The Daily Stoic - AJ Jacobs on the Enduring Power of Puzzles and Memento Mori

Episode Date: May 14, 2022

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.

Hey, prime members, you can listen to the Daily Stoic podcast early and add free on Amazon music. Download the app today. 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, and most

importantly to prepare for what the week ahead may bring. Hi I'm David Brown, the host of Wundery's podcast business wars, and in our new season for what the week ahead may bring. 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 obstacles away is coming out. I think might have been growth echo. I was in Toronto, I was giving a talk as it's talk called Mastermind Talks. It had been to many times put on by my friend Jason Gainard. 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. Anyways, I went up to the hotel gym to work out 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 AJ Jacobs, today's guest. And it makes sense that he had this rather strange work set up 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 sold a bazillion copies, been turned into TV shows. He's a favorite of my friend Tim Ferris, a favorite of mine. He's an editor at large at Esquire magazine, a commentator on NPR, economist 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 dailystoke.com a couple years ago where he, it was all about gratitude and he went to go express 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. AJ 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 cross-worder. And this is what inspired his new book, The Puzzler, One Man's Quest to solve the most baffling puzzles ever

from crosswords to jigss to the meaning 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 AJ'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. Chronicles is journey to understand the enduring power of puzzles, why we love them, but 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 going to 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, It's All the Most Baffling Puzzles Ever from Crosswords to Jigsaw's To The Meaning of Life. You can check out his book, The Year of Living Biblically, The Know It All, Drop Dead Healthy, Thanks 1000. It's all relative. It ventures up and down the world's family tree. We look into geneogy, and a bunch of his articles on Esquire enjoy this episode with the one and only AJ Jacobs. 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. That's it, 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, yeah, everything's a puzzle. Nice to see you. Nice to see you. Nice to see you. Nice to see you. Nice to see you. Nice to see you.

Nice to see you. Nice to see you. Nice to see you. Nice to see you. Nice to see you. Nice to see you. Nice to see you. Nice to see you. Nice to see you. Nice to see you. Nice to see you. Nice to see you. Nice to see you. Nice to see you. Nice to see you. Nice to see you. Nice to see you. Nice to see you. Nice to see you. Nice to see you. Nice to see you. Nice to see you. Nice to see you. Nice to see you. Nice to see you. Nice to see you. Nice to see you. Nice to see you. Nice to see you. Nice to see you. Nice to see you. Nice to see you. Nice to see you. Nice to see you. Nice to see you. Nice to see you. Nice to see you. Nice to see you. Nice to see you. Nice to see you. Nice to see you. Nice to see you. Nice to see you. Nice to see you. Nice to see you. Nice to see you. Nice to see you. Nice to see you. Nice to, 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.

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 out how hard I can blow this off without getting in an argument instead. You know, so that's the real puzzle for me. It's like, how can I not participate in something that borrows me and then also avoid getting in an argument? Well, you infer the worst possible answers so that she knows never to ask you again. That's one solution. 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, they're actually figuring out of like weird numeric puzzles and stuff. Right.

But like what I've always not liked about sci-fi is like when I wanna get like immersed in a world, I don't wanna have to go like, okay, wait, is there gravity here? And like who are these ghouls or gov? 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. I you know what I am way. I'm not gonna argue that I prefer the the history I love partly because I love seeing how horrible life was and it feels a little better and we've talked about that But yeah, I don't think you need to love sci-fi, to love puzzles. As I say, you know, puzzles are, I seriously think that a lot of your life has been a putt. You figured out one of the many solutions to life's puzzle with stoicism. I mean, that's a very, that to me is the biggest puzzle is our mind. 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. Well, I want to talk about the, I want to talk about the big questions

because the, 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 using puzzles to refer to like games, what am I missing by not being interested in games? Well, to me, I think there are so many benefits, and I'm not gonna 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 Ferris, 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, you come to a puzzle and you are just baffled, you try a hundred 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 in the theme of my career as experiments. And puzzles are basically just one big experiment. Are video games puzzles in your mind? Oh, yeah.

