Why Success Is Making You Dumber | Ryan Holiday

Ryan Holiday explores how wisdom isn't innate—it's earned through deliberate practices. The most actionable insight: Create a 'second brain' by actively processing what you learn. Don't just read—take notes, extract key ideas onto index cards or a digital system, and organize them by theme. This tra

1h 20m
10% Happier

Key Takeaway

Ryan Holiday explores how wisdom isn't innate—it's earned through deliberate practices. The most actionable insight: Create a 'second brain' by actively processing what you learn. Don't just read—take notes, extract key ideas onto index cards or a digital system, and organize them by theme. This transforms passive consumption into accessible wisdom you can draw upon when needed, just as Ronald Reagan did throughout his career with his 3x5 note card system.

Episode Overview

In this episode, Ryan Holiday discusses his new book 'Wisdom Takes Work' and breaks down the ancient Stoic approach to cultivating wisdom. He explains that wisdom—one of the four cardinal virtues of Stoicism (along with courage, temperance, and justice)—is the mother of all other virtues because it informs and instructs how to practice them. Holiday emphasizes that wisdom isn't something you're born with or acquire by chance; it requires consistent, deliberate practices like reading, questioning, focused work, and creating systems to capture and organize insights. The conversation explores practical methods for doing the 'work' of wisdom, including maintaining a commonplace book or note-card system, protecting your peak focus hours, seeking teachers and mentors, and understanding your own patterns and limitations.

Key Insights

Wisdom Requires Work and Cannot Be Acquired by Chance

The Stoic philosopher Seneca emphasized that nobody achieves wisdom by chance—it's not innate, can't be given to you, and only comes through deliberate effort. Rather than trying to define wisdom precisely (which itself may indicate you lack it), focus on the timeless practices and processes that produce it as a byproduct.

Intelligence Without Social Awareness Can Be Dangerous

Socrates, despite being one of history's wisest philosophers, was so socially tone-deaf during his trial that more jurors voted to sentence him to death than had voted for his guilt. This illustrates that you can possess tremendous knowledge yet lack critical wisdom in reading people and situations—a form of intelligence often underrated but essential for applying knowledge effectively.

Deep Study Transforms Moral Instinct Into Effective Action

Both Thomas Clarkson and Abraham Lincoln felt instinctively that slavery was wrong, but what made them effective abolitionists was their multi-year deep dives into the institution's history, legal foundations, and economic underpinnings. Wisdom isn't just having the right values—it's developing the technical competence and understanding to communicate them and identify where to direct your efforts for maximum impact.

Books Are Conversations With the Dead

The founder of Stoicism, Zeno, discovered at the Temple of Apollo that he would 'achieve wisdom when he began to have conversations with the dead'—which he later realized meant reading books. Philosophy and the classics represent an ongoing dialogue with the wisest people who ever lived, most of whom are long gone, giving us access to accumulated wisdom we'd otherwise have to learn through painful trial and error.

Reading Without a Capture System Is Learning Lost

You're lying to yourself if you think what you read is simply stored in your mind—it's going into a black hole. Wisdom requires actively processing what you learn through a 'second brain' system: note-taking, extracting key ideas, organizing them by theme. Ronald Reagan's legendary folksy wisdom and perfect anecdotes weren't organic—they came from decades of recording insights on 3x5 cards organized in photo binders by theme.

Know Yourself to Optimize Your Best Work

Self-knowledge is fundamental wisdom—knowing when you're at your best, understanding your limitations and vulnerabilities. This changes over time (before kids vs. after, younger vs. older). Once you identify your peak focus window (e.g., 7-11 AM), you must have the discipline to structure your life around it, protecting that time for your most important thinking and creative work.

Asking Good Questions Opens Doors You Didn't Know Existed

Zeno's life-changing question ('What's the secret to the good life?') and the Nobel Prize-winning physicist whose mother asked him daily 'Did you ask any good questions?' illustrate how our journey to wisdom hinges on curiosity and questioning. The best teachers are 'door openers' who reveal rooms we didn't know existed—but only if we ask.

