How to Win the War with Yourself | Ryan Holiday

AI transcript
0:00:05 You’ve said before that life is always whispering at you and if you’re not paying attention it’ll
0:00:11 eventually scream at you. In sobriety circles they talk about like two cars in the garage addicts.
0:00:17 What rock bottom is for you is a choice that you kind of get to make. So do you realize
0:00:22 that you’re heading down a bad path after you’ve had to sell your house and your cars and you’ve
0:00:29 lost literally everything or is it that embarrassing evening at the company Christmas party that
0:00:35 serves to send the message? How are you hearing what the world is trying to tell you
0:00:41 or are you very much not hearing it and at some point is it going to have to hold you down and
0:00:57 scream it into your ear? Welcome to the Knowledge Project Podcast. I’m your host, Shane Parrish,
0:01:02 in a world where knowledge is power this podcast is your tool kit for mastering the best what other
0:01:07 people have already figured out. Can you do me a quick favor most people who listen to the show
0:01:13 are not subscribers? Go ahead and hit that follow button right now. Thank you. My guest today is
0:01:18 the modern day philosopher king Ryan Holiday. His books on helping people live better and more
0:01:23 meaningful lives have sold millions of copies. Building a meaningful life isn’t just about
0:01:28 inspiration. It’s about action and today Ryan shares the practical ancient strategies that have
0:01:34 helped the world class athletes, artists and entrepreneurs transform their lives. It’s time
0:01:43 to listen and learn. There are too many podcasts and not enough time. What if you could skip the
0:01:48 noise and get just the insightful moments even from shows you didn’t know existed?
0:01:54 That’s what overlap does. Overlap is an AI driven podcast app that uses large language models to
0:02:00 curate the best moments from episodes. Imagine having a smart assistant who reads through every
0:02:05 transcript finds just the best parts and serves them up based on whatever topic you’re interested in.
0:02:12 I use overlap every day to research, guess, explore and learn. Give it a try and start
0:02:19 discovering the best moments from the best podcast. Go to joinoverlap.com. That’s joinoverlap.com.
0:02:27 Some things require a lot of work to grow, like plants, hair, babies or your savings. But when
0:02:31 you run a business, you already have enough on your plate. Scotiabank’s right size savings for
0:02:35 business account can help you grow your savings with ease. For a limited time, open a new account
0:02:40 and earn up to 4.65% interest for the first six months. Before you know it, your savings will
0:02:44 grow without you even noticing. Ooh, which reminds me, I need a haircut. Conditions apply.
0:02:48 Ends December 15th. Greatest annual calculated daily and will vary based on account balance. Visit
0:02:54 Scotiabank.com/rightsizesavings for full details. Help turn off hesitation, turn off doubt,
0:03:00 turn off fears. The YMCA is a charity that helps people turn off whatever’s holding them back
0:03:06 so they can let their potential shine. With your support, you can help us turn on confidence,
0:03:11 connections and possibilities. Whether it’s supporting families, building life skills or
0:03:16 fostering well-being, the YMCA offers a wide range of programs that empower people to shine
0:03:20 their brightest. Visit our website to see how you can help today.
0:03:26 How do we separate this signal from the noise? Like in a world of social media,
0:03:31 you’re getting feedback all the time. How do you distinguish what’s valid and sort of helpful
0:03:36 feedback and a whisper versus this is noise and it offers no value? Yeah, this is really hard.
0:03:44 You can see that often to be successful as an entrepreneur, you get there by not listening.
0:03:50 You get there by not listening to the odds, not listening to the doubts, not listening to the
0:03:57 critics and then you succeed. So then you get this very wicked learning environment where
0:04:03 you succeeded precisely because you did not listen to the message that the world was trying to send
0:04:08 you. But if what you generalized from that is never listen to people, you’re going to be a
0:04:13 really tough spot. So take Elon Musk. When Elon Musk was planning what became SpaceX,
0:04:20 his friends held a literal AA style intervention that said you cannot start a rocket company.
0:04:24 This is the worst idea. You will lose all your money. Obviously, he was correct and there were
0:04:30 moments when he probably, the conventional wisdom or the data or the advice from the investors
0:04:37 overwhelmingly was to sell Tesla or to do X, Y, and C. So what happens when it’s sort of a passing
0:04:44 fancy or an impulse consideration to buy Twitter? Some people told them it was a good idea. Some
0:04:47 people told them it was a really, really bad idea. Some people told them most totally outside of his
0:04:52 domain of expertise and all these things. How do you know whether to listen or not? This is like
0:05:00 the essential question. The quote is something like a reasonable person adapts to the world.
0:05:05 And an unreasonable man adapts the world to themselves. And so therefore,
0:05:12 all progress depends on the unreasonable man. So often this thing that makes one a groundbreaking
0:05:22 artist, a discoverer, an inventor, an entrepreneur, an artist, whatever it is. The thing that makes
0:05:29 you great is this ability to not listen to feedback. At some point, invariably, you come
0:05:36 across feedback that you should listen to. You go past the point that you aimed for. You go
0:05:43 past a convention that is there for a good reason. And we only see the survivors. We never see the
0:05:49 people who didn’t listen and failed because they just sort of become noise, if you will, in the
0:05:54 process. Whereas Elon gets held up as like, “Oh, I’ve done all of these things and people have
0:05:58 told me I couldn’t do them. I shouldn’t do them. They can’t be done and yet I’ve done them.”
0:06:03 Yeah. And what we take from that is not, he was right in these specific instances for these
0:06:08 reasons. What we tend to take from that is the shorthand of don’t listen to other people or
0:06:13 conventional wisdom is always wrong. But of course, many, many people had failed. There was a graveyard
0:06:18 of millionaires and billionaires who’d lost their fortunes starting private space companies.
0:06:24 I think a good part is like not taking these sort of like business book, headline,
0:06:35 cover story narratives from people’s trajectories or from history, but actually really drilling
0:06:41 down and getting to the actual reason as to why something worked or didn’t work. Elon Musk sees
0:06:48 himself as this groundbreaking, precedent-shattering entrepreneur. And another version to look at
0:06:54 is this guy who took massive government subsidies at critical points that allowed him to do those
0:06:59 things. A story you tell yourself about your own experiences is really interesting. And then the
0:07:05 story that society says about your experiences is also really interesting too. Can you give me
0:07:10 an example of where you’ve missed a whisper and it’s gotten louder and louder and then you’re like,
0:07:14 “Oh, shit.” Well, I think we all have these in our personal lives, right? Like you sensed you were
0:07:23 coming across some sort of personal limitation or you sensed that you were straining a relationship.
0:07:30 Working with someone that you didn’t quite think was right, but you ignore that and then it
0:07:36 becomes very clear why you should have listened to that kind of gut level instincts. I just take
0:07:42 on too much and then I’m like, “Oh, okay.” Like earlier this year, I had rolled my ankle really
0:07:48 bad. I had to go to the yard and they were like, “You got to take like six weeks off.” And I took
0:07:54 like a week and a half off. I heard it again so badly. I thought when I looked down, I would
0:08:00 see the bone sticking out of my leg. It wasn’t. Thankfully, I’d been given a very clear message,
0:08:04 not just from my own body, but from a medical professional. I said, “You got to slow down
0:08:10 and take a break.” And I didn’t listen. And the irony whenever I do this, and I’ve done this many
0:08:19 times, you end up losing more time than you would if you’d just taken the prescription when it was
0:08:25 there. It’s when we rush the comeback or we rush the recovery. What I say is a lack of patience
0:08:31 changes the outcome. And if you think about money, that’s a great area where people just try to get
0:08:38 rich quick, whereas the path or formula to get rich over time is pretty clear. And it’s available
0:08:43 to almost anybody, but you get into trouble when you start trying to rush the timeline.
0:08:49 Yeah, there’s a Latin expression called “festina lente,” which means to make haste slowly. We often
0:08:57 look for shortcuts and it takes longer than if we just sort of done it slow instead. It is amazing
0:09:05 at some level how it all can be reduced down to something in Aesop’s fables or a cliche or a
0:09:11 little proverb. I’ve been amazed lately at the idea that somebody said that for the first time.
0:09:15 Someone will invent a new word to express a concept or someone will invent a new way of
0:09:19 thinking about things and say, “Oh, that’s great.” But a lot of these things that we take for granted,
0:09:26 it’s not like they’re hardwired into our DNA. And so somebody who’s now lost
0:09:33 came up with that idea, the timelessness of the truth of that I just love. And then it’s been
0:09:39 true for 2,300 years or whatever. And it’ll be true for 2,300 more years. Yeah, almost certainly.
0:09:45 I was listening to our old episode and one thing I never asked you was, “How would you define stoicism?”
0:09:49 I’ve come to define it as this idea that we don’t control what happens, but we control how we
0:09:54 respond to what happens. And then when people go, “What does that mean? I usually follow this idea.”
0:10:01 And then stoic is predicated on this idea that you can respond with virtue or irritate annoying
0:10:09 people, a natural disaster, extreme success, death sentence. You don’t control that that happened.
0:10:13 Maybe you controlled whether it was or wasn’t going to happen, but now it is happening.
0:10:17 And to me, stoicism is the framework for which you orient your response.
0:10:23 Is it harder if we caused it versus something we didn’t cause? Is it harder to handle a situation
0:10:27 where we messed up versus we get a cancer diagnosis?
0:10:32 I think so, yeah, because we have guilt and shame and frustration, but it doesn’t change
0:10:37 the fact that it’s now there. And I think that’s part of what stoicism is, is the ability to go,
0:10:44 “Okay, how I got here is separate and independent from the fact that I currently am here.”
0:10:53 I might need to at some point examine those causes so I can learn from it, but my impulse to dissect
0:11:01 and blame and question what has happened is actually just a really convenient distraction
0:11:06 from the choice in front of me right now, which is what am I going to do about it?
0:11:10 There’s a passage in Meditations where Marx realizes, sort of criticizing the people who are
0:11:15 always trying to delve into what lies beneath. Like they’re always like, “Well, what does this mean?”
0:11:19 or “What does that word mean?” or “Why is it this way?” or “Who’s fault? What are the root causes?”
0:11:24 And again, that all matters, but usually not in the moment. In the moment it’s, “Well, what are you
0:11:33 going to do?” When should we look back and reflect on that situation so that we can actually learn from
0:11:40 it? What is our contribution to it? For me, it’s always once the strong emotions about it have
0:11:47 dissipated. How do you reflect? Do you write or do you think? To me, stoicism is journaling and
0:11:53 journaling is stoicism. Journaling is to stoicism as meditation is to Buddhism. It is the practice of
0:11:59 having a conversation with yourself about your thoughts and beliefs and values and actions.
0:12:04 And that, I don’t think it’s a coincidence that Marx realizes, his sole philosophical work was
0:12:10 entitled Meditations, which the Greek title was just to himself. Almost certainly he did not give
0:12:17 it a title. And what makes it such a remarkable work is that he didn’t intend it as a work.
0:12:23 It is a work in progress, that dialogue with the self. And so, yeah, I’m usually doing it there.
0:12:29 And then obviously the benefit of being a writer, and you know this, is like you have this sort of
0:12:37 forced self-reflection that if I was just a regular person, I think I would do a lot more
0:12:41 journaling than I do, given that I have to wake up and think about all these things and write
0:12:45 about them and talk about them. And I get asked questions about them. So there’s sort of a,
0:12:51 there’s something, there’s a benefit to the profession certainly also. You just kind of
0:12:56 ping it around in your head. I don’t think you’re going to be doing it. It’s because the thoughts
0:13:00 in our heads sort of make sense in our head. But when we put them on paper, they don’t.
0:13:07 Yeah, it’s like also what I’m hearing right now as I’m talking is an understanding of my
0:13:11 voice that when I listen to a recording of this, you see very clearly do not match up.
0:13:17 And that’s to me a metaphor for so much of the human experience, which is that it feels one
0:13:22 way to us as we’re feeling it, or as it’s coming out. And then with distance or from a different
0:13:29 lens or a, you know, a different medium, it suddenly sounds and feels and looks very different.
0:13:33 And I think it’s because it’s like, I’m hearing it through my own head right now,
0:13:39 like my, the way the sound waves are literally going through the bones in my own head are different
0:13:44 than when I’m have headphones on and it’s been recorded afterwards. Yeah, you grow up thinking
0:13:48 your voice sounds like one thing. And then you hear it recording like, Oh, I’m, I’m actually a very
0:13:55 different voice. You have these thoughts about things that feel like they make sense until you
