Stoic Practices for Getting Rid of Mental Junk, Your Morning Routine, and Talking to the Dead | Ryan Holiday

This is the 10% happier podcast. I'm Dan Harris. Hello, my fellow suffering beings, how we doing today? Today we're talking to a guy who has quickly become one of my favorite return guests. Ryan Holiday, the stoic philosopher and uber prolific author on all things stoicism. Today we're talking about how to be wise or how to cultivate wisdom as you'll hear me joke to Ryan. Wisdom is kind of a funny term because it's hard to define and often either ungraspable or totally confusing. But actually, as Ryan talks about in his new book, which is called Wisdom Takes Work, there are tons of things you can do that will improve your life out of which wisdom may well emerge. So in this conversation, we talk about how to talk to the dead. He'll explain what that means. The value of asking questions, including impertinent questions, how to create a second brain, how to find a teacher for yourself, how to manage your ego and navigate your blind spots, how to get rid of mental junk, how to cool off your brain, how not to be and know it all, how to achieve focus through having a morning routine or any kind of routine, depending on what time of day works for you, how to seek out criticism, how to embrace complexity, how to learn how to die, and much more. A little bit more on Ryan before we dive in here, Ryan Holiday has written many, many, many best-selling books, including The Daily Stoic, The Obstacle is the Way, Ego is the Enemy, and Stillness is the Key. He's got a popular podcast called The Daily Stoic, and again, he's got a new book called Wisdom Takes Work. Real quick, before we dive in here, don't forget to check out my new app. It's called 10% with Dan Harris, and you can sign up at danheras.com, the most egotistical web address in the world. There's a free 14-day trial if you want to check out the app before you buy it. Let me just tell you, though, we've got an amazing and growing library of guided meditations from amazing teachers, including people like Joseph Goldstein. We also do weekly live video meditation and Q&A sessions, so you can get your questions answered, and we've set it up so that you can connect with your fellow meditators and great relationships, so you don't feel so alone in this weird thing called meditation. We'll get started with Ryan Holiday right after this. Have you ever wished you could make something happen just by thinking about it? Wix may have just answered your prayers. Wix's new Harmony Editor makes it so easy to create a website exactly how you imagined it, that it's almost like you're just thinking out loud. Experience the new way to create websites? 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I can't tell you how often scrolling and I get served ads for stuff I have no interest in. So when you want to reach the right professionals, use LinkedIn ads. LinkedIn has grown to a network over a billion professionals, including 130 million decision makers. And that's where it stands apart from other ad buys. You can target your buyers by job title, industry, company roles, and yard-y skills, company revenue. So you can stop wasting budget on the wrong audience. It's why LinkedIn ads generates the highest B to B return on ad spend of all major ad networks. Seriously, all of them. Spend $250 on your first campaign on LinkedIn ads and get a $250 credit for the next one. Just go to LinkedIn.com slash happier. That's LinkedIn.com slash happier terms and conditions apply. Ryan Holiday, welcome back to the show. Yeah, thanks for having me. It's a pleasure to have you back. All right, well, let me start with some basic questions. Deal. The book is called Wisdom Takes Work. What do you mean by wisdom? It's one of those words that like you say it and you picture it like dumbledore. What do you mean specifically by wisdom? Yeah, it's a tricky one. What is the definition of wisdom? I've come to understand that it is many things. Right. So obviously it's experiences. It is reading. I guess what I figured out doing this book. So I've been doing this series on the Cardinal virtues. The four virtues for people don't know of stoicism or courage, temperance or self discipline, justice and wisdom. So they're all kind of basic words that are pretty obvious. And then as soon as you start to drill down on them, you realize, oh, there are many things and there are sort of sub virtues underneath each one. And so my definition of wisdom is that there is no definition. The thing that there is a clean one sentence definition is probably some sign that whatever wisdom is, you don't have it. It's a complicated thing, comprising intelligence and creativity and experience and age. It's wit. It's all of these things and more. And yet at some level, it is incredibly elusive and it's hard to point to any one person that has it. Which ultimately comes to the title of the book, which you mentioned. Senna is saying the one thing that we can all agree on as far as wisdom is that nobody gets it by chance. It's not something you're born with. It's not something anyone can give you. It only comes the stoic say as a result of a lot of work. And so that's basically the premise of the book that it's sort of this byproduct of this kind of timeless methodology or process. These sort of basic practices and it's probably better to focus more on doing those things than trying to ascertain whether you have it or don't, if that makes sense. Yeah, it's like you do the work with them is the emerging property and it's somewhat ineffable, indescribable. Yes. But you kind of know it when you see it or experience it. It alludes your grasp, right? Even if you like the paradoxical nature of it is that if you were I were to agree on someone that we both think is wise. And then we asked them not just are you wise, but how did you get wise? They would almost certainly not describe themselves in that way. And there would be, as you said, a certain ineffability to how they got to wherever they got because it's such a long and gradual process. You mentioned Seneca for people who don't know who that is. Can you just fill us in? Yeah. Seneca is one of the wisest philosophers of the ancient world. He lives in the time of Nero. He's a Roman senator who becomes a stoic philosopher, a complicated, fascinating guy who writes quite eloquently and persuasively about all these stoic ideals and the pursuit of wisdom. And then I think to go to our point that even the wisest people have huge blind spots and make all sorts of mistakes. He is Nero's teacher, one of the worst emperors that ever lived. He sort of caught up in this political mess. One of the things I end up talking about in the book actually is this idea of like why so often very smart people, academics or philosophers or gurus or whatever. Find themselves drawn into the service or the orbit of profoundly bad people and seem to be genuinely bad at reading those people. Plato does the same thing. I'm fascinated with that as well. Yeah, me see it was Jeffrey Epstein. I mean, he had all these smart people in his orbit. I mean, maybe it speaks to the difference between intelligence or being smart and wisdom. Yes, also though, like when we're talking about intelligence, social intelligence is such an underrated form of it. Like one of my favorite stories in the book and not everyone agrees with me on it. But I think it's fascinating. So Socrates, we hold up as this great wise philosopher, this brave man who is brought up on these trumped up charges and goes bravely to his death. But to me, the illustrative thing about Socrates is, okay, so Socrates is brought up on trial for impiety and corrupting the youth and he's only narrowly convicted by the jury, right? The juries in ancient Athens were hundreds of people, but he's like narrowly convicted of the crime. But then he's given the opportunity to suggest his own punishment, right? He's allowed to address the court. And after Socrates addresses the court, he gives such a bad speech like he reads the room so poorly and he's so obnoxious. He says, actually, not only should I not have been convicted, you should give me a pension like my punishment should be a reward. And