Ryan Holiday: How to Win the War with Yourself

29:17Is the connection with really, instead of sports and military, if we sort of generalize that, is the connection just with anybody who's doing hard things and yet we tend to hold up these professions? I think so. I mean, that's what sports are, is a metaphor for any kind of pursuit of excellence. It's just the most visible. you know it's a very visible because it's a game with rules at a beginning and an end the most observable form of excellence right an entertaining form of excellence and look in the ancient world they're using sports metaphors then too because it's the same the same process one of the stokes is talking about how he thinks that a philosopher has to be like an athlete he's just like a ball player, you catch the ball and throw it back, catch the ball and throw it back.

30:13And whether it's a good throw or a bad throw, you still have to catch it. He considers Socrates like the greatest athlete of all time because he deals with the things that life throws at him, including this death sentence. There's weightlifting metaphors and racing metaphors. And some of the Stoics were also athletes. So I think there's something about sports that is the sort of unmitigated pursuit of excellence. And yet it's also not unmitigated because we expect our athletes to exhibit sportsmanship and grace and coolness and depression. You know, we like all these traits that go into being a full, well-rounded person are at play in sports.

30:56This is, I think, why the Olympics are this sort of enduring thing. We still observe some of the same exact sports almost that the Stokes would have been very familiar with. Do you think anybody can be at the far right of the curve in whatever domain they're an expert or a sports or skill and be a normal sort of person? I think about this all the time. I would like to be both. And I think you do realize there are trade-offs. There is something inherently unbalanced about excellence in a singular domain because you are focusing all of your energy on one thing. There's something dysmorphic about the athlete's physique.

31:49And that's probably just the physical manifestation of also. So if you could look at their mind and their priorities, probably equally out of whack. But if they weren't out of whack, then they wouldn't be on the right end. Yeah. I mean, what I really admire, and I've gotten to meet a handful of them over the years, and I'm always reluctant to be like, well, this one is a good example of this because you don't really know what's happening in anyone's personal life. But I think it's really something special when you meet someone who has inarguably attained the heights of their profession or, you know, in some sort of all time greats, you know, great achieve the great prizes of their thing, whether it's politics, sports, business, art.

32:36And they seem reasonably well adjusted. They haven't left a trail of bodies behind them, literal or otherwise. You know, their family wasn't utterly neglected. Their health wasn't utterly neglected. Their moral priorities weren't so, weren't grotesquely out of alignment. So when you meet someone and you're like, oh, they did it as good as it can really be done, but they didn't have to turn themselves into a monster to do it. That's, I would argue, a much rarer feat. Power corrupts, absolute power corrupts, absolutely. So what I think makes Marx really such a fascinating example is here you have one of the few humans to hold absolute power as we would really define it and doesn't seem to have become deranged or grotesque is into an overwhelmingly cautionary tale.

33:38So that to me is a rarer feat than if you told me he had won the single greatest military victory of all time. Like the greatest victory, the Stokes would say, would be the victory over those very impulses. There's another Roman, I think it was like a Cincinnati, you know your history way better than I do, Cincinnatus who like gave up power. Yeah, I tell this story to my son all the time. But Cincinnati's is maybe not real, maybe real. But his example was certainly very real to the Greeks. Oh, I guess to the Romans, not to the Greeks. But yeah, Rome sends out its army in this big battle and they're defeated and the army's trapped.

34:25And so Rome had this sort of emergency, you know, smash in case of emergency button that said, you know, you could make someone dictator to save the Republic. And so they go to Cincinnatus, who had been a general, and they make him dictator. and he rounds up every straggling man and boy in Rome at this time and he marches out and he rescues the army, he defeats the enemy and then he returns to Rome, resigns as dictator after like 17 days and then he returns to his farm. He just goes back to his regular civilian life. And it's this example that is told for generations and generations and generations, so much so that George Washington hears it as a young boy and he resigns his commission repeatedly.

35:24I was just in Annapolis a couple weeks ago, and you can stand in the courthouse where he resides his military commission, and then when he resides after two terms as president. But King George, when he hears after the revolution, he's, you know, what is to become of George Washington? He's told that, you know, I think he intends to return to his farm to not make himself and the Washington name, you know, a hereditary monarchy. and King George says, you know, if he can do that, he will be the greatest man on earth. And there is something about relinquishing power or walking away that takes an incredible amount of discipline and strength.

36:09And that we don't usually appreciate in the moment. And in fact, we tend to ridicule and mock it. Like, uh, you know, Andrew Luck, the quarterback, he walked away and we don't hear about him anymore. So he's not out there like fighting for his legacy, arguing about his accomplishments. He's not on TV. So he just sort of recedes from memory. But he also made like$100 million playing football. He, as far as we know, escaped without any serious long-term brain injuries. I don't know what he does all day, but the idea is... And he walked away at the top. Yes. Yes. Has there been any boxer in history that's walked away too early?

36:56Probably not. It clearly takes more discipline to walk away early or on top than it does to go for the sixth ring or the three-peat or whatever. Those things are extraordinarily hard. But clearly, if less people do this other feat, it must be because it's even harder. Do you ever think of, of walking away from writing? Yeah. Why do you think, do you think it's time for me to retire? No, that's not what I was saying at all. You're, you're sort of like, you're in the middle of it, right? Like you're like, what? 12, 13, 14 books. Like the thing that for me is that's the part that I like doing. And it's probably the least hard on me.

37:40Right. It'd be the other stuff that I think would, would be like the bookstore or YouTube. No, yeah, like YouTube or podcasts or speaking or to just be like, no, I'm just going to do this one part. I don't know how people do podcasts once a week or more. Like I find once every two weeks hard. How often do you do it? 26 times a year. Is that a deliberate choice? Yeah, I don't think I could remain intellectually. Like I don't think it would be genuine if I was doing it weekly. I'd be finding people that I could talk to, not people that I wanted to talk to. You know what I mean? Like I'd be filling a slot versus I really want to talk to this person.

