The Exchanges

Q So when do you write? Do you write in the mornings? Are you writing for the same period of time every day? Is it like two hours? Is it 90 minutes? Is it?

A Yeah, almost always the morning, although, like, I'm in the middle of the launch on this new book, and so my routine's a bit exploded, um, but, like, my thing is I really don't schedule anything in my calendar. Like, we're doing this at 11 central. This is, like, the first thing in my calendar, and usually I'll do, tend to do a little bit later. I want the mornings free, so probably, um, You know, from 8:30 to, like, 11, uh, 1130 is, like, loosely writing time, so that might be, like, thinking about the writing, that might be reviewing some writing, might be going through note cards, or it's just uninterrupted, like, sitting down writing, but that's, I make a big distinction between, like, book writing and other forms of writing that I do. By that I don't mean, like, Writing emails to people, but like, if I'm editing a book for someone or, or for myself, I can do that later in the day. I can, you know, write newsletters or blog posts. I can do those kinds of writing, but I feel like book writing demands a level of concentration and focus and frankly, energy that you only have when you are fresh at the beginning of the day.

AI assessment note: “almost always the morning... from 8:30 to, like, 11, uh, 1130 is, like, loosely writing time”

Q Let's talk about what you've been writing about for, but the, ever since I've met you, I think we've known each other, what, seven, eight years now. So let's talk about stoicism a little bit. What is stoicism?

A It's a philosophy that originates in ancient Athens, makes its way to Rome over the next several centuries, and becomes, I think, the most interesting and practical of the ancient philosophies. Like when, I, I'm, I'm sure when people hear ancient philosophy, they go, that's really interesting intellectually. But of very little use to me as, uh, insert whatever it is that you do. What I love about stoicism, what gets me excited about it, is that all of the stoics were, like, active elite professionals at whatever they did, and stoicism was a guiding force, a thing that allowed them to do that, and guided the decisions they made inside that field, but it wasn't You know, they weren't Diogenes the Cynic, or a Buddhist monk, uh, or, or, or anyone whose pursuit of a philosophy or a set of ideas took them away from the world. To me, what I love about Stoicism is that it's very much philosophy for the world. I mean, it's literally founded, one, by a merchant who loses everything in a shipwreck, um, and two, it's founded in the Athenian Agora, like in the center of Athens, In the marketplace where it's battling for, like from day one, limited attention from busy people who have actual lives.

AI assessment note: “It's a philosophy that originates in ancient Athens, makes its way to Rome”

Q they're committed to something like whether it's sort of like building a company, whether it's character or virtue, uh, but they don't waver. They're just a hundred percent committed to that. And so often, like not only like a lot of us are like sister, like we're channel surfing, we're looking for that thing and we're not committing to anything. What's your response? Like, how do you respond to that?

A There's this great moment where, uh, after Caesar comes to power, and Cicero had, up until this point, been this, like, lover of the Republic, and then he just sort of rolls over and lets Caesar do what he does, but he sort of kept one foot in both camps, and this guy gives this speech where he sort of criticizes Caesar to his face. You know, Cicero congratulates the guy after, he says, come over here and sit with us, sit next to me, and the guy, he's like, I'm surprised there's a chair next to you, Because you sit on two stools, meaning that he, he always does precisely that. He tries to play both sides. Basically, Rome has two civil wars in his lifetime, and he goes, I'm just going to wait, pick the, when the winner, uh, reveals themselves, that's who I'm going to side with. Well, so he barely survives the first civil war. Uh, he's always regarded as, with suspicion, and then the second civil war happens, and then, uh, you know, eventually, uh, uh, It, it, it shakes itself out, and Cicero gets killed anyway, because they saw, like, it was so preposterously transparent. This idea that you can play it both ways, it never works, right? Um, it, eventually, the music stops, and they see you for what you are.

AI assessment note: “This idea that you can play it both ways, it never works, right?”