Notable Quotes

"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."

— Ryan Holiday

"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 Stoics say, as a result of a lot of work."

— Ryan Holiday

"It is impossible to learn that which you think you already know."

— Ryan Holiday

"You can have all the knowledge in the world but be stupid at some level."

— Ryan Holiday

"The irony of humility is that it actually makes you smarter."

— Ryan Holiday

Action Items

  • 1
    Create Your Second Brain System Today

    Start a commonplace book, note-card system, or digital knowledge management tool (like Notion or Obsidian). When you read something valuable, don't just highlight it—extract the key ideas, write them in your own words, and organize them by theme. Process books shortly after reading by reviewing your highlights and transferring insights to this system.

  • 2
    Protect Your Peak Focus Hours

    Identify when you do your best thinking (often early morning for most people). Block this time for your most important creative or strategic work—before checking email, taking meetings, or looking at your phone. Structure your day so routine tasks happen during lower-energy periods. Experiment to discover your personal patterns and be willing to adjust as your life circumstances change.

  • 3
    Cultivate the Habit of Asking Good Questions

    Instead of just consuming information passively, actively question what you're learning. Ask 'impertinent questions' that challenge assumptions. If you have children, ask them daily 'What good questions did you ask today?' rather than 'What did you learn?' Model intellectual curiosity and reward questioning, even when the questions are uncomfortable or challenging.

  • 4
    Find a Teacher or Door Opener

    Identify someone wise in an area you want to develop and find ways to learn from them—whether through mentorship, their published work, podcasts, or courses. Don't be satisfied with just reading about wisdom; seek living examples who can open doors to rooms you didn't know existed. Be willing to ask for book recommendations and guidance from people further along the path.

Full Transcript

Transcript of Why Success Is Making You Dumber | Ryan Holiday from 10% Happier. Auto-generated from episode audio; may contain minor errors.

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. Problem with success is that the stakes become ever higher and your access to accurate information, feedback, and criticism is less and less. You can have all the knowledge in the world but be stupid at some level. It is impossible to learn that which you think you already know.

The irony of humility is that it actually makes you smarter. It's very hard to achieve any kind of real or lasting wisdom without paying for it. 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 Stoics say, as a result of a lot of work. So, let's talk about how to do this work. 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.

basic questions. basic questions. Deal. Deal. Deal. The book is called Wisdom Takes Work. What do you mean by wisdom? I It's one of those words that like, you know, you say it and you picture like Dumbledore. Um, so like what what do you mean specifically by wisdom? Yeah, it's a it's a tricky one, right? What is the definition of wisdom? Uh I've come to understand that it is many things right. So obviously it's experiences, experiences, experiences, it is it is it is reading, it is the advice we get.

You know it I guess what I what I what I figured out doing this book. So I I've been doing this series on the cardinal virtues. Uh and what I find is so the four virtues for people don't know of stoicism are 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 there are many things and there are sort of sub virtues underneath each one.

And so my my my definition of wisdom wisdom wisdom is uh that there is no definition. And to think that there is a a a clean one-s sentence definition is probably some sign that whatever wisdom is you don't have it right. Uh it's it's a complicated thing comprising you know intelligence and creativity and experience and age. um it's wit, you know, it's uh it's it's all of these things and more. And yet at some level it is uh incredibly elusive and it's hard to point to any one person that has it which sort of ultimately comes to to the title of the book which you mentioned.

Senica is saying um like the one thing that we can all agree on as far as wisdom is that nobody gets it by chance, right? It's not something you're born with. It's not something anyone can give you. It only comes, the Stoics 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 uh it's probably better to focus more on doing those things than trying to ascertain whether you have it or don't.