38:20Sure. That is. Well, you also do your interviews are longer, right? So you might be able to say if somebody is doing, uh, two a week and they're an hour, that's the same as you doing. But I find all the work that goes into it. It's not like I show up. I got this one page thing, but this is like nine, 10 hours. When I had my marketing company, one of the reasons I never wanted to hire employees was that I was skeptical that there were enough projects that I would be interested in working on to pay for the people. which meant if I hired someone, they would represent a certain number of projects per year just to get back to even.

39:14I go back and forth between whether that was a constraining, kind of limiting belief, or if that was actually a pure and admirable stance. And you kind of distance yourself from the work too, right? So if I hired somebody to do the research for the podcast, I could show up, there'd be a list of questions, but part of what I enjoy about it is actually doing all the research and the work. The pressure to scale. Like I know a lot of people in the this kind of information media space that have taken on like private equity investments. Like there's like the Chernin group. And so they'll buy like half of the business or all of the business.

39:57And then the idea is like, well, how do we scale this into a much larger company? I've expressed no interest in doing that because, to me, part of the whole joy of doing it is not having a boss and not needing to get to a certain level or do a certain amount of things, which you are foregoing when you bring on somebody else. I was talking to John Mackey about this, the Whole Foods guy. And he sort of said, I love this analogy. He's like, when you bring people on, they're usually hitchhikers. So they'll be in the car with you. And as long as you're going in the right direction at the right speed, they'll pay for the gas.

40:41But the minute you're like, oh, I'm really curious what's over here. They're going to be like, no, what are you doing? You can't do that. And then all of a sudden you have a boss and you have all this pressure. And they own half of your business. Yeah, it's more like you went from being the driver to being the passenger. Kind of, yeah. The other person is like, they have a brake, and they have their own steering wheel, and they have their own accelerator. The pressure to scale is obviously a first world problem. Because most people, and not that long ago for me, the problem was breaking through or breaking out.

41:15Once you do that, because that is so rare, there's an immense amount of structural pressure, economic pressure, cultural pressure to take a winner and turn it into a big winner as opposed to just being like, this is nice. Even with the bookstore, every couple weeks I'll get an email being like, hey, have you thought about opening another one? And it's like, I already hit the lottery by not failing. Do I need to start a chain of bookstores? I don't think that I do. And I don't think that would improve my life quality at all. But it's easy to be disciplined in some areas and not in other areas. So when you're successful, one of the tendencies is to start saying yes to all these other projects.

42:05Start hiring a team and then you're distanced from the work and you can be like, you go do this. And then all of a sudden you start taking on projects just to do them. Yes. How can we use stoicism as a means to sort of focus our energy and remove distractions? Mark Serios writes in Meditation, you can imagine the immense pressure and inbound that's coming at the emperor of 50 million people. He says, in everything you do and say and think, you have to ask yourself, is this essential? And he says, because most of what we do and say and think is not essential. And he says, when you eliminate the inessential, you get the double benefit of doing the essential things better.

42:42knowing that what you're saying yes to means saying no to other things and conversely saying no to things means saying yes to things is like the very tricky never gets easy balance that i was struggling with like even this morning my wife and i were like okay i got offered to do this and i got offered to do that what do we want to say yes to what do we want to say no to and then just the you would think at some point not needing it would make it easier to say no but opportunity costs you get more opportunities yes and success tends to sow the seeds of its own yes destruction it'd be easy to say like oh when you're you know be disciplined while you're successful you know don't don't take on too much you say no to a lot of things but in sports or entertainment or art or even you know whatever it is that you do you don't do it forever you have a narrow window and there's going to be at some point where it dries up and so are you going to look back and go there was almost a bit of ego in my in my selection process because I was assuming that I would get to do it forever.

44:01I continue to wrestle with that constantly. How do you think about opportunity cost? Is it always increasing for you or is it based sort of like on the workload right in front of you? I was thinking about how kind of like what seemed like a lot of money to you as a kid always remains a lot of money to you. even as your income goes up it's hard for you it's hard for me to pass on things because that seems like a lot even though proportionally it no longer is i'm trying to do work and get more clear get more objective about like no hey actually yes that to and to you 10 years ago to any person on the street that is a lot but given what your time is actually worth at its current valuation, that's actually something you should say no to.

44:52That's hard. Imagine if you're a billionaire, how hard that must get. No one's throwing them a pity party, but that must be very disorienting and destabilizing to not have a good way to value what to say yes or no to. The problem is financial upside is always clear. opportunity costs are sometimes clear, but often not clear. If I get offered to do, I don't know, a speaking gig, that's the opportunity cost of saying no, or whatever they're offering. The opportunity cost of saying yes, is whatever creative work I might've done had I stayed home. And then also intangibles like, the rhythm of our households, my personal happiness, how easy things are.

45:47And so the downside is, in one sense, is very quantifiable. And the upside in the other case is very hard to quantify. And in some cases, the consequences of it are quite lagging. And so you're faced with briefcase with cash in it. and hey, isn't this a bit much? We're all tired. How do you balance that? My uncle taught me this thing when I was a teenager about how he used to price his business. So he was up, he ran a plumbing company. What he did was basically the first 75 % of hours were priced at 100%. So the regular rate, but 75 to 80, he would increase the rate 80 to 100. He'd increase it and over 100 % of like a normal work week.

46:35Then he'd increase it even more. and he was super transparent with people about this like i'm really busy right now i hate to give you this quote but to do the job properly here's what we'd have to price it at and he's 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 like i'll figure out how to do it for this price and he's like was so surprised by the number of people who said yes in part because of his honesty right but i use this this is sort of like one of the simple principles that i use which is like if i'm super busy i'm going to price it more because I actually kind of want you to say no.

47:08Right. But if you're going to say yes, then I'll make it work. But it's at a certain price. And so the pricing that we use is dynamic in some ways. And there's like a baseline, which is like, here's the minimum. And you need a certain amount of self-confidence and security to be able to do that. And you can see why if you're like, if you have just an adorbitant void inside you, how vulnerable that makes you. Yeah. Because you want to be wanted. You want the validation. You want the cha-ching. Because that feels good. But like you, I get five speaking requests a week. Yeah. And there's no way you can say yes to everything.