0:14:03 interrogate them or ask, is that true? Thoughts aside, like I never thought about my voice until
0:14:08 I heard myself. Yeah. And apparently I have a very distinct voice that a lot of people don’t like.
0:14:14 It’s a feedback on the audio book is like Shane should not read books.
0:14:18 Interesting. And then I get this thing where I’m like, I was in a hot tub in Hawaii and this guy’s
0:14:22 like, I know your voice from somewhere. And I was like, no, all Canadians sound like this.
0:14:26 He’s like, no, it’s such a distinct voice. You just can’t pinpoint where it’s from.
0:14:30 But when I listened to myself talk, I don’t, I don’t hear any of that.
0:14:35 You realize in that moment, just how different objective reality and perception are how
0:14:41 sometimes it’s good to get external feedback. And sometimes it’s good to be in a bubble because
0:14:47 can you do anything about your voice? No. My therapist uses this phrase that I think about a lot.
0:14:52 And she catches herself doing it and so on. I catch myself doing it. But she’ll, you know,
0:14:56 somebody does something and then you’re like, well, what that means or what you’re saying.
0:15:03 And she always says you should preface it with this phrase. What I make up about that is what
0:15:08 they’re saying, what they’re doing, it means something to them. And then you’re having an
0:15:16 interpretation of it. It is a remark. And then you are saying it’s rude or it’s manipulative or
0:15:24 it’s provocative or offensive or loving or not loving. You’re interpreting what it is. And
0:15:28 this is a very core idea in Stoicism that Epictetus said that, you know, it’s not
0:15:33 things that upset us. It’s our opinion about things. It’s the way the voice sounds to us.
0:15:38 That is the problem, not the, not the voice. And when you realize that doesn’t magically give you
0:15:44 the ability to not have the opinion, but it does help you realize, I’m bringing a lot to this.
0:15:49 I’m making something up about that. That’s what an assumption is. I am assuming something. And
0:15:56 usually those things are making stuff harder, not easier.
0:16:00 There’s an interesting quirk to when you’re talking with people, if you say something like
0:16:06 the story I’m telling myself is, and it’s wrong, people have a tendency to correct you.
0:16:11 Yes. And so they’ll actually inform you. It’s like, no, that’s not what’s happening,
0:16:14 but you have to be brave enough to sort of put it out there.
0:16:17 Yeah. And when thinking about how much less threatening it is to say the story I’m telling
0:16:22 myself about that is this, as opposed to, I don’t like that what you’re doing is this.
0:16:30 Because one implies judgment and then the other implies not just a certain interpretation about
0:16:37 that, but an interpretation plus a loosely heldness, right? By you saying what I, what I make up about
0:16:43 that is, or the story I tell myself about that is, or the way that sounds to me is, you are not
0:16:50 expressing your interpretation of reality as reality. And therefore you are offering the person
0:16:55 the opportunity to correct or update or contextualize that thing.
0:17:03 A lot of people think stoicism is simply suppressing your emotion. How would you respond to that?
0:17:10 The Stoics got married. The Stoics had children. The Stoics went to the theater. The Stoics wrote
0:17:16 moving works that were performed in the theater. The Stoics fought in battle. The Stoics participated
0:17:22 in politics and, you know, the great causes of their time. The idea that these people had no
0:17:29 emotions is, to me, totally belied by their actual day-to-day existences that we have a lot of
0:17:35 evidence for. And when you look at Marx’s views as meditations, you’re not seeing
0:17:39 a person who is devoid of emotion. You are trying to see a person who’s
0:17:49 attempting to be less emotional in high-stakes situations or in stressful situations. But,
0:17:55 to me, that’s very different than denying or disregarding the emotions altogether.
0:17:59 It’s almost like you have a narrower band, so you don’t have these big oscillations.
0:18:04 Yeah. I mean, I make a distinction between being angry and doing something out of anger.
0:18:13 I think that’s like a pretty basic being, you know, being sad and then being in despair,
0:18:21 again, very different. And so I think, to me, Stoicism is a set of exercises and insights
0:18:28 and practices to help you understand those emotions, process those emotions, and not be
0:18:35 ruled by those emotions. But I don’t think there’s ever this place where you’re able
0:18:39 to fully transcend them. And I’m not sure you would want to. The Stoics weren’t saying, like,
0:18:43 you should never laugh. You should never have fun. You should never experience pleasure.
0:18:47 I think they were saying, hey, you know, this thing that feels pleasurable in the moment,
0:18:53 how do you feel after? And so let’s try to have a fuller picture of that thing. And they’re saying,
0:19:02 you know, if you’re wrecked every time you lose someone, life’s going to be very hard because
0:19:10 losing people is a part of life. So I think they’re trying to balance both a healthy set of
0:19:20 emotions and an unpredictable, often painful existence. And this sort of lower case Stoicism
0:19:26 that we have is about as far from the mark as lower case Epicureanism is from the philosophy
0:19:33 of Epicurus, who didn’t eat at fine restaurants or engage in orgies or, you know, truly give his
0:19:42 life over to pleasure as we understand that to me now. Can we experience like pure joy and really
0:19:49 high highs without really low lows? Or do we need the lows to actually give us the variation?
0:19:56 Yeah, I’m not sure one has to make room for the low lows in the sense that life will
0:20:02 force that upon you. I think when the Stoics talk about joy, they are trying to remind you
0:20:12 that if joy for you is only possible when things are going amazing, your joy or your happiness
0:20:19 is therefore out of your hands. Like one of the sort of philosophical questions that we get from
0:20:25 a lot of the ancients is like, could a person be happy like on the rack? Like could you experience
0:20:30 happiness as you’re being tortured to death? And I don’t think they necessarily thought you could,
0:20:35 but it is an interesting thought experiment. The idea like if joy and happiness are dependent
0:20:44 on external circumstances, how good is it? And therefore how fragile it is. And so the idea
0:20:53 to be able to experience joy and happiness in any and all situations is, I think, provocative and
0:20:56 interesting. There’s this woman, she wrote this book called Bomb Shelter. I think about it all the
0:21:02 time. She had what she thought was a normal childhood. Her name is Mary Philpott, I think.
0:21:07 She had what she thought was a normal childhood. And then she only found out later that her father,
0:21:14 they lived outside Washington DC, that her father’s job was to basically set up the government
0:21:19 facilities. He was a doctor, so he would have gone to in there if it happened, but to set up
0:21:27 basically the government in exile underground in the case of a nuclear strike on Washington.
0:21:34 And so she’s kind of thinking about what it must have been like for her father to go to his kids’
0:21:42 soccer games or punish them for not doing their homework or do anything at home with
0:21:49 like a literal sort of domicile over him at all moments. His job was to prepare for a,
0:21:59 was to assume that it was likely that they would all be evaporated in that nuclear strike.
0:22:09 And if that was to happen, part of his job was to flee and survive. It’s not like
0:22:14 the doctor got to take their family with him. So she was just talking about like compartmentalization
0:22:19 that that would require. And I think that’s interesting because one, that is actually,
0:22:24 I think, more relatable to every parent than you think it would be. You’re always thinking about
0:22:30 stuff. Yeah, you’re always thinking about stuff. And yet you also have to listen to this ridiculous
0:22:35 story about a video game character or something. You have to be present even though you’re waiting
0:22:41 for an email telling you that your job has been made redundant and you’re about to be laid off,
0:22:48 or you have to have fun with your kids at an amusement park as somebody you know is dying
0:22:54 in a hospital or whatever. And I think when the Stoics thought about joy and happiness,
0:23:02 they were thinking about a more resilient form of that emotion, not fun, smiling, cheerfulness,
0:23:08 happiness, but like a happiness of a person who is surviving the blows of
0:23:15 fate and flourishing as a human being in good situations and bad ones. There’s a story about
0:23:26 this one Stoic named Agrippinus. And he’s he’s exiled for running a fowl of Nero. And he’s told
0:23:34 that he’s been convicted. And you know, he has like, there’s like an hour before the verdict
0:23:39 comes down. And I think he exercises or something. He just like does whatever he just goes about his
0:23:45 day. And then they’re told, okay, you’re being you’re being exiled and you can take some of your
0:23:50 property with you. Was it going to be a penniless exile or not? He finds out he can take some of
0:23:54 his property that he says to his friend, okay, we’ll have our lunch on the road then. Or I forget
0:23:59 what it’s Attica or something. He’s like, we shall have our lunch in Attica. You know, he’s
0:24:04 like basically like, what is going on the road? And to me, there’s that is close to the Stoic idea
0:24:13 of joy and happiness of you just just got told everything was stolen from you. You just got
0:24:21 told you have cancer. You just got told, you know, insert horrendous event. Does it break you? Or do
0:24:27 you just go, okay, what’s next? So it’s not arguing with the reality or the situation as as it’s been
0:24:32 given to you or the hand that you’ve been dealt. It’s just how do I play this hand to the best of
0:24:37 my ability? Yeah, there’s no complaint about the unfairness, the preciousness, the surprise. Just
0:24:43 what are we having for lunch? Can you train yourself to think that way? Or is it something you
0:24:49 think is more there’s people disposed to that? I know I’m not born that way. I wouldn’t say that
0:24:57 I am now that way. But I think I am further along in becoming that way than I was at the beginning.
0:25:04 I think it’s probably true for a lot of the decision making and cognitive stuff that you
0:25:09 talk about, which is like, are there people who are naturally gifted and have this sort of a
0:25:16 computer, you know, mind? Yes. And then there are those of us that are not that way. But in the
0:25:23 process of studying and thinking about them, can we slow that process down? Can we be more conscious
0:25:31 of the things less of a slave to the things? I would say yes. I find it easier for me to like
0:25:37 in these moments where something is happening, we’re stuck in traffic. I love it when the kids
0:25:41 are in the car. Because when the kids are in the car, I can be like, oh, this is a good teaching
0:25:44 moment, right? Like, there’s not much we can do about it. Might as well make the best of it. Let’s
0:25:48 put some music on. Let’s have a conversation. Let’s do XYZ. But if they’re not in the car,
0:25:53 my immediate temptation is sort of like, oh, traffic, you know, we’re really good at giving
0:25:58 advice to other people and then not so good at applying it ourselves. Because we have that
0:26:05 cognitive distance, you know, we’re able to, it’s our identity is less at stake or our emotions are
0:26:17 less tied up in it. With your kids, you’re able to see the impotence and the unfundness of the
0:26:26 frustration. And you also feel obligated to help them with the meta skill of that. Because of the
0:26:32 specific instances with a kid, you’re like, well, what, how is this going to matter for their life?
0:26:39 But we’re not as good as that for us. We’re like, I’m mad that someone said XYZ, not, hey,
0:26:44 how can I get better in my life at not responding when people say XYZ.
0:26:51 So yeah, you learn as you teach the stoics. What other misconceptions do you run into about
0:27:01 stoicism? Well, that it’s all old rich white dudes with a lot of merit and a desire to
0:27:08 point out the biases and sort of structural patterns of not just the ancient world, but all
0:27:16 forms of history, just to focus on what was obscured or what’s not included. We forget just how
0:27:23 enormous the Roman Empire was. I mean, the Roman Empire makes contact with the Han dynasty during
0:27:30 Marcus Aurelius’s reign, and it stretches as far as England and Africa and the Middle East. And
0:27:40 you have Epictetus, who’s a slave. You have Marcus Aurelius, who’s the emperor, Zeno, the founder
0:27:49 of stoicism. Some people were convinced he is black. He’s described interestingly in some of the
0:27:55 few descriptions we have of his physical form. But in the case, he’s like a Mediterranean merchant.
0:28:02 And so just the idea that that it was like all people of the same social class, just because
0:28:08 Rome was a caste society, doesn’t mean that all the philosophers perfectly conformed to
0:28:14 that caste. Just because we hear mostly of the men doesn’t mean there weren’t stoic women.
0:28:19 Cato’s daughter, Portia, is involved in the assassination of Julius Caesar.
0:28:27 All the stoics would have had wives and daughters. There’s a fascinating essay from Mussodes Rufus,
0:28:34 who’s not just Epictetus’ philosophy teacher, so he’s teaching a slave, but he writes this essay
0:28:38 about why women should be taught philosophy. So we know he has female students. We just don’t know
0:28:43 any of their names. And there’s been a backlash about stoicism. It’s like, oh, this is a bro of
0:28:50 philosophy for bros in Silicon Valley, or this is for meatheads, or this is for soldiers.
0:28:55 Yeah, there is, I think, a connection to certain masculine worlds in stoicism. But I mean,
0:29:04 a huge percent of my audience is not male. But I also, just on a historical basis, that’s not true.