he's so annoying that a larger percentage of the jury votes to convict him to death, to sentence him to death, then voted for his guilt in the first place. Oh, wow. So what this means is that some people who thought he was innocent still wanted him sentenced to death. Yeah, my point is that Socrates is one of the wisest people who ever lived and yet he's obnoxious. He's not just obnoxious, but he seems to poorly perceive how he comes off to people like he would describe himself as the gadfly of Athens. But people hate flies, right? Like that's a bad thing to be. So I think there is a tendency and I think we see this in these extreme examples and then we want to wonder where we're doing it. My point is just if you're smart, but your intelligence leads you to get sentenced to death, avoidably so, maybe you're not so smart, right? Maybe you're lacking some element of wisdom. So you said earlier that wisdom is one of the four cardinal virtues. Yeah. And then you walked us through what they were and I can't remember the justice, temperance, courage, maybe. And you got him. Thank you. I'm going to say this, but you say it in the book that wisdom is the mother of all of these virtues. So why is that? What's the most important of the virtues? Obviously at some level they're inseparable and all interdependent on each other. A great example of this would be courage and justice. Courage in pursuit of a profoundly evil or selfish aim, like an unjust or an injust aim, is obviously not an admirable or a virtuous form of courage. So I think we can say that all the other virtues descend from wisdom because wisdom informs or instructs us on what they are. So the cause that you pick is not just informed by wisdom, but then you are understanding of how to bring that justice into the world has to be shaped by wisdom. And I think the example that I given this actually to fascinating examples, Thomas Clarkson and Abraham Lincoln, the two individuals most responsible for the eradication of slavery in the Western world. At some kind of moral personal level, they just instinctively believe that slavery is wrong. It's fascinating about both of them if you study their journey from just two individuals who disliked slavery to two crusading activists who bring about its demise. Thomas Clarkson for people though no is in England. He starts the abolitionist movement and leads to the the invention of most modern political activism nonviolent activism. Both he and Lincoln do is they say, okay, I have this sense that this thing is wrong, but they do these multi year deep dives into the history of the institution, both its legality, its philosophical roots, its economic underpinnings, like Lincoln goes to the library of Congress and reads as much original documentation debates amongst the founders, letters, bullet points from senatorial and congressional debates, Clarkson does the same thing. He goes and actually visits a slave ship like that famous drawing of what a slave the inside of a slave ship looks like that comes from Clarkson. So my point is that both the interests like the curiosity and then the technical competence to go wrap your arms around a subject or a topic is a part of wisdom. It's not, oh, I think this thing is wrong and therefore everyone should agree with me. What both of them do in their crusade is they go and understand the thing and figure out how to communicate it. And then also figure out its center of gravity that they're then able to attack courageously with discipline to make a more just world. As we've been saying the book is called wisdom takes work. So let's talk about how to do this work. You divide it into three areas. Part one is called the training ground or the a gauche. Is that the technical term via go get a go get that's how I pronounce it. I don't know if I've ever heard anyone say it. So I'm just guessing but yes, that's like the training ground in classical Greece. That's where you went to train both in military training and in your education. So there are a bunch of entries under training ground. I'm going to avoid pronouncing that word. And so I'm just going to pick a few and talk to you and get you to talk to him about it. One of them is talk to the dead. What does that mean? The founder of stoicism is this guy's you know he's a merchant in the Mediterranean and he deals in this thing called tyrion purple which is this rare purple die that would make cloaks and fabulous garments in the ancient world. So he's your ordinary merchant but like most of the Greeks he worships the gods. And so at some point he stops in Delphi and visits the temple of Apollo. He makes his way up the sacred way washes his hands in the sacred spring lights his incense and then he asks the priestess at the temple of Apollo. What's the secret to the good life? And she tells him in sort of typical cryptic terms that you will achieve wisdom when you begin to have conversations with the dead. He has no idea what this means for many years until eventually he suffers this shipwreck he washes up penniless and Athens and there in the agora another term which I'm a little bit more confident in my pronunciation. There in the agora he stops by a bookseller who's you know a cart of scrolls and books and the booksellers reading aloud a passage from Xenophon actually it's a it's called the choice of hercules which comes to us from socrates which I open all four books of the virtue series with he's reading this story about hercules coming to a crossroads to metaphor about choosing the easy way or the hard way in life. Anyways it's here where he hears socrates long since dead coming alive from a book reading that Xenophon realizes what the priestess was telling him all along that books are a way to have conversations with the dead that philosophy is a way to communicate with the wisest people who have ever lived most of them who lived a very long. Time ago I think this is why we tend to call the classics the great conversation right this sort of continual conversation with Aristotle and Plato and Xenophon and Socrates and Cicero and all the Greeks and the Romans so when we say talk to the dead we're talking about reading obviously there's this sort of dichotomy which I think is a false dichotomy of do you learn from books or do you learn from the streets or you book smarter street smart and the answer is you want to be both. And I think anything you can learn from books that you don't have to learn on the street is both an efficiency and a way to spare yourself some painful trial and error so that's what it means to talk to the dead. And to your credit you've built a really cool career around talking to the dead. But let me move on to some of the other suggestions in this part of the book just to reset for the listener we're talking about how to do the work of wisdom the work that produces wisdom we've just talked about talking to the dead another of your suggestions here is to ask him pertinent questions. Yeah, you know you think about the question that Xenophon goes and asks the priest right what's the secret to the good life my own life my introduction to stoicism hinges on the fact that I was at a conference when I was 19 years old and I asked for a book recommendation our life can hinge on these questions that we ask or don't ask. And so I think so much of our journey to wisdom begins with whether we're going to be curious or not whether we're going to ask or not sometimes you'll like the answer sometimes you won't like the answer but I think the act of questioning is just such an essential part of this journey so what I was trying to just sort of lay out these kind of basic principles and the story I tell is about this Nobel Prize winning physicist who ever wanted to be a person who was a person who was a person who was a person who was a person who was a person who was a person who was a person who was a person who was a person who was a person who was a person who was a person who was a person who was a person who was a person who was a person who was a person who was a person who was a person who was a person who was a person who was a person who was a person who was a person who was a person who was a person who was a person who was a person who was