I mean, first of all, there are video games that are very puzzling, 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 Machikaji 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. You've got to, you can't be all about the exclamation point,

because you may never get to the exclamation point. So I think it's a more poetic way of saying, love the journey, not the destination. Yeah, my son's obsessed with Minecraft, and which is obviously this sort of weird, puzzling sort of world-building game. But what I've been, like there obviously this sort of weird, puzzly sort of world building game. But what I've been, 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's only six. And so he wants to 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, I wanna watch this channel. And it's like, okay, well, what sound does it start with? And then we can work through what letters go to spell that thing that he wants to look up. So I guess if we have this sort of expansive definition as to what is a puzzle, maybe 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. So I probably started playing video games when I was like 12 or 13 and all my friends were like, you actually the opposite, I guess you're happy about that. 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. I'm like, oh, I like, that just, I was just never into that. I never, I never figured it out. So I 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, I'm sure it's fun. But like, I feel like the, I, I have to imagine part of the reason

that puzzles are fun is one has some aptitude for, like people who are just horrible at them, probably are having less fun than people who are good at that. Well, yes, 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 can barely find my house if I'm three blocks away. So I'm not good at the Rubik's view. 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. Yeah, it's like probably like learning languages like the earlier you do it the better, but you can do it the better, but You can do it any the age. I feel like this is one thing as someone was asking me something about like the city I live in which is Austin and I was like you have to understand I

Move to Austin when I was like 28 after having lived in a lot of other cities I have no conception of how the city works or is laid out. 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 for Southeast Austin, versus, you know, like, I don't get how it works. I think there's cross, there's no zombie apocalypse and the internet stays around so you can find your way. Yeah, no, I'm the same way. I have terrible.

Even though I have lived in New York City all of my life, I still can't find my way. 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. 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 and I wait in the line that goes quickly, I like, I have to say to myself out loud, remember this, you idiot, like there, there are times when the 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. 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. 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. 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. 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 the themes of the book as it's an ode to curiosity.

I said curiosity and gratitude, my two favorite human drives. And he had a great quote about curiosity that on a 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 take the most stereotypically boring topics, like accounting or something, I'm sure that if I scratch the surface, it would be fascinating. Because it's not just about numbers,

it's about people and their businesses and passion and love. And it is, everything can be interesting if you can just ramp up your curiosity. So that's a lot of fun. And also, it's interesting that it's interesting to other people. So if it borers you and you're like, I don't get 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 in account or whatever. 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. 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 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 you believe? Why do I believe what I believe? Is there any way to change our minds, any evidence is there, 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 the phrase that I picked up that I love is don't get furious get curious so the puzzling is sort of a way to encourage that curiosity sort of a way to the Baby Mrs. Kiki Palmer podcast. I'm putting my friends, family, and some of the dopest experts in the hot seat to ask them the questions that have been burning in my mind. What will former child stars be if they weren't actors? What happened to sitcoms? It's only fans, only bad. I want to know. So I asked my mom about it. These are the questions that keep me up at night, but I'm taking these questions out of my head and I'm bringing them to you. Because on Baby This Is Kiki Palmer, no topic is off limits.

Follow Baby This Is Kiki Palmer, whatever you get your podcast. Hey Prime members, you can listen early and app free on Amazon Music. Download the Amazon music app today. Yeah, like Socrates have 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 is the grocery store do 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

read like there's 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. There's some reason that it is that way. And I think oftentimes we're so close-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. 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 in people in them, 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 they're logic, because they are going to have logic, even if it's crazy logic. Well, and it's unlikely, I think the epistematic humility is, it's unlikely that this thing that I have thought about for seven seconds, that 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's, 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. Right. I mean, that, I love that is sort of the, the, the, uh, one size fits all answer to almost any big question is, well, it depends. It's complicated. And people that drives people crazy. But it's true.

