I, uh, as you say, it's just five minutes, but five minutes a day, it adds up. So I am, uh, I am a big fan of either trading worries or just asking someone, "Do you mind worrying about this for me?"

• 58:03Ryan Holiday?

  So have you, have you solved the riddle though, what, what the meaning of life is? Have you figured it out?

• 58:10Speaker 01

  Well, there's, yeah. I mean, there's the Douglas Adams. Do you like, oh, you don't like, uh, sci-fi?

• 58:16Ryan Holiday?

  I don't like sci-fi.

• 58:17Speaker 01

  This is, this is one of the, my favorite sci-fi is, is The Hitchhiker's Guide to the Galaxy. I think you would like that. It's very funny. Uh, but anyway, he always said the, the secret to life was forty-two. I, I'm gonna go back to my answer, which I believe is not a cop-out, but is truly the answer, the secret to life. Is partly, at least, in the search for the secret to life. It is the curiosity, it is embracing learning and new experiences and trying to figure it out. It's the arrow that we were talking about between the question mark and the exclamation point. The arrow is the meaning of life.

• 59:00Ryan Holiday?

  Well, if you said that puzzles were asking, or puzzles were about seeing things from a different perspective, then I think the ultimate answer to this question is Viktor Frankl's In Man's Search for Meaning, coming out of the Holocaust, he says, you know, "We ask life, you know, we say outwardly, 'What is the meaning of life?'" As if someone else can tell us there's some objective answer. And he's saying, "Actually, we get it wrong. Life is asking us the question, right? Like, what is the meaning of you, right? What's the meaning of your life?" And he's saying, "Our actions, the way we live, that's the answer." So instead of thinking of it as this thing that you pose,

• 59:41Ryan Holiday?

  it's instead something that you have to answer with the choices you make and the person you choose to be. I think that is a kind of a beautiful, but also kind of mind-blowing way to think about it.

• 59:56Speaker 01

  Yeah, that is great. And yeah, like you say, it's thinking of a different perspective. I also think that when you ask that question, one of the first things you could ask is, "What is the meaning of meaning?" Because the word "mean" has dozens of definitions. You know, it can mean nasty, it can mean a type of average, it can mean cheap. So we've got to ask ourselves, "What is the meaning of meaning?" Before we ask ourselves, "What is the meaning of life?"

• 1:00:23Ryan Holiday?

  Or you could take the sort of Clinton lawyerly approach and ask, "What does 'is' even mean?"

• 1:00:28Speaker 01

  You know, he always gets crap for that. I think, I want to defend him. You know, obviously, he was a sleaze ball and did some, you know... But that sentence, I don't blame him for that sentence, because I do think that we should think about what is the meaning of "is" in more situations.

• 1:00:47Ryan Holiday?

  I agree. Well, that's an amazing, totally inconclusive place to cut this off. I love the book. I love all your books. And I think we've known each other like 10 years now. I was just thinking about it. It's pretty crazy.

• 1:01:01Speaker 01

  Oh, yeah. No, I love. I will say, one of the highest compliments anyone ever paid was, you and I were staying at a hotel in Canada, I think Toronto, and I had, we both went to the gym, and I set up a desk, my treadmill desk.

• 1:01:17Ryan Holiday?

  Yeah, you set up a walking desk of the treadmill.

• 1:01:19Speaker 01

  Yeah. And you were like, that is awesome. And, you know, instead of making fun of me, which is what I think most people would do. And it just, it gives me joy. I think about it. I mean, I'm on the treadmill every day, working, and I often think, hey, Ryan Holiday says that this is a good thing. So.

• 1:01:37Ryan Holiday?

  Whatever. I respected the dedication and the insistence on whatever works, you know, it's like, whatever, whatever works for you, man. That's what I'm good with.

• 1:01:47Speaker 01

  I love it. Well, thank you, Ryan. That was a pleasure.

• 1:01:52Ryan Holiday?

  All right, cool, man. We'll talk soon.

• 1:01:54Speaker 01

  All right, great.

• 1:01:58Ryan Holiday?

  Thanks so much for listening. If you could rate this podcast and leave a review on iTunes, that would mean so much to us, and it would really help the show. We appreciate it. And I'll see you next episode.