Uh if that makes sense. Yeah. It's like you do the work. Wisdom is the emerging property and and it's somewhat ineffable, indescribable, but you kind of know it when you see it. Yeah. It eludes your grasp, right? Even even even if you like the paradoxical nature of it is that like um if you if you or I were to agree on someone that we both think is wise and then we asked them like not just uh are you wise but how did you get wise? uh there there they would almost certainly not describe themselves in that way and there would be as you said a certain ineffibility um to how they got to wherever they got because uh it's such a long and uh gradual process.

gradual process. gradual process. You mentioned Senica for people who don't know who that is can you just fill us in? us in? us in? Yeah. Senica is one of the the wisest philosophers of the ancient world. He lives in the time of Nero. He's a Roman senator who uh you know becomes a stoic philosopher. Um a complicated fascinating guy who 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.

you know, he is Nero's teacher, one of the worst emperors that ever lived. sort of caught up in this uh uh political mess that um one of the things I end up talking about in the book actually is is this idea of like why so often very smart people often academics or philosophers or gurus or whatever find themselves drawn into the service or the orbit of profoundly bad people and and seem to be genuinely bad at reading those people that that Plato does the same thing.

Um, so I'm I'm fascinated with that as well. Yeah. I mean, you see it with 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. Yes. Well, and and that also though, like when we're talking about intelligence, intelligence, intelligence, social intelligence is such a an underrated form of it. Like one of my favorite stories in the book, and not everyone uh agrees with me on it, but I think it's fascinating.

So, so Socrates we hold up as this great wise philosopher uh this brave man who you know uh is is brought up on these trumped up charges and you know goes bravely to his death. But to me the illustrative thing about Socrates is okay so Socrates is brought up on trial for impunity and corrupting the youth and and he's only narrowly convicted by the jury right uh the juries in ancient Athens were hundreds of people but he's like narrowly convicted of the crime. Um but then he's asked uh he he's given the opportunity to suggest his own punishment, right?

He's 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 he says, "Actually, not only um 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 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. first place.

first place. Oh wow. Oh wow. Oh wow. And so so what this means is that some people who thought he was innocent still wanted him wanted him wanted him sentenced to death. And and so my my point is that that Socrates is is one of the wisest men in the in wisest people who ever lived. And yet he's obnoxious and he he's not just obnoxious, but he seems to poorly perceive how he comes off to people. Like he he would describe himself as the gadfly of Athens, but people hate flies, right?

Like that's a bad thing to be. So, so, so I I I think um there is a tendency and I think we see this in we can see it in these extreme examples and then we want to wonder where we're doing it. My my my point is just um 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. Yeah. So you said earlier that wisdom is one of the four cardinal virtues.

Yeah. Yeah. Yeah. Yeah. And then you you walked us through what they were and I can't remember the justice, temperance, something else. Courage maybe. Courage maybe. Courage maybe. And thank you. Um you said wisdom is the mother or you didn't say this but you say it in the book that wisdom is the mother of all of these virtues. So why is that? is that? is that? Yeah. So it's it's like what's the most important of the virtues? Obviously at some level they're inseparable and all interdependent on on each other.

A great example of this would be courage and justice. Uh courage in pursuit of a profoundly profoundly profoundly evil or selfish aim like an in an unjust or an injust aim is obviously not an admirable or a virtuous form of courage. So so I I think we can say that all the other virtues descend from wisdom because wisdom informs or instructs us on what they are. Right? Um so the the cause that you pick uh is not just informed by wisdom but then your understanding of how to bring that justice in the world into the world has to be uh shaped by by uh justice or sorry by wisdom like the example that I I give in this actually two fascinating examples uh Thomas Clarkson and Abraham Lincoln the two individuals most responsible uh for the eradication of slavery in the western world at some kind of moral personal level they just instinctively believe that slavery is wrong.

But what's fascinating about both of them if you study their journey to being uh from just two individuals who disliked slavery to two sort of crusading activists who who who bring about its demise. Uh Thomas Clarkson for people don't know is is in England. He starts the abolitionist movement and and and leads to the uh basically the invention of most sort of modern political activism uh non-violent activism like but what both he and Lincoln do is they 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 its legality its philosophical roots its economic underpinnings like like Lincoln goes to the library of Congress and reads as much original documentation, debates uh amongst the founders, letters, you know, um uh bullet points from from senatorial and and congressional debates.