There's not, you know, you've got to delve in and look at the nuances on anything. And that, you know, again, that comes back to curiosity and not having this black and white picture of the world. 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 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, that's not to say they are sort of unthinkingly. That's not to say they're doing a good job or that it's perfect, because I think Twitter is a cesspool. But these obvious off-the-cuff things

that you just experienced as a user, like, hey, why isn't there an edit button, or why isn't this? Like, some of the smartest people in the world have been working at this company for 10 years. Like they they they've thought about this. It's it's like it it's complicated as one answer. The other is like, let me tell you all these other things that you don't know are happening behind the scenes. I heard a good like I heard that like when you become

president, 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. Right. Right. Right. Right. Right. It seems simple, but like that's because you don't have the full story. And that's the puzzle. Right. That is a huge puzzle. Yeah. You don't know what you don't know as people say. And also, you know, it relates to who said you don't have to have an opinion. Marcus really? Yes. Yes. Right.

With the Twitter and Elon Musk, I have my gut opinion, but I don't want to express it yet because I want to really think about it. That is another part of Stores' is in my love. We don't have to rush into it. Just I love, so that is another part of Stosis of my 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.

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 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 sound bite, 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, you can't, civics isn't, is it 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. 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? 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 I've been thinking about that a lot because civics, that is a huge word. That can mean a hundred different things. 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, RUN 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 a hundred things sure? You know I am I am you know pro capitalism overall

But I think there should be constraints so if someone says, you're messing with the free market, freedom, oh, that's great. It has a positive connotation. But it has many other means. What about the freedom to choose to shop at not a monopoly? What about the freedom to make a wage? So, to puzzles, word puzzles, I think are good in that they train you to look at the words very carefully. How's that? Did I get a word? Words matter, right? And if you're not someone that actually thinks about

what's happening, you can very easily be deceived or you fall for empty slogans. Again, Elon Musk thinks, Elon Musk is like, I'm a believer in free speech. I think 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 going to do that. And he's like, and I'm going to 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- Right. I think it's- That's so rebellion, yeah. Yeah, exactly. And so, in a way, propaganda and understanding what things mean, like slogan, this is a puzzle too. Like, what does that mean? What are they really saying?

Like, does that even make sense? Right. And you love puzzles, I knew it. I got you. Well, writing is a puzzle, right? Like, Mark Twain said, you know, or maybe he didn't say, And you love puzzles. I knew it. I got you. I got writing is a puzzle right like You know, Mark Twain said you know, or maybe he didn't say but whatever the quote is about the right word is the difference between lightning and lightning bug Right 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 tree is like, how do you say the thing most effectively with the fewest or the most or the best words? So I like puzzles in that sense. And yeah, I definitely, 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. Are you? Yeah, I just find it very, I don't know. It's solitary and depressing for me 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 that way I wasn't as miserable. I still prefer the research in talking to people, but it was better. What I love about, right, there is that expression, painters like painting, writers like having written, which I find to generally be true, but I do, like when I, 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 going to, is this book going to be three parts or two parts? Is it gonna have 15 chapters or is it gonna have six chapters?

Right, are they long chapters or short chapters? Like, what is the intro to each chapter look like? And once you crack that, 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. That's like walking without GPS. Right? Yes. Exactly. Well, I am totally with you. I am a huge structure, a hall like 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. Of course, you didn't do that. Yeah, I'm embarrassed. No, that is something I, because 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, did I rush it? And there was this, you know, I go, like right now, for instance, this is the first time

I've ever done this. 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, because now I'm thinking, well, okay, this chapter could go in the courage book, but is it actually an example of justice or self-discipline, right? And so like having to move things around, but once each book is published,

you now have fewer options. So it's like, you know, it'd be like doing a crossword puzzle or once you guess, like, you know, it's your stuck or something, right? Like 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 having to then be conscious of not just this singular project, but how it fits in a larger universe is something I've never, never done before. Yeah, that is, that's a good challenge. Well, it's, I had 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 too am battling regret.