47:49So you have to have a system to sort of... Well, I think the first step is you have to have someone between you and the thing. Oh, totally. To just eliminate three of the five that were not serious. or not even not serious, but we're at a number that might be tempting, but it's better for you not to see. Because you're more likely to say, yeah. What can happen as you become successful is you can become jaded and entitled and you want to be the, like, you want to keep yourself as the good guy, the nice guy, the person who is saying yes. Yes. So you have to set some boundaries and then task other people with enforcing them.

48:25Yeah. I think some people will go, oh, is it, you know you want to pay these people commissions you just do it yourself and i think there's a danger in doing it yourself which is that totally it almost it can go to your head and also kind of uh and then when it goes away what yes this i worry about this all the time right it's like well five and i'm like saying no you read that book die with zero yeah it's a great book but the idea is you know thinking about what are you what are you trying to do all this for you try to accumulate a large amount of money that you don't get to take with you when you die we are borrowing money from our poorer selves to loan to our future richer self the example that he uses the book which i think is a good one he's talking about like a med student who's like living way below their means saving up money they know in the future they're going to make a lot of money it's very clear how that profession works right and so they'd be more effective maybe not racking up a ton of debt but like not living as if they don't know for certain their financials they're they're not actually, you know, making$30 ,000 a year.

49:29They're just temporarily making that. Anyways, that advice is very helpful in clarifying in more predictive linear professions. But that would be bad advice to give to a rookie in the NBA because they may only be able to do it for two years. I think it is tricky when you have a very clear element of unpredictability and a very, historically, a very clear drop off. Like at some point, you age out. At some point, your trend or moment goes away. And maybe you survive long enough for it to come back. but like the idea that for me as our author that my sales are only going to go like this it's preposterously naive that it adds this layer to like okay so you're saying no because you're too busy right now yeah but in six years you'll you'll feel like an idiot you wish for this request to come back yeah is it ever okay to lose your cool like is there strategic points where it actually makes sense to sort of not be stoic and to to i wouldn't say completely lose control but to have more variation.

50:42We have this idea that like crying is, is not manly, right? Like being overwhelmed with your emotions is somehow a weakness, but we make an exception culturally for anger. If you went through some problematic work thing and you cried in front of your whole team, you would reasonably expect that team would be like, what's wrong with Shane, right? I'm not saying that that's right and they just would but if you got so angry that you punched a wall not only might not you be judged for that that might be like part of the legend of shame right which is interesting and the stoics would point out that like those are both the same process of being overwhelmed by our emotions and one is actively harmful to you and your world and the other is not.

51:37And so it's kind of strange. So it's interesting. We have a couple of stories of Mark's realest crying, but we don't have any stories of him losing his temper. And I think he was chastened by the fact there's a story about Hadrian, his predecessor, who gets frustrated with his secretary. He grabs the secretary's pen and he stabs it in the man's eye. Like this is the thing that the emperor could get away with, literally anything. And so I do think it's interesting, the allowances we make, particularly with men, for certain kinds of emotions and not other kinds of emotions. And I'm not saying, oh, hey, we should be all with one or all with the other.

52:15It's just the idea of the Stoic suppressing their tears and sadness and love and affection, but then being a vortex of temper and rage strikes me as a contradiction that doesn't make any sense. And the idea would be to be kind of an even keel across the board. That being said, there is a difference between being angry and doing something out of anger. And then there's a third, which is the performative element of anger. You're a head basketball coach, and you've gotten a series of bad calls. Losing your temper, screaming at the ref, and getting ejected not only doesn't help your team, but it costs your team points because you get two technicals.

53:05But if you are so even keeled that you're just allowing the refs to run over you or you're allowing a lackadaisical effort from your team to go unchastened, also probably not good. And so I am fascinated by the way that a great coach can turn up or down certain levers. I was at a Spurs game one time, and I watched Greg Popovich get ejected, and Tim Duncan took over. And the team was down by seven or eight points, and Tim Duncan coached the rest of the game. and they came very narrowly within winning. It came down to the last two seconds and they didn't win, but they almost did. And somebody told me after that Pop had looked at Duncan and said, I'm going to get myself thrown out.

54:01You're going to handle the rest of this game. And he saw that the team needed an energy shift and that that was a tool in his toolkit. I find that very interesting. I want to move on and talk about discipline for a second. When we think of discipline, I mean, the image that comes to mind for me and probably a lot of other people is like the army drill sergeant. What is discipline? I'm talking about self-discipline. So the discipline of an army sergeant is obviously important, but I don't think that's a virtue because it's being imposed on you. Of course, essential that an army is disciplined. How would you define self-discipline?

54:42But the virtue of self-discipline is the discipline that you insist upon yourself. So it's what you do when no one's watching. It's what you do with the discretion that is given to you. And I think when we think of self-discipline, we shouldn't just be thinking of physical discipline. It's not just how does your uniform look and how far can you march. And self-discipline is, can you keep your head about you when things are falling apart? Can you be a calm, reassuring presence? can you keep your emotions in check? So self-discipline is sometimes rendered as the idea of temperance, which just doesn't have a good connotation in the English language.

55:21But it is, the Stoics would say, the greatest empire is command of oneself. And so whether you're the emperor or a slave, whether you're a soldier or a CEO, it's this idea of not like, what are you allowed to get away with? What is being asked of you? And it's more like, what are you asking of and insisting of yourself. To me, that's what self-discipline is. Where do you struggle the most with it? Knowing one's limitations, setting reasonable bounds on things. I don't have a problem getting up and working. I have a problem getting up from and stopping working. I mean, I have other vices too, whether it's food or my screen or devices or whatever.

56:03But I think for the most part, it's discipline for me is closer to balance and saying no than it is to insisting on yes. For a lot of people, it's sort of the discipline to eat healthy, the discipline to go to the gym, the discipline. And then if we miss one, we think it's like it's over. Like we've, how do we get back on track? You told me something though that I've been thinking about where you said that you're, you go to the gym every day. Yeah. As opposed to I work out three days a week. Yeah. Because there's a consistency to everydayness and. It's not a choice then. Yes. It takes away the lie you can tell yourself, which is I'm doing it tomorrow.