Uh Clarkson does the same thing. He 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. And so so my point is that um the the the both the uh interest like the curiosity and then the technical competence to go wrap your arms around a subject or a topic is a is a part of wisdom. It's not it's not just oh I I think this thing is wrong and therefore everyone should agree with me.

What both of them do in in in their sort of crusade is they 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 you know and then obviously to to 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 into three areas. Uh part one is called the training ground or the ago.

Is that the technical term? Uh the agogi. It's it's the it's the the Greek word. That's how I pronounce it. Uh I don't know. No, I don't know if I've ever heard anyone say it. So uh uh I'm just guessing. But um but uh yes that that that's that's like uh the training ground in in in classical Greece Greek. That's where you went to train both in in sort of military training and and in in your education. So there are a bunch of entries under uh training ground.

I'm going to avoid pronouncing that word. Um uh 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? So the the founder of stoicism is this guy Zeno. And he's an Athenian. He's a he's a merchant. He's uh in the in the Mediterranean. And he deals in in this thing called Tyrion purple, which is this rare purple dye that would make uh you know, cloaks and and uh you know, fabulous garments in the ancient world.

So he's he's your ordinary merchant, but but like most of the Greeks, he worships the gods. And so at some point he stops in Deli uh and visits the temple of Apollo. So he makes his way up the the sacred way. He washes his hands in the sacred spring, lights his incense, and then he asks the the the priestess at the temple of Apollo says, you know, what's the secret to the good life? And she tells him in sort of typical cryptic terms, uh that you will achieve wisdom when you begin to have conversations with the dead.

Uh he has no idea what this means for many years until uh eventually he suffers this shipwreck. He washes up penniless in Athens. And there in the agora, another uh another term which I'm a little bit more confident in my pronunciation. Uh there in the agora, he stops by a book seller who's you know a cart of scrolls and books. And the the book seller is is reading aloud uh a passage from Zenifan. Actually, it's uh the story. It's called The Choice of Hercules, which comes to us from Socrates, which I I open all four books of the virtue series with.

He's reading this story about uh Hercules coming to a crossroads. It's a metaphor about choosing the easy way or the hard way in life. Anyways, it's here where he hears Socrates Socrates Socrates uh long since dead coming alive right from a book reading that Zeno 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.

This 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 Zeno and Socrates and Cicero and all all the the Greeks and the Romans. So when we say talk to the dead, we're talking about reading. Um obviously there's there's this um sort of dichotomy which I think is a false dichotomy of you know do you learn do you learn from from books or do you learn from the streets? Are you books smart or street smart?

And the answer is you want to be both. And and I think anything you can learn from books that you don't have to learn on the street is uh is is both an efficiency and uh 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 you've built a a a really cool career around talking to the dead. Um but let me move on to some of the other um uh suggestions in in in this part of the book.

Um another is and again this is the 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 to the dead. Another of your suggestions here is to ask impermanent impertinent questions. Yeah. Well, I you know, you think about the question that Zeno goes and asks the priest, right? Uh what's the secret to the good life? I 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.

Um the our life can hinge on these questions that we ask or don't ask, right? And and so I think so much of our our journey to wisdom begins with whether we're gonna we're going to be curious or not, whether we're going to ask or not. Um sometimes you'll like the answer, sometimes you won't like the answer. Uh but 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, you know, these kind of basic principles and the the story I I tell is about this uh Nobel Prize-winning physicist who, you know, every day when he would come home from school, his mother wouldn't ask, you know, how'd you do on the test?

What are your grades? You know, did you did you stand at the head of your class, you know, any of that. She she would ask him every day, you know, did you ask any good questions? And I just think that's such a a wonderful habit to inculcate in a child and it's something that I try to teach my own children and I I you just realize that like so often what we are implicitly encouraging is not the questioning it's the output of the question uh or or it's it's things like grades the superficial stuff and not did you ask the good questions and I think even you know we we actively discourage this questioning often because those questions that our kids ask us make us uncomfortable or are challenging.