0:29:12 And so this idea, if stoicism is like for dudes of the army, and it’s about suppressing their
0:29:18 emotions, I get why it’s not going to be attractive. But that’s not what it is. Just like if you think
0:29:23 Epicureanism is orgies and parties and retreating from the world, you’re going to be like, what is
0:29:30 this? But that’s not what Epicurus was talking about either. I thought it was, not Zeno, I thought
0:29:36 it was Sisyphus, who, maybe I’m getting really confused here, who created like the first sort of
0:29:43 stoic? Chrysippus? Yes, that was the one. Created what? Sorry. Stoicism. No, Zeno was the founder
0:29:50 of stoicism. Zeno studies under this cynic philosopher named Cretis. By the way, Cretis is
0:29:56 an equal partner with his philosophical wife in Athens. There’s always been a female influence
0:30:02 from the beginning. But Zeno is credited as the founder of stoicism. He sets it up on the stoa
0:30:09 pochile, this porch in the Athenian Agora. That’s where stoicism comes from. Then there’s Cleanthes
0:30:14 and then Chrysippus. But it doesn’t really become a real school philosophy until later with sort of
0:30:21 codified. But Zeno is considered the founder of stoicism. Is the connection with really, instead
0:30:27 of sports and military, if we sort of generalize that, is the connection just with anybody who’s
0:30:33 doing hard things and yet we tend to hold up these professions? I think so. I mean, that’s what
0:30:40 sports are, is a metaphor for any kind of pursuit of excellence. It’s just the most
0:30:49 visible. Because it’s a game with rules at the beginning and an end, the most observable form
0:30:58 of excellence. An entertaining form of excellence. And look, in the ancient world, they’re using
0:31:04 sports metaphors then too because it’s the same process. One of the stoics is talking about how
0:31:11 he thinks that a philosopher has to be like an athlete. He’s just like a ball player. You
0:31:16 catch the ball and throw it back, catch the ball and throw it back. And whether it’s a good throw
0:31:20 or a bad throw, you still have to catch it. He considers Socrates like the greatest athlete of
0:31:26 all time because he deals with the things that life throws. And I’m including this as death
0:31:31 sentence. There’s weightlifting metaphors and racing metaphors and some of the stoics were also
0:31:37 athletes. So I think there’s something about sports that is the sort of unmitigated pursuit of
0:31:44 excellence. And yet it’s also not unmitigated because we expect our athletes to exhibit sportsmanship
0:31:52 and grace and coolness and repression. All these traits that go into being a full well-rounded
0:32:02 person are at play in sports. This is I think why the Olympics are this sort of enduring thing.
0:32:07 We still observe some of the same exact sports almost that the stoics would have been very
0:32:13 familiar with. Do you think anybody can be at the far right of the curve in whatever domain
0:32:20 they’re an expert or a sports or skill and be a normal sort of person? I think about this all
0:32:30 the time. I would like to be both. And I think you do realize there are trade-offs part. There is
0:32:41 something inherently unbalanced about excellence in a singular domain because you are focusing
0:32:48 all of your energy on one thing. There’s something dysmorphic about like the athlete’s physique.
0:32:55 And that’s probably just the physical manifestation of also if you could look at their mind
0:33:03 and their priorities probably equally out of whack. But if they weren’t out of whack then they
0:33:09 wouldn’t be on the right end. Yeah. I mean what I really admire and I’ve gotten to meet a handful
0:33:13 of them over the years and I’m always reluctant to be like well this one is a good example of this
0:33:17 because you don’t really know what’s happening in anyone’s personal life. But I think it’s really
0:33:23 something special when you meet someone who has inarguably attained the
0:33:32 heights of their profession or in some sort of all-time greats achieve the great prizes of their
0:33:40 thing whether it’s politics, sports, business, art and they seem reasonably well adjusted.
0:33:49 They haven’t left a trail of bodies behind them, literal or otherwise. Their family wasn’t
0:33:55 utterly neglected. Their health wasn’t utterly neglected. Their moral priorities weren’t so
0:34:00 weren’t grotesquely out of alignment. So when you meet someone you’re like oh
0:34:07 they did it as good as it can really be done but they didn’t have to turn themselves into
0:34:14 a monster to do it that’s that’s all I would argue a much rarer feat. Power corrupts, absolute
0:34:19 power corrupts absolutely. So what I think makes Marx really such a fascinating example is here you
0:34:26 have one of the few humans to hold absolute power as we would really define it and
0:34:39 doesn’t seem to have become deranged or grotesque is into an overwhelmingly cautionary tale. That
0:34:49 to me is a rarer feat than if you told me he had won the single greatest you know military victory
0:34:54 of all time. Like the greatest victory of the Stokes would say would be the victory over those
0:35:01 very impulses. There’s another Roman I think it was like a Cincinnati you know your history
0:35:06 way better than I do. Cincinnati’s who like gave up power. Yeah I tell this story to my son all the
0:35:14 time Cincinnati’s is maybe not real maybe real but his example was certainly very real to the
0:35:21 Greeks and the oh I guess to the Romans not to the Greeks but yeah Rome is sends out its army
0:35:30 in this big battle and they’re defeated and the army’s trapped and so Rome had this sort of emergency
0:35:39 you know smash in case of emergency button that said you know you could make someone dictator
0:35:46 to save the Republic and so they go to Cincinnati who had been in general and they make him dictator
0:35:54 and he rounds up every you know straggling man and boy in Rome at this time and he marches out and he
0:36:00 defeats he rescues the army he defeats the enemy and then he returns to Rome
0:36:08 resigns as dictator after like 17 days and then he returns to his farm. He just goes back
0:36:16 to his regular civilian life and it’s this example that is told for generations and generations and
0:36:23 generations so much so that George Washington hears it as a young boy and he resigns his
0:36:29 commission repeatedly. I was just in Annapolis a couple weeks ago and you can stand in the
0:36:34 courthouse where he resigns his military commission and then when he resigns after two terms as
0:36:40 president but King George when he hears after the revolution he’s you know what it’s to become
0:36:48 of George Washington he’s told that you know I think he intends to return to his farm to not
0:36:56 make himself and the Washington name you know a hereditary monarchy and King George says you
0:37:03 know if he can do that he will be the greatest man on earth and there is something about relinquishing
0:37:10 power or walking away that takes an incredible amount of discipline and strength and then we
0:37:15 don’t usually appreciate in the moment and in fact we tend to ridicule and mock it like
0:37:22 you know Andrew Luck the quarterback he walked away and we don’t hear about him anymore so he’s
0:37:28 not out there like fighting for his legacy arguing about his accomplishments he’s not on tv so he
0:37:33 just sort of recedes from memory but he also made like a hundred million dollars playing football
0:37:41 he as far as we know escaped without any serious long-term you know brain injuries I don’t know
0:37:51 what he does all day but you know the idea is any walk away at the top yes yes to be out there has
0:37:59 there been any boxer in history that’s walked away too early probably not it clearly takes more
0:38:10 discipline to walk away early or on top than it does to go for the sixth ring or the three
0:38:17 feet or whatever those things are extraordinarily hard but clearly if less people do this other
0:38:23 feet it must be because it’s even harder do you ever think of of walking away from writing
0:38:29 yeah why did you think it’s time for me to retire oh that’s the one I was saying at all
0:38:34 you’re you’re sort of like you’re in the middle of it right like yeah you’re like what 12 13 14
0:38:39 books so many like the thing that for me is that’s the part that I like doing you like and it’s
0:38:46 probably the least hard on me right it’d be the other stuff that I think would would be like the
0:38:52 bookstore or youtube no yeah like youtube or podcasts or speaking or to just be like now I’m
0:38:58 just just going to do this one part I don’t know how people do podcasts once a week or more like
0:39:03 I found once every two weeks hard how often do you do it 26 times a year is that a deliberate choice
0:39:10 yeah I don’t think I could remain intellectually like I don’t think it would be genuine if I was
0:39:15 doing it weekly I’d be finding people that I could talk to you not people that I wanted to
0:39:21 talk to you know what I mean like I’d be filling a slot versus I really want to talk to this person
0:39:25 well you also do your interviews are longer right so
0:39:30 you might be able to say if somebody’s doing
0:39:37 two a week and they’re an hour that’s the same as you doing but I find all the work that goes
0:39:43 into it sure it’s not like I show up I got this one page thing but this is like nine ten hours
0:39:49 when I had my marketing company one of the reasons I never wanted to hire employees
0:39:59 was that I was skeptical that there were enough projects that I would be interested in working
0:40:10 on to pay for and the people which meant if I hired someone they would represent a certain
0:40:16 number of projects per year just to get back to even I go back and forth between whether that was
0:40:26 a constraining kind of limiting belief or if that was actually like a pure and like admirable
0:40:30 stance and you kind of distance yourself from the work too right like so if I hired somebody to do
0:40:35 the research for the podcast I could show up there’d be a list of questions but part of what I enjoy
0:40:42 about it is actually doing all the research in the work the pressure to scale like I know a lot
0:40:51 of people in the this kind of information media space that have taken on like private equity
0:40:57 investments like there’s like the churnham group and so they’ll buy like half of the business or
0:41:02 all the business and then the idea is like well how do we scale this into a much larger company
0:41:09 I’ve expressed no interest in doing that because like to me part of the whole joy of doing it
0:41:16 is not having a boss and not needing to get at us to a certain level or do a certain amount of
0:41:26 things which you are forgoing with you bring on somebody else I was starting to John Mackey
0:41:32 about this the Whole Foods guy and he sort of said I love this analogy he’s like when you bring
0:41:38 people on they’re usually hitchhikers so they’ll be in the car with you and as long as you’re going
0:41:43 in the right direction at the right speed they’ll pay for the gas but the minute you you’re like
0:41:48 oh I’m really curious what’s over here they’re going to be like no what do you do you can’t do
0:41:52 that and then all of a sudden you have a boss and you have all this pressure and you know they own
0:41:58 half of your yeah it’s more like you went from being the driver to being the passenger kind of yeah
0:42:01 the other person is like has a they have a break and they have their own steering wheel
0:42:08 and they have their own accelerator the pressure to scale is obviously a first world problem because
0:42:15 you’re most people and not that long ago for me that the problem was breaking through or breaking
0:42:23 out yeah once you do that because that is so rare there’s an immense amount of structural pressure
0:42:31 economic pressure cultural pressure to you know take a winner and turn it into a big winner
0:42:37 as opposed to just being like this is nice even with the bookstore every couple weeks I’ll get
0:42:41 an email being like hey if you thought about opening another one and it’s like I already
0:42:51 hit the lottery by not failing do I need to start a chain of bookstores I don’t think that I do
0:42:59 and I don’t think that would improve my life quality at all but we it’s easy to be disciplined
0:43:04 in some areas and not in other areas so when you’re successful one of the tendencies is to
0:43:08 start saying yes to all these other projects start hiring a team and then your distance from the work
0:43:12 and you can be like you go do this and then all of a sudden you start taking on projects just to do
0:43:20 them yes how can we use stoicism as a means to sort of focus our energy and remove distractions
0:43:26 Marx just writes in meditation you can imagine the immense pressure and inbound that’s coming at
0:43:31 the emperor of 50 million people he says in everything that you do and say in the thing you
0:43:36 have to ask yourself is this essential and he says because most of what we do and say and think is
0:43:41 non-essential and he says when you eliminate the inessential you get the double benefit of doing
0:43:47 the essential things better knowing that what you’re saying yes to means saying no to other things
0:43:55 and conversely saying no to things means saying yes to things is like the very tricky never gets
0:44:00 easy balance that I was struggling with like even this morning my wife and I were like okay I got
0:44:04 offered to do this and I got offered to do that what do we want to say yes to what do we want to
0:44:12 say no to and then just the you would think at some point not needing it would make it easier
0:44:18 to say no but opportunity costs you get more opportunities yes and success tends to sow the
0:44:24 seeds of its own destruction it’d be easy to say like oh when you’re you know be disciplined
0:44:33 while you’re successful you know don’t don’t take on too much you say no to a lot of things but
0:44:44 in sports or entertainment or art or even you know whatever it is that you do you don’t do it
0:44:49 forever do you have a narrow window and there’s going to be at some point where it dries up and so