56:43Yeah. You can change like duration or scope, but like work out sweat every day. It's like, it's so life changing for me and other people who've tried it after listening to me, it's been life changing for them too. No, it's a great way of thinking. I try to write every day. Um, or try to do a little something every day. And that's better for me than, okay, I'm not doing it. And then next month I'm going to start doing it but so you use the word try like i try to write every day so like how do you get back on track if you you went two or three days you're traveling you're talking you're just busy with all the stuff that goes on you get home the family needs you and then all of a sudden it's three four days i almost always have the opposite problem which is telling myself that being five minutes late on this is not as big a deal as it feels in the moment.

57:35I am tending to fight the compulsive side of it. And so the battle for me is going, let's just have a nice weekend, as opposed to I'm behind. I'm going to blow apart this nice weekend to check some arbitrary box in a race that I am preposterously ahead on. And by the way, don't even need to be doing. But if you don't push yourself, like what's the flip side of that? What do you worry about? Are you scared you'll just stop and be lazy? I mean, that's the thing about most compulsive tendencies is they're not based on anything. You have this belief that if you don't do it, things will fall apart.

58:17I'm the same way. Like I work every day. Yeah, it's not based on anything real. And most of the time what you get is not even the reward for doing it. you get the relief for having not not done it. the feeling is not i'm proud of myself i did a great job this made a huge difference the reward is see you're not a piece of shit and that is not not a way to go through life does your workaholism sort of i'm using that no no go for it but does that cause issues in your relationship yeah of course uh i think it always has um and so what you you oftentimes workaholism or any kind of sort of compulsive tendency to do is adapting from some sort of either childhood wound or insufficiency, or it's sort of a way of soothing something that you feel.

59:13But unlike a lot of addictions or compulsions, it's... Somewhat productive. It's somewhat productive, and it's socially adaptive. Doing heroin or drinking all night tends not to have positive social reinforcement, but being really good at what you do and thriving on that feeling of being validated for being good at what you do is nevertheless a pretty wicked feedback loop. Are you sort of like motivated? I think about this all the time and it like, sometimes it motivates me and sometimes I'm like, Oh, it's hopeless. You know, there's like this gap between where I think I could be and where I am.

59:59And no matter where that is on a relative, like Y axis, it's like that gap is what I focus on, which is like, how do I shrink this gap? And then, you know, like where I think I could be is probably growing slightly faster than where I am. And so the gap is widening. and then it's like I need to there's so many things I want to do and I have so much excitement and energy around it what they do throw on top of that like what you hear other people are doing yes it's even more hard to run your own race said it guy has this word euthymia and he talks about being on the path that you're on this is not being distracted by the paths that crisscross yours he says especially the paths of those who are lost and I think about that all the time You don't know where someone's trying to end up.

1:00:46You don't know where they're going to end up. You also don't know what is propelling them. Addiction or psychological issue, what's propelling them is millions of dollars of a fortune they inherited or, you know, some dark money, you know, donor. It could be a bazillion things. You don't know. And so I think the more indifferent and probably ignorant you are of what your peers are doing, the healthier you are and the cleaner your compass reading will be. i think of it as like swimming in your own lanes and there was this video i think it was from the olympics post 20 i forget what year it was but this guy is swimming and he looks over at his competitor and it ends up distracting him just enough that he loses the race yeah because he's like one he's not worried about him and his lane and his goals and his stroke and yes he looks over just enough to distract and he lost by like milliseconds yeah there's that although the other one that keeps me up there was a there was like a mountain bike race in the japan olympics i think and the woman thought she was in first place but she was actually in second place oh so she let up because like it's sometimes you know like in swimming you're all right next to each other like the marathon or something the longer races you might be it might be two minutes that's a closable gap but you can't see what the other people are doing even if it was an insurmountable lead for her to get first, her second place time was not the best that it could be.

1:02:22Right. So clearly at some level, we understand that competition is healthy and motivating, and yet too much competition is disorienting and ultimately self-defeating. And so that balance is tough. What can we do to cultivate more discipline? i mean look i think having a physical practice is a way to cultivate more mental and cognitive discipline like going to the gym or running running swimming biking like i do endurance sports and they help me as a writer like i couldn't do what i do as a writer without those physical components uh even like i have a cold plunge and there's something about like I'm going to get in this thing that is uncomfortable and I'm going to decide how long I'm going to stay in it, whether or not it has any health benefits whatsoever.

1:03:14And I'm pretty skeptical at this point of all of those claims because I've seen what nonsense these same communities will propagate. So to me, the benefit is purely that it's hard and that I am doing the hard thing. And how do you sort of teach your kids or instill discipline in that? It's tough. My kids are still pretty young, and so I am hesitant to give them my somewhat unhealthy adult levels of discipline. Part of me is just like letting them, enjoying letting them just not be. My assumption is that they have whatever I have. And so allowing them to enjoy not having it is part of how I think about it.

1:03:58Because I watch as they get into things. They don't just like kind of get into things. They go all in. They're like, I need all of this. I read a story about Tom Brady watching his son playing video games and his son getting so upset. And he throws the controller at the TV or whatever. And he was like, dude, I have that. And it doesn't always take you where you want it to take you. And so I suspect that that part's there. It can help you, but it can also get in your way. Yeah. Yeah. And would you wish it on someone, especially someone who right now is young and pure and has no, none of these adult notions.

1:04:41A lot of people with dyslexia talk about how that dyslexia is shaped and informed the success they have. Then if you ask them, would you want your kids to have it? They're like, are you fucking out of your mind? We know like hard things and struggle and adversity. We know it's good for us. and yet we don't want them for our kids we don't want it for our kids and and we also know though like if we hadn't had that we probably just would have had something else like i've never met someone who had zero adversity in their like sometimes people ask me hey should i create adversity in my kids lives or do i need to seek out obstacles and i'm of two butts i think like having a physical practice is obviously a way of creating adversity at the same time you know was it dostoyevsky would like gamble all his money away so that he would write better i don't know if you need to how would you define character i just heard something someone said like character like your reputation is what other people think of you and character is like what you do and people don't see there's like an element of right and wrong embedded in this but who who sort of defines what's right and wrong.