I am 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 that is just, it's not helping me. It's not helping the world. So what would the stoic response to regret be? Well, 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 addition or whatever, right?

So first off, you have to actually do the math. 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. The real thing to take out of it is, well, what factors contributed to me making that wrong decision? I'll give you an example, something I forgot.

So I have, the obstacle is the way tattooed on this arm, and you go as the enemy tattooed on this arm. Now, I went to two different tattoo shops, and I'm not really a super visual person, so I didn't remember what the font was on the 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? Right. Every, every day I look at it and I go, God, damn it. What was I think? Like, you know, right there, day I look at it and I go, God damn it. What does it feel like? You know, right there.

You can't escape it. You can't put it in the closet, Song You Skin. Like, three, you know, basically I rushed a decision. 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, right? 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.

So interesting. So 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 account and adjust for that? So if it can have an effect on the future, then it is worth thinking about it. 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. Sure. 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 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 53,999th piece, and the last one was missing. And he just freaked out, you know, he couldn't sleep, he couldn't need, he tore up his house, he tore up his vacuum cleaner. So my hope was, for the end of the story, that he just left it like that. And as like, here is a, like, you know,

sort of a tribute to the fact that like, 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,

can you imagine though, like he spent like a year getting to that point? I think what happens is often, often the thing that makes you want to do puzzles or write something or do like be great at something is, uh, this is where the stoke virtue of temperance comes in. It's hard to turn it off, right? Like it's hard to not be, 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. Like, for instance, the Apple Watch is kind of a gamified puzzle. It turns exercise into a puzzle, right? I have an exercise goal, a standing goal, an active calorie goal, and I have to sometimes actively decide that I'm in charge and not the watch.

You know what I mean? Because it'll be like, well, if I don't get to break a thousand or whatever the thing is, I'll lose. But then it's like, what am I winning? I don't get any points here. Who's in charge here? Right. They're not going to throw me a parade.

This is a made up game. And I have to go, you know what? 900 out of a thousand is still an A. You know, like, it's not all or nothing. I bet to him to not do that final piece was the same as not doing it at all. You know what I mean? It was like undone by missing a piece instead of being 99.9% complete. He saw it as a failure. 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 because 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 puzzles. I do think puzzles teach you to think probabilistically because you cannot be good at crosswords. You cannot be certain that this is the answer. You have to write it in pencil. Like some people are like, oh, I do crosswords in pen. And that's fine. You know, you're cool. You're macho. But

I do crosswords and pen and that's fine. You're cool, you're macho. But actually, it's much better. I think in life and in puzzles to say, I think 80% chance this is the right answer. But let's keep in mind it's not always the right answer. So, yeah, to me, that is the way out of black Black and White thinking which is really screw this up big time and speaking of which weren't you an answer in the New York Times Crossword puzzle? I was and actually I'm interested in the stoic version of this because here here's the story I've always been a word nerd. So about five years ago. I

Was the answer to one down in the New York Times Cross repuzzle. And is that, by the way, is there a status into like where you are? Is one down like, is that, is that, is that, is that, is that, is that, is that, is that, is that, is that, is that, is that, is that, is that, is that, is that, is that, is that, is that, is that, is that, is that, is that, is that, is that, is that, is that, is that, is that, is that, is that, is that, is that, is that, is that, is that, is that, is that, is that, is that, is that, is that, is that, is that, is that, is that, is that, is that, is that, is that, is that, is that, is that, is that, is that, is that, is that, is that, is that, is that, is that, is that, is that, is that, is that, is that, is that, is that, is that, is that, is, is that, is that, is that, is that, is that, is that, is that, is that, is, is that, is that, is that, is that, is that, is that, is that, is that, is that, is that, is that, is that, is, is that, is that, is that, is that, is that, is that, is that, is that, is that, is that, is that, is that, is that, is that, is that, is that, is that, is that, is, is that, is that, is, is that, is that, is that, is that, is that, is that, is that, is that, is, is that, is, is that, is that, is that, is that, is that, is that, is that, is, is that 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 in my life. My kids being born, that was pretty good, but I'm in the New York Times Cross proposal. And then my brother-in-law emailed me, he did congratulate me, so I wanna get that out there. But he also pointed out that I was in the Saturday New York Times Cross repulsed.