0:44:58 are you going to look back and go there was almost a bit of ego in my in my selection process because
0:45:04 I was assuming that I would get to do it forever I continue to wrestle with that constantly how do
0:45:09 you think about opportunity cost is it always increasing for you or is it based sort of like on
0:45:14 the workload right in front of you or I was thinking about how kind of like what seems like a lot of
0:45:20 money to you as a kid always remains a lot of money to you even as your income goes up
0:45:28 it’s hard for you it’s hard for me to pass on things because that seems like a lot even though
0:45:34 proportionally it no longer is I’m trying to do work and get more clear get more objective about
0:45:41 like no hey actually yes that to and to you 10 years ago to any person on the street
0:45:50 that is a lot but given what your time is actually worth at its current valuation that’s actually
0:45:56 something you should say no to that’s hard imagine if you’re a billionaire how hard that must
0:46:03 get no one’s throwing them a pity party but like that must be very disorienting and destabilizing
0:46:12 to not have a good way to value what to say yes or no to the problem is financial upside is always clear
0:46:21 opportunity opportunity costs are sometimes clear but often not clear if I get offered to
0:46:29 do I don’t know speaking gig that’s the opportunity cost of saying no or whatever they’re offering
0:46:37 the opportunity cost of saying yes is whatever creative work I might have done had I stayed home
0:46:46 and then also intangibles like the rhythm of our households my personal happiness how easy things
0:46:54 are and so one is the the the downside is in one sense is very quantifiable and the upside in the
0:47:02 other case is very hard to quantify and in in some cases the consequences of it are are quite lagging
0:47:13 and so you’re faced with briefcase with cash in it and hey isn’t this a bit much we’re all tired
0:47:17 how do you balance that my uncle taught me this thing when I was a teenager about how he used to
0:47:23 price his business so he was a he ran a plumbing company what he did was basically the first 75
0:47:30 percent of hours were priced at 100 percent so the regular rate but 75 to 80 he would increase the
0:47:36 rate 80 to 100 you’d increase and over 100 percent of like a normal work week then it increased it
0:47:41 even more and it was super transparent with people about this like I’m really busy right now I hate to
0:47:46 give you this quote but to do the job properly here’s what we’d have to price it at and he’s
0:47:51 pricing it at like 150 because he wants them to say no he doesn’t want to be the one to say no he’s
0:47:55 like I’ll figure out how to do it for this price and he’s like was so surprised by the number of
0:48:01 people who said yes in part because of his honesty right but I use this this is sort of like one of
0:48:06 the simple principles that I use which is like if I’m super busy I’m going to price it more because
0:48:10 I actually kind of want you to say no right but if you’re going to say yes then I’ll make it work
0:48:16 but it’s at a certain price and so the pricing that we use is dynamic in some ways and there’s
0:48:22 like a baseline which is like here’s the minimum and you need a certain amount of self-confidence
0:48:29 and security to be able to do that and you can see why if you’re like if you ever just said
0:48:37 endorphins void inside you how vulnerable that makes you yeah because you want to be wanted you
0:48:45 want the validation you want the cha-ching yeah that feels good but like you like I get I get
0:48:50 five speaking requests a week yeah and there’s no way you can say yes to everything so you have to
0:48:56 have a system to sort of well if I think the first step is you have to have someone between you and
0:49:02 the thing oh totally just eliminate three of the five that were not serious or not even not serious
0:49:07 but we’re at a number that might be tempting but it’s better for you not to see because you’re
0:49:11 more likely to say yeah what could happen as you become successful is you can become jaded and
0:49:16 entitled yeah and you want to be like you want to keep yourself as the good guy the nice guy that
0:49:24 the person who is saying yes yes so you have to set some boundaries and then task other people
0:49:29 with enforcing them yeah I think some people go oh is it you know you want to pay these people
0:49:34 commissions you just do it yourself and I think there’s a danger in doing yourself which is that
0:49:41 totally it almost it can go to your head and also kind of and then when it goes away what yes this I
0:49:45 worry about this all the time right it’s like well five and I’m like saying no you’re at that book die
0:49:52 was zero yeah it’s a great book but the idea is you know thinking about what are you what are you
0:49:56 trying to do all this for you try to accumulate a large amount of money that you don’t get to take
0:50:01 with you when you die we are borrowing money from our poorer selves to loan to our future richer
0:50:05 self the example that is the book which I think is a good one he’s talking about like a medsoon
0:50:10 who’s like living way below their means saving up money they know in the future they’re going to
0:50:16 make a lot of money it’s very clear how that profession works right and so they’d be more
0:50:23 effective maybe not racking up a ton of debt but like not living as if they don’t know for certain
0:50:29 their financials they’re they’re not actually you know making thirty thousand dollars a year
0:50:38 they’re just temporarily making that anyways that advice is very helpful in clarifying in more
0:50:44 predictive linear professions but that would be bad advice to give to a rookie in the NBA
0:50:50 because they may only be able to do it for two years I think it is tricky when you have
0:51:00 a very clear element of unpredictability and a very historically a very clear drop off
0:51:10 like at some point you age out at some point yeah your trend or moment goes away and maybe
0:51:15 it comes you survive long enough for it to come back but like the idea that for me as their author
0:51:20 that my sales are only going to go like this it’s preposterously naive that it adds this layer to
0:51:27 like okay so you’re saying no because you’re too busy right now yeah but in six years you’ll you’ll
0:51:33 feel like an idiot you wish for this request to come back yeah is it ever okay to lose your cool
0:51:38 like is there strategic points where it actually makes sense to sort of not be stoic and to to
0:51:44 I wouldn’t say completely lose control but to have more variation we had this idea
0:51:54 that like crying is is not manly right like being overwhelmed with your emotions is somehow a weakness
0:52:01 but we make an exception culturally for anger if you went through some problematic work thing
0:52:07 and you cried in front of your whole team you would reasonably expect that team would be like
0:52:12 what’s wrong with Shane right I’m not saying that that’s right they just would but if you
0:52:18 got so angry that you punched a wall not only might not you be judged for that that might be
0:52:22 like part of the legend of Shane right which is interesting and the stoics would point out that
0:52:31 like those are both the same process of being overwhelmed by our emotions and one is actively
0:52:39 harmful to you and your world and the other is not and so it’s kind of strange so it’s it’s
0:52:42 interesting we have a couple of stories and Mark’s realist crying but we don’t have any stories of
0:52:48 him losing his temper and I think he was chastened by the fact there’s a story about Hadrian his
0:52:54 predecessor who’s gets frustrated with his secretarity he grabs the secretary’s pet and he
0:52:58 stabs it in the man’s eye like this is the thing that the king could the emperor could get away
0:53:08 with literally anything and so I I do think it’s interesting the allowances we make particularly
0:53:13 with men for certain kinds of emotions and not other kinds of emotions and I’m I’m not saying oh
0:53:19 hey we should be all with one or all with the other it’s just the idea of the the stoic
0:53:29 suppressing their tears and sadness and love and affection but then you know being a vortex of
0:53:34 temper and rage strikes me as a contradiction that doesn’t make any sense and the idea would
0:53:41 be to be kind of an even keel across the board that being said there is a difference between
0:53:47 being angry and doing something out of anger and then there’s a third which is
0:53:54 the performative element of anger your head basketball coach and you’ve gotten a series of bad
0:54:02 calls losing your temper screaming at the ref and getting ejected not only doesn’t help your team
0:54:08 but it costs your team points because you get two technicals but if you are so even healed
0:54:14 that you’re just allowing the refs to run over you or you’re allowing a lackadaisical effort from
0:54:23 your team to go unchastened also probably not good and so I am fascinated by the way that a great
0:54:36 coach can turn up or down certain levers I was at a spurs game one time and I watched Greg Popovich
0:54:46 get ejected and Tim Duncan took over and the team was down my seven or eight points and Tim Duncan
0:54:55 coached the rest of the game and they came very narrowly within winning like it came down to like
0:54:59 the last two seconds and they didn’t win but they almost did and somebody told me after that Pop had
0:55:03 looked at Duncan and said I’m going to get myself thrown out you’re going to you’re going to handle
0:55:08 the rest of this game and he was just he he saw that the team needed an energy shift and that
0:55:15 that was a tool in his toolkit I find that very interesting I want to move on and talk about
0:55:19 discipline okay for a second when we think of discipline I mean the image that comes to mind
0:55:25 for me and probably a lot of other people is like the army drill sergeant what is discipline I’m
0:55:34 talking about self-discipline so the the discipline of an army sergeant is obviously important but I
0:55:40 don’t think that’s a virtue because it’s being imposed on you of course essential that an army
0:55:46 is disciplined how would you define self-discipline but the virtue of self-discipline is the discipline
0:55:51 that you insist upon yourself so it’s what you do when no one’s watching it’s what you do with the
0:55:57 discretion that is given to you and I think when we think of self-discipline we shouldn’t just be
0:56:01 thinking of physical discipline it’s not just how does your uniform look and how far can you march
0:56:08 and self-discipline is can you keep your head about you when things are falling apart can you
0:56:18 be a calm you know reassuring presence can you keep your emotions in check so so self-discipline
0:56:21 is sometimes rendered as the idea of temperance which just doesn’t have a good connotation in
0:56:27 the initial language but it it is the soaks would say the greatest empire is command of oneself
0:56:33 and so whether you’re the emperor or a slave whether you’re a soldier or a ceo it’s this idea
0:56:39 of not like what are you allowed to get away with what is being asked of you and it’s more like what
0:56:45 are you asking of and insisting of yourself to me that’s what self-discipline is or do you struggle
0:56:52 the most with it knowing one’s limitations setting reasonable bounds on things i don’t have a problem
0:56:58 getting up and working i have a problem getting up from and stopping working i mean i have other
0:57:04 vices too whether it’s food or you know my screen or devices or whatever but i think for the most
0:57:13 part it’s discipline for me is closer to balance and saying no than it is to insisting on yes for a
0:57:18 lot of people it’s sort of uh the discipline to eat healthy the discipline to go to the gym the
0:57:23 discipline and then if we miss one we think it’s like it’s over like we’ve how do we get back on
0:57:27 track you told me something though that i’ve been thinking about where you said that you’re you go to
0:57:34 the gym every day yeah as opposed to i work out three days a week yeah because there’s a consistency
0:57:42 to every dayness and it’s not a choice then yes it takes away the lie you can tell yourself which
0:57:47 is i’m doing it tomorrow yeah you can do it you can change like duration or scope but like work
0:57:53 out sweat every day it’s like it’s so life changing for me and yeah other people who’ve tried it after
0:57:57 listening to me it’s been life changing for them too no it’s a great way to think about i try to
0:58:03 write every day um we’re trying to do a little something every day and that’s better for me than
0:58:09 okay i’m not doing it and then next month i’m going to start doing it this you use the word
0:58:15 try like i try to write every day so like how do you get back on track if you you went two or three
0:58:19 days you’re traveling you’re talking you’re just busy with all the stuff that goes on you get home
0:58:25 the family needs you and then all of a sudden it’s three four days i always always have the opposite
0:58:35 problem which is telling myself that being five minutes late on this is not as big a deal as it
0:58:40 feels in the moment i am tending to fight the compulsive side of it and so the battle for me
0:58:47 is going let’s just have a nice weekend as opposed to i’m behind right i’m going to
0:58:57 blow apart this nice weekend to check some arbitrary box in a race that i am preposterously
0:59:02 ahead on and by the way don’t even need to be doing but if you don’t push yourself like what’s
0:59:08 the flip side of that what do you worry about are you scared you’ll just stop and be lazy or i
0:59:13 mean that’s the thing about most compulsive tendencies is they’re not based on anything
0:59:18 you have this belief that if you don’t do it things will fall apart i’m the same way like
0:59:24 i work every day yeah it’s not based on anything real and most of the time what you get is not even
0:59:34 the reward for doing it you get the relief for having not not done it the feeling is not i’m
0:59:40 proud of myself i did a great job this made a huge difference the reward is see you’re not a piece of