a person who was a person who was a person who was a person who was a person who was a person who was a person who was a person who was a person who was a person who was a person who was a person who was a person who was a person who was a person who was a person who was a person who was a person who was a person who was a person who was a person who was a person who was a person who was a person who was a person who was a person who was a person who was a person who was a person who was a person who was a person who was a person who was a person who was a person who was a person who was a person who was a person who was a person who was a person who was a person who was a person who was a person who was a person who was a person who was a person who was a person who was a person who was a person who was a person who was a person who was a person who was a person who was a person who was a person who was a person who was a person who was a person who was a person who was a person output of the question, it's things like grades, the superficial stuff, and not, did you ask the good questions? And I think even we actively discourage this questioning often because those questions that our kids ask us make us uncomfortable or are challenging the hated question of why, why, why. You stamp that out of your child, that your peril, I think, as many of us had it stamped out of us. Okay, ticking down the list here, you've got a recommendation that you call focus, focus, focus. We all know focusing is important. I'm just curious. First of all, I want to hear why you're recommending it, but specifically I want to hear, how does one focus in this era of mass distraction? Well, the importance of a disease year to express than the magical solution to it. I think it's very hard to learn or understand anything to get to any kind of wisdom or insight without long uninterrupted periods of concentration and focus. I don't know about you, but one of the things I think you find is that there's your first appreciation of something, and then there's what you appreciate or understand about it after hours and hours and hours of study about it, and then there's what you understand and appreciate it. After many years of focus on it, I've often thought that the Zen Coins of that we sometimes hold up these kind of riddle questions that Eastern philosophers would contemplate. I'm not actually sure there is an answer to them. I think the whole point is that it's supposed to be perplexing and paradoxical, and you're just supposed to spend a lot of time thinking about it, and it's weirdly the sort of, byproduct of that thinking that produces the enlightenment, not some wonderful singular moment where you know what the sound of one hand clapping is. Yes, I'm not a Zen master, but my understanding of these Zen Coins is that it's supposed to kind of ride the flawed horse of your thinking mind all the way to the transcendence of the thinking mind by breaking the thinking mind. I think that's exactly right. And so having things that you contemplate and consider on a regular basis is to me a big part of it. This is my journaling practice is a big part of, like I try to start my morning, not getting sucked into the phone, not getting sucked into meetings. I try to leave that early period of the day when I am freshest, when it's quietest, when there are the fewest interruptions to sort of do that focus. And again, all of these things are interrelated. Like focus is obviously a part and parcel of wisdom, and yet it requires an immense amount of discipline or self mastery, which would be the second virtue of stoicism. I tell this story in the discipline book that's one of my favorites. I tell it to people all the time. Tony Morris and people don't know before she was a novelist, she was an editor at Random House, as well as being a single mother. And so as she's working on her novels and then doing her two other day jobs, being a parent and editing other people's books, what she would have to do is she would have to get up every morning before dawn, and she wanted to be writing as the sun came up, which she would watch happen out of her window. But she said that she learned that it was important for her to get all or most of her writing done before she heard the word mom for the first time. Focus is this matter of willpower to be sure, but it's also, I think, a matter of planning and structure. So whenever I write, or whenever I try to work on some problem or solve something at two in the afternoon, I'm reminded why I don't do it then most of the time. You know, I'm like, oh, this ship has sailed. Like I have depleted whatever my focus capacity or reservoir is for the day. I could read a memo now, or I could have a decently productive brainstorming session, but I'm not gonna write anything that I'm proud of or have any creative breakthroughs that I'm proud of. That part of the day is over. Now, that's when it works for me. Other people you talked to them, they're like, no, no, I do my best work at two in the morning. And so you got a structure and build your life and day around that. I'm so with you on the morning thing as a fellow writer, although I turn out one book in the time that you turn out six. I noticed I've got this window of a couple of hours in the morning where all the good stuff is gonna happen. And then later in the day, my brain's still online, but just not in as focused a way or as a clear or creative way. I think what you're saying here is your answer to my question, yeah, we get it focus is important. How do we do it is know yourself, know what are the times when you can clear everything out if that's possible, given your life circumstances, and make a hard run at the thing that matters most to you in the time that is most fruitful for you. I think that's absolutely right. And I think what you just said there knowing yourself is obviously one of the most essential forms of wisdom, which by the way was inscribed in the rock over the temple of Apollo for a reason. You've got to know when you're at your best, you've got to know your limitations, you've got to know your weaknesses and your vulnerabilities. And what I have found too is it's not this singular thing. So today or now I'm a person who has to get their best work done in the morning. Before I had kids when I was younger, that window you're talking about of like when the best stuff was gonna happen, that was a bigger, more flexible window. You know, I used to be able to think and work productively on airplanes, for example. And now because I've got young kids, like the second I'm on an airplane by myself, I immediately fall asleep, right? And I can't concentrate for anything there. And so just knowing both your evolution as a person, knowing your body, knowing how you evolve and change, knowing that these things come and go in various seasons, this is an essential form of wisdom because once you know, okay, hey, my best work, my best thinking comes at between 7 a.m. and 11 a.m. then you've got to have the discipline to make decisions around that, but then to make a comfortable circle, that produces the kinds of insights or understanding that you're trying to produce. So again, all these things are very interrelated, but they descend as we're saying, that knowing yourself, knowing your environment, being able to look and observe patterns in both yourself in the world and other people is an essential thing that you have to do. Coming up Ryan Holiday talks about how to create a second brain, how to find a teacher for yourself, how to manage your ego, how to navigate your blind spots, and much more. I was not great at math as a student growing up. What I did love, the one subject that really did it for me, foreign languages. I took French from seventh grade all the way up until my senior year in college. And then as a grown up, I spent a lot of time in foreign countries as a journalist and always enjoyed learning the local languages after 9-11. I spent a lot of time in Arab countries, and I got pretty good at Arabic after a while. Anyway, a long way of saying that learning new languages can be really fun. And if that's your bag, you should check out Rosetta Stone. Learning a new language is one of those skills that really stays with you, and it's incredibly rewarding once you start caring yourself, understand and speak it naturally. Rosetta Stone makes it simple to get started and easy to keep going. 