And maybe your wife can tell you that 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. This is proof you are totally, no one knows who you are that you're obscure. And it's like, if you get in a month, it seems to me that- It just seems to me that-

It just seems to me that you're a popularity. Right, it was proof of my irrelevance is his point. And I was devastated. And 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 Joe Biden or Lady Gaga, those kind of people are in a two. It's not Monday, but Tuesday is still pretty.

So then he did that and that was the truly greatest moment in 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, but I would say even that you were that when you were just out doing what you do, that your dissatisfaction or your foe hurt with your placement, the fact that that was picked up by an editor of the New York Times is also a state, 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? That's a pretty big statement, right? Oh, I like that spin. I like that. So I also think it's one of the things as a writer, I do trying to do is to create a story out of pain. I know a lot of the times it's a false story or at least sort of selective, 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 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 and take control of it, and I think that, you know, even as long as you're aware that you're kind of doing that and don't delude yourself that that is the ultimate reality, I think it's really good for my mental health anyway. 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. That's hilarious, very ironic. That's a tough one. What do you do about that? I know. I thought it was pretty cool. No, 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? You know, are they, are they implying that I'm well known or not well known? So one of the things you talk about is like the joy of optical illusions, which are another kind 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 you realize, oh, there's two ways of seeing this

same image. Like the image is static, 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 stoicism. Epic Titus 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. It does kind of humble us that like, oh yeah, what my initial reaction is was wildly off base. Yeah. Well, that is great. I mean, it's what you say all the time. You can't control what happens to you, but you can control how you react to it. And 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 feeling jittery before a speech, am I, is that because I'm nervous or excited? I just tell myself it's excited. And then I'm in a better position. 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 because 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 tell an inspiring story. So framing to me is absolutely, and I love that the Stoics were behind this idea as well. 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 an obscene image, right?

And so it's like, I saw that one. Yeah. So it's like, do you have a dirty mind 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 make the decision. You're, the Stokes also say, we're complicit when we get offended. Right?

So the idea that like the story we tell ourselves, 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 world around us. Right. That is so. I mean, that reminds me of why I think about words a lot partly because I did this book on 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're just a reflex. You hear that word.

You have no control. And you are immediately set off into a spiral. So I am very much against, I think there's a huge problem with vitriol and people using words in terrible ways, but I don't think that we should call it triggering. We should come up with a more active and empowering way. Because to me, 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 just feel you're taking away some of the power that you could express in trying

to stop these things. 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're a powerless automaton that does not control whether it upsets you, whether you're hurt, whether you can deal with it or not. 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 find like when people get really upset

about microaggressions, like I understand, you should try to be sensitive, you don't wanna try to hurt other people, you wanna think about how your actions affect other people. 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 you are saying that this is the smallest aggression, as the least amount of aggression possible, right?

Like you were saying that this is the smallest aggression, the smallest inflection of pain or distress possible. And then you're acting as if it is a regular aggression, right? And so I think the words we use are illustrative and oftentimes we use those words with no, or 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 is.

It's kind of strange how people use language. 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,, that is 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, 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. I think that's right. I think that's right. I was thinking about the big question of the book, which is a 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, what about this, why, what about this, what about this, right? Like, to me that 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 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? I think 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 is inherently in philosophy the pursuit of answers to life's most difficult puzzles. Absolutely. Yeah, I love that and that's like what I was saying when I talked to someone who's on the other side of the spectrum, the puzzle is why do I believe what I believe and why do they believe what they believe? 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 part of my answer is the meaning of life is partly in the search for meaning of life at the end. 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 in the process. So that I totally agree with. And philosophy and puzzles, they're very similar. Well, Seneca says that the ultimate puzzle in life is as 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 resources much more precious than the other. I love that. I'm going to have to think about that. I don't have an opinion like workers really is right now, but I'm going to 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 one of our huge blind spots is just how fast time goes and how life can be over in a flash. And that's why we've talked about this. I love Momentumori. I'm a huge Momentumori. And actually as part of this puzzle book, I kind of created a Momentumori in puzzle form because I teamed up with this designer,