Q And do you map it out in that, like, today I'm going to do this section, tomorrow I'm going to do this section. Are you doing anything else while you're doing this?

A It's not scheduled, like, on Tuesday I'm doing this, and Wednesday I'm doing this. It's more like, You have to go from A to Z, and so you're starting in A, and then when you're done with A, then you move on to B. Um, but, like, I don't write full-time. Like, I could, but I have a company, and I, I try to write one or two articles a week. I have my own site. Um, I do a lot of consulting. Um, for the first three books, I was also working in American Apparel. So, I tend to, I don't know how someone writes for an entire day. So, um, I write, I usually get up early. I love your stuff about, you know, if you want to be more productive, wake up early. I wake up around seven. I try to start writing by like eight, and I write usually like at like 11, 11 30, like I'm done. There's, it's, it's hard.

AI assessment note: “It's not scheduled, like, on Tuesday I'm doing this... I don't write full-time.”

Q Whether single parents or together, it's, it's a lot going on. You've said that writing helps clarify your thinking. Can you double click on that a little bit?

A I actually have a chapter about this in the book that I'm doing now. Um, you know, Amazon has this culture where they, uh, 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 could sit down and do it. And 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 Uh, Eisenhower at the outbreak of the Second World War. Marshall is Chief of Staff of the U.S. Army, and he, he's, he's bet Eisenhower before. He sees, uh, some promise to the sound officer, and he calls him in, and he says, um, 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, you know, pulled an answer off the top of his head and riffed, and he says, can I have a desk in two hours? And I, and Marshall says, um, 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 Uh, you know, he's done a lot, but he gets it on paper, and I think there…

AI assessment note: “the act of having to put your thoughts and the agenda... on paper is essential”

Q Let's switch gears a little bit because I want to get into some more meaty questions here. What do you know about making decisions that most people miss?

A I do tend to find we often spend too much time thinking about the decision, uh, instead of just fucking making it and dealing with the consequences of it. So I, there's a story I tell about George Marshall where he goes, don't fight the problem, decide the problem. So I tend to find in my thing, like, I'm a big believer in momentum, and I'm a big believer in crossing things off the list. So sometimes this costs me because I'll be hastier than I should have been, but like, What'll be frustrating to me, especially with someone I work for, I'd be like, I'll bring something up and be like, hey, you know, you have to decide whether we're doing this or this, right? And then like three days later, three months later, I'll check in on and they'll be like, oh, I'm still thinking about it. It's like, okay, but you just cost us three months of not having it either way. And whatever the margin of error would be between one decision or the other is far smaller than whatever the opportunity costs of not having it done. And moved on to the next thing are.

AI assessment note: “we often spend too much time thinking about the decision, uh, instead of just”

Q Totally. Do you do you want to go a little deeper on that in terms of like momentum and how that works for you and how you think about that in the context of decision making?

A Well, so as a writer, for instance, I'm all about momentum. So every day, like I told you about how I sort of work on books, but I'm, I break each thing up into smaller pieces, and so I want to have the sense that I'm crossing things off, that I'm making forward progress. Let's say, um, I have a bunch of chapters I have to write for this section. Now, there's one section that I kind of knew what I wanted to do, and another section that I could do it this way, I could do it this way, I don't really have the right example, Am I going to do the hard one first or the easier one first? In this case, I'm going to do the easier one first because stalling out is the main thing that I want to avoid. It's not that I'm going towards the path of least resistance, but I'm going towards where I'm going to make forward progress, and so I like to do things in order. For instance, I like to do them according to plan, but if you're telling me that I'm starting to get dammed up over here, I'm going to pivot, and maybe I will flash forward, and like the book that I'm working on now, which is about self-discipline, I didn't have enough material to write the main chapter for the second part of the book, but I did know all the subsequent chapters I was going to write in the book, so I started with the subsequent chapters, and then only last week did I circle back to put in the main thing, so instead …

AI assessment note: “In this case, I'm going to do the easier one first because stalling out”

Q 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, or?