0:59:49 shit and that is not not a way to go through life does your work haul is a sort of an amazing
0:59:54 that no no go for it but does that cause issues in your relationship yeah of course uh i think it
1:00:01 always has um and so what you you oftentimes workaholism or any kind of sort of compulsive
1:00:10 tendency to do is adapting from some sort of either childhood wound or insufficiency or it’s
1:00:17 it’s sort of a way of soothing something that you feel but unlike a lot of addictions or compulsions
1:00:24 it’s uh somewhat productive it’s somewhat productive and it’s socially adaptive
1:00:34 doing heroin or you know uh drinking all night tends not to have positive social reinforcement
1:00:42 but being really good at what you do and thriving on that feeling of being validated
1:00:48 for being good at what you do is a is nevertheless a pretty wicked feedback loop
1:00:53 are you sort of like motivated i think about this all the time and it like sometimes it motivates me
1:00:58 and sometimes i’m like oh it’s hopeless you know there’s like this gap between where i think i could
1:01:05 be and where i am and no matter where that is on a relative like y axis it’s like that gap is what
1:01:11 i’ve focused on which is like how do i shrink this gap and then you know like where i think i could
1:01:16 be is probably growing slightly faster than where i am and so the gap is widening yeah and then it’s
1:01:21 like i need to there’s so many things i want to do there and i have so much excitement and energy
1:01:28 around it what did you throw on top of that like what you hear other people are doing yes it’s even
1:01:34 more hard to run your own race instead of guys this word euthymia and he talks about being on the
1:01:41 path that you’re on this is not being distracted by the paths that crisscross yours says especially
1:01:46 the paths of those who are lost and i think about that all the time you don’t know where someone’s
1:01:50 trying to end up you don’t know where they’re going to end up you also don’t know what is propelling
1:01:57 them addiction or psychological issue what’s propelling them is millions of dollars of a fortune
1:02:04 they inherited or you know some dark money you know donor it could be a bazillion things you
1:02:12 don’t know and so i think the more indifferent and probably ignorant you are of what your peers are
1:02:21 doing the healthier you are and the the cleaner your compass reading will be i think of it is
1:02:27 like swimming in your own lands and there was this video i think it was from the olympics post 20 i
1:02:33 forget what year it was but this guy is swimming and he looks over at his competitor and it ends
1:02:38 up distracting him just enough that he loses the race yeah because he’s like one he’s not worried
1:02:44 about him and his land and his goals and his stroke and yes he looks over just enough to distract
1:02:48 and he lost by like milliseconds yeah there’s that although the other one that keeps me up there
1:02:56 was a there was like a mountain bike race and the japan olympics i think and the woman thought she
1:03:02 was in first place but she was actually in second place oh so she let up because like it’s sometimes
1:03:06 you know like in swimming you’re only next to each other like the marathon or something longer
1:03:11 races you might be might be two minutes that’s a closeable gap but you can’t see what the other
1:03:20 people are doing even if it was an insurmountable lead for her to get first her second place time
1:03:26 was not the best that it could be right so clearly at some level we understand that competition is
1:03:34 healthy and motivating and yet too much competition is disorienting and ultimately is self-defeating
1:03:39 and so that balance is tough what can we do to cultivate more discipline
1:03:48 oh i mean look i think having a physical practice is a way to cultivate more mental
1:03:54 and cognitive discipline like going to the gym or running running swimming biking like i do at
1:03:59 during sports and they help me as a rider like i couldn’t do what i do as a rider without those
1:04:05 physical components uh even like i have a cold plunge and there’s something about like i’m going
1:04:10 to get in this thing that is uncomfortable and i’m going to decide how long i’m going to stay in it
1:04:16 whether or not it has any health benefits whatsoever and i’m pretty skeptical at this point
1:04:21 of like all of those claims because i’ve seen what nonsense like these same communities will
1:04:29 propagate so to me the benefit is is purely that it’s hard that it’s hard and then i am doing the
1:04:34 hard thing and how do you sort of teach your kids or instill discipline and then it’s tough my kids
1:04:43 are still pretty young and so i am i am hesitant to give them my somewhat unhealthy adult levels
1:04:49 of discipline part of me is just like letting them enjoying letting them just not be my assumption
1:04:57 is that they have whatever i have and so allowing them to enjoy not having it is part of how i think
1:05:04 about it because i watch as they get into things they don’t just like kind of get into things they
1:05:09 go all in they need they’re like i need all of this i read a story about tom brady watching his
1:05:15 son playing video games and his son getting so upset and he like throws the camera throws the
1:05:22 controller the tv or whatever and is just like he was like dude i have that and it it doesn’t always
1:05:29 take you where you want it to take you and so i i suspect that that part’s there so it can help you
1:05:36 but it can also get in your way yeah and would you wish it on someone especially someone who right
1:05:43 now is young and pure and has no none of these adult notions a lot of people with dyslexia talk
1:05:51 about how that dyslexia is shaped and informed the success they have then if you ask them would
1:05:56 you want your kids to have it they’re like are you fucking out of your mind we know like hard
1:06:04 things and struggle and adversity we know it’s good for us and yet we don’t want them for our kids
1:06:09 we don’t want it for our kids and and we also know though like if we hadn’t had that we probably
1:06:13 just would have had something else yeah like i’ve never met someone who had zero adversity in there
1:06:20 like sometimes people ask me hey should i create adversity in my kids’ lives or do i need to seek
1:06:25 out obstacles and i’m of two butts i think like having a physical practice is obviously a way
1:06:31 of creating adversity at the same time you know was it dosto eski would like gamble all this buddy
1:06:38 away so that he would write better i don’t know if you need to how would you define character
1:06:44 ooh i just heard something someone said like character like your reputation is what other
1:06:50 people think of you and characters like what you do and people don’t see there’s like an element of
1:06:55 right and wrong embedded in this but who who sort of defines what’s right and wrong that’s the hard
1:07:00 part i so i just i’ve been doing this series of the cardinal virtues so i’d encourage and discipline
1:07:05 and justice and on one level yeah i would go how do we know what’s right and wrong is it the 10
1:07:12 commandments is there some you know scientific basis or utilitarian argument for what’s okay about
1:07:22 and then it is remarkable how much societies and cultures all agree on some fundamental level
1:07:27 as to what yeah there’s disagreement some people some countries burn their dead some bury their
1:07:34 dead some you know do this or that pretty much every culture religious tradition and philosophical
1:07:41 school has formulated some conception of the golden rule and all the philosophers that you know come
1:07:45 to some level of like well what would happen if everyone did that one of the things i don’t like
1:07:53 about philosophy is the way that it looks at these moral questions and it makes them so complicated
1:07:59 as to make them almost worthless like how do you know what’s right and wrong what about this what
1:08:05 like we it’s like we almost focus on the edge cases as a way of there’s such a middle ground that
1:08:12 we can all agree on yeah that’s like 95 percent you know we’re like should you know a nazi’s begging
1:08:18 on your door they want to know if you have a jew in your basement should you lie to them or
1:08:24 should you tell the truth because you know like this is a cons categorical imperative you know a
1:08:30 trolley is racing down a track and it’s going to kill five people but if you pull this lever it’ll
1:08:37 go here and kill one person what would you do it’s a way of abstracting away from the fact that we
1:08:45 have morally charged decisions in front of us all the time and we don’t think about it and don’t
1:08:50 do anything about it and that that middle ground if everyone just did a little bit better on this
1:08:56 middle ground the whole world would be immensely better we’ve all sort of had moments where we
1:09:01 didn’t act to the person we didn’t choose the action to the person that we’re capable of being
1:09:07 totally how do you live up to the best version of yourself we think of virtue as this thing that you
1:09:14 have or don’t have think of it as a noun when it’d be far better to think of virtue as a verb
1:09:20 Aristotle says like how do you get better at playing the flute it’s by playing the flute
1:09:26 how do you become a more generous person it’s by doing more generous actions he sort of compares
1:09:34 virtue to any other craft that you know a carpenter builds stuff and that’s how they
1:09:41 become a carpenter so a good person does good things not the way we sometimes think about it
1:09:47 which is like go through your regular life and then perhaps you will find yourself in some
1:09:54 decision of enormous moral consequence upon which the fate of the world will depend and then let’s
1:10:01 hope that you draw from this ethical framework that you read about in a book and will make everyone
1:10:08 proud but in fact it’s like a series of small daily decisions just like any other discipline
1:10:11 and that’s why these virtues are so related like there’s a discipline to justice
1:10:17 I keep my word I help people I
1:10:27 think about the consequences of my actions on other people I don’t do insert x y or z thing
1:10:33 that might be legal but not right and so if you think about it as a practice
1:10:38 you can get yourself not only can you get yourself to a place where you’re capable of
1:10:43 doing it but by nature of doing the practice it’s never going to happen we’re just going to pick
1:10:48 some random ass person and put the fate of the world on their shoulders you have to be
1:10:56 involved in the thick of things making decisions of consequence to ever find yourself in a position
1:11:04 of decisions of consequence we live in a world where your slip up in character which we all make
1:11:09 yes can now become viral on the internet it’s like you yelled at somebody you weren’t generous
1:11:13 when you could have been generous you did something stupid somebody had their phone out
1:11:19 and now you can’t recover from this you know the profumo scandal in uh London in the 60s there was
1:11:25 this uh cabinet officer in the British government who has this affair so he’s cheating on his wife
1:11:33 he’s cheating on his wife with a prostitute that turns out to be a russian spy and he lies about it
1:11:39 and it ends up bringing about the fall of i forget which government but it brings about the
1:11:49 prime minister vouches for him and then uh has to apologize and ends up resigning as a result
1:11:54 and i tell the story of profumo because i think he’s so interesting so he destroys his political
1:12:00 career and you know today we would say he was cancelled and what would happen today is that
1:12:09 this person would be basically shunned by one half of society and then perversely like embraced by
1:12:17 another darker side of society that doesn’t like those people right and you would see him get radicalized
1:12:22 and fight against cancel culture you know you would you we almost know exactly how that scandal
1:12:27 would go he would like get rid of all of his political beliefs from before embrace a different
1:12:31 set of political beliefs and kind of become almost like they become almost like these
1:12:37 joker like figures and instead he just quietly shows up one day at this charity i’m forgetting
1:12:47 the name of it um it was like a like a salvation army style charity house and he shows up one day
1:12:52 and asks if they need any help and they put him to work in the kitchen like he’s washing dishes
1:12:57 and he volunteers there every day for like the next 40 years and he becomes it’s like chief
1:13:05 fundraiser and it’s main leader and he just quietly goes about his life doing good work
1:13:11 and eventually there is an arc of redemption to it that you can’t do good every day for decades
1:13:17 without it inevitably being noticed did he get his political career back no did everyone forgive him
1:13:25 no is his name still inextricably linked with a certain scandal sure but on net most people look
1:13:35 back and go probably overreacted we certainly made judgments about this person based on a singular
1:13:43 set of decisions that his subsequent actions revealed to be more complicated an aberration
1:13:51 yeah sort of care exactly and and i think uh to me that’s the danger in today’s world it’s not
1:13:55 so much that you’ll make a mistake and people will judge and criticize you for it because i think
1:14:00 that’s always been true it you’re you’re right the internet makes the internet is not a place where
1:14:07 grace is commonplace and where things can be wretched out of context and all of that and yet
1:14:14 actual danger is that in all of that scandal and attention and negativity
1:14:21 does it change who you are like i am fascinated by people who are
1:14:28 fascinated by and impressed by the people who have messed up had scandals and the subjects of
1:14:38 cancel culture or moms or whatever and then they emerged from it not caricatures of themselves
1:14:44 that it it actually wasn’t this life-defining formative change like the stoics talk about like