You know, the the the hated question of why why why um you know, you can you can uh you stamp that out of your child at your peril. I think as as many of us had it stamped out of us. Okay. Ticking down the list here, you've got a a a recommendation that you call focus, focus, focus. We all we all know focusing is important. I'm just curious first of all why you re 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.

distraction. distraction. Well the importance of it is easier to express than the uh than than the magical solution to it. But I I 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. And I don't know about you, but one of the things I think you find is that 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 sort of 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 uh singular moment where you know what the sound of one hand clapping is.

Yes. I mean, I'm not a Zen master, but my understanding of these Zen coons 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 I think that's exactly right. And so, you know, having things that you contemplate and consider on a regular basis is to me a a big part of it. This my 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 that early period of the day when I am freshest, when it's quietest, when there are the fewest interruptions interruptions interruptions um to to to sort of do that focus and and again all of these uh uh things are interrelated like like focus is obviously a a part part and parcel of of wisdom and yet it requires an immense amount of discipline or selfmastery which would be the the the second virtue of stoicism. And so, uh, I I love I tell this story in the discipline book that's one of my favorites.

I tell it to people all the time to Tony Morrison. People don't know before she was a novelist, she was a an editor at at at at Random House and as well as being a single mother. And so as she's working on her novels and then, you know, doing her two other day jobs, being a parent and and and editing other people's books, she what she would have to do is she would have to get up every morning before dawn and she wanted to be writing as as the sun came up, which she would look she would watch happen out of her window.

But she said that she learned that it was important for her to get all all or most of her writing done before she heard the word mom for the first time. and and so so it's like I think focus is is this matter of willpower to be sure but it's also I think a matter of planning and structure um so you are like like whenever I write or whenever I try to work on some problem or solve something at 2 in the afternoon I'm reminded why I don't do it then most of the time you know I'm like oh it's this ship has sailed like I depleted whatever my focus capacity or reservoir is for the day.

And uh you know, I could I could read a memo now or I could have a decently productive brainstorming session, but I'm not going to write anything that I'm proud of or have any creative breakthroughs that I'm proud of. Like that that that part of the day is is over. Now, for me, that's that's when it works for me. Other people, you talk to them, they're like, "No, no, I do my best work at 2 in the morning." And so you got to structure and build your life and day around that.

I'm so with you on the morning thing as a fellow writer. Although I I turn out one book in the time that you turn out six. Um uh I'm just a a shitty writer. Um you Um you Um you I I notice like I've got this window of a couple of hours in the morning where all the good stuff is going to happen. Yeah. happen. Yeah. happen. Yeah. And then later in the day I can do, you know, I can my brain's still online but just not in as focused a way or as a clear or creative way.

And so I say I 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 you you you know yourself. know yourself. know yourself. 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. for you. for you. I think that's absolutely right and and 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 of Apollo for a reason.

Um, 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, you know, your vulnerabilities. And, and what I have found too is it's it's not this singular thing. So, you know, today or now I'm a I'm a person who has to get the best work their best work done when in the morning. You know, before I had kids, when I was younger, I my my wi that window you're talking about of like when the best stuff was going to happen, that was a bigger, more flexible window.

You know, I used to be able to to 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? Uh but and and I can't concentrate uh for anything there. And so just knowing both your evolution as a person, knowing your body, knowing how you evolve and change, uh knowing that thing these things come and go in various seasons. I think this is like this is an essential form of wisdom because once you know okay hey I my best work my best thinking comes at you know between 7 a.m.

and 11:00 a.m. then you've got to have the discipline uh to to make decisions around that that then you know to make it come full circle that produces the kinds of insights or understanding that you you know you um you're trying to produce. So again, all these things are very interrelated, but they they descend as we're saying or the mother of the ver that knowing yourself, knowing your environment, being able to look and and observe patterns in both yourself and the world and other people is is an essential thing that you have to do.

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Uh but another of your recommendations is to create a second brain. What does that mean? It's a it's a it's an amazing term this idea of creating a second brain because it's a it's a term that I think was invented in like 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 like a commonplace book or a journal you know um the idea of reading talking to the dead as we talked about, but then finding some some way to synthesize and transfer that knowledge into knowledge into knowledge into uh uh uh into a form that you can easily access, carry with you uh and cultivate over the course of your life is what we're talking about there.