1:05:55That's the hard part. So I just, I've been doing this series on the cardinal virtues so I did courage and discipline and then justice. And on one level, yeah, we go, how do we know what's right and wrong? Is it the Ten Commandments? Is there some, you know, scientific basis or utilitarian argument for what's okay about? And then it is remarkable how much societies and cultures all agree on some fundamental level as to what, yeah, there's disagreements. Some countries burn their dead, some bury their dead, some do this or that. Pretty much every culture, religious tradition, and philosophical school has formulated some conception of the golden rule.

1:06:38And all the philosophers come to some level of like, well, what would happen if everyone did that? One of the things I don't like about philosophy is the way that it looks at these moral questions and it makes them so complicated as to make them almost worthless. Like, how do you know what's right and wrong? What about this? It's like we almost focus on the edge cases as a way of... There's such a middle ground that we can all agree on. Yeah, that's like 95%. We're like, should... A Nazi's banging on your door. They want to know if you have a Jew in your basement. Should you lie to them or should you tell the truth?

1:07:20You know, like this is a cons categorical imperative. You know, a trolley is racing down a track and it's going to kill five people. But if you pull this lever, it'll go here and kill one person. What would you do? It's a way of abstracting away from the fact that we have morally charged decisions in front of us all the time. And we don't think about it and don't do anything about it. And that middle ground, if everyone just did a little bit better on this middle ground, the whole world would be immensely better. We've all sort of had moments where we didn't act to the person. We didn't choose the action to the person that we're capable of being.

1:08:01How do you live up to the best version of yourself? We think of virtue as this thing that you have or don't have. Think of it as a noun. When it'd be far better to think of virtue as a verb. Aristotle says, like, how do you get better at playing the flute? It's by playing the flute. How do you become a more generous person? It's by doing more generous actions. He sort of compares virtue to any other craft that, you know, a carpenter builds stuff and that's how they become a carpenter. So a good person does good things. not the way we sometimes think about it, which is like, go through your regular life.

1:08:42And then perhaps you will find yourself in some decision of enormous moral consequence upon which the fate of the world will depend. And then let's hope that you draw from this ethical framework that you read about in a book and will make everyone proud. But in fact, it's like a series of small daily decisions, just like any other discipline. And that's why these virtues are so related. Like there's a discipline to justice. I keep my word. I help people. I think about the consequences of my actions on other people. I don't do, insert X, Y, or Z thing that might be legal, but not right. and so if you think about it as a practice you can get yourself not only can you get yourself to a place where you're capable of doing it but by nature of doing the practice it's never going to happen we're just going to pick some random ass person and put the fate of the world on their shoulders you have to be involved in the thick of things making decisions of consequence to ever find yourself in a position of decisions of consequence.

1:10:00We live in a world where your slip up in character, which we all make, can now become viral on the internet. It's like you yelled at somebody. You weren't generous when you could have been generous. You did something stupid. Somebody had their phone out and now you can't recover from this. You know the Profumo scandal in London in the 60s? There was this cabinet officer in the British government who has this affair. So he's cheating on his wife. He's cheating on his wife with a prostitute that turns out to be a Russian spy. And then he lies about it. And it ends up bringing about the fall of, I forget which government, but it brings about the prime minister vouches for him.

1:10:43And then has to apologize and ends up resigning as a result. And I tell the story of Perfuma because I think he's so interesting. So he destroys his political career. And today we would say he was canceled. And what would happen today is that this person would be basically shunned by one half of society and then perversely embraced by another darker side of society that doesn't like those people. Right. And you would see him get radicalized and fight against cancel culture. You know, we almost know exactly how that scandal would go. He would like get rid of all of his political beliefs from before, embrace a different set of political beliefs, and kind of become almost like these Joker-like figures.

1:11:32And instead, he just quietly shows up one day at this charity. I'm forgetting the name of it. It was like a Salvation Army-style charity house. And he shows up one day and asks if they need any help. and they put him to work in the kitchen like he's washing dishes and he volunteers there every day for like the next 40 years and he becomes it's like chief fundraiser and its main leader and he just quietly goes about his life doing good work and eventually there is an arc of redemption to it that you can't do good every day for decades without it inevitably being noticed did he get his political career back?

1:12:14No. Did everyone forgive him? No. Is his name still inextricably linked with a certain scandal? Sure. But on net, most people look back and go, probably overreacted. We certainly made judgments about this person based on a singular set of decisions that his subsequent actions revealed to be more complicated. An aberration of sort of character. Exactly. And I think, to me, that's the danger in today's world. It's not so much that you'll make a mistake and people will judge and criticize you for it. Because I think that's always been true. You're right. The internet is not a place where grace is commonplace and where things can be wretched out of context and all of that.

1:13:06And yet, actual danger is that in all of that scandal and attention and negativity, does it change who you are? Like I am fascinated by people who are fascinated by and impressed by the people who have messed up, had scandals in the subjects of cancel culture or mobs or whatever. And then they emerged from it, not caricatures of themselves, that it actually wasn't this life defining formative change. Like the Stoics talk about like, look, people can come and take all your stuff from you and you can be treated profoundly unjustly. But like no one can affect your character. That is the thing you have.

1:13:56But oftentimes that's the first thing to go because we're angry or we feel mistreated or because our willpower collapses or whatever. So so like, can you not turn into a radicalized asshole is to me the interesting question. there's another sort of subset to this that we sort of sometimes will behave better than we want to because we know we're being recorded we know we're being watched and then it's it's not character anymore because if character is sort of like what you do nobody's watching and yeah look philosophers can debate that question too like is it good if you're doing good because you want a reward or because you're following it should just be enough to do good because you're doing good yeah but if I had to choose you know like people are today are like oh it's all this virtue signaling you know it's like certainly better than the alternative you know totally I'm not sure this sort of like this the cruelty is the point vice signaling is preferable even if it's more honest I would love people to be signaling work they say what um uh hypocrisy is the uh is the credit that vice plays to virtue.