A I was thinking about how kind of like what seems 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 clarity, get more objective about like, no, Hey, actually, yes, that to, 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. That's hard. Imagine if you're a billionaire, how hard that must, again, no one's throwing them a pity party, but like, 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 have done had I stayed home, and then also Intangibles like the rhythm of our households, my personal happiness, how easy things are. And so one is the, the, the downside is in one sense is very quantifiable and the upside in the other case is very hard to quantify. And in, in some cases, the con…

AI assessment note: “Opportunity costs are sometimes clear, but often not clear. If I get offered”

Q That's awesome. Um, let's geek out for a second, because the number one question I got when I told people I was interviewing you is, they want to know about this infamous note card system. Can you walk me through, uh, Robert's system, and then how you've adapted that to your system now?

A Sure, so Robert does, uh, he's not quite Robert Caro, who writes everything longhand, but Robert, uh, Um, I would say probably 80% of his work is in the research, and 20% is in the writing. And all the writing is done on these note cards. So you would read a book, he would read a book, go through it, and take notes, uh, mark things that he liked, and then he would transfer that knowledge onto note cards. And then if you note, like, so the 48 laws of power might be 48 sections, and then each law is supported by note cards. And so the way that works with a research assistant is like, my job is to find materials, to go in the note cards.

AI assessment note: “he would transfer that knowledge onto note cards”

Q There's, like, an element of right and wrong embedded in this, but who, who sort of defines what's right and wrong?

A That's the hard part. I, so I just, I've been doing this series of the cardinal virtues, so I did courage and discipline and justice. And on one level, yeah, we go, how do we know what's right and wrong? Is it the 10 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 disagreement. Some people, some countries burn their dead, some bury their dead, some, you know, do this or that. Pretty much every culture, religious tradition, and philosophical school has formulated some conception of the golden rule. And all the philosophers have, you know, 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? What, like, we, it's like we almost focus on the edge cases as a way of.

AI assessment note: “Pretty much every culture, religious tradition, and philosophical school has formulated some conception”

Q Can we experience like pure joy and really high highs without really low lows, or do we need the lows to actually give us the variation?

A Yeah, I'm not sure one has to make room for the low lows in the sense that life will force that upon you. I think when the Stoics talk about joy, they are trying to remind you that if joy for you is only possible when things are going amazing, your joy or your happiness is therefore out of your hands. Like one of the Sort of philosophical questions that we get from a lot of the ancients is like, could a person be happy, like on the rack? Like, could you experience happiness as you're being tortured to death? And I don't think they necessarily thought you could, but it is an interesting thought experiment. The idea, like, if joy and happiness are dependent on external circumstances, how, how good is it? And therefore, how fragile it is. And so the idea to be able to experience joy and happiness in any and all situations is I think provocative and interesting. There's this woman, she wrote this book called Bomb Shelter, and I think about it all the time.

AI assessment note: “I'm not sure one has to make room for the low lows”

Q focusing on personal directives in life. And finally, Ed Lattimore will teach you about the most important element for creating happiness and self-development that almost everyone gets wrong and explains how happiness isn't a rate, but a rate of change. It's time to listen and learn. From episode one 28, here is Ryan Holiday. Going on to the next sort of topic, how can we learn to manage our anger?