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In my view, we'll accelerate your business meaningfully. Make this the year where no opportunity and no customer slips away, try Quo for free plus 20% off your first six months when you go to Quo.com slash happier. That's quo.com slash happier. Quo, no missed calls, no missed customers. Another thing you talk about in the book, and again, this is all onto the first part of the book where you talk about the training ground for wisdom and we'll get to the later parts of the book later. But another of your recommendations is to create a second brain. What does that mean? It's an amazing term, this idea of creating a second brain. It's a term that I think was invented in the last 10 years. But it describes a very timeless thing that almost all the philosophical and literary and creative minds that we admire have practiced for centuries, which is this idea of a commonplace book or a journal. The idea of reading, talking to the dead, as we talked about, but then finding some way to synthesize and transfer that knowledge into a form that you can easily access, carry with you, and cultivate over the course of your life is what we're talking about there. So for me, I use note cards, I read a book, I fold pages, I write in the margins as I do, and then after I let it sit for a bit, I process, I take extracts out of the book, ideas that it brought up, quotes that I like, things that I want to research, and I transfer that onto these note cards, which then become the building blocks of my books, but also just changes things I do in my life and my business, all of this. So it's not just enough to read and explore and be intellectually curious. You're just lying to yourself if you think that it's just being stored in your mind somewhere. It's not. It's going into a black hole for the most part. So I spend a lot of time talking about strategies from different people over the centuries. Emerson's system is a little bit different than Eric Hopper's, which is a little bit different than Montains, which is a little bit different than Joan Dittians, but what is the process by which you are recording and organizing what you're learning? Because if you're not, you're not really learning it. Do you think people like us mean you have an advantage in this regard because we have the excuse of our writing careers and our podcasting careers that we, if forces a kind of internalization that the casual reader who's got a whole other life to worry about can't often access. Yes, although I'll give you just because I'm an index card nerd, I gave a talk several years ago at the Reagan Library and I agreed to do it in exchange. I said, look, I'll come do this talk, but I would like to go through the archive and look at Ronald Reagan's note cards. And they were like, we're actually surprised that you know about them because they're not super well known. But Ronald Reagan from his earliest days as a movie star, then later his days as a spokesman, he was a pitchman and a spokesman, I think for a general electric. And then when he became sort of a political, I think he ran the screen actors guild, then he ran for governor and then president, what he would do is he was always reading and talking to people. And then he would write things down on three by five note cards and then he would store them in these photo binders organized by theme. And so his reputation later, and we don't have to get into his specific politics as you can take him or leave him, but his sort of genius as this folksy guy who always had the perfect story, the perfect anecdote, the right little statistic or yarn, that seemed like it was organic and natural, but it was in fact incredibly studious and well researched. And so most of the people that you admire, that you think are winging it and in fact have some sort of system like this. So I don't think it just works for writers, yes, it's a wonderful excuse for all of us, but if you're the CEO of a company, if you are trying to teach something to your 16 year old, it's better that you don't have to go, I think I read somewhere one time, there was this idea about X, Y, or Z, or I heard ones from somebody, I don't remember the exact wording of it, you're gonna wanna draw on these things. And at some point in your life, you're gonna wanna draw on this store of wisdom or knowledge. And if you haven't done the work before you know that you're gonna need it, it's not gonna be there for you to draw on. Another thing you recommend is to find a teacher. This is actually a question I get a lot because this is gonna reveal me to be the type of Shima who reads his comments, but I read a comment recently somewhere that was complaining about this podcast and the fact that many of the people I bring on are Buddhist teachers who are friends of mine and are legitimately my teachers too. And this person was saying, I think with some justification, you're kind of a dick for that because it's kind of flaunting to us that you have all of these teachers that we don't have access to. So I'm curious to hear what you say. When you recommend to people find your teacher, what does that look like? Well, I wanna let you out the hook first because I think you could say that what you're doing is actually an act of service and even generosity instead of just pursuing this stuff on your own. You're choosing to interview and talk to these people in a way that makes it public. And by the way, free, you've put out hundreds and hundreds of hours of these discussions that to otherwise access these teachers' wisdoms would either be expensive or impossible because they don't just take on random students. And so we talked about cheating earlier. Part of the cheat code that you and I have figured out is that hey, we can have access to people that we otherwise wouldn't have access to because we're gonna share that knowledge with a wider audience and it allows it to scale. I think you figured something out there and I think it's very much of use. But I told you that story about Zeno. So Zeno ends up in the Agura. He hears the reading of Socrates. He's having this conversation with the dead. But he isn't content just to talk to the dead. Actually, his first question to that bookseller is where can I find a man like that? Meaning Socrates. Like where can I find someone like Socrates? Because Socrates is dead and although it's wonderful to read his dialogues, it would be ideal to have a dialogue with someone as wise or approaching the wisdom of Socrates. And as it happens, a cynic philosopher named Cratees is walking by at this very moment. The bookseller simply raises his hand and points at him. And Zeno becomes a student of Cratees and his wife just to give credit to the female philosophers of the ancient world. His wife has a very difficult to pronounce name so I won't embarrass myself. But she was not a nameless individual. But the point is this sort of philosophical team of Cratees and his wife are the foremost philosophical influences of Zeno's life. And Cratees' nickname in Athens was the door opener, which I think is such a great way of expressing what the best teachers do. They not only open doors. They open doors to rooms we didn't even know existed. And so yeah, who is your teacher on your journey? I talk in the book both about teachers and mentors. Can you draw a clear line between one or the other? I don't know where one begins and the other ends exactly. But who are you learning from? Whose feet are you studying at? Obviously, there are some people who are totally self-taught, who find they learn by experience and books exclusively. That is more the exception than the rule. You've got to find the people who you can ask a million questions, too, to go back to what we were talking about. That patient teacher who is willing to direct and orient you towards the things that you need and want to know. Feels to me like there are many options here and many levels to this. There's the parasocial teaching relationship you can have with people