Jeff Waldman on Craftsmanship, Memento Mori, and Developing Competence | It’s Not That You Read, It’s How You Read

Ryan reads today’s daily meditation and talks to Jeff Waldman about his new book “Tools: The Ultimate Guide” (which you can get a signed copy of at the Painted Porch), the Stoic concept of Memento Mori, why it’s so vital to develop competence, and more. Jeff Waldman is a maker, builder and creator with a talent for connecting with interesting people and even more interesting projects. With the help of their friends, he and his partner designed and hand-built their own cabin and communal getaway in the Santa Cruz Mountains of California. You can often find him tinkering in his shop where he works to build similar experiences for many others from different walks of life. Jeff’s book, Tools, launches this week. This is the book for answering all your tool questions, gaining knowledge before hiring a professional, or rifling through just for the joy of learning something new about the objects that shape our world. If you want to become a great reader, the Stoics can help. We built out their best insights into our Read to Lead: A Daily Stoic Reading Challenge. Since it first launched in 2019, Read to Lead has been our most popular challenge, taken on by almost ten thousand participants. Today, we’re excited to announce that, for the first time ever, registration to join the 2022 live cohort is officially open. Kion Aminos is backed by over 20 years of clinical research, has the highest quality ingredients, no fillers or junk, undergoes rigorous quality testing, and tastes amazing with all-natural flavors. Go to getkion.com/dailystoic to save 20% on subscriptions and 10% on one-time purchases. The Jordan Harbinger Show is one of the most interesting podcasts on the web, with guests like Kobe Bryant, Mark Manson, Eric Schmidt, and more. Listen to one of Ryan's episodes right now (1, 2), and subscribe to the Jordan Harbinger Show today. Talkspace is an online and mobile therapy company. Visit talkspace.com and get $100 off your first month when you use promo code STOIC at sign-up. That’s $100 off at talkspace.com, promo code STOIC. Right now, when you purchase a 3-month Babbel subscription, you’ll get an additional 3 months for FREE. That’s 6 months, for the price of 3! Just go to Babbel.com and use promo code DAILYSTOIC. 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, FacebookFollow Jeff Waldman: Website, InstagramSee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

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

• 0:06Ryan Holiday?

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

• 0:46Ryan Holiday?

  As you know, the human body is mostly water. What you didn't know is that everything else in your body is basically 50% amino acids. And these building blocks are essential to health and fitness in life. And if you like to move, which I do, amino acids are essential. And that's why Kion Aminos is a fundamental supplement for fitness. You can drink them every day for energy, to build muscle and recover faster. It's got the highest quality ingredients, no fillers, no junk. Every product undergoes rigorous quality testing. It tastes amazing with all-natural flavors. If you want more energy, lean muscle, faster recovery, you have to get Kion Aminos. And you can save 20% now on subscriptions,

• 1:30Ryan Holiday?

  or 10% off one-time purchase. Just go to getkion.com/dailystoic. I'll spell it out for you. That's G-E-T-K-I-O-N.com/dailystoic. To get this awesome supplement for fitness, that's Kion Aminos. And check it out.

• 1:48Ryan Holiday?

  It's not what you read, it's how you read. We tend to think that how much we read is proof that we're making progress. We like to show off our library. We listen to audiobooks on 2 or 3X speed. We think less is more, quality over quantity, not with books. We think that because reading is a good thing, wouldn't more be better?

• 2:12Ryan Holiday?

  But the answer is no. Not all reading is created equal. As Epictetus said, "I cannot call someone hardworking knowing only that they read, even if all night long is added. I cannot say it," he says, "not until I know the focus of all this energy." Of course, spending hours or days in front of books is better than, say, hours watching stupid internet videos. But it can still be a waste of time. "Far too many brains," Seneca said, "have been afflicted by the pointless enthusiasm for useless knowledge." To be a great reader, it is not enough that you read, it's how you read. It's not about reading to impress people or for mental gymnastics.

• 2:56Ryan Holiday?

  It's not about pouring inputs into your brain. It's about getting better. It's about filtering what gets into your brain. It's about finding useful knowledge, knowledge you can use in your actual life. It's about putting the information up to the test, examining it, seeing how it applies to your life, asking yourself how you might use it and what it's prompting you to think. Well, and if you want to be a great reader, the Stoics can help. And over the years, we've built out their best insights into what we're calling the Read to Lead Daily Stoic Reading Challenge. And since it first launched in 2019, Read to Lead has been our most popular challenge here at Daily Stoic, taken by almost 10,000 participants.

• 3:39Ryan Holiday?

  And today, we're excited to announce that for the first time ever, registration to join the 2022 cohort is open. It's going to take place across five weeks, two emails a week, 30,000 words of content about being a better reader. Learn how to get the most out of your reading, how to read more, how to find books with the potential of changing our life, how to think more critically, how to find more time to read, how to digest books above your level, and a lot more. And look, there's going to be weekly live videos with me, written my fair share, books about Stoic philosophy. My reading list newsletter goes out to almost 300,000 people.

• 4:22Ryan Holiday?

  And videos about my own reading habits have gotten millions and millions of views. And I think you're really going to like, this is the practice that I use to be a better reader. You'll become a better reader, you'll build a better reading habit, you'll get to learn. From me. It's going to start on Monday, May 17th. We all move this course together at the same time. Registration is now officially open, but registration will close on Sunday, May 16th at midnight. That's your last chance to join us all as part of this cohort. Participate in the sessions with me. So sign up at dailystoic.com/reading.

• 5:04Ryan Holiday?

  Hey, it's Ryan Holiday. Welcome to another episode of the Daily Stoic Podcast. When I dropped out of college, I moved to a house in Los Angeles. Crenshaw in Venice or thereabouts, I think Arlington in Venice. I'm trying to remember the exact address. Let's just say it was not a nice part of town. Like one time, a dog, clearly tragically part of a dog fighting ring, just walked into our front yard, which was concrete and just died. So that's the kind of neighborhood it was. Anyways, I lived on a mattress. So I was working for this author and he was like, come live with me.

• 5:45Ryan Holiday?

  I'll teach you how to be a writer. You work this talent agency in Hollywood, which is what I was doing. And he was like, I got a place for you to stay. So I remember pulling away from Samantha, my wife's apartment in Riverside for the summer, not fully knowing I was dropping out yet, but I moved to LA, you know, thinking I'm, I don't know. I had some, some vision that it was going to be like the television show Entourage, not fully understanding the economics of, of, of the author world. Anyways, I get there and they point to me that they have a mattress for me on the floor in the living room. And I was later informed that they'd found the mattress outside in said disgusting neighborhood, but it was enough for me and it set in motion my whole career and life.

• 6:30Ryan Holiday?

  And I wouldn't trade that experience for just about anything. But the person in the bedroom across from the mattress that I was living on was my guest today, the one and only Jeff Waldman. Today, you might know him as a maker and builder and creator. His incredible Instagram account, Elevated Spaces, makes some cool ass shit, houses.

• 6:56Ryan Holiday?

  Cabins, tree forts. And in fact, if you have followed my Instagram or watched the Daily Stoic videos, you might have seen the the tree fort on my farm here in Austin, Texas. Jeff helped me build that a couple of years ago. But if you have been to the Painted Porch, you've definitely seen Jeff's handiwork. Because in February, Jeff came out and apropos of his new book, Tools, The Ultimate Guide, 500 Tools, an ultimate guide, basically a history and breakdown of how some of the great tools of history were made, how they work, what they do, how to think about them, how to use them.

• 7:36Ryan Holiday?

  It's his first book. It's a spectacular book. I think a great dad gift, a great grad gift, a great coffee table book, a really fun book. Anyway, apropos of that book, he'd actually come out to Austin as I was thinking about doing the bookstore when he helped me build the tree fort. And I showed him the property and he was into it. And he was like, let's come out and do a project together. That's who Jeff is. Jeff's like, what's a cool thing you're trying to do at your house? Let me come over and help you do it. He's just like a great friend, great person, very different than I remember him 15 years ago, as we'll talk about in today's episode. But anyways, he came out and I had this crazy idea. I wanted to do something extra cool for the story. So you've seen our cool like book tower, which is like 20 feet of books made out of brick,

• 8:19Ryan Holiday?

  books stacked like bricks, going all the way up to the ceiling along the fireplace on the right hand wall of the bookstore. I wanted to do something even cooler than that. And so I said, Jeff, wouldn't it be cool if it looked like a tree was growing out of the floor of the bookstore, all the way up to the 20 foot ceilings and then out the ceiling. And Jeff being Jeff and Jeff knowing his way around tools, he was like, I can figure out how to do that. And so he came out and we just had an awesome time. We found this huge tree that fell in the ice storm in 2021. And we chopped it up into pieces. We had to use all the tools he's talking about chainsaws and saws

• 8:59Ryan Holiday?

  and drills and hammers and everything else you can imagine, ropes and winches, levers. And we Moved this thousand pound or so tree in pieces. The actual tree was about 30 feet. We cut it down to about 17. It comes up from the floor. It goes into the balcony underneath some of the offices, grows through the balcony, and then up and out through the ceiling. And some of them reach straight out into the store. It's just one of the coolest things that I've seen, and I'm just so proud of it. Every time Jeff comes, he makes me proud of what I'm capable of doing that I don't feel like I'm ordinarily capable of doing. And I'm just so excited to have him on the podcast.