Um so for me, I use uh I use note cards. I read a book, I fold pages, I write in the margins as I do, and then after I I let it sit for a bit, I process, I take extracts out of the book, ideas that it brought up, you know, quotes that I like, uh, things that I want to research, um, uh, and, and I transfer that onto these note cards, which then become the building blocks of my books, but also, you know, just changes things I do in my life, in my business, all all of this.

So the 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. Like you it's not it's going into a black hole for the most part. So So I I spend a lot of time talking about you know strategies from different people over the centuries. You know, Emerson's system is a little bit different than Eric Hoffers, which is a little bit different than Montaigne's, which is a little bit different than Joan Ddian's.

But what is the process by which you are recording and organizing what you're learning? Because uh if you're not, you're not really learning it. Don't you think people like us mean me and you have an advantage in this regard because we have the excuse of our our writing careers and our podcasting careers that we it just it it forces a kind of internalization that the casual reader who's got a whole other life to worry about about about can't often access. Yes. Although I'll give you just because I'm an index card nerd.

Uh, I gave a talk uh several years ago at the Reagan Library and uh I agreed to do it in exchange. I said, "Look, I I'll come do this talk, but I would like to go through the archive and and look at Ronald Reagan's note cards." And they were like, "We're actually surprised that you you know about them because they're not super wellknown." But but Ronald Reagan from his earliest days as a movie star, then later his his days as a spokesman. he was a like a pitchman, a spokesman I think for General Electric and then uh when he became became became sort of a political I think he ran the Screen Actors Guild then then he ran for governor and then president.

Um what he would do is he was always reading and you know talking to people and then he would write things down on 3x5 note cards and then he would store them in these photo binders and organized by theme. And so his reputation later, and we don't have to get into his specific politics as you could take him or leave him, but his his sort of genius as this um folksy um folksy um folksy uh uh guy who always had the perfect story, the perfect anecdote, uh the right little statistic or yarn.

um that that seemed like it was organic and natural but is was in fact incredibly studious and and uh and well researched and so you know most of the people that you admire that you think are are winging it and in fact have some sort of system like this. So uh 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, you know, trying to teach something to your 16-year-old, it's better that you don't have to go, you know, I think I read somewhere one time there was this idea about X, Y, or Z or, you know, um, I heard once from somebody, I don't remember the exact wording of it, like it you're going to want to draw on these things and and, uh, to me creating that like there's going to be at At some point in your life, you're going to want to draw on this store of wisdom or knowledge.

Um, and uh, if you haven't done the work before you know uh, that you're going to need it, it's not going to 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 I actually saw Yeah. And this is going to reveal me to be the type of schmuck who reads his comments. Um, but I I read uh a comment recently somewhere uh that was complaining about this podcast in the fact that many of the people I bring on are you know Buddhist teachers who are friends of mine and are legitimately my teachers too.

And this person was saying, I think with some justification that kind of you're you're kind of uh 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 when you I'm curious to hear what you say like when you say recommend when you recommend to people find your teacher, what does that look like? Well, I want to let you off the hook first because I I could I think you could say that what you're doing is actually an act of service and and even generosity instead of just pursuing this stuff on your own.

You're choosing to to interview and talk to these people in a way that makes it public and by the way free. you know that you've you've put out hundreds and hundreds and of hours of these discussions that you know to otherwise access these teachers wisdoms would would either be expensive or impossible because they don't just take on random students. And so part of uh what I we talked about cheating earlier. Part of the the cheat code that you and I have figured out is that hey, we can we can have access to people that we otherwise wouldn't have access to because we're going to share that knowledge with a wider audience and it allows it to scale.

So I I I think you figured something out there and I think it's it's very much of use. But you know, I told you that story about Zeno. So Zeno ends up in the agora. He he hears the the the reading of Socrates. He's having this conversation with the dead, but but but he isn't content just to talk to the dead. Actually, his first question to that book seller 