you believe to be wise out in the world who are dead or alive, like the dead people that we talked about earlier or alive people who are podcasters or authors giving speeches that you can attend. So there's that and you can do your best to get close to them if that's within your realm of possibility. But then there are also people in your life who are never going to be on mic on a podcast. Yes. But are just naturally wise to experience your grandmother. Yes. Some teacher you had in high school that you reconnect with, et cetera, it's a boss at the office who, or even a colleague at the office who just seems to have some aspect of wisdom that you can, they don't have to be a perfect teacher, but they can be good enough and you can accumulate enough of them to triangulate your way toward progress. There's a lot of things that you can learn from people telling you. That's a talk you would attend or a book you would read or a video you would watch or a podcast you might listen to. And then there's some things that I think you kind of need to be shown. And that's probably where your teacher comes in. And there's some things that need to be tailored exactly to you. I talk a lot in the book about Montagne, the French thinker. He talks about while he was at school, he has this teacher that understands, he doesn't name the teacher, we can sort of triangulate and guess who it was. But this teacher understands that even the curriculum in class and the assigned reading is not going to be everything that Montagne needs. And so they work out this agreement that he gives him access, books being rare in these days, the printing press being a relatively recent invention, that he's allowed to raid his teacher's bookshelf. And we can imagine the teacher also picking out some specific titles and going, hey, I need you to read this one. I'm writing right now about Admiral James Stockdale is one of the few sort of modern proponents of stoicism. And I'm just getting to the point right now where he's at Stanford, he's getting a graduate degree. And everything he learns in all of his classes is great. But then he has this sort of side relationship with a professor named Philip Reinlander, who begins to sort of do a series of extracurricular assignments for him. Books that he has to read and then Stockdale comes and they schedule one hour a week for discussion where they just talk about these books. I think most of us, and if not, then I think we should all count ourselves as incredibly fortunate to have this. Have one of those kind of intellectual relationships in our life. Someone further ahead than us, someone we admire, someone who possesses some amount of wisdom, who sort of charts out a course of study or experiences for us. And we either listen to them or we don't. But when we look back, we go, I wouldn't have gotten where I am without that kind of one-on-one instruction. Okay, I'm going to reset for the listener. We're talking about Ryan's new book, Wisdom Takes Work. The book is divided into three parts. We're never going to cover everything in the book. You should go buy it and read it. We've just spent some time talking about a few of the aspects of part one of the book, which is the training ground for wisdom. The second part of the book is about the shit you should avoid, the sirens, the perilous rocks of which you must beware. Before I get into the specific sirens, why dedicate a whole section of the book to the stuff you must avoid on the path toward wisdom? If we think that wisdom is simply the acquisition of knowledge and experience and teachings and advice, we're obviously missing something because you can learn a whole lot. But if you don't remove certain tendencies, if you don't avoid certain pitfalls, you can end up being something that I think appears in most of the different philosophical and spiritual traditions, which is the intelligent fool. You can have all the knowledge in the world, but be stupid at some level. And so I came to understand that wisdom is both all these things that you're learning. And then it's also all this foolishness that you're trying to avoid or excise. There's the learning, and then there's, I don't know, but either the first time you sort of are informed about all these different cognitive biases that humans are susceptible to. So on the one hand, you're learning something, and then what you're actually learning is how to beware or avoid these sort of timeless traps or blind spots that all of us have. And so I wanted to spend a lot of time on that because I think that's probably what causes most of the suffering and the evil in the world is not ignorance per se. It's something different. Okay, so under sirens in this section where we're talking not so much about co-mission, but omission. Yeah. One of the entries is called empty the cup. Yeah, what does that mean? Well, this is the famous end story of the teacher and the student sitting down for tea. The teacher goes to fill the cup and it overflows and he says, you know, our mind is like this cup. If it's not empty, I can't take any knowledge in. I wanted to talk about a couple things there. One ego being a thing that often fills our cup and prevents us from learning. And then also the biases and the prejudices or the habits or the preconceived notions, whatever you want to call them, that, wow, perhaps they don't fill the cup exactly. What they tend to do is poison or taint whatever you put in the cup. And so the idea of sort of clearing the mind, understanding what we're bringing to things and trying to empty that out as much as possible to me as seems like an essential part of this sort of wisdom journey. What are your modalities for doing that? Yeah, that's a good question. To me, journaling is a big one. I tend to like stoic philosophy is this idea of sort of pausing and reflecting. So I try to go, okay, I have this opinion. I have this view. This is my first impression of the matter and not allowing myself to go with that, but to stop and go, okay, what's acting on my opinion here? What is informing my impression here? The stoics talk about taking all of our emotions, our judgments, our views of things and putting them to the test. So this kind of process of not going with your first instinct or reacting immediately in the moment is I think one of the more essential parts of it. And ego is one of the ones that I'm always trying to check for. My view is sort of ego is the root of most of the big failures and conflicts of the world. And whenever we can ask ourselves, hey, am I acting out of ego here? Where is my ego distorting what I'm seeing and feeling and experiencing? And how can I remove that from the equation? The better we're going to do. And by ego, but I know you wrote a whole book about the ego. So I'm going to be annoying and ask for another definitional question. Do you mean just like an inflated sense of this self? Yeah, not the Freudian ego exactly, but that sort of colloquial ego, Donald Trump being the embodiment of that ego probably, right? The sort of narcissism and inflated sense of worth, as you said, maybe another less triggering way to think about is like your identity as a person, right? I am this, I am that. I don't want to be this. I don't want to be that. That thing getting in the way of what is actually, you know, a little bit of feedback or what's actually a totally innocent remark or something that has absolutely nothing to do with you. That's where ego gets in the way. In recovery, they sometimes talk about ego as being a conscious separation from. I think that's an interesting definition. Yeah. It's something that's getting in between you and whatever is happening. Yeah. Actually, the acronym they sometimes use and I don't even think this necessarily has to be religious, but they said ego stands for edging God out. You know, it's just something that's like pushing away this because it threatens the identity or your sense of self. Yeah, that's actually quite profound. I have not spent a lot of time in the recovery world, but every time somebody talks about it, I'm like, yeah, they're really onto something there. And that sense of separation, I mean, that goes really deep like we have this sense of ourselves as encased in