• 9:43Ryan Holiday?

  Jeff Waldman's new book, Tools, The Ultimate Guide, it features over 500 tools. You can hear, those are the tabs of the book that he sent me the copy and he tagged all the important parts. This is a great book. He's a great dude. You can go to his website, elevatedspaces.ca. You can follow him on Instagram, @elevatedspaces. And you may be remembering Jeff vaguely, because Jeff is in the first chapter of Trust Me, I'm Line. He did this other awesome thing where he went up and he set up swings all over California, like these rope swings, this sort of really low, like no frills swings, like two ropes, a piece of wood. And he just put up these swings and people could swing on them and they helped them

• 10:28Ryan Holiday?

  recapture their childhood. And I got to show him how I worked. I helped do some of the marketing for it and ended up blowing up, becoming this whole thing. It became an international commercial for Coca-Cola and blew up all over and set Jeff on this cool path that ended now in this book and building the tree in the bookstore. I am really excited for you to check out this book. I think we have some signed copies in the Painted Porch. If you want to check it out, you can get the books anywhere books are sold. It's published by Chronicle Books and it's fantastic. Tools, The Ultimate Guide. Check out Jeff's website, elevatedspaces.com. He also sells cool plans for his different cabins. So if you're thinking about building a cabin on your property, you want a tree for it, I know it's kind of a niche thing, but it's a great business for him.

• 11:13Ryan Holiday?

  You can check those out too and follow him on Instagram, @elevatedspaces. And come check out his handiwork here at the Painted Porch. It will hopefully be here for a very long time. And here's my conversation about craftsmanship, memento mori, embracing change and developing competence, which I think is a critical part of confidence, with the one and only Jeff Waldman.

• 11:40Ryan Holiday?

  I was trying to think when we met each other. So it would have been 2007 or was it 2008? Something like that, right? It was at a PF Chang's or something?

• 11:49Speaker 01

  It was 2007 or maybe even 2006.

• 11:54Ryan Holiday?

  Maybe, maybe.

• 11:56Speaker 01

  It definitely wasn't 2008. By 2008, we're kind of into the swing of things movie wise. It was before that.

• 12:02Ryan Holiday?

  Right, we were already, yeah, we would have been living together then. I lived on the, on the pee stained dog mattress.

• 12:08Speaker 01

  Yeah, when you lived on the pee stained dog mattress, at what, what year was that? When did you leave college?

• 12:14Ryan Holiday?

  That would have been, well, so I left college after that, but that would have been the summer of 2007.

• 12:22Speaker 01

  Okay, I think maybe early 2007, possibly like late 2006.

• 12:27Ryan Holiday?

  That sounds right. That sounds right.

• 12:29Speaker 01

  So that's, how many years is that? Is that like 15 years?

• 12:33Ryan Holiday?

  Yeah, that's crazy.

• 12:34Speaker 01

  Jesus.

• 12:36Ryan Holiday?

  That's fair. That, that is, that is an insane, that is an insane amount of time. That's, well, it's also weird now, like, um, I don't know, as you get older, you're like, you're stopped. Like I had to ask Samantha how, how old I was the other day. I was like, how old am I again? But like, also that I could say something that's 15 years and that's not half or more of my life is also a new thing I'm having to think about.

• 13:02Speaker 01

  Yeah, I remember when I was a kid, my dad used to brag to me. He'd be like, oh, I've had this down jacket for 20 years. And it seemed at the time, I was like, wow, that seems like a really long time. And now I'm like, yeah, I think I've got like a bunch of stuff that's 20 years old.

• 13:16Speaker 01

  It moves fast.

• 13:17Ryan Holiday?

  You and I talked about Chuck Klosterman and he, I never, and I interviewed him, but he never talked about this in the book, I don't think. But like, when someone pointed out to me that the nineties, which is the subject of his new book, we are as distant from the nineties as the nineties were from the sixties. It's like, appallingly, uh, uh, hits you appallingly hard. You're like, whoa, okay, that is like crazy.

• 13:43Speaker 01

  Well, yeah, cause when we were kids, I mean, you and I are a little bit different in age, but I remember in the nineties being in like middle school. Folks were really into that late 60s, 70s stuff and it felt decidedly retro, entirely from a different era. And to think about it now has been like, oh, that was just people being into what was 20 years ago. It's the same thing as the 90s now. Like, I don't know, it just, it makes me look at that past very differently. It felt like we weren't just looking back on a couple of decades because that's what everyone always does. It felt like we were looking back on a very specific time and place in American culture where you're like, oh, this is the retro time. But like, no, it's just a couple decades back.

• 14:23Ryan Holiday?

  But also, I feel like the world seemed like, and this is one of the things he talks about in the 90s, which is that like, the 60s to the 90s felt like an unfathomable gulf between them. Like, these are different worlds, right? Like, the 60s was still a part of the world where the 40s was recent. Do you know what I mean? Like, it's felt so long ago. And then like, 90s, 2000s, 2010s, those, those do blur together in a way that it doesn't feel like, even 9/11 doesn't feel like some moment where it was like, although the geopolitical stage changed, it doesn't feel like how the world was constituted and what it was made up by, that that changed.

• 15:09Ryan Holiday?

  Like, things are still mass-produced, things are still digital, you know, like, that is, like, it feels more constant in that sense.

• 15:17Speaker 01

  Yeah, I don't remember if he used this word in the book, but it was basically alluding to like, the homogenization of culture over the past couple decades. And it's like, it really does blur together. The caveat to that, though, is that I remember thinking in the 90s, I was like, oh, man, it's weird that every era had a look to it and a certain fashion style. And we just don't. We just, our clothes look totally normal. But now, when you look back 20 years, you go, no, those clothes definitely look like the 90s. So I wonder if in looking back, what feels very homogenized now will feel a lot more stratified in the future.

• 15:51Ryan Holiday?

  Yeah, no, funny enough, the Stoics do kind of talk about that. He talks about like, how different these names sound. You know, he's like, naming off the different emperors and they're like, the most powerful people, like how the names sound so anachronistic and weird, even though, like, they were, they thought that they would be remembered forever. And it is weird, like, how the things that seem like a big deal. Like, just with the passage of not that much time, suddenly don't feel like being such a big deal. And then the things that you thought were normal, as you're saying, like with clothes, you're like, oh, I'm, I'm, I'm just a normal person. I'm wearing a, a regular shirt and regular pants. And you don't realize the, the degree to which the things you're taken for granted are

• 16:36Ryan Holiday?

  actually the products of trends and fads and of the moments. And then you look at the pants 20 years later and you're like, that's so lame. Like, that's like, I was trying so hard, even though I thought I wasn't trying.

• 16:49Speaker 01

  Sure. Yeah. I mean, it's hard to see that whole fish tank when you're inside of it, I think.

• 16:54Ryan Holiday?

  But that's, but the other thing is like, okay, so 15 years ago, it doesn't seem that long ago. But then if you think about who you were, or I was 15 years ago, that seems as distant to me as the 60s. Like, I, I have no conception of who that person was, or was thinking or doing, because it's like another person to me.

• 17:15Speaker 01

  Yeah, that I agree with completely. Does that bring you shame? Like, does that make you feel negative feelings when you look back at yourself from 15 years ago? Or do you just accept it as, hey, it's, I'm a work in progress, it's all good?

• 17:29Ryan Holiday?

  That's a good question. I think it's both. There are definitely moments, as, as the word very much of the moment, there are definitely moments of cringe when I look back. Definitely with writing, like, it's also weird to me. So, Trust Me, My Mind, my first book, is, is, is 10 years old. This summer is 10 years old. And, and actually, Obstacle came out eight years ago yesterday, which is also, like, insane to me. When I read stuff that I wrote that long ago, the thing that strikes me, it's not that I feel shame, but I sort of feel like I was being way too certain, or like, like, I'm, I'm sort of embarrassed at the forcefulness with which I

• 18:12Ryan Holiday?

  held opinions and expressed those opinions, that now, in retrospect, since I don't agree with, I think, well, that was stupid.

• 18:20Speaker 01

  Yeah. Yeah. Any of those beliefs that you're binding too tightly to, it's like, you don't know anything. I I got into a little bit of an argument with a guy that I'm in this I've been in this group therapy thing for like 10 years and there was a guy in there that he was he was saying the truth is the truth and I know what it is and like because I was arguing that there's a lot of ambiguity in things a lot of gray area and it's some of this stuff is unknowable and he said no it's I know it for a fact and I said yeah but I've been in this group with you for like 10 years I remember eight years ago you had different stances on things and he goes yeah I was wrong then but I'm not wrong now it's like come on if you accept that you were wrong then then maybe you just shouldn't hold too tightly to those beliefs.

• 19:04Ryan Holiday?