a Dutch puzzle designer, he's crazy and he makes these, they're mechanical puzzles like where you twist things and rubics you. 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 Disciilion 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 this because to me it's what's called a generation puzzle. So you're passing it down from you, to your kids, to that, to their kids, and no one's going to 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 think about people in the future and try to make the world better for them. But be the momentum worry. We're only here for a little bit. Let's try to make the most of it. Yeah, it's that you can spend your whole life for rowing your brow at this puzzle, but it will outlive you and all of your descendants. Right. Many times over, there's this humility in that.

Right. Yes, it is very humbling. And I think that's a good thing that puzzle sometimes do is humble you. We just did one for daily stoic that's, it's a, 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 you have left, but how much have you already died? Oh, I love that. Because actually that is another thing I

talking 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 wouldn't go into use. I'll give you credit. Or, uh, this no excredit. All right, I'll give Santa a quick credit. 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 we fundamentally,

you brought capital, capitalism is paying with your labor, with your life, for money. But we don't think about,'t think about the exchange going often only in one direction. I give me $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. Yeah, that was great. Or to this thing that I regret.

You said five minutes. Five minutes 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. Absolutely. Yeah. I mean, it's funny. One, the first, the reason I met Tim Ferris was our mutual friend was that I wrote

an article called My Outsource Life. I tried to outsource everything. I outsourced my phone calls, my emails, but one of the other things I did, I hired this lovely woman in Bangalore, India. One of the things I asked her to do for me was, can you worry for five minutes a day on my behalf. And because 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, and I said, I'll even worry about something in your life for you, because then it doesn't have the emotional heft.

So outsourcing your worry, I think, is, believe it or not, that was one of the most effective things in that experiment was outsourcing my worry, having someone else worry for me. And I, as you say, it's just five minutes, but five minutes a day, it adds up. So I am a big fan of either trading worries or just asking someone, you mind worrying about this for me? So have you solved the riddle though? What the meaning of life is? We figured it out. Well, there's the Douglas Adam. Do you like, oh, you don't like sci-fi?

I don't like sci-fi. This is one of my favorite sci-fi is the was the Hitchhiker's Guide to the Galaxy. I think you would like that. It's very funny. But anyway, he always said the secret to life was 42. I'm going to 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. 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 the arrow that we were talking about between the question mark and the exclamation point that arrow is the meaning of life well if you said that puzzles were asking, or puzzles were about seeing things from a different perspective, then I think the ultimate answer this question is Victor Frankl's, in Mancerns for Meaning, coming out of the Holocaust, he says, we ask life, 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 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 what what 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 is this thing that you pose, 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 kind of a beautiful but also kind of mind blowing way to think about it. 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 can 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 meaning before we ask ourselves, what is the meaning of life? Or you could take the sort of clinton, lawyerly approach and ask, what is is even mean? You know, he always gets crap for that. I think, I want to defend him. Obviously, he was a sleaze ball and did some, 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. 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. 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

and Canada, I think Toronto and I had, we both went to the gym and I set up a desk, my treadmill. Yeah, you set up a walking desk of the treadmill. 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 whatever. I respected the dedication and the insistence on whatever works, you know,

it's like whatever works for you, man, that's what I'm good with. I love it. Well, thank you, Ryan. That was a pleasure. All right, cool, man. We'll talk soon. All right, great. 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. Hey Prime Members, you can listen to the Daily Stoke early and ad-free on Amazon Music, download the Amazon Music app today, or you can listen early and ad-free on Amazon Music, download the Amazon Music app today, or you can listen early and ad-free with Wondery Plus in Apple podcasts.