1:14:51 look people can come and take all your stuff from you and you can be treated profoundly unjustly
1:14:58 but like no one can affect your character that is the thing you have but oftentimes that’s the
1:15:06 first thing to go because we’re angry or we feel mistreated or because our willpower collapses
1:15:11 or whatever so so like can you not turn into a radicalized asshole is to me the interesting
1:15:17 question there’s another sort of subset to this that we sort of sometimes will behave better than
1:15:22 we want to because we know we’re being recorded we know we’re being watched and then it’s it’s not
1:15:26 character anymore because if character is sort of like what you do when nobody’s watching and
1:15:32 yeah look philosophers can debate that question too like is it good if you’re doing good because
1:15:38 you want a reward or because you’re following it should just be enough to do good because you’re
1:15:42 doing good yeah but if i had to choose you know like people are today are like oh it’s all this
1:15:49 virtue signaling you know it’s like certainly better than the alternative you know totally i’m
1:15:58 not sure this sort of input like this the cruelty is the point vice signaling is preferable even if
1:16:05 it’s more honest i would like people to be signaling work the as they say what um uh hypocrisy is the
1:16:13 is the credit that vice plays to virtue never like like you’re at least saying that you think it’s
1:16:19 important even if you can’t live up to it you know i would rather have virtue signaling than
1:16:27 than not than the nihilism of like lol nothing matters where in life do you have the highest
1:16:33 standards the easy answer would be professionally because it’s easiest and it’s the most measurable
1:16:42 and you get the most feedback is there something a little shameful and sad about that probably i
1:16:48 don’t know anyone that’s like i suck at work but i’m great at home so we we we naturally
1:16:58 are unbalanced like i don’t work as hard at being a parent as i do at being a great writer
1:17:04 but at the end which is which am i gonna think is more meaningful but when so much more measurable
1:17:09 more people care about the other one because it affects more people at least in the
1:17:13 short term without you what do you feel like you have the highest standards
1:17:20 oh i hope myself to these like unrealistic expectations in every domain i want to be
1:17:29 the best father i also want to be super successful at what i do at work and trying to pursue those
1:17:35 two things i want to be a great son to my parents i want to be right you know i want to be the best
1:17:41 of whatever it is that i’m doing and i go through these oscillations where i think of it as harmony
1:17:47 not balance because i can’t balance being great at work and being a great father and so sometimes
1:17:52 like it’s going to be busy for the next couple months i’m traveling a lot and we’re going to you
1:17:56 know my kids are teenagers now so it’s a little easier but like we’re going to figure this out
1:18:01 together right and then it’ll come back and it’ll restore and they’ll sort of be a different balance
1:18:05 but i also like it’s caused me to do these crazy things where it’s like i am home every day when
1:18:11 the kids get home from school my work day when i have the kids is basically like nine to three
1:18:16 and in that period i got to work out and so my work day is really short and then when i don’t
1:18:20 have them i’m like okay i gotta make up for this lost time because yeah it’s not coming at the
1:18:26 expense of being a great father or a great parent or a present parent and then when i fail at these
1:18:31 things like the parenting thing man like i’ve gone to bed crying you know just being like
1:18:37 man i lost my cool in the kids you know i wasn’t a good dad today and then you kind of beat yourself
1:18:42 up but you’re holding yourself to this expectation it is interesting how this is like basically every
1:18:48 woman’s experience up until very recently and almost no men were thinking about these things
1:18:57 were dealing with a set of expectations and a set of responsibilities for which there is not
1:19:06 centuries of cultural experience and lessons and examples to draw on yeah you know what i mean
1:19:12 like your dad wasn’t ever doing that and your grandfather certainly wasn’t ever doing that
1:19:16 and then you go back a couple generations and they’re like you probably even know all their
1:19:23 kids names it has changed way for the better but yeah i think about that too you go okay
1:19:30 i try to i i’m i’m either dropping my kids off or picking them up or sometimes both every day
1:19:36 that i’m in town i’m not always in town but when i’m home i’m doing that and so yeah very quickly
1:19:44 your day is super circumscribed and then there is this challenge or tension of like can you be great
1:19:52 at what you do working not even bankers hours but like stay at home mom hours or something you know
1:19:57 well it pushes me they go to bed so i’ll be like i gotta log in and i gotta do work you know we used
1:20:02 to travel in the summers and go away for kind of like a month and we just pick a random place and
1:20:08 we’d live there and i would be present with them all day and then as soon as they went to bed i’m
1:20:12 like oh god i gotta work right and now it’s easier because they sleep in so i get a full work day and
1:20:18 before they get out of bed yeah uh tony morrison talked about how she wanted to do all her writing
1:20:22 before she heard the work mom and so she would have to get up at like four in the morning she’d
1:20:28 ride until six or something i’m not quite on that schedule but i do yeah i try to like my day is
1:20:36 circumscribed by their day and i also go how the fuck are other people doing it this is crazy
1:20:42 i could pick my own schedule i could stop working if i wanted to but like how can you expect society
1:20:48 to function and you’re in canada so you have some social safety net but like how could you expect
1:20:55 your average american parent to drop their kid off at school sometime between nine or seven and nine
1:21:01 and then pick them up between two and four if you’ve got and then also let’s say you’re two
1:21:07 different kids at two different schools or more yeah it’s insane no one no society can’t function
1:21:12 this way we’re expecting rightfully so for parents spend a lot of time with their children
1:21:20 but the world is not conducive to that in all unless you’ve retired or you’re not working
1:21:25 i think about this all the time right like i have a eight minute commute to work in the morning and
1:21:29 i’m like i don’t know how people would do 30 minutes you know like that’s an extra almost
1:21:35 an hour a day you’re gonna lose just on commuting and then i think about family and the role of like
1:21:42 i’m so blessed to have my parents close by some active part of my life and my kids life and there’s
1:21:49 a lot of people who don’t have any family support in the city that they live in and i i wonder like
1:21:54 how they do it all the time crazy then i get texts from people going like oh god i just had the kids
1:21:58 alone for a weekend i don’t know how you do this all the time and i’m like okay maybe i’m not that
1:22:04 bad but also just think about the fact that like for basically up until let’s say 20 years ago
1:22:07 and that might be generous and and we’re not on different scales but like
1:22:14 only one parent was thinking about these things really at all and so the just the immense cognitive
1:22:26 load and only one of the genders is aware of it in any way yeah is insane in retrospect sad unfair
1:22:34 and then still doesn’t change the fact that it’s now different and not a lot has gone into helping
1:22:40 people manage that i have a lot of respect for the parents out there yeah whether single parents
1:22:45 are together it’s it’s a lot going on you’ve said that writing helps clarify your thinking
1:22:49 can you double click on that a little bit i actually have a chat about this in the book that i’m
1:22:56 doing now um you know amazon has this culture where they uh you’re not allowed to call a meeting
1:23:00 unless you’ve written a memo about what’s going to be discussed at the meeting and
1:23:05 multiple people have to edit that memo before you could sit down and do it and why is that it’s not
1:23:11 because memos are fun or anyone likes reading memos it’s that the act of having to put your thoughts
1:23:16 and the agenda and the purpose of the meeting on paper is essential there’s this story about
1:23:22 eisenhower at the outbreak of the second world war marshal his chief staff the us army
1:23:28 and he’s he’s bet eisenhower before he sees uh some promise in the sound officer
1:23:36 and he calls him in and he says uh you know it looks like world war two is about to break out
1:23:43 japan’s on the march what do you do and it’s a job interview and the eisenhower could have just
1:23:49 you know pulled an answerer off the top of his head and rift and he says can i have a desk in two hours
1:23:54 and marshal says um sure and he goes he gets a typewriter he sits down and he basically types
1:24:00 out a memo everything he has studied and learned and thought about this exact problem his whole
1:24:06 military career he’s been in the philippines he’s been in south america he’s been uh you know he’s
1:24:13 done a lot but he gets it on paper and i think there’s something about getting it on paper instead of
1:24:20 spouting it off whenever my aunt like the answer i just gave you is not as good as the answer
1:24:25 or the analysis of that problem that i wrote in the book that i’m doing right now that’s
1:24:28 how my mind works and i think that’s how most minds work they’re the process of really
1:24:36 stopping to think and clarifying and going over joe diddy and said that writing is a hostile act
1:24:42 because you’re having to convince someone to see things the way that you see them or think the way
1:24:48 that you think and that’s like it takes an immense amount of skill to do that very few people can do
1:24:53 that off the top of their head kind of have to meet people where they are and then take them
1:24:58 where you want them to go yeah you zoom out you zoom in yeah you know thomas merton the catholic
1:25:05 monk he becomes this monk and he’s a trappist monk which they didn’t technically take a vow of silence
1:25:10 but they are supposed to spend their lives in contemplation but he becomes this prolific writer
1:25:14 and a lot of people are upset because it’s somehow a violation of the vow and he was
1:25:20 saying no like writing is contemplation i’m thinking about what i think
1:25:25 and for people who are not writers maybe that doesn’t make sense to me writing my impulse to
1:25:34 write comes from my inability or the insufficiency of what i can come up with off the top of my head
1:25:41 my belief in my ability if i sit down have an uninterrupted bit of focus and concentration
1:25:48 but i can get it i can i can do that hostile act of changing your thinking as a writer
1:26:00 how do you see the impact of ai i haven’t seen it do anything that even a pretty good writer
1:26:09 can do but it can do things a lot better than people who are bad at writing we clearly have
1:26:18 problems in our society with people who are extremely credulous and susceptible to misinformation
1:26:22 and disinformation and conspiracy theories and nonsense i don’t know about you but
1:26:28 when you interact with ai about something you really know about you realize it’s not very good
1:26:35 and it’s very very prone to telling you what it thinks you want it to hear and so one of the
1:26:43 things i’m nervous about is people’s inability to handle that like one of the things you learn
1:26:49 as a project manager like if you’re working with someone who has technical expertise is you have
1:26:54 to know enough and they have to know that you know enough that they can’t bullshit you like they
1:27:00 can’t say no that’s not possible right or that’s going to take six months or that’s going to cost
1:27:05 this amount of money you have to have enough technical domain expertise that you can push back
1:27:12 and get to the truth of things and when i’ve worked with ai and i’m i’m needing it to track
1:27:16 something down that maybe i’m doing i’m like hey didn’t so-and-so say something about this and they
1:27:23 go oh yeah they said this and then i go wait or was it actually so-and-so and they go yeah yeah it was
1:27:30 that and and what it’s doing is it’s telling me what i wanted to hear in the same way that people
1:27:35 google stuff or see stuff on social media and they go that feels true that’s it if what human beings
1:27:40 are good at is using tools and using and cooperating with other people what we’re gonna have to have in
1:27:55 this age of ai is a strong sense for bullshit and an ability to know when to push back and to examine
1:28:02 and when to verify because a lot of what it’s going to spit out is not true or is only partially true
1:28:10 and if you’re just defaulting to it you’re gonna be embarrassed do you use it for any writing or
1:28:17 any purpose i mean i use it when i do presentations i have it do like uh i want a picture of insert
1:28:23 a thing that’s never been painted by a renaissance painter before so right you know like i when i’m
1:28:29 trying to visualize things i use it and sometimes we’ll use it in videos i’m gonna like you know
1:28:34 show marcus realius like in a suit of armor show marcus real is like so i use it for things like
1:28:42 that like track stuff down but then i i verify i have to i have to get a second opinion i have to
1:28:49 have it verified in some way because i’m that skepticism keeps me up because it the the costs
1:28:53 the reputational costs are bored it’s like trusting wikipedia you know it’s good if it’s right
1:29:00 the reputational hit is felt by you alone totally do you use it yeah we use it all the time at home
1:29:05 the kids like will write their essay the way that i i encourage it at home is like you’re
1:29:10 growing up in this well like you need to use it but here’s the appropriate use the appropriate use