  No, I think one thing reflecting on who you were in the past it should make you more humble and less tightly held to your opinions now because you're like oh it's like it's like okay you felt some intense amount of pain like you stubbed your toe you're like that passes right the same will be true with the opinions or the things that you're really worked up about because there's significance in the world changes you change the facts change whatever it is I I find certainty and arrogance do not age well.

• 19:37Speaker 01

  Yeah, yeah, I mean what positions could you possibly hold in your twenties that are just going to continually stand up yeah I going back to your cringe thing now I think sometime in the past five years I've gotten to the point where I can flip through photos and go through old emails and I can do it kind of peacefully.

• 19:57Ryan Holiday?

  Yes.

• 19:58Speaker 01

  But for almost my entire history up until about five years ago to even look at old photos or to look through old emails would make me cringe so hard that I would like close the laptop and like I couldn't even do it I couldn't revisit the past and the acknowledgement of like who I was and be like nope looking forward can't look back.

• 20:15Ryan Holiday?

  Yeah, the Stoics talk a little bit about being kind to yourself I think it's hard to look back at who you were and what you were doing and not be very judgmental in a way that you wouldn't be that judgmental if it was another person like if you're looking at an embarrassing photo of someone from the 90s you would laugh you'd be like oh that's so funny but you you're like what a loser you know like it's it's it's meaner when you look at it with yourself for some reason I feel like.

• 20:41Speaker 01

  Yeah, I mean, I agree with that, but the counter to it is that we often grant ourselves so much more latitude than we're willing to give others. Like, you'll judge, you'll judge somebody by a soundbite, or by a single wrong action, when you yourself, like, you know that you're a more complete picture, and that you would hope that nobody would judge you by the single screw-up thing you said on your friend's podcast.

• 21:03Ryan Holiday?

  That's true. We do that with sort of what they're calling cancel culture, which we don't need to get into a whole thing about, but like, like, like, the idea that, like, the person, like, the person that said this thing in a moment of anger in a private communication 20 years ago, that that is fully who they are. Do you know what I mean? And that you don't have tons of those skeletons in your closet. Like, it seems like in very, I remember there was this one, it was like the editor of Vogue, or Teen Vogue, or something, she'd like, said some racist things in like, emails or on Facebook when she was like, in college. And like, the main person who'd attacked her and gotten her fired, like, it turned out she also had done that, like, it's, it's, you know, it's that idea of not casting stones,

• 21:48Ryan Holiday?

  and reminding that, like, everyone was an idiot 10 years ago. Like, and you aren't, in 10 years, you will think of yourself as an idiot.

• 21:57Speaker 01

  Yeah. I mean, you knew me 10 years ago, 15 years ago, I was a real idiot.

• 22:02Ryan Holiday?

  Well, no, that's what I was, I was actually gonna ask you some version of the how do you think about it, because that seems so different, and we were both sort of, uh, very, we'd both inherited a set of certain opinions about how the world would work, and how things were gonna go, and then we both had our own sort of issues and demons that we had to deal with. How do you think back to who you were then, and could you have imagined that 15 years later, you'd be like, a builder on the internet who sells like, plans for, for exotic treehouses? Like, that's the, that's the other thing that's really humbling, is like,

• 22:38Ryan Holiday?

  Conceiving of where, could you have conceived of where you are now then? And like, just how random life is and where it takes you?

• 22:46Speaker 01

  Yeah, I couldn't have conceived of it at all.

• 22:52Speaker 01

  Yeah, I think that just speaks to something about like, the uncertainty of your path. Like, you just don't know the direction things are gonna go. And that kind of goes back to what you were saying about being a little bit softer with like, the opinions and the things that you hold on to dearly, because like, that certainty, I don't know, it's just gonna bog you down. Yeah, I don't know, like, 15 years ago, I think that I was a very different person. I had a very different outlook, was a lot angrier. I didn't really have a sense of who I was. I didn't have a lot of confidence in myself. I didn't really feel like, you know, I loved myself and that therefore, like, other people would kind of like me. So I was sort of trying on a lot of different hats and identities, which you sort of saw a lot of back then. And I just, you know, I couldn't have imagined like, the path that things would take.

• 23:35Speaker 01

  It's, you know, a strange turn of events. I mean, and I'm sure the same for you. Like, you had your eye on writing, but, you know, beyond that, like, you couldn't really predict the trajectory of things were gonna go on.

• 23:48Ryan Holiday?

  One thing the Stoics all have in common is that they love to learn. They love to learn from people who had experiences, had insights, had interesting lives. That's one of the things I love about podcasts. It's like, an hour, or two hours, or three hours sometimes, right into the brain of a person who thinks very differently, or has experienced things very different from what you've experienced. And that's something I always feel when I listen to my friend Jordan Harbinger's podcast, The Jordan Harbinger Show, which is the sponsor of today's episode. His show has interviewed basically everywhere. You can listen to his episode with Robert Greene on the laws of human nature, or both my episodes, where I talk about solving for what you want in life.

• 24:32Ryan Holiday?

  Talk about my book Conspiracy, or Stillness is Key. I mean, he's had literally everyone you can imagine on, professional art forgers, to billionaire entrepreneurs, to mafia hitmen, to models, to professional athletes. He did this episode about birth control, and how it alters the partners we pick, and how medicine can affect elements of our personalities. He talks about Just everything you can imagine. It's just a great show. Recommend it. The podcast covers a lot, but I think the one thing that's constant is he always pulls useful bits of advice from his guests, and I can say that from experience. I always feel like the interviews I do on the Jordan Harbinger Show get something out of me that I didn't talk about the interview I did

• 25:15Ryan Holiday?

  just a few days earlier. Like, when I would point you to those interviews, if I would say, hey, someone's like, hey, what's a podcast you were on? I'd connect you, I might link you to one of my episodes of Jordan, because it would be different from all the other ones. And I think that's all you can really ask for from a podcast. I enjoy it. I recommend it. There's so much there. You can check out jordanharbinger.com/start for episode recommendations, or just look for The Jordan Harbinger Show on Apple Podcasts, Spotify, or wherever you listen to podcasts. Thank you to Jordan for sponsoring this podcast, and I hope you give it a listen.

• 25:53Ryan Holiday?

  Yeah, that's why I think it's weird when people have very specific goals or ideas. I think you want to have like a general point on the horizon you're aiming towards, and then you're sort of, you have no idea the terrain that's going to exist between you and there, and the obstacles you're going to encounter, and you have to be willing, I think, to be flexible and adjust to the facts as you find them along the way. Yeah, I mean, it's a, it's a long journey. Yeah, I mean, you're just going to come up against so many impediments. And I mean, it's like that, you know, the Mike Tyson quote about everybody's got a plan until they get punched in the face, you know, like, you can, you can be

• 26:37Ryan Holiday?

  fixated on this is my life goal, this is the thing I'm going to do, like, I've got a, but it's not going to work out that way. It's just not going to pan out the way that you need it to. And if you're not flexible enough, I feel like you're just going to break. And then, like, I do remember you being a very angry person, and that being sort of who I thought you were. And I remember being very surprised meeting, seeing you for something, or talking to you something, several years later, and then, this would sound like...

• 27:08Ryan Holiday?

  The absence of that, it was like, it wasn't like there was a hole, but that was like, what, what you were built around, right?

• 27:19Speaker 01

  No.

• 27:19Ryan Holiday?

  So it was, it was weird to see that disappear. And then, like, I guess anything could have rushed in to fill that hole, right? And then, but, but like, we're, I think very rarely do you see it get filled with the opposite of what was there before, which is a roundabout way of complimenting you, which is I think you replace what was anger with like a lot of kindness and niceness, which again was very unexpected, weirdly.

• 27:49Speaker 01

  Yeah, I mean, I think if I dig down deep and I kind of look back through years of therapy and self-examination, the problem that I had going on was that I didn't feel good about myself, I didn't feel confident, I didn't feel like I had a sort of identity and a craft and a trade. I'm sure plumbers feel really good because their contribution to society is that they plum. And I didn't, like, my, sure, my stuff was a little bit more open-ended. And because of that, like, I just, I thought, like, I'm gonna be rejected. And one of the ways that I pushed back against that, or I felt some power, is like, I'm gonna be angry, I'm gonna push back first, I'm gonna control the situation, and, you know, at least I can kind of, you know, garner an identity as like, I don't know, an angry,

• 28:34Speaker 01

  volatile person, volatile person, which isn't much of an identity at all. But that's coming from a place of like yearning, right? Like, I want a community, I want the friends, I want to be accepted, I want to feel like I have a place in the community and something to contribute.

• 28:47Ryan Holiday?

  Like preemptively rejecting it.

• 28:48Speaker 01

  Yeah. And so if I can eventually get to a place where that's sort of quelled, and like you said, now there's a vacuum, like, what's gonna rush in? I mean, the things that I was sort of yearning to fill it in, and I was just doing it in a very misguided way, are like, okay, community building and feeling good about myself and, you know, creating an identity and a craft and a trade. And so now, like, I find myself in a place where I'm working very hard to build friendships and build skills, working with my hands, doing a bunch of like, kind of community building type things that all, all the stuff that I do in terms of building is really just like, you know, making stuff with my friends and wanting to, you know, be a part of workshops and put on workshops, that type of thing.