some sort of armor separate from a dangerous universe. When in fact, I mean, that's all an illusion. You are created entirely from non-Ryan stuff. And yet you feel very much like Ryan. And so how can you not let that sense of Ryan, which is true on some level? If you look in the mirror, you'll see Ryan, but on some deep level is actually an illusion. How can you not let that separation fuck up your decisions? When, as years where I experienced it quite practically, right, like the stereotype of like the egotistical artist or the egotistical politician or the egotistical CEO, the problem with that ego is that what each of those people is doing is fundamentally about someone else, right? Like you're making art that's supposed to sure speak to your experience, but it has to resonate with other people. The CEO is making something of value that other people will willingly exchange time and money for. The politician has to be the representative of the people, has to like the people, has to understand what they're experiencing and what their needs are and what their emotions are. And so the problem with ego is that it makes everything about you. And most of what we're doing in life professionally and personally is by definition not about us. And so that's where ego really gets in the way of what you're trying to do or really what you need to do to be successful at that thing. So along those lines, there's another entry in this part of the book around the sirens, the dangerous stuff on the path to wisdom. There's another little chapter here called don't be a know-it-all. Epic Titus' line was remember it is impossible to learn that which you think you already know. And I think that gets right to it, right? Because there's something self-fulfilling about being a know-it-all. It's not that you know everything, but you know all that it's possible for you to know, right? Because you don't think there's anything else for you to learn. And so the irony of humility is that it actually makes you smarter. We've been talking about the Oracle of Delphi. At some point Athens dispatches someone to the Oracle. And it actually wasn't until I was in Greece this summer that I truly understood how far the Oracle is from Athens. Like it was a several hour drive, right? And then I'm like, oh, how did they get here in the ancient world? Like it occurred to me that part of the function of the Oracle must have been as a cooling off mechanism. Like it's going to take them a week or two by boat or a month or two by foot to get there. Like it must have functioned as the founders supposedly said the Senate was supposed to. There's the saucer that cools the cup. But at some point Athens dispatches a messenger to the Oracle to ask, you know, is there anyone wiser than Socrates? And the answer comes back, no, no one is wiser than Socrates. And this is all quite baffling to Socrates because he doesn't feel that he's wise. And it's only as he you know takes his quiet time to focus and reflect that he realizes that perhaps this is what the Oracle meant, that his lack of certainty about his wisdom, his intellectual humility, his interest in asking questions instead of providing answers that is in fact the source of whatever wisdom he does possess. And so if we can understand that the more we focus on what we don't know, the more we will come to know. And the less we sort of reflect and glory in all that we have learned, the better we're going to be. Didn't stop Socrates from getting himself killed. It's true. Maybe that was him being a little proud of himself. This is a total digression, but I just read this novel set in the ancient world, set in Syracuse called Glorious Exploits. Have you read it? Who's it by? It's by a first time Irish novelist whose name is evading me now. But will I will put it in the show notes? My friends have recommended this book. It's very funny. And to me, what's coming to mind right now is it gave me this feeling that listening to you gives me to, which is just a centilla of a taste of what it must have been like to live at that time. The reason I ask is like the best book that I read this year, by the way, talking about speaking to the dead, often my favorite book of the year is like never published in that year that I'm reading it. It's often like some book that was incredibly popular 20 years ago, 50 years ago, 500 years ago, and I'm just hearing about it for the first time. But I read this book The Last of the Wine by Mary Renult, which is a novel about basically paracly and Athens. Socrates is one of the main characters. And it was like hugely popular many, many years ago. It's so easy to think about these historical figures as like, you know, you think of Socrates walking around Athens and his toga. Oh, it was so wonderful. And they're just kicking around ideas. I mean, Socrates lives through a great power conflict between Athens and Sparta, a series of wars, one of which he fights in, which his country loses, by the way. And then he lives through a time called the 30 tyrants. And then later he's put to death like he lived in this incredibly fitful, uncertain, chaotic, stressful time. And we just totally misremember what the past was actually like, like the past was exactly like things are right now, which is to say a complete mess feels like the world is ending all the time. Feels like everyone is uniquely awful and stupid and cruel. And we're going to fuck it all up. And it's like, that's what they felt like. Montagne lived through the Reformation and the counter Reformation, like his whole period of like retreating to his study to think about things. That wasn't a voluntary choice. He was worried about being burned at the stake. And that's why he retires from public life. So just to pick up on that, what you said about Socrates and the Athenians losing wars, this book, glorious exploits, is set in, I said Syracuse, and I didn't know until I read the book, that Syracuse was on Sicily. And the Athenians had invaded at the point in this where this book takes place and had lost. And they were keeping a bunch of the POWs, the prisoners of war, in the bottom of a quarry. Yes. And some locals got this mad cap idea to put on an Athenian play using the Athenian prisoners, hilarity and soons. So two things related to that, right? How interconnected all this stuff was that failed flawed invasion is led by Alcy Abides, whose Socrates' student slash protege, whose your classic example of a brilliant, egotistical, narcissistic, fool. And those prisoners, because the Athenians get like absolutely decimated, just went through. They were basically like worked to death in these horrible camps. And they almost all died. It was brutal. But I didn't know about this novel. And now I'm very excited to read it. Listeners should know that Ryan is the proprietor of a bookstore. If you find yourself in Austin, Texas or the environs, you should go check out his bookstore, which is called the painted porch, just to make it all full circle. That's where Xeno sets up in the Agura. It's the stoa poquile or the painted porch is where he begins to host his philosophical discussions. So that's where the name comes from. Let's keep going with some of the sirens. Yeah. This is more of a commission than omission, but it's I think worth talking about. Seek criticism. Yeah. The problem with success is that the stakes become ever higher. And the your access to accurate information, feedback, and criticism is less and less. I've thought about this practically on this very book. I sent in the first draft of it. And my publisher was like, sounds good. I have a decent track record. We've worked together a long time. And they basically were just like, okay, this is good to go. And I had to go, no, no, no, no, no, no, it's definitely not. There is no way that it was, right? And so it's funny earlier in my career, both out of ego and then also, you know, as you're sort of fighting to do what you're trying to do. My problem was too much feedback, too much criticism. People trying to tell me what I could and couldn't do. And you have this kind of antagonistic relationship with feedback. And then the irony is once you succeed at some level, that goes away. And that's actually not a