1:29:17 isn’t like i need for an essay on the civil war that’s 2,500 words go the appropriate use is you
1:29:23 write something reasonably good yes and i want to see your full history so yeah like i always
1:29:27 keep the kids full history but you submit it and you’re like you’re a grade nine teacher what would
1:29:32 you say are the weak points of my argument so it’s like almost like a personal tutor yeah and then
1:29:37 i’ll submit like here’s a draft chapter like what did i miss what what do you think and sometimes
1:29:42 it’s pretty insightful i’ve used it with my kids will have fun like they’ll be like draw this or
1:29:50 make that they get increasingly excited about making it do more absurd things and the idea of
1:29:55 seeing it as a as a tool as opposed to a replacement for something i think is really important i want
1:30:01 them to be familiarized with the inherent limitations of it yeah right so it’s like you say
1:30:07 draw you know it i had to do i was doing a slide and i was like how to draw this the socrates doing
1:30:13 x y z and then one of the characters in the back had glasses on and i was like this doesn’t make
1:30:19 any sense they didn’t have glasses so like get rid of the glasses and then it’s like they redid it
1:30:26 and then now more people have glasses you know like yeah and it’s also its inability to to iterate
1:30:34 like it’s not very good at this i want this but five percent different it starts from scratch
1:30:40 you know and so again yeah i think the more you learn the limitations of it and the logic of it
1:30:47 and if you can get good at prompting like prompting as a skill um i want my kids to have that so here’s
1:30:52 a like interest i actually get it to write its own prompts i am going to prompt ai i want a
1:30:59 a summary of this podcast and then it’ll give me like a five sentence thing that i could basically
1:31:04 just submit back to itself and tweak a few things here and there but it gives me a much better
1:31:10 prompt than i would give it this is the worst it’s ever probably going to be yeah right much
1:31:16 much better and so it’s going to get exponentially better over the next decade or 20 years and it’d
1:31:20 be interesting to see how we use it and i find it interesting because the schools are like don’t
1:31:25 use it and i’m like you can use it i need the chat history because i want to go in if i have to
1:31:30 argue with your teacher i want to say here’s what you submit it here’s your first draft and now that
1:31:35 they’ve done this thing where they make them write a draft in the school and they take a picture of it
1:31:42 and so your final submission can’t differ too much from the original submission well so i do this
1:31:48 thing so when i read a book i often type up the passages that i liked in the book yeah and sometimes
1:31:52 because i’m just sending it to myself to print back the office or whatever i’ll do it in gmail
1:31:57 and gmail has always had this kind of predictive ai in it where it’s guessing the end of what you’re
1:32:03 saying and i always found it really interesting as a writer so i’m typing some sentence from Hemingway
1:32:09 so this is a sentence that has been written before unlike you know my average yeah i’m making it up
1:32:15 this is a sentence that exists so something there’s a right answer but there is an answer
1:32:22 and we’re largely in agreement that Hemingway did a good job right um he’s considered one of the
1:32:29 great writers so it’s like it’s like you’re you’re doing a simulation of a path that someone actually
1:32:36 flew never is the ai able to predict the next couple words in that sentence i’ve always found
1:32:42 that very interesting and it’s a reminder to me that still the the act of creative genius of of
1:32:49 doing not any sentence but like the right sentence the right way with the right words like Twain said
1:32:53 that you know that’s the difference between lightning and lightning bug you do get a sense of the
1:33:01 limitations of ai when you can see how insufficient it is compared to really great stuff Tyler Cowan
1:33:07 wrote this book like 10 years ago called averages over and i think that kind of defines my philosophy
1:33:14 of life which is that a lot these technologies aren’t eliminating they’re going to be eliminating
1:33:18 large chunks of the people who are able to do that thing but the people who could do that thing
1:33:25 at an elite or an excellent level yeah will probably it’s leverage will be better at it and
1:33:31 be more highly compensated and the importance of it will be higher and so you you have to figure out
1:33:35 what is the thing that you’re going to be excellent at and then you have to be as we’re saying somewhat
1:33:42 disunbalanced in the pursuit of that excellence but it’s like the cost of being mediocre get higher
1:33:48 and higher one thing i have noticed is like the length of emails and the grammatical perfection
1:33:54 in emails has increased quite a bit and i’m like i know you there’s no way you wrote 16 sentences
1:33:58 without making your grammatical error spelling error people are just putting you know their
1:34:03 point form and being like generate a nonviolent race you know email to send to this person put
1:34:07 this in nonviolent communication then you get it and you’re like this is half a page it should be
1:34:12 like two sentences we’re just like social media’s bots talking to bots like a lot of our life is
1:34:17 going to be like ai talking to ai like if i open an email and i don’t know the person it’s more
1:34:21 than like five sentences now i’m just delete right i don’t know yeah well you’re gonna have to get
1:34:25 better just like you have to get good at spotting most of it you’re gonna have to be good at spotting
1:34:31 ai versus non ai yeah because the cost to generate an ai email is zero at least before you had to
1:34:37 type something in or copy paste email like you’ve gotten those emails it’s like dear joe and you’re
1:34:44 like wait my name’s ryan like uh what are you reading right now that’s challenging your thinking
1:34:49 i just i’ve read these three huge books on linkedin so i’ve been doing a huge deep dive into
1:34:55 linkedin for the book that i’m writing now um and i think that’s like you know maybe earlier in my
1:35:00 writing career i would have read one book and called it and now i’m like i’m gonna read another
1:35:06 and another and another and so i’m just going deeper and deeper and stuff um i’m reading this
1:35:10 book now about the founding of australia the i’m finding really interesting called the fatal shore
1:35:16 about like why why did they start a penal colony on the other side of the earth was it was well the
1:35:26 argument was that uh london had an extremely strict legal system uh an abysmal for-profit prison
1:35:34 system and a belief that like there was essentially a race of people that were criminals as opposed to
1:35:43 crimes being an act of opportunity or desperation and that reform was possible then america rebelled
1:35:50 and the ability to send colonists or the undesirables across the atlantic to america
1:35:57 evaporated and they had to find some new place to do it that’s crazy it’s fascinating do you
1:36:01 read many business books like what are the best business biographies you’ve read best business
1:36:07 biographies i don’t read that many business biographies uh i like my dream book is like
1:36:15 a 900 page biography of someone i know nothing about or someone that i know a lot about
1:36:24 because you want the detail and then yeah i’m looking for illustrative stories or insights into
1:36:29 how that person operated or solved problems so like you know i read a book about lincoln
1:36:34 specifically as a politician i read a book you know specifically about lincoln’s cabinet i read a
1:36:41 book specifically about you know lincoln and literary inclination you know like yeah i want
1:36:48 to go really deep in a specific thing and and then i’m finding stuff that didn’t appear in one but
1:36:53 appears in the other and that’s how i’m building out the chapter that i’m writing and do you do that
1:36:58 without having the story in mind you’re like oh this story is representative of xyz tag it sometimes
1:37:02 i’m just reading generally about something and like i’m not writing anything about australia i’m
1:37:07 just was there and now i’m interested in it and i have some basis of knowledge i’m building on
1:37:14 and then it’ll help me understand the 1700s the 1800s and often it’s i’m i’m chasing something
1:37:22 down that i think i know is down this hallway how do you define success today and how has it changed
1:37:26 do you remember what i said the other times no i still think my definition of success is autonomy
1:37:32 like i’ve been saying recently like success is how much you see your kids and power is how much
1:37:38 control you have over your schedule my son school called and he was sick and i was like all right
1:37:44 i’ll be right there you know i like that to me that’s that’s both success and power i didn’t
1:37:52 have to ask anyone’s permission i didn’t need to worry about the cost of yeah missing a day’s work
1:37:56 or whatever i just could handle it turns out it wasn’t actually sick you know he’s just had a
1:38:01 cough or something and so we just hung out all day and then i had to talk that afternoon and
1:38:06 he came with me how has that changed from like a decade ago when you would define success when
1:38:13 you were younger i think success was often more predicated on like either very specific things
1:38:22 or relative to other people and their accomplishments and i think i’ve gotten closer and closer to
1:38:28 just not really caring and part of that is living where i live how my life is set up just
1:38:32 valuing different things the relative thing is fascinating because if you compare yourself to
1:38:38 people who are relatively you know not pursuing the same goals not maybe not as successful as you are
1:38:43 you sort of feel good about yourself like maybe you’re not reaching your potential because you
1:38:48 can sort of coast a little bit and if you compare yourself to people who are better or more successful
1:38:54 then you’re perpetually sort of like not where you want to be and it can sort of like destroy your
1:38:59 your satisfaction i try to remind myself that i write about an obscure school of ancient philosophy
1:39:04 that there’s a floor and a ceiling to that look if we compare ourselves to james clear we’re all
1:39:11 failure yeah and for our book sales but if you compare yourself to the millions of people who
1:39:16 would kill to even have a meeting with an editor it’s a huge success sometimes it can be helpful
1:39:22 to really think about how modest you would have previously defined success oh total and then there’s
1:39:27 there’s also like a relative or sort of like a relative success and absolute success which is
1:39:32 you know if you sell i think i don’t know what the actual number i heard it was like 50 000 books
1:39:38 yeah you’re in the top one percent of books ever published in the history of humanity yeah so like
1:39:42 there’s always a different way to change your perspective on where you’re at and sort of and
1:39:47 what a friend of mine used to say this like if we threw everybody’s shoes in a big pile
1:39:50 and you picked out the shoes and you got all the problems with it you probably pick your own shoes
1:39:55 like the whole world basically you know you could pick anybody’s problem a year most of the time
1:39:59 you’re gonna pick yours there’s a lot of people who would try to pick our problems when i feel
1:40:05 jealousy i try to remind myself that you can’t pick and choose like if you want what someone has
1:40:10 you have to trade your whole life and in that case you almost would never take it
1:40:15 or maybe not even your whole life but let’s just say like oh why did they get this opportunity
1:40:20 i should have got this but it’s no you have to swap your whole career for theirs would you do it
1:40:25 and it becomes more complicated it’s it’s it’s we want you know we want to be a little from here a
1:40:30 little from here a little from here but that’s not a possible combination because every decision
1:40:40 every goal inherently is making things not goals there’s trade-offs yeah and yeah you can’t be like
1:40:47 i want to be classical musician and then compare yourself to Taylor Swift they’re just they’re
1:40:53 different genres of music that have different floors and ceilings so like you know it might be
1:40:57 easier to break out as a classical musician i’m not saying it’s easy but like you know there’s a
1:41:05 there’s a set audience and there’s also a ceiling you’re never going to be the number one album in
1:41:13 the country but by going for the number one album in the country you might get nothing and just
1:41:22 understanding that you made certain choices and that you can’t strategy is by definition
1:41:30 choosing certain objectives and not choosing other objectives and if you try to straddle to
1:41:43 strategies you’ll destroy yourself thanks for listening and learning with us for a complete
1:41:52 list of episodes show notes transcripts and more go to fs.blog/podcast or just google the knowledge
1:41:57 project recently i’ve started to record my reflections and thoughts about the interview
1:42:03 after the interview i sit down highlight the key moments that stood out for me and i also talk about
1:42:08 other connections to episodes and sort of what’s got me pondering that i maybe haven’t quite figured
1:42:16 out this is available to supporting members of the knowledge project you can go to fs.blog/membership
1:42:20 check out the show notes for a link and you can sign up today and my reflections will just be
1:42:25 available in your private podcast feed you’ll also skip all the ads at the front of the episode
1:42:30 the front of street blog is also where you can learn more about my new book clear thinking
1:42:36 turning ordinary moments into extraordinary results it’s a transformative guide that hands you the
1:42:43 tools to master your fate sharpen your decision making and set yourself up for unparalleled success
1:42:54 learn more at fs.blog/clear until next time
1:43:04 [BLANK_AUDIO]