• 29:32Speaker 01

  And so like, that's filling the void that I was, I don't know, kind of replacing before with anger. Cause I think you look at it as the polar opposite, but really, it's just like, you know, what is that anger a placeholder for? And now like, I can confidently sort of, you look at what I've got going on now, and I think that's what the anger was a placeholder for.

• 29:52Ryan Holiday?

  It's also weird, lucky, fortuitous, I don't know how you wanna say it, but like, so you have this coping mechanism, whatever it is, it's anger, you know, it's an addiction, whatever the thing the person has, and it's sort of a, uh, not constructive, it's destructive, right?

• 30:08Speaker 01

  Yeah.

• 30:09Ryan Holiday?

  And so you get in this sort of downward spiral with it. But then, if you switch to something that's positive, that makes the world better, sometimes you get lucky and it becomes a positive feedback loop. So like, you know, you did that, I remember you did the first thing with the swings, where you put up the swings all over San Francisco and LA, and people started liking it, and then it got attention, and then it became a coat commercial, and that, but like, I think about that as like, you kind of trying on a very different thing, and it being rewarded and creating a different kind of loop. Do you know what I mean? Like, and, and I kind of think about that with my career too, whereas like, I was on this marketing track, and it was very successful, and was making money, I wouldn't exactly describe it as constructive,

• 30:53Ryan Holiday?

  but the Stoicism stuff becomes suddenly, it's like, first off, I'm interested in it, first off, I like it, but then, because it actually does something for people in a way that's not extractive, the way the other stuff was, suddenly it becomes this whole thing, and, and you can, you can sort of build your life around this new thing, that because it's making the world better, you actually get encouragement for, as opposed to just like, you know, like, things you like, like, you're not forcing it, it's the opposite, you're being like, pulled instead of pushing.

• 31:25Speaker 01

  Yeah. Yeah, and I think that speaks to the flexibility you were talking about before, cause it took, you know, stumbling into those paths to find that positive feedback loop. You know, I just kind of... I mean, I liked playing in the park with friends and hanging out and doing some weird things, but like hanging those swings and sort of touching upon like, oh, this has some positive thing here. I'm doing something that's creating a feedback loop that's helpful. And same thing with building stuff out in our land and finding that, I don't know, working with my hands and that kind of design and trade like had a positive thing. I mean, in you with Stoicism, like, I don't know, it just, it takes, it's not like 15

• 32:06Speaker 01

  years ago, you had said, I'm going to build a career and a path about writing about the Stoics. Like, you had to stumble into that.

• 32:13Ryan Holiday?

  Yeah.

• 32:14Speaker 01

  And to be into the sort of direction it might go. And then to also recognize, you know, here's, here's something positive in my life. People are vibing on this. It's working for me. Like, maybe there's something here. I should pull this thread a little bit.

• 32:28Ryan Holiday?

  What is weird, because people ask me about that, like, they sort of, like, so I was interested, I read the Stoics before I met you. So this would have been 2006-ish.

• 32:38Speaker 01

  Yeah.

• 32:38Ryan Holiday?

  And I was interested in that. That's what I wanted to write about. And that's what I was writing about on my blog that nobody read. But then, but

• 32:45Speaker 01

  I read your blog.

• 32:47Ryan Holiday?

  Yes, I read yours as well. But we were like the only ones. But, but like, I just remember, like, I think people think about it as like, I was on this marketing track for a long time, and then I switched. And you didn't realize that actually, one predated the other. It was just sort of, like, I actually, I say this, and trust me, I'm lying. You know, the word disintegrated, disintegrated, right? We think of disintegrated means like falling, falling apart, right? Like a plane disintegrates in the, you know, in the air. But it also means not integrated, right? That I sort of had these different parts. Like, I was interested in this thing. I was interested in this thing. I was interested in this thing. I was ambitious. I was young, whatever. But it wasn't all, it didn't, it

• 33:32Ryan Holiday?

  was, it was not put together in any sensical way. So like, most of my energy and time and ambition was dedicated towards this one career path. But really, the thing that I was interested in and cared the most about was this other thing.

• 33:46Speaker 01

  Yeah.

• 33:47Ryan Holiday?

  And it took a longer amount of time for them to be integrated, for me to get rid of the stuff that wasn't working, for me to ramp up the stuff that was working. But It was just a weird period, that whole, like, my whole mid twenties was just a weird period, or early twenties.

• 34:04Speaker 01

  But that means that somewhere along the way, there was an alignment of, like, how you saw yourself and the things you wanted to write about, and how the public was seeing you and what you wanted to write about.

• 34:15Ryan Holiday?

  That's right.

• 34:16Speaker 01

  Does some peace come from that? And just before you answer that, the reason I'm bringing it up is there's, I gotta, can't remember who it was now, but there was somebody that used to write about addicts, and they were talking about the thing that addicts were sort of medicating away, was this disconnect between how they saw themselves and how they felt the world saw themselves. And because there wasn't an alignment there, there was a great dissatisfaction.

• 34:39Ryan Holiday?

  I think that's right. It's like, you can be very good at something, you can be very well-liked for something, you can be very well compensated for something, and it not be what you were meant to do.

• 34:51Speaker 01

  Yeah.

• 34:51Ryan Holiday?

  You know, and if you're spending most of your time doing what you're not willing to do, or being the person you're not willing to be, I think that causes a kind of distress or suffering that you can either address by looking in the mirror and making hard decisions, right, and like painful, costly choices, or you can go get drunk, or you can work a lot, or you can have, like, you can be consumed by your sex life, or, you know, you can get in trouble. Like, there's a bunch of things you can do to distract you from that distress.

• 35:27Speaker 01

  Either way.

• 35:28Ryan Holiday?

  Or you can address it. Yeah.

• 35:30Speaker 01

  Yeah. Yeah. I think distress is the right word for it. Yeah.

• 35:34Ryan Holiday?

  Well, the Buddhist, it's dukkha, I think is how you say it, but it's like suffering or like pain. It's just that, like, that, uh, it's just the things that cause you distress, you know? And, you know, how do you treat that distress? Do you get to the root symptoms? Or, or do you get to the root causes, or do you medicate the symptoms more and more until eventually you, you know, reach some sort of crisis?

• 36:05Speaker 01

  Well, yeah, and I mean, speaking from experience, the, the risk in that medicating away the symptoms as an addict is that you build up these patterns of avoidance, and you never really learn how to deal with it, you know, to begin with. And, I mean, it just gets harder and harder to dig yourself out of that hole.

• 36:19Ryan Holiday?

  Yeah, and just you're doing a thing compulsively and then it becomes its own. You do it, you don't even, like, there's this great expression that traditions are are solutions to problems we forgot about. Right? So if you think about like, why do we do it this way? It's probably because at one point someone was like, we should solve this problem. This is why we have this policy, you know? And I think oftentimes the things we do or how we spend our time are solutions to distress or anxieties or fears or bad advice or, you know, things we've internalized. And then we do them for so long that we don't even remember why we do them. We just do them and it feels painful to not do them. Or it feels stupid to stop doing it.

• 37:04Ryan Holiday?

  You're like, I make $200,000 a year as an executive at this company. I should just leave it because I actually have more fun doing X? That sounds insane. You know what I mean? And so either, you know, this is obviously the plot of Fight Club. Like, he has this life that deep down he knows is wrong and his subconscious has to destroy it for him to be able to leave it. I think that is flaws of the book and movie aside, that is a very common modern predicament.

• 37:35Speaker 01

  Yeah, I mean, then it brings up a complicated relationship with like bucking convention and changing things up. Because on the one hand, you go, well, this has probably been done this way for a while. But on the other, you know, sometimes like it feels like you need to kind of shake things up and do it a little bit differently.

• 37:57Speaker 01

  There is also like when it comes to behaviors, like, you know, I mean, how many, I know I keep coming back to the addict thing, but like, how many alcoholics have said like, well, now I think I can have a drink because like, things are going pretty good for me. And they're forgetting like, the reason things are going good for you is because you haven't been drinking. So like, there's a, that that push-pull relationship with the, I think that I should change things up dramatically because there might be some good that'll come from it or to buck convention of how things are typically done. But then on the flip side of it, it's like, well, perhaps things have been done that way for a reason and perhaps you shouldn't rock the boat too much.

• 38:34Ryan Holiday?

  Yes. Yes.

• 38:36Speaker 01

  Which I guess goes back to the very first part of this conversation, which is like not holding too tightly to any one idea.

• 38:42Ryan Holiday?

  No, I think that's right. I think that's right. No, so it was, I don't think I would have predicted the direction you ended up going, but it's been very interesting to like, I think that's the other thing that I do like about the economy and how the world works is like, you really can do, like, you can have weird jobs. Like, that can be a thing that you do, right? Like, you're like, oh, I bake tree houses for a living, or whatever. Like, you're like, that's a thing? You can do that? Even, even now, I think, like, it's like, oh, yeah, I talk about an obscure school of ancient philosophy. That's my job. And they're like, oh, did you go to philosophy school? No. Like, oh, do you teach at a university?