privilege. It's a kind of a curse. You know, I ended up having to do quite a bit of work to get the feedback and criticism that I needed to get the book where I think it needed to end up. Obviously, you know, this is a minor example, but you can imagine the president doesn't get many people telling them they're not doing a good job. There's a story that Gerald Ford, speaking of presidents, Gerald Ford was fond of this story about Abraham Lincoln when he was inspecting the defenses around the Union lines. He's obviously so tall that a Confederate sharpshooter takes a shot at Lincoln and just barely misses and a union soldier, you know, petrified, goes, get down you fool. And he said, that may have been the only and the last time that anyone called an American president a fool to their face. That is, let's say, less a risk in a democracy where you have freedom of speech, but you can imagine not many people are able to tell Vladimir Putin that he's fucking up this Ukraine thing and that he made a colossal mistake and needs to back out, right? Dictators, presidents, celebrities, CEOs, etc. don't get the feedback or criticism that they need to improve and get better. And so if you don't cultivate a practice in your life and as well as a network, later in the book, I talk about cultivating a board of advisors. If you don't cultivate that, you're not just going to stop getting better. You're going to start getting worse. You can see it in Kim Jong-un's fashion choices. Yeah. And this is why you read the comments on your videos, right? Thank you for putting my dumb behavior into the most positive light. I will say just one thing, what feedback to let in and not let in is really the question, is it feedback from random people on the internet? Probably not, right? And so that is the art of it. It's not what everyone thinks, but how do you get it from the right people in the right way? Having up Ryan talks about how to seek out criticism, embrace complexity, and how to learn how to die. Keep it here. It never happens at a good time. The pipe bursts at midnight. The heater quits on the coldest night. Suddenly, you're overwhelmed. That's when home service here. For 499 a month, you're never alone. Just call their 24-7 hotline and the local pro is on the way. Trusted by millions, home-served delivers peace of mind when you need it most. For plans starting at just 499 a month, go to home-served.com. That's home-served.com. Not available everywhere. Most plans range between 499 to 1199 a month your first year. Terms apply are covered with repairs. Underwear drawers are like the wild west of war droves. You never know what pair you're going to pull out or what shape it's in. It's time to upgrade your underwear drawer with a buttery soft comfort of me undies. Me undies signature fabric is a soft as a warm hug from your favorite sweater. Plus it's breathable and oh so comfy, making it ideal for all day wear. Get 20% off your first order plus free shipping at me undies.com slash comfort. Enter promo code comfort. That's me undies.com slash comfort code comfort. We talked about the first two parts of the book, the training ground and then the sirens, the stuff you should avoid on route hopefully to wisdom. Part three of the book is called the apotheosis or the touching of the divine. What does that mean? What's the relationship to wisdom? Yeah. So what I ended up kind of doing in each of the four books in this series is kind of like there's like your beginner level, there's your intermediate level and then there's your sort of advanced level. There's some kind of transcendent level of each of these virtues. There's a sort of ordinary courage of a person who gets up and speaks their mind and then there's the courage of the person who's willing to go to jail for an idea or willing to be executed for said idea, right? And I think with wisdom, there's obviously the sort of educational process we all have to undergo. There's the sort of foolishness and error that we try to to avoid and then there is some level of kind of transcendent wisdom. Gandhi's education is fascinating to me, right? He has some ordinary school in India. Then he goes to London for law school, which is where he really becomes a critical thinker and engages with a bunch of the intellectual ideas that shape him for the rest of his life. But we don't call him the Mahatma because he got a degree in London and the law, right? There's some other level of education and learning and insight and understanding that he learns first in South Africa, both as a practicing lawyer and then as a fledgling activist. And then later when he goes back to India, so my point in the third part of the book is just the ideal, the highest level of wisdom. And I talk a lot about Lincoln because Lincoln's fascinating in this regard. He sort of mirrors all these different levels. His self-education as a young man was obviously essential. But it's actually later in life, kind of the last 15 or so years of his life that he becomes the sort of Abraham Lincoln, the great man of history. And that education and that transformation is what I'm sort of not just most interested in, but I think we all ought to aspire to at some level. So let's talk about the how of that. You have a lot of recommendations, but let me throw a couple of them at you and get you to hold forth. One of them, you've got a chapter here under this third part of the book called Embrace the Mystery. What do you mean by that? Before you know stuff, you think the world is very simple. And then you study and you learn, and it becomes a little bit more complex. And then you study it more and more and it becomes simple again. And then you study more and more and it becomes complex again. I guess what I'm talking about, I talk about this a lot in part three of the book, is the complexity and contradiction, the ineffability of things like even the idea of wisdom. I think I've gotten better at going like, I actually don't know how to define wisdom exactly. I don't think, and perhaps the definition of it is actually not the important thing. So I just wanted to spend some time in the book talking about that ineffability, that contradiction, that complexity. I think this is why often some of the wisest people love fiction and poetry and the arts. They're in a way almost a poem comes better to encapsulating the truth of something than a textbook can, even though it's attacking the problem from a very different angle. Speaking of truth, there's also a chapter here called Suffer into Truth. Yeah, it's very hard to achieve any kind of real or lasting wisdom without paying for it. The engine said we suffer into truth. That was Escalus, which by the way, Robert F. Kennedy, the first one, famously quotes this line to a rockess crowd in Indianapolis the night that they all simultaneously learn that Martin Luther King Jr. has been killed. He was speaking of his own painful lessons from his brother's death, that you want to be angry, you want to rage, and then he just sort of wared his violence in this way, take you. He was just talking about these lessons that we have learned painfully over our experience as a human race, and then also individually in our own lives. And so when we talk about learning by trial and error, some of those errors are going to be embarrassing and humiliating and costly and expensive. And the redeeming quality that comes out of them has to be the insight and the understanding. You can suffer and screw up and not take wisdom out of it, too, I guess. So that's the choice that you have. I shudder to think how many times I've made the wrong choice in this regard, but moving along, there's another chapter here I want to hear you talk about, which is called Grass the Essence. The story I tell in that chapter is about Lincoln writing the Gettysburg address, which is word for word, pound for pound, one of the greatest things ever written in the English language, and then also most impactful things ever written in the English language. I talked about his sort of deep dive into slavery and the history of America there. That speech is the distillation of all of that study, of all of those talks, of all of that suffering that he had experienced personally and