In this episode, Ryan Holiday unpacks the subtle and not-so-subtle messages life sends us—and what happens when we ignore them. From mismatched tattoos and injured ankles, Ryan reflects on the lessons he’s learned about preparation, awareness, and humility. Using examples ranging from personal missteps to famous entrepreneurial gambles, this episode is a deep dive into the art of learning from experience, knowing when to listen, and the cost of stubbornness. Plus, Holiday revisits his roots to discuss how Stoic principles can guide you in navigating feedback, balancing ambition with self-awareness, and understanding the fine line between determination and delusion.

Holiday is a New York Times bestselling authorHe has written over 10 books, covering both the fundamentals of Stoicism as well as key elements of modern-day marketing and media. His most recent release is Right Thing, Right Now. Holiday has been a guest on the podcast twice before.

Newsletter – The Brain Food newsletter delivers actionable insights and thoughtful ideas every Sunday. It takes 5 minutes to read, and it’s completely free. Learn more and sign up at https://fs.blog/newsletter/

Upgrade — If you want to hear my thoughts and reflections at the end of the episode, join our membership: ⁠⁠⁠⁠⁠⁠⁠https://fs.blog/membership/⁠⁠ and get your own private feed.

Follow me: ⁠⁠⁠⁠⁠⁠⁠⁠https://beacons.ai/shaneparrish⁠⁠⁠⁠⁠⁠⁠⁠

Watch on YouTube: https://www.youtube.com/@tkppodcast

(00:00) Intro

(02:20) When to Ignore Advice

(04:49) The Importance of Reflection and Journaling

(07:26) Balancing Emotions and Stoic Practices

(24:34) Misconceptions and Historical Context of Stoicism

(29:53) The Pursuit of Excellence and Its Trade-offs

(40:58) The Power of Saying No and Opportunity Costs

(49:09) The Role of Anger and Emotional Control

(52:58) Defining Self-Discipline

(53:43) The Essence of Self-Discipline

(54:29) Balancing Discipline and Life

(55:09) Consistency and Overcoming Setbacks

(56:09) The Struggle with Compulsive Tendencies

(58:33) Navigating Competition and Personal Goals

(01:01:22) Cultivating Discipline Through Physical Practice

(01:02:15) Instilling Discipline in Children

(01:04:22) Understanding Character and Virtue

(01:23:32) The Impact of Modern Technology on Writing

(01:35:04) Defining Success and Managing Expectations

Leave a Comment