• 39:21Ryan Holiday?

  No. How does it work? I don't know. It just works, you know? Like, so that is the, the tricky thing about those conventions, too, is like, some of them exist for a reason, and some of them are totally made up dumb stuff. And you have to know which ones you can sort of knock the legs out from under.

• 39:39Speaker 01

  Yeah. Yeah, you, you talked about this on your podcast with Chuck Klosterman. You're talking about movie making, and like, some of the approaches there, and like, well, why do we need to do it this way? It's like, well, there's a reason, because everybody's been making movies this way for a while. Like, they've worked out the kinks. Not all conventions need to be bucked. Yeah.

• 40:00Ryan Holiday?

  Well, no, it's, it's extra tricky. If you have built a career breaking conventions, how do you then respect the conventions? Right?

• 40:08Speaker 01

  Yeah, totally.

• 40:09Ryan Holiday?

  Like, Elon Musk, right? Every company, everything he's ever done, they're like, that won't work for the following reasons, right? But I saw this at American Apparel. If that becomes your identity, like, I, I break conventions. I don't think about what those people, what, you know, the DJ Khaled, they. I don't listen to what they say. Well, sometimes, in fact, a lot of times, they are right, right? And so, you're like, if you develop this sort of, this is where, I think the colloquial definition for this would be ego. If you develop the identity that you intuitively and instinctively know better than everyone, eventually you will bump into the thing in which that is not

• 40:52Ryan Holiday?

  true, and that will be your Waterloo, you know, like, rock bottom crash. That will be the thing that brings you back down to earth.

• 41:03Speaker 01

  Yeah. Well, I mean, I've been seeing a bunch of stuff on social media in terms of like people's profile pictures and their bios, talking about making fun of the fact that folks are into the current thing, whatever the current thing is.

• 41:17Ryan Holiday?

  Yeah, Mark Andreessen talks about this.

• 41:18Speaker 01

  Yeah. And so there are many people I've come across now where their entire identity is pushing back against that, to lampoon it and to say, I am not for the current thing. Well, if that's your entire identity pushing back against the conventional wisdom of whatever the population is generally into, you are also going to find yourself in a position at some point where you are absolutely on the wrong side of a topic. Like, you can't just bind that tightly to the like, I buck convention. I do what others tell me I shouldn't do. I do what they say we shouldn't, and they are wrong about the current thing. Like, to just push back against the nebulous "they" is always going to leave you in a bad place eventually.

• 42:01Ryan Holiday?

  Mark says, you know, you gotta do what's essential, focus on what's essential to you. But sometimes we don't know what that is, or sometimes we get caught up and think the wrong things are essential. And one of the places you can dive into what makes you tick, why you want the things you want, why you get distracted by the things that you don't want, is therapy. And I'm not ashamed to say that I go to therapy, that I've gone to therapy, and I love having advertisers like Talkspace sponsor the podcast because I think the service is important. Are you taking care of yourself? Are you being vulnerable? Are you putting yourself out there? You shouldn't be afraid to ask for help, and you shouldn't be afraid to make time to get that help. And that's where

• 42:43Ryan Holiday?

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• 43:25Ryan Holiday?

  the promo code STOIC. That's 100 bucks off at talkspace.com promo code STOIC.

• 43:34Ryan Holiday?

  Yeah, well, Peter Thiel says, you know, like, it can't just be, uh, you put a minus sign in front of stuff. Like, that doesn't, that doesn't work. Because, yeah, eventually, it's, you're putting the negative sign in front of a life-saving medical technique, or what, like, I, I saw that, I actually saw Andreessen and, uh, you know, Musk talking about this the other day, where they were like, like, all of us, like, they started, they were talking about free speech and this and that, and then all of a sudden, they're like, opining about, like, uh, SSRIs and antidepressants. And it's like, look, first off, you might be right. The chances of you being right are very low, because you have zero

• 44:14Ryan Holiday?

  understanding or, uh, training in this thing. And also, this isn't the same as speculating about, you know, whether, uh, the Patriots should draft so-and-so or not, right? Like, you're talking about a thing that millions of people depend on, or believe they depend on, to literally not commit suicide. So maybe just shut the fuck up, because, like, the caught, like, you know what I'm saying? Like, this sort of intuitive, reflexive, like, my identity is I challenge whatever those people think. And I think what's happening, and you and I both know some people who, whose identity has been warped by this, because those people were rude to you,

• 44:56Ryan Holiday?

  or dismissive, or wrong about you in the past, um, you, your identity is now, fuck whatever they like, believe, care about. It, so it's, it's even pettier than just like, I think the opposite of whatever the crowd thinks. It's more like spite, like, politics of spite, like, I don't like those people, so whatever they like, or think about, or support, I'm gonna reject, even if they happen to be right about this, that, or the other. And it, it takes you down a dark corridor.

• 45:27Speaker 01

  I mean, that, now you're just speaking to, like, the sort of national division and culture wars in this country.

• 45:32Ryan Holiday?

  Of course.

• 45:32Speaker 01

  But also, like, what you're talking about, Andreessen and, um, Musk, that's the, the downside of that positive feedback loop we were talking about earlier, where you see success in a thing, you get rewarded for your expertise in one sector, and like, society loves you for it. You got fans, you're doing well, things are great, and now you feel comfortable stepping outside of your lane, you know? Um, I've seen, uh, what's his name?

• 45:59Speaker 01

  Ah, the astronomer guy.

• 46:01Ryan Holiday?

  Oh, Neil deGrasse Tyson.

• 46:02Speaker 01

  Neil deGrasse Tyson. Like, I've seen him speak about a few things where I think he got really enabled by such a positive feedback in terms of like his contributions to the scientific community and, you know, specifically in his field. And then he'll speak about other stuff that's way outside of his lane. It's not quite as far outside of his lane as Musk talking about SSRIs, but it's like, ah, I don't know, man. I think maybe you should just keep talking about stars.

• 46:28Ryan Holiday?

  I read an interesting study once that was saying that, you know, oftentimes conspiracy theorists are, like, obviously, there's the Alex Jones sort of whack jobs out there. That's not who we're talking about. But like, the people that propagate the sort of real big conspiracy theories are almost always academic experts in something else. So they're an astronomer, or a sociologist, or an expert in this kind of medicine, or on this diet. And what happens, this is what ego does, ego makes you think, I'm an expert here, I'm

• 47:08Ryan Holiday?

  an expert in all things. Like, you carry on the certainty built from years of study in X field, you carry it around like a backpack. You know, they talk when they talk about privilege, the invisible backpack. The uncertainty is your, or the certainty is your invisible backpack. Like, you're just walking around convinced that this thing that you thought about for three seconds is rooted in the same 20 years of study as your scientific observations in that exact field. And they're not. And that's why you're being a crazy person.

• 47:42Speaker 01

  Yeah. I mean, you hit the nail on the head with that word certainty. Like, that's, I don't know, that's what I've kind of come to see as the poison. And it's, it creates like a little bit of a weird relationship with the truth, because I want to feel good about certain things. You know, I want to listen to experts when they tell me I should do this or do that. But by and large, like certainty, real diehard certainty is something that I see is, I don't know, a negative thing in my life. And I certainly don't appreciate it generally when I tend to hear it from most folks. Like, I just, how can you be so sure about everything? I mean, and of course, that's a conversation that used to be less problematic. Now we're dealing with people who think the earth is flat, and I feel like you can be pretty certain

• 48:27Speaker 01

  that the earth is a sphere. But yeah, it's, I don't know, that certainty and ego, like, it's been poisonous for a long time.

• 48:34Ryan Holiday?

  Well, that's the tricky part too, right? So like, conspiracy theorists that like say believe the world is flat, or anti-vaxxers, or whatever, they're like into, they're wrong about a lot of stuff. But you have to, you have to then go, you have to, you can't be like, what does Alex Jones think about X? I think the opposite of X. Right?

• 48:55Speaker 01

  Right, reflexive pushback.

• 48:57Ryan Holiday?

  Yeah, because you're actually doing the same thing. You have to go, putting aside what everyone thinks, what do I think about this independently? Do you know what I mean? Like politically, like, let's say you find like Musk repulsive for like the things we were just talking about him saying and other things. Like, if you then predict he's going to be a failure and everything because you don't like him personally, that's going to cost you. Right? Like, or if you, you know, if you are repulsed by this political figure, and therefore reject every part of the plank that their party or that their campaign is built on, you're going to miss the handful of things that they're actually not wrong about. So you have to, you have to have this discipline to be like, I, that's what, and

• 49:40Ryan Holiday?

  that's what Teal told me, his definition of, of sort of being anti-mimetic is, mimesis coming from the philosopher Rene Girard, is it's not that you just do the opposite of whatever the crowd is. It's that you try not to think about what the crowd thinks, and you try to come up with your own opinion based on as much independent information as possible.