then witnessed as he toured these battlefields and read the casualty counts. What Lincoln is doing there is articulating fundamentally what America is should be and could be. And the fact that he does it in like 260 somewhat words is all the more remarkable when you learn, and I didn't learn this in school, that he was not the main speaker of the day. Edward Everett was widely considered America's greatest order at that time. He spoke for two hours before Lincoln. The Gettysburg address was shorter than the invocation, the prayer that kicked off the events there at Gettysburg. But Everett tells Lincoln that either that evening or the next day that he came closer to expressing the essence of what needed to be expressed in two minutes than Everett had done in two hours. That was not a magic trick. That was the culmination of an intellectual and spiritual journey that had gone back to Lincoln's earliest days. I can't remember if the words I'm about to utter come from the Gettysburg address or the second inaugural, but the idea of malice toward none and charity toward all that just seems to me to be desperately lacking in our culture right now. You're totally right. It is in the second inaugural. But to go to our point about expressing the essence, the idea, if you've been to the Lincoln Memorial, that his two greatest pieces of writing, and Lincoln was a writer, there's actually a great book called Lincoln Biography of a writer that I recommend to a lot of people. We think of them as a politician giving speeches, but these were meticulously crafted documents that oftentimes he just read. He fished a scrap of paper out of his pocket and read the Gettysburg address. But the fact that those two speeches could fit on, I think, three tablets in the Lincoln Memorial is just a magnificent statement of brevity and distillation. I think the second inaugural address is like one of the shortest inaugural addresses. And yet it is the best. Someone pointed out to me once and I don't know if it's true. And I don't want to look it up because I just like thinking about it that every sentence and phrase in the second inaugural has become a book title. And you go, yeah, it probably because every phrase in it is perfect. A couple more questions for you before I let you go. There's a chapter here right at the end called Past the Final Test. Yeah. Siseroe said that to philosophize is to learn how to die, that the whole point of philosophy was to prepare us for the one thing that we're all going to do. So of all the things that I'm writing about in the book, this is obviously the one I have the least experience in. And I have no idea whether I'm right or not. But if the dead can teach us anything, I'm just trying to sort of channel what they have spoken to us about. The idea being that that all philosophy is aimed at both living well and then ultimately dying well. I wanted to talk about sort of some of the lessons that death teaches us. And then sort of how we orient ourselves. I opened the book with Montan and I ended it with Montan and he loved that line from Siseroe. But he had written that he hopes death will find him planting cabbages. And what he meant was that he hoped death would find him in the course of an ordinary regular moment of life that he was living well. And I think there's something kind of zen about that. It's kind of the perfect expression. But you know, death is ever present. The Stoics want us to remember that death is in a thing that happens at the end. That in fact, death is happening now. So Senica would say that actually I do have some familiarity with death because I've already died nearly 40 years. That if we think about death as this thing that is a part of our existence and a part of our life, not just that the people we love and know are dying all around us all the time, but that we ourselves are dying with the passage of time. I think we are grasping a fundamental piece of wisdom that can be life changing. This is final phrase I want to ask you about. Val maist. Ooh, yes. This is Steinbeck. Have you read it East of Eden? A long time ago. It is worth rereading because it is an incredible book. I reread it early in the pandemic. A beautiful, magnificent kind of epic novel, which by the way has a lot of Stoicism in it, leave the Chinese servant to the main family is this philosopher who's always quoting Marcus Aurelius to the two boys. In any case, Steinbeck writes this book about writing East of Eden. It's called Letters from a novel, I think. Anyways, he's talking to his editor and he says basically the fundamental premise of the book, and he thinks this is his insight into the ancient traditions too, is that the commandments are not thou shalt not as in like you absolutely are not allowed to do these things, but that thou maest that you have the choice not to and that who we are is ultimately about making this choice. That free will is the essential part of the Christian tradition part of the virtue tradition, which is that no one is making you do or not do these things and that perhaps hell or heaven is the wrong way to think about it too because then it's like you've got a gun to your head that there's a punishment for doing or not doing the right thing. He's saying that it's a choice and that this choice is the thing that matters, that says who we are. And so I begin and end the series calling back to that story about the choice of Hercules, which was so informative for Socrates and then later for Zeno, the choice of Hercules being this very idea that Hercules comes to the crossroads, the choice between virtue and vice. And the path of vice he's told will be easy and straightforward and wonderful and pleasurable in all of these things and that the path to virtue will be hard and difficult and may not pay off and which one is he going to choose, that that's the choice of Hercules and that's the choice that we have to make as individuals. And by the way, just like a little crazy thing I was surprised to learn, John Adams thought that the choice of Hercules should be what's on the seal of the United States, not the eagle. He thought the choice of Hercules was fundamentally what a country built around liberty was saying that the government can't tell you to do or not do these things, but you as the individual given the choice may or may not do these things and what you choose is who you are. It's always great to talk to you. I'm going to ask the two questions I always ask at the end of the show, habitually. The first is, is there anything you were hoping that we would get to that we didn't get to? Now this is amazing. I always look talking with you. The second question is, just can you remind everybody of the books you've written and any other stuff that they should know about from you, the Daily Stoic, etc., please just step into the plug zone. Oh yeah, well ego wise, this one's much easier for me. So the Stuart Virtue series, Courage is Calling, Discipline is Destiny, right thing right now, and Wisdom takes work. That's what I just finished. Those are available anywhere. And then I'm probably best known for my book, The Daily Stoic, and then DailyStoic.com, which is a stoic inspired email every day and then podcast and YouTube stuff. So that you can find at Daily Stoic pretty much everywhere you would go. Right, thanks again for making time for this awesome to talk to you always. Now this is amazing. All right, hope to see you soon. Thanks again to Ryan Holiday, as I said at the top, I love having that guy in the show. Before I leave you, just want to remind you to sign up for my new app, 10% with Dan Harris, my new meditation app. You can sign up over at DanHarris.com. There's a free 14-day trial. If you want to try before you buy, lots of amazing stuff going on over there. I'm really proud of my team for all the work they're doing over there. And finally, I just want to thank everybody who worked so hard to make this show. Our producers are Tara Anderson and Eleanor Vasilie are recording and engineering is handled by the great folks over at PodPyple. Lauren Smith is our managing producer, Marissa Schneiderman is our senior producer. DJ Cashmere is our executive producer and Nick Thorburn of Band Islands, wrote our theme.