1:15:10Never heard that. Like, you're at least saying that you think it's important, even if you can't live up to it. You know, I would rather have virtue signaling than... Than not. Than the nihilism of, like, lol, nothing matters. Where in life do you have the highest standards? The easy answer would be professionally, because it's easiest, and it's the most measurable. And you get the most feedback. Is there something a little shameful and sad about that? Probably. I don't know anyone that's like, I suck at work, but I'm great at all. So we naturally are unbalanced. Like, I don't work as hard at being a parent as I do at being a great writer.

1:15:57But at the end, which am I going to think is more meaningful? But one's so much more measurable. more people care about the other one because it affects more people, at least in the short term. What about you? What do you feel like you have the highest standards? I hold myself to these unrealistic expectations in every domain. I want to be the best father. I also want to be super successful at what I do at work and trying to pursue those two things. is I want to be a great son to my parents. I want to be, you know, I want to be the best at whatever it is that I'm doing. And I go through these oscillations where I think of it as harmony, not balance, because I can't balance being great at work and being a great father.

1:16:45And so sometimes I'm like, it's going to be busy for the next couple of months. I'm traveling a lot and we're going to, you know, my kids are teenagers now, so it's a little easier, but like we're going to figure this out together. Right. And then it'll come back and it'll restore and they'll sort of be a different balance. But I also like, it's caused me to do these crazy things where it's like, I am home every day when the kids get home from school. My workday when I have the kids is basically like nine to three. And in that period, I got to work out. And so my workday is really short. And then when I don't have them, I'm like, okay, I got to make up for this lost time because it's not coming at the expense of being a great father or a great parent or a present parent.

1:17:24And then when I fail at these things, like the parenting thing, man, Like I've gone to bed crying, you know, just being like, man, I lost my cool in the kids. You know, I wasn't a good dad today. And then you kind of beat yourself up, but you're holding yourself to this expectation. It is interesting how this is like basically every woman's experience up until very recently. And almost no men were thinking about these things. We're dealing with a set of expectations and a set of responsibilities for which there is not centuries of cultural experience and lessons and examples to draw on. You know what I mean?

1:18:06Like your dad wasn't ever doing that. And your grandfather certainly wasn't ever doing that. And then you go back a couple of generations and they're like, probably didn't even know all their kids' names. It has changed way for the better. But yeah, I think about that too. You go, okay, I try to, I'm either dropping my kids off or picking them up or sometimes both every day. 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 your day is super circumscribed. And then there is this challenge or tension of like, can you be great at what you do?

1:18:45working not even banker's hours but like stay-at-home mom hours or something you know it pushes me they go to bed so i'll be like i gotta log in i gotta do work you know we used to travel in the summers and go away for kind of like a month and we just pick a random place and we'd live there and i would be present with them all day and then as soon as they went to bed i'm like oh god i gotta work right and now it's easier because they sleep in so i get a full work day and before they get out of bed. Yeah. Toni Morrison talked about how she wanted to do all her writing before she heard the work mom.

1:19:19And so she would have to get up at like four in the morning and she'd write until six or something. I'm not quite on that schedule, but I do. Yeah, I try to, like my day is circumscribed by their day. And I also go, how the fuck are other people doing it? This is crazy. I can pick my own schedule. I could stop working if I wanted to. But like, how can you expect society to function and you're in Canada, so you have some social safety net. But how could you expect your average American parent to drop their kid off at school sometime between 7 and 9 and then pick them up between 2 and 4 if you've got...

1:19:59And then also, let's say, you're two different kids at two different schools or more. It's insane. Society can't function this way. We're expecting, rightfully so, for parents to spend a lot of time with their children. but the world is not conducive to that at all unless you've retired or you're not working. I think about this all the time, right? Like I have an eight minute commute to work in the morning and I'm like, I don't know how people would do 30 minutes, you know, like that's an extra, almost an hour a day you're going to lose just on commuting. And then I think about family and the role of like, I'm so blessed to have my parents close by who are an active part of my life and my kids' life.

1:20:41And there's a lot of people who don't have any family support in the city that they live in. And I wonder like how they do it all the time. Crazy. And then I get texts from people going like, oh, God, I just had the kids alone for a weekend. I don't know how you do this all the time. And I'm like, OK, maybe I'm not that bad. But also just think about the fact that like for basically up until, let's say, 20 years ago, and that might be generous and we're not all on different scales, but like only one parent was thinking about these things really at all. And so just the immense cognitive load, and only one of the genders is aware of it in any way, is insane in retrospect.

1:21:24Sad, unfair, and then still doesn't change the fact that it's now different, and not a lot has gone into helping people manage that. I have a lot of respect for the parents out there. Yeah. Whether single parents or together, it's a lot going on. You've said that writing helps clarify your thinking. Can you double click on that a little bit? I actually have a chapter about this in the book that I'm doing now. Amazon has this culture where you're not allowed to call a meeting unless you've written a memo about what's going to be discussed at the meeting. And multiple people have to edit that memo before you can sit down and do it.

1:22:03And why is that? It's not because memos are fun or anyone likes reading memos. It's that the act of having to put your thoughts and the agenda and the purpose of the meeting on paper is essential. There's this story about Eisenhower at the outbreak of the Second World War. Marshall is chief of staff of the U.S. Army, and he's bet Eisenhower before. He sees some promise in this town officer, and he calls him in and he says, you know, it looks like World War II is about to break out. Japan's on the march. What do you do? And it's a job interview. And Eisenhower could have just pulled an answer off the top of his head and riffed.

1:22:46And he says, can I have a desk in two hours? And Marshall says, sure. And he goes, he gets a typewriter, he sits down and he basically types out a memo. Everything he has studied and learned and thought about this exact problem, his whole military career, he's been in the Philippines, he's been in South America, he's been, you know, he's done a lot. But he gets it on paper. And I think there's something about getting it on paper instead of spouting it off. Whatever my answer, like the answer I just gave you is not as good as the answer or the analysis of that problem that I wrote in the book that I'm doing right now.