• 50:02Speaker 01

  Yeah, and the benefit of that is that whatever certainty that affords you in the moment, that philosophy means that you're always open to new information. So you're flexible, you're moving with it, you're allowing your opinions to be changed, which frankly, these days is about the biggest compliment I can kind of give somebody, is that I see that their opinions are sort of open to be changed with new information.

• 50:22Ryan Holiday?

  That's right.

• 50:23Speaker 01

  Yeah.

• 50:24Ryan Holiday?

  All right, I wanted to ask you about something. So you sort of built up this whole new life, and then suddenly, all the work that you'd done literally burnt to the ground. Talk to me about the fire and how you responded, because I remember, I remember finding, again, for a person who'd been angry and had some issues in the past, I remember finding your reaction to it to be, to have, I remember finding it remarkably self-controlled and calm, considering the circumstances.

• 50:55Speaker 01

  Sure. You want me to give a little background on that property? It's not just you and I here, right?

• 51:00Ryan Holiday?

  Yes.

• 51:01Speaker 01

  So, like, six years ago, my wife and now-wife and I bought a property up in the mountains, it was just like a piece of dirt, recreational land. We were like, okay, we can't really leave our house just yet, we don't want to leave the city of San Francisco, we want to have a place where we can kind of like host friends and gather and, you know, like spend kind of quality time that we'd done at like friends' ranches and Airbnbs. So we're like, we're gonna buy this land and we're gonna kind of build it out. And then we just spent the next four years building. And I didn't, when we entered into it, we didn't have much of a skill set. Like, I think, I mean, you having known me for like 15 years, you know that I was probably the guy you might call over to help you try and fix your dishwasher, but I didn't really

• 51:45Speaker 01

  know what I, like, I tinkered, but I didn't really know what I was doing, building-wise. And so we just started plotting down this road of like, okay, we'll bring some friends over and we'll clear some trees and we'll build a picnic table. And then we'll bring some more friends over and we'll try our hand at like a little pavilion. And then maybe like, I don't know, let's organize a big weekend get-together and have a friend fly in from out of town, and we'll try building a deck up in the trees, like a little treehouse deck. And we just kept doing that until after a few years in, we had a cabin. It was like featured in magazines and stuff. We had a network of tree decks, a wood fired hot tub up in the tree, a very nice outhouse,

• 52:26Speaker 01

  sheds and hammock stands and hammock hooks in the trees and a fire pit and a little network of trails. Like we built out this full little adult retreat center. It was just for us and our friends to use. And when we would do these big annual gatherings or like weekend hangs, the invite list, what started out going out to maybe like six or so people, toward the end there was going out to about 60 or 70, just because the build parties and the big hangs and stuff, it just attracted like minded people, good quality friends of friends, that type of thing. So we had, you know, got archery and axe throwing, summer camp vibes. It was just a total zen retreat space that everybody

• 53:10Speaker 01

  loved. It was like a place and a reason to gather. We had a bunch of friends that would fly in a couple of times a year. It was a whole thing. It was really beautiful. And then California wildfires of 2020, one came through and just burnt it all to the ground.

• 53:32Speaker 01

  And I didn't really touch on this a second ago, but like, I mean, we built out the plumbing in that place, all of the trails, every bit of infrastructure, the roads, like, other than planting the trees, if there was anything there that looked like it had a human hand on it, it was something that we did, you know, we didn't really hire anyone to do anything. So yeah, 2020, August 17th, I think, wildfire came through and just annihilated it. Nothing was left standing, except for like the larger trees, all the small ones burned, everything that we built, you know, roads remain, but that's about it. And yeah,

• 54:17Speaker 01

  my reaction to it was.

• 54:23Speaker 01

  I said this a bunch of times to people and it's sort of the cliche thing to say, but I don't mind losing the stuff so much because it was the experience that was gained and like the quality time with friends. And I have a bunch of caveats to that, but the

• 54:42Speaker 01

  the reason the cliche is true, and I'm not just saying it to sound nice, is because during the past five years or so of building there, and there was just a lot of personal growth. I really came to understand who I was, to see my value in the community, to kind of come to love myself and, you know, the sort of service and identity I provide. It enriched the relationships that I had with friends. It cemented like a firm feeling of like, okay, I know who I am, I know what I can do, I know what my contribution is. Like, I figured out who I was in that place. And I figured out what it was that I kind of desired in life.

• 55:24Speaker 01

  And we saw enough of it through that even post-fire, it's like, okay, what I'm left with is such important lifelong lessons that, you know, that can't really be taken away. The caveat to all that is that what goes hand in hand with it is that thing was a huge social tool. It was a reason and a place to gather. Like I said, we had friends flying in, we're doing big events. And the truth is, good habits and good practices and good community, like, those things are all great, but they're certainly enabled by the tools that can enable them. And having that infrastructure in that place, like, you know, socially, things have taken a little bit of a

• 56:05Speaker 01

  hit, but it also came during the pandemic and people leaving cities and stuff. But yeah, it's, um...

• 56:11Ryan Holiday?

  Didn't you tell me you looked at it kind of like a mandala, that Buddhist kind of art, where it's like you make the thing, and then it wipes it clean, and then you get to do it again?

• 56:21Speaker 01

  Totally. And I mean, we've, you know, built a new outhouse and a new little A-frame cabin, and I'm currently working on putting in some new water. I will concede that the...

• 56:35Speaker 01

  The drive is a little bit different just because there's a mild amount of trepidation. So, you know, in terms of investing like a lot of time and money, it's like, well, maybe we don't go at it at the exact same speed as which we did before. The approach is a little bit different. But yeah, it's total mandala. Like, the truth is, what I really enjoyed from that place was seeing a project through and doing it with friends. So we'd get together for a weekend. I would have all the plans in place in terms of amassing a bunch of lumber and tools. And, you know, I've thought through every bit of this because you only get one shot at it. And we're gonna do a wall raising and we're gonna build a pavilion.

• 57:16Speaker 01

  Building that thing in a weekend and sitting underneath it on Sunday and eating with friends and that kind of shared sense of accomplishment of this thing didn't exist, but now it does. Like, that's all I was really living for, and that was the best part for me. And then just like having it in perpetuity, I can take it or leave it. And if you wipe the slate clean and you tell me that I just get to do it all over again and I get a fresh project, it's kind of exciting because it's just, I don't know, it's the process and not, you know, ultimately having the thing at the end of it.

• 57:47Ryan Holiday?

  Well, that's kind of that way in writing, right? Like, you're writing something and then a computer eats it or it gets destroyed. Theoretically, you could just write it again because it's in your head, right? You can't take away the idea. And you can still, there's, and you could see it as an opportunity to do it again better, right? But there is something less fun about doing it the second time in that it's not, what you have lost is the first time-ness, right?

• 58:19Speaker 01

  Yeah.

• 58:20Ryan Holiday?

  You've lost doing it uniquely for the first time, which is probably why driving back from a trip is not as fun as driving there. Like, you already saw it.

• 58:28Speaker 01

  Yeah. The comparison I would make to writing is I don't look at this property as a single entity where it's like, I did it once and now I'm doing it again.

• 58:39Ryan Holiday?

  Sure.

• 58:40Speaker 01

  Instead, it's just sort of a venue for this continued process of like, learning how to design and build and host events and gather. So it's kind of like if...

• 58:51Speaker 01

  You wrote your book, you completed it. You closed that laptop and you were like, it's done. I've finished it, maybe even sent it off to the publisher. And then for whatever reason, they just lost all the copies of it.

• 59:01Ryan Holiday?

  Yeah.

• 59:02Speaker 01

  But like that satisfaction of like you kind of saw it through. That's what I have. It doesn't exist in perpetuity. It's not still on the shelves for people to buy. But like I saw that project through and now I just get to kind of start on the new book. It doesn't really feel to me like the computer ate it halfway through.

• 59:20Ryan Holiday?

  But that that requires a certain philosophical understanding that the thing was was process, not outcomes. Right? So it's like if the purpose for doing the book was where it hits on the bestseller list, or if the purpose of the book was impressing fancy people or whatever that stuff is, then the losing of the manuscript is the tragedy. Right? Like I did this book, I did Lives of the Stoics. Obviously, I wanted to do well, but part of the reason I wrote it was there was a bunch of Stoics that I didn't know very well. Right? And so even if that book had never come out, or even if it had sold zero copies,

• 1:00:02Ryan Holiday?

  I would be better because of what I learned to write the book. Right? And so if you can think about doing the things, to me, that's the ultimate distinction about process versus outcomes. Are you doing it because you enjoy the process? Are you doing it for what you get out of the process? Or are you doing it for what happens at the end, for the reward at the end of the process? Those are very different mindsets and one is much more fragile and vulnerable to what happens in the world than the other.

• 1:00:31Speaker 01

  Yeah. I mean, I hate to like just categorize something as wrong or worse, but it feels like you're hanging a lot on that second one. Things that are beyond your control. You just don't know how it's going to turn out.

• 1:00:45Ryan Holiday?