A I was thinking about this with a course that we made for Daily Stoic. I was saying that, like, just because you don't have an anger problem doesn't mean that anger is not a problem for you, right? Like, when I look at most of the mistakes that I made, most of the things that I regret, most of the things that I wish I could undo, usually anger is a pretty big part of that. Right. Like anger was a driving factor in why I wrote the email and sent it. Right. It was why I, uh, chose not to do X, Y, or Z. You know, it's why I was speaking this way or that way. So I think, you know, the, the question about anger is like, does it actually make you better at what you do? It, it may in the short term. Right. And, and to go to our point, Earlier about sustainability. Is it fuel, uh, that, that can get you where you want to go over the long term, or is it really corrosive? And usually I tend to find that it's pretty corrosive fuel. So I think if we just start with like, Let, let me make sure I'm not lying to myself about my temper, right? Cause a lot of us tell ourselves like, oh, uh, it's cause I really care or it's what drives me. I'm not as bad as my boss or my dad or whatever. But like, if you really step back and you said like, what is this actually adding and what are the costs that it's coming at? It usually becomes pretty illustrated that it's, it's not a positive force in our live…

AI assessment note: “start with like, Let, let me make sure I'm not lying to myself”

Q to research, guess, explore, and learn. Give it a try and start discovering the best moments from the best podcasts. Go to joinoverlap.com. That's joinoverlap.com. How do we separate the signal from the noise? Like in a world of social media, you're getting feedback all the time. How do you distinguish what's valid and sort of helpful feedback and a whisper versus this is noise and it offers no value?

A Yeah, this is really hard. Uh, you can see that often to be successful as an entrepreneur, you get there by not listening. You get there by not listening to the odds, not listening to the doubts, not listening to the critics, and then You succeed. So then you get this very wicked learning environment where you succeeded precisely because you did not listen to the message that the world was trying to send you. But if what you generalize from that is never listen to people, You're going to be a really tough spot. So take Elon Musk, right? When Elon Musk was planning what became SpaceX, his friends held a literal AA style intervention that said, you cannot start a rocket company. This is the worst idea. You will lose all your money. Obviously he was correct. And there were moments when he probably, uh, the, the conventional wisdom or the data or the advice from the investors overwhelmingly was to sell Tesla or to do X, Y, and Z. So what happens when You know, it's sort of a passing fancy or, you know, an impulse consideration to buy Twitter. Some people told him it was a good idea. Some people told him it was a really, really bad idea. Some people told him it was totally outside of his domain of expertise and all these things. How do you know whether to listen or not? This is like the essential question. The quote is something like, uh, a reasonable person adapts to the world. And…

AI assessment note: “How do you know whether to listen or not? This is like the essential question.”

Q a book a year, how stoicism can help us make better decisions, the value of journaling, and the four virtues, courage, self-control, temperance, and justice. It's time to listen and learn. Let's start with your book writing process. You're prolific, man. You do like a book a year. How do you do that? What's your process for writing? What does that look like? Take us inside and behind the scenes.

A It's weird, uh, because obviously I sort of know objectively that I'm prolific and people tell me that I'm prolific, but to me, I am more curious that other people are not so prolific. I mean, I realize that different authors do different kinds of books, but I, I do feel like if this is the job and you're waking up and Doing it every day. It does seem to me that, like, more published work for people should come out of the other side. And, but I am kind of amazed. Maybe it's because writing is a creative profession that people don't treat, like, uh, professional sports or, you know, trading or anything where it's just sort of excuse, like, because people think it's hard and they don't understand how it works. They're just a really tolerant of sort of spotty output. Do you know what I mean?

AI assessment note: “to me, I am more curious that other people are not so prolific”

Q Can you walk me through that decision and what you did right after that?

A Well, I mean, one of the first things I like to do, if only for my own sake, is I, even though I, like, look, I wrote my biography, so I'm responsible for the people who say, like, hey, um, you know, you dropped out of college at 19, but it's interesting how things can become, in retrospect, more significant than they are, and Nassim Taleb calls this the, uh, the narrative fallacy. Um, you, you tell yourself a story about your life. So it's like, Call the, my sophomore year of college ended, you know, two weeks before my next, 20th birthday, and that's when I stopped going to school. So did I drop out when I was 19 or did I drop out when I was 20? Um, is that semantic or is that a, that's a very significant.

AI assessment note: “Nassim Taleb calls this the, uh, the narrative fallacy.”