1:23:24That's how my mind works. And I think that's how most minds work. The process of really stopping to think and clarifying and going over. Joan Didion said that writing is a hostile act. because you're having to convince someone to see things the way that you see them or think the way that you think. And that's like it takes an immense amount of skill to do that. Very few people can do that off the top of their head. Kind of have to meet people where they are and then take them where you want them to go. Yeah, you zoom out, you zoom in. You know Thomas Merton, the Catholic monk? He becomes this monk and he's a Trappist monk, which they didn't technically take a vow of silence, but they are supposed to spend their lives in contemplation.

1:24:07But he becomes this prolific writer. And a lot of people are upset because it's somehow a violation of the vow. And he was saying, no, like writing is contemplation. I'm thinking about what I think. And for people who are not writers, maybe that doesn't make sense. To me, writing, my impulse to write comes from my inability or the insufficiency of what I can come up with off the top of my head. My belief in my ability, if I sit down and have an uninterrupted bit of focus and concentration, that I can get it. I can do that hostile act of changing your thinking. As a writer, how do you see the impact of AI?

1:24:51I haven't seen it do anything that even a pretty good writer can do. but it can do things a lot better than people who are bad at writing. We clearly have problems in our society with people who are extremely credulous and susceptible to misinformation and disinformation and conspiracy theories and nonsense. I don't know about you, but when you interact with AI about something you really know about, you realize it's not very good, and it's very, very prone to telling you what it thinks you want it to hear. And so one of the things I'm nervous about is people's inability to handle that. Like one of the things you learn as a project manager, like if you're working with someone who has technical expertise is you have to know enough and they have to know that you know enough that they can't bullshit you.

1:25:53Like they can't say, no, that's not possible. Right. Or that's going to take six months or that's going to cost this amount of money. You have to have enough technical domain expertise that you can push back and get to the truth of things. And when I've worked with AI and I'm needing it to track something down that maybe I'm like, hey, didn't so-and-so say something about this? And they 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 that. And what it's doing is it's telling me what I wanted to hear in the same way that people Google stuff or see stuff on social media and they go, that feels true.

1:26:33That's it. If what human beings are good at is using tools and using and cooperating with other people, what we're going to have to have in this age of AI is a strong sense for bullshit and an ability to know when to push back and to examine and when to verify. Because a lot of what it's going to spit out is not true or is only partially true. And if you're just defaulting to it, you're going to be embarrassed. Do you use it for any writing or any purpose? I mean, I use it when I do presentations. I have it do, like, I want a picture of insert a thing that's never been painted by a Renaissance painter before.

1:27:21or something you know like i when i'm trying to visualize things i use it and sometimes we'll use it in videos and we're like you know show marcus aurelius like in a suit of armor show marcus like so i use it for things like that like track stuff down but then i i verify i have to i have to get a second opinion i have to have it verified in some way because i'm that skepticism keeps me up in it because it the the costs the reputational costs are bored it's like trusting wikipedia you know it's good if it's right the reputational hit is felt by you alone totally do you use it yeah we use it all the time at home the kids like will write their essay the way that i i encourage it at home is like you're growing up in this world like you need to use it but here's the appropriate use the appropriate use isn't like i need to write an essay on the civil war that's 2 ,500 words go the appropriate use is you write something reasonably good.

1:28:19Yes. And I want to see your full history. So like I always keep the kids full history, but you submit it and you're like, you're a grade nine teacher. What would you say are the weak points in my argument? So it's like almost like a personal tutor. Yeah. And then I'll submit like, here's a draft chapter. Like, what did I miss? What do you think? And sometimes it's pretty insightful. I've used it with my kids. We'll have fun. Like. they'll be like draw this or make that they get increasingly excited about making it do more and more absurd things and the idea of seeing it as a as a tool as opposed to a replacement for something i think is really important i want them to be familiarized with the inherent limitations of it yeah right so it's like you say draw you know it i had to do i was doing a slide and i was like draw this socrates doing x y z and then one of the characters in the back had glasses on and i was like this doesn't make any sense they didn't have glasses so like get rid of the glasses and then it's like they redid it and then now more people have glasses you know like yeah and it's also it's inability to to iterate like it's not very good at this i want this but five percent different, it starts from scratch, you know?

1:29:35And so again, yeah, I think the more you learn the limitations of it and the logic of it, and if you can get good at prompting, like prompting as a skill, I want my kids to have that. So here's the like interest. I actually get it to write its own prompts. I am going to prompt AI. I want a summary of this podcast. And then it'll give me like a five sentence thing that I could basically just submit back to itself and tweak a few things here and there, but it gives me a much better prompt than I would give it. This is the worst it's ever probably going to be. Yeah, much, much better. And so it's going to get exponentially better over the next decade or 20 years.

1:30:15And it'll be interesting to see how we use it. And I find it interesting because the schools are like, don't 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 argue with your teacher. I want to say, here's what you submitted. Here's your first draft. And now they've done this thing where they make them write a draft in the school and they take a picture of it. And so your final submission can't differ too much from the original submission. Well, so I do this thing. So when I read a book, I often type up the passages that I liked in the book. Yeah.

1:30:46And sometimes because I'm just sending it to myself to print back the office or whatever. I'll do it in Gmail. And Gmail has always had this kind of predictive AI in it where it's guessing the end of what you're saying. Yeah. And I always found it really interesting as a writer. So I'm typing some sentence from Hemingway. So this is a sentence that has been written before. Unlike, you know, my average sentence, I'm making it up. This is a sentence that exists. So it's not that there's a right answer, but there is an answer. And we're largely in agreement that Hemingway did a good job, right? Because he's considered one of the great writers.

1:31:22So it's like you're doing a simulation of a path that someone actually flew. Never is the AI able to predict the next couple words in that sentence. I've always found that very interesting. And it's a reminder to me that still the act of creative genius of doing not any sentence, but like the right sentence, the right way with the right words. Like Twain said that, you know, that's the difference between lightning and lightning bug. you do get a sense of the limitations of ai when you can see how insufficient it is compared to really great stuff tyler cowan wrote this book like 10 years ago called average is over and i think that kind of defines my philosophy of life which is a lot these technologies aren't eliminating they're going to be eliminating large chunks of the people who are able to do that thing but the people who could do that thing at an elite or an excellent level will probably it's leverage will be better at it and be more highly compensated and the importance of it will be higher and so you you have to figure out what is the thing that you're going to be excellent at and then you have to be as we were saying somewhat dis unbalanced in the pursuit of that excellence but it's like the cost of being mediocre get higher and higher one thing i have noticed is like the length of emails and the grammatical perfection in emails has increased quite a bit.

1:32:50And I'm like, I know you, there's no way you wrote 16 sentences without making a grammatical error, spelling error. People are just putting, you know, their point form and being like, generate a nonviolent race, you know, email to send to this person, put this in nonviolent communication. Then you get it and you're like, this is half a page. It should be like two sentences. Well, just like social media is bots talking to bots. Like a lot of our life is going to be like ai talking to ai like if i open an email and i don't know the person it's more than like five sentences now i'm just delete right i don't even yeah well you're gonna have to get better just like you have to get good at spotting bullshit you're gonna have to be good at spotting ai versus non-ai yeah because the cost to generate an ai email is zero at least before you had to type something in or copy paste you know like you've gotten those emails it's like dear joe And you're like, wait, my name's Ryan.

1:33:40What are you reading right now that's challenging your thinking? I just read these three huge books on LinkedIn. So I've been doing a huge deep dive into LinkedIn for the book that I'm writing now. And I think that's like, you know, maybe earlier in my writing career, I would have read one book and called it. And now I'm like, I'm going to read another and another and another. And so I'm just going deeper and deeper and stuff. um i'm reading this book now about the founding of australia that i'm finding really interesting called the fatal shore about like why why did they start a penal colony on the other side of the earth what's it what's the well the argument was that uh london had extremely strict legal system uh an abysmal for-profit prison system and a belief that like there was essentially a race of people that were criminals as opposed to crimes being an act of opportunity or desperation and that reform was possible then america rebelled and the ability to send colonists or the undesirables across the atlantic to america evaporated and they had to find some new place to do it that's crazy it's fascinating do you read many business books like what are the best business biographies you've best business biographies i don't read that many business biographies uh i like my dream book is like a 900 page biography of someone i know nothing about or someone that i know a lot about because you want the detail and then yeah i'm looking for illustrative stories or insights into how that person operated or solved problems so like you know i read a book about lincoln specifically as a politician.

1:35:30I read a book, you know, specifically about Lincoln's cabinet. I read a book specifically about, you know, Lincoln and literary inclination. You know, like I want to go really deep in a specific thing. And then I'm finding stuff that didn't appear in one, but appears in the other. And that's how I'm building out the chapter that I'm writing. And do you do that without having this story in mind? You're like, oh, this story is representative of XYZ, tag it. Sometimes I'm just reading generally about something. Like, I'm not writing anything about Australia. I just was there, and now I'm interested in it.

1:36:04And I have some basis of knowledge that I'm building on. And then it'll help me understand the 1700s, the 1800s. And often, I'm chasing something down that I think I know is down this hallway. How do you define success today, and how has it changed? Do you remember what I said the other times? No. I still think my definition of success is autonomy. me. Like I've been saying recently, like success is how much you see your kids and power is how much control you have over your schedule. My son's school called and he was sick and I was like, all right, I'll be right there. You know, I like that to me.

1:36:40That's, that's both success and power. I didn't have to ask anyone's permission. I didn't need to worry about the cost of missing a day's work or whatever. I just could handle it. It turns out it wasn't actually sick, You know, he just had a cough or something. And so we just hung out all day. And then I had a talk that afternoon and he came with me. How has that changed from like a decade ago when you would define success when you were younger? I think success was often more predicated on like either very specific things or relative to other people and their accomplishments. And I think I've gotten closer and closer to just not really caring.

1:37:24And part of that is living where I live, how my life is set up, just valuing different things. The relative thing is fascinating because if you compare yourself to people who are relatively not pursuing the same goals, maybe not as successful as you are, you sort of feel good about yourself. but maybe you're not reaching your potential because you can sort of coast a little bit. And if you compare yourself to people who are better or more successful, then you're perpetually sort of like not where you want to be. And it can sort of like destroy your, your satisfaction. I try to remind myself that I write about an obscure school of ancient philosophy, that there's a floor and a ceiling to that.

1:38:02Look, if we compare ourselves to James Clear, we're all failures. Yeah. And far as book sales. But if you compare yourself to the millions of people who would kill to even have a meeting with an editor, it's a huge success. Sometimes it can be helpful to really think about how bodice you would have previously defined success. Oh, totally. And then there's also like a relative or sort of like a relative success and absolute success, which is, you know, if you sell, I think, I don't know what the actual number. I heard it was like 50 ,000 books. Yeah. You're in the top 1 % of books ever published in the history of humanity.

1:38:37So there's always a different way to change your perspective on where you're at. And what a friend of mine used to say, if we threw everybody's shoes in a big pile and you picked out the shoes and you got all the problems with it, you'd probably pick your own shoes. The whole world, basically, you could pick anybody's problem. Most of the time, you're going to pick yours. There's a lot of people who would try to pick our problems. When I feel jealousy, I try to remind myself that you can't pick and choose. like if you want what someone has you have to trade your whole life and in that case you almost would never take it or maybe not even your whole life but let's just say like oh why did they get this opportunity i should have got this but it's no no you have to swap your whole career for theirs would you do it and it becomes more complicated it's it's it's we want you know we want to be a little from here a little from here a little from here but that's not a possible combination because every decision every goal inherently is making things not goals there's trade-offs yeah and yeah you can't be like i want to be classical musician and then compare yourself to taylor swift they're just they're different genres of music that have different floors and ceilings so like you know it might be easier to break out as a classical musician i'm not saying it's easy but But there's a set audience and there's also a ceiling.

1:40:03You're never going to be the number one album in the country. But by going for the number one album in the country, you might get nothing. And just understanding that you made certain choices and that you can't. strategy is by definition choosing certain objectives and not choosing other objectives. And if you try to straddle two strategies, you'll destroy yourself.

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