  As Epictetus says, "It's impossible to learn that which you think you already know." "You should be a student," he's saying. "Try to always learn." He also says, "You can't get better unless you're willing to look a little bit foolish." One thing that I think humbles us, but also makes us better, is learning languages. Babbel, the language learning app, has sold more than 10 million subscriptions for this reason. It takes 15-minute lessons that are designed to help you learn a new language on the go. Other language learning apps use AI for their lesson plans, but Babbel lessons were created with over 100 different language experts, and their teaching method has been scientifically proven to be effective. You can choose from 14 languages: Spanish, French, Italian, and German. And their speech recognition technology helps you improve your pronunciation and accent.

• 1:01:29Ryan Holiday?

  Right now, when you purchase a three-month Babbel subscription, you get an additional three months free. That's six months for the price of three, so 50% off. You can go to babbel.com and use promo code DAILYSTOIC. That's B-A-B-B-E-L dot com. Use code DAILYSTOIC. Babbel, language for life.

• 1:01:50Ryan Holiday?

  That's right. You know, in Obstacle, I tell this story about Edison. And this is when his Menlo Park laboratory burns up. And I say this line in all my talks, because people love it. But, you know, he rushes in, his factory's on fire, and he stands his son. He finds his son standing there, and he goes, "Go get your mother, and all her friends will never see a fire like this again." And I love that, because it's not just like the, "Oh, I'm not going to be bitter about it afterwards." But also like, man, this is cool. Like, even if you're like, it's like, it's like when you're a kid. You build the, I do this with my kids all the time, you build the thing. The fun part is knocking it down, right? Like, it's not that you made it, and now you have to protect it forever and keep it exactly as it is. That is not only not fun, it's the opposite of fun.

• 1:02:35Ryan Holiday?

  Because now, like, you're walking on eggshells, and you can't, you know, you're like, you're scared all the time. And I think that one of the tragedies of people who become successful or do stuff is that you become very risk averse, you become very protectionist, because you can't fathom not having what you didn't have not that long ago.

• 1:02:55Speaker 01

  Yeah, I mean, it's just a dangerous road to go down because now, I mean, there's just so much that's beyond your control. You want to steel yourself against all the things that are bound to happen in the world, you know?

• 1:03:05Ryan Holiday?

  And don't you think, like, I wrote an email about this a while ago, which is like, obviously, you're scared about someone taking this thing from you, your house burning down, even losing people that you love. I was saying like, they can take it from you, the they again, life can take it from you, but it can't take that you had it from you, if that distinction makes sense.

• 1:03:30Speaker 01

  Oh, of course.

• 1:03:31Ryan Holiday?

  And if we can remember that, I think it does make us much more resilient. It's like, yeah, the marriage blew up, but like, the 10 years were good. And you can't take that away. Like, I control the memory of the thing, short of Alzheimer's, or whatever, is always yours.

• 1:03:49Speaker 01

  No, that's funny, you talk about the marriage there. People talk about like, you know, failed marriages, the marriage failed after 20 years. They talk the same thing about businesses, you know, the business failed, like, yeah, but it was doing well for like 25 years. It didn't fail. Like, yeah, there's an idea that something's supposed to persist in perpetuity, I guess. Yeah, I've said this to a bunch of people, like, I wish I could have seen the cabin burn down. It must have been an awesome fire.

• 1:04:19Ryan Holiday?

  Yes.

• 1:04:19Speaker 01

  The handle, when Molly and I went back to the wreckage, we were thinking we might be able to salvage some souvenirs. You know, I thought like, oh, my cast iron pans might be in there or something. The handles melted off the cast iron pans. Our stove melted, the wood stove that's supposed to hold up to a fire inside of it, it melted. Now.

• 1:04:37Ryan Holiday?

  That's crazy.

• 1:04:38Speaker 01

  It must have been awesome.

• 1:04:40Ryan Holiday?

  Yeah, just think about the sheer power of nature and what it can do when it's at full force is, it's humbling and then also literally awesome.

• 1:04:55Speaker 01

  Yeah. Yeah. I mean, in the truest sense of the word. But yeah, I mean, if you think about that. Who am I to think that I can control that? Like, you can't control against that. You can't stop the power of a fire that's so strong it makes trees explode from the sap boiling inside. So, you know, it's just, it's a mandala.

• 1:05:15Ryan Holiday?

  Yeah, to me, the saddest part about a fire like that is not the buildings, etc., no offense. It's the, it's the things that can't come back in terms of like, this tree took 100 years to become what it is. You know what I mean? When I think about the, just the, it's not even a loss, because I guess it's nature. But just like when something like that happens and you know, like you know eventually it will come back, but it will not be something that you are able to appreciate.

• 1:05:43Speaker 01

  Yeah, I mean, the landscape is going to be forever altered. Things are looking better over at our property now because there's new growth and we got rid of a bunch of the dead trees. But those trees are black and the bark is, on the redwoods, redwoods is going to remain black for hundreds of years. It's just always going to be that way.

• 1:05:58Ryan Holiday?

  Yeah.

• 1:06:00Speaker 01

  But yeah, I mean, on the flip side, like, I don't know. I got a bunch of random commenters on the internet who were lamenting the damage to the forest. The forest is fine. It's part of its process.

• 1:06:08Ryan Holiday?

  Probably better, yeah.

• 1:06:09Speaker 01

  Yeah, the redwood trees, like their bark is fire resistant. They're fine. It's just the shit we put in the forest that burns.

• 1:06:17Ryan Holiday?

  Well, and it's, you're anti-mandolinist, right? They're like, I like this forest the way that I saw it when I was a kid or the way I was there. As if it's not just whatever forest is there since they clear cut it 100 years ago. Since before, you know, act like, like, we have this sense of like, keeping nature the way we like it, as if nature itself isn't constantly changing and going in different directions and doesn't, doesn't care what we think about it at all.

• 1:06:49Speaker 01

  Yeah, well, that's one of the flaws in those very rigid arguments that are always pushing for, we absolutely need to preserve this or go back to this or whatever. They're often predicated on a very small snapshot of time. It's like you forget that these things have been in a constant state of evolution for so long. You know, your desire, your demand that we need to go back to how things were at the time of European contact or that, just the way that you like, remember them as a kid during your formative years. Like, no, that's when it was best. No, that's when it just was. It just, you know, things are constantly changing and evolving. And you're right, like, we're, I don't know, we like them to stay the same. It's a human thing that you kind of have to fight back against.

• 1:07:29Ryan Holiday?

  Well, let's talk about the new book, which I loved. I love the idea of thinking intellectually about a thing that we often sort of see almost as anti-intellectual. Like, when I was interviewing Steve Brunello, we were talking about, like, how the high five was kind of recently invented and like different techniques. It's weird to think like every single tool in this book was like a massive innovation. Like, someone was like, what if we put, like, someone designed each one of these things? And it literally, in some cases, changed the course of human history. That someone was like, you know, if you do this, suddenly, boom.

• 1:08:14Speaker 01

  Yeah.

• 1:08:15Ryan Holiday?

  But we just take it for granted.

• 1:08:17Speaker 01

  Yeah, that's true. I mean, I mean, I'm standing in a house and, you know, you are as well. Most people don't really look around their houses and consider what it took for it to kind of get there. But yeah, I mean, I mean, I talk about this in the intro of that book, like, our history as humans is chronicled by the tools that we've used. Like, people talk about the Stone Age and Bronze Age. And I mean, you know, big shifts in humanity in terms of what we were able to accomplish and how we were able to shape our landscape came around when they figured out that new thing. They're like, holy shit, I can make a saw blade out of metal and put it on a stick. And like, all of a sudden, the world's different.

• 1:08:52Ryan Holiday?

  Well, I was, I was telling the kids this morning, we were on a walk along the river, the Colorado River, behind the bookstore where you helped us install the tree that now towers from floor to ceiling. And there was like a tree in the middle of the river that had fallen down. And I was, I was telling them, I was like, okay, the pine trees that grow in this town, originally Bastrop was a lumber town. And I was like, guys, this is gonna blow your mind. But at one time, there were not trucks and there were not trains. And so, how do you think they moved?

• 1:09:28Ryan Holiday?

  These giant trees, after they cut them down, how did they get them all over the And I was explaining that they would cut the trees, roll them into the river, and then float them from Bastrop to the Gulf of Mexico, out, and then it was like, so they did, because they couldn't travel them on roads, they would just float them down, like hundreds and hundreds of miles of curvy river, they would float these logs down, until they got out to the open ocean, and then they would load them onto boats, and they would take them all over. And I was also telling them, they loved this, that like, what would happen is these massive bottlenecks would happen, like, one tree would go sideways, then it would create enormous, enormous log, like literal log jams, and they would just blow it up with dynamite.

• 1:10:13Ryan Holiday?

  And, but anyways, just when you think about just how hard the world was, and what a minor, what a major intervention, one of these minor inventions must have been. It's kind of, it's, it's insane to consider.

• 1:10:31Speaker 01

  Oh, yeah, completely. I mean, just figuring out leverage the wheel. Look what the wheel has done for us. You don't hear people talking about it a lot.

• 1:10:40Ryan Holiday?

  Yeah. But so, so what is your fascination with tools? Is it what tools do for you? Is it what goes into tool? Like, why do you end up writing a book about tools?

• 1:10:51Speaker 01

  It is the ability to create, to like, make something that didn't exist before. Because, I don't know, like, or just to repair things, which I think comes with a feeling of capability.

• 1:11:02Ryan Holiday?

  Sure.

• 1:11:03Speaker 01

  And I like feeling capable. It makes me feel kind of powerful, makes me feel like I have something to contribute, makes me feel like I'm worth something. And, I don't know, it stands in contrast with a lot of folks that I've met who do not feel capable. And for them, like, that's a sort of, I don't know, it's a detriment. So, I don't know, it's knowing how to wield a tool, knowing how to speak that language, knowing the landscape so that you can go into the hardware store to ask the right question, because it's a sort of like, it's an unknowably vast thing, right? But if you have enough of a base knowledge where you're like, okay, I can talk to the repair guy, or I can kind of, I know how to research a problem to solve it. It puts you in a position where, I don't know, like, I can solve problems. I can, I-

• 1:11:47Speaker 01

  There's a hammock stand in my front yard right now and there wasn't yesterday. Yesterday, I was like, I kinda want a hammock stand here and I realized that um we just moved into a new house and my friends used to live here. He left a bunch of lumber in the backyard. I was like, I can make a hammock stand from that lumber. And I made it and my wife was here and her parents were here and they were marveling at it and she laid in the hammock and she got some joy from it. Like, I don't know, just being able to create that to, I don't know, like to shape my world and fix problems, it's just great. And you can't really do that without tools. And I mean, it's a broad definition, like this book, I tend to cover tools that are just in the shop, garage, you know, home, apartment, that sort of thing.

• 1:12:30Speaker 01

  But the truth is, like, if you're cooking or knitting or whatever, like, the world's full of tools. Um, and so they kind of enable us humans to get shit done.

• 1:12:39Ryan Holiday?

  It sounds like you're also talking about the distinction between, or the link between confidence and competence. Like, when you know how to do something, when you have a skill set or a uh a base of knowledge, it allows you to be like, yeah, I can handle that. Or it allows you to just be more resilient because you know, okay, it won't go the way I want it to go. But I believe I have evidence in my ability to figure my way out of here.

• 1:13:10Speaker 01

  Yeah, I mean, look, I'm on this planet for like eight years or something, if I'm lucky. And feeling like I'm not too scared by the process is pretty important. And, you know, as we're social creatures, feeling like I have something to contribute to my community, like that seems pretty important. And tools and just a general competence and confidence about like, I know how to problem solve, I know how to fix things, I can make stuff happen, I have a trade. They enable all that immensely.

• 1:13:40Ryan Holiday?

  Yeah, yeah, yeah, that makes sense. What do you think of the, um, the, uh, the remark from Aristotle? That the, uh, the, the most important thing in life is figuring out how you spend your leisure time? Like, the idea that you figure out what your hobbies are. Like, what do you do with, like, your free time? It strikes me as you have a pretty good answer to that question, but what do you think of the question?

• 1:14:06Speaker 01

  Yeah, I mean, I guess that's just Aristotle getting down to like, what matters to you, you know? Because like, that's what you do with your, your free time. You do the things that matter to you. And there's that incongruence between the things that matter to you and the things that you have to do. Um, as we said before, it kind of brings you a lot of displeasure and discomfort. Yeah, there's, well, I mean, I was about to say, like, you know, a lot of folks would strive to, uh, figure out how to, you know, do the thing you love and you'll never work a day in your life. And there's kind of some truth to that, but it also seems like a path to pervert the thing that you love. So there's, I don't know. Um, but yeah, it's, it computes for me that you, you want to figure out,

• 1:14:50Speaker 01

  what is it at my core that I value? What are my values? What matters to me? If, if I don't have anything standing in my way, what do I want to do that's important to me? And how do I want to spend my time? And I'm very fortunate that I've stumbled down a path that has put me in a position where that's just all of my time now. I don't do anything that I don't want to do. I work on projects that bring me joy and I help out friends. I drove halfway across the country to help you put that tree up. It makes me very happy that I was able to do that. Like, that, that's a sort of dream existence for me.

• 1:15:25Ryan Holiday?

  Well, that was the, yeah. That was the last thing I was going to ask you, which is you told me that, uh, the sort of Stoic idea of memento mori was in part, or was part of that, like, why am I spending my time on this? How am I going to spend my time? Walk, walk me through how you came to that.

• 1:15:48Ryan Holiday?

  How, how, why you decided to give up a pretty well-paying job to change your life to just sort of do cool-ass projects?

• 1:15:56Speaker 01

  Yeah. For years, I have been inching closer and closer to kind of that position and a decision point of like, you know, I could leave my job to spend my time doing the things that matter to me. But it is so hard to make that jump because you're sitting on a cushy paycheck. It's stable. It's got nice, nice health insurance. I was making more money than I've ever made for what was honestly probably the easiest job I've ever had. And it's very difficult to turn that down. And every year that goes by that I'm going deeper into it is just like more money than I'm saving for retirement or more money that I'm socking away.

• 1:16:39Speaker 01

  Like the math says you shouldn't leave your job.

• 1:16:42Ryan Holiday?

  Yeah.

• 1:16:43Speaker 01

  So I kind of kept putting that decision off for quite a while. And then somewhere deep into the territory of thinking about it, I don't know, I got like your seventh email talking about, you know,

• 1:16:54Ryan Holiday?

  How dare you?

• 1:16:55Speaker 01

  The Marcus Aurelius quote of like, you know, you could live, you could die tomorrow, let that determine what you say and do and think now, something to that effect.

• 1:17:02Ryan Holiday?

  That's exactly.

• 1:17:03Speaker 01

  And I do remember that one of those struck a bit of a chord. And I was like, fuck, like I totally, like I could die tomorrow, you know, like, um, and yeah, so I just, I made the decision. I was like, all right, like I'm actually gonna leave my job. And that, I left it, I made the decision to leave and then my property burned down and I still left. So I was like, no, like this is, um, I, I made the decision large, in large part to leave and to focus on things in my property. And even after it burned down, I was like, well, it wasn't the place, it's the process. I'm still doing this. And now like, you know, I just spend all my time working on personal projects and projects

• 1:17:44Speaker 01

  with friends and it's, it was absolutely the right decision, but, um, it came in large part from thinking about that quote. Yeah.

• 1:17:55Ryan Holiday?

  Yeah, it's funny, people sometimes like, "Why do you say the same thing over and over again?" Because not everyone gets it the first time, for starters. And, you know, it's not like there's anything in that quote that you haven't heard of. Like, we all know you only have so much time and blah, blah, blah. But it's like, can it get you at the right time, when you're in the right position? You know, the timing of it is everything, right? Like, and this is the other stoic idea, if we don't step in the same river twice. Are you in a position where it can hit you? Then it might work. And you might have to hear it like 500 times before it makes sense to you.

• 1:18:37Speaker 01

  Totally. I mean, it just doesn't always land the same way every time. You gotta be in the right headspace. And then also, I think that it's kind of the tenet of advertising, right? To continually keep planting the seed. And eventually, if you see Coca-Cola enough times, maybe by the 10th time, you're like, "I think I need a Coca-Cola." So, I mean, I think that it works that way a little bit as well. Like, you planted that seed, and it was in there sort of gnawing away for a while. And then, you know, one day, you read it the eighth time, and you're like, "It lands a little different today, for whatever reason." And it motivates that change.

• 1:19:10Ryan Holiday?

  Yeah, what's the expression?

• 1:19:15Ryan Holiday?

  "When the student is ready, the teacher appears."

• 1:19:18Speaker 01

  Yeah.

• 1:19:21Speaker 01

  It's been good. I appreciate it. Thanks for blasting those emails out all the time.

• 1:19:24Ryan Holiday?

  Yeah, of course. That's my job. I like building those. I like the ephemerality of like, "I wrote this thing. It will go out to a group of people. And then it might as well not even exist anymore." Do you know what I mean? And then, so, six months later, I can do it again. Because everyone forgot what I said the last. But those are the things that I like building. I like the little puzzle of the daily email.

• 1:19:48Speaker 01

  Yeah, I totally get it. I felt similarly about the book and finishing it up. Like, I felt really good about the research I put into it, and figuring out how to organize all those different tools and just sort of catalog those things. And now that it's done, I'm good. I don't actually care if anybody buys it. Like, I'm satisfied.

• 1:20:10Ryan Holiday?

  Well, don't tell the publisher that, but I very much relate to the expression.

• 1:20:16Ryan Holiday?

  All right, man. This is awesome. I appreciate it. The book is great. This is my marked up copy that you gave me. And there is a physical manifestation of it, not just in the store, but at my house, in the treehouse that you helped me build also. Nice. I'm glad that thing's still up. It hasn't collapsed yet. It has not collapsed yet, and it's going strong. Cool. Good talking with you. All right, see you, man.

• 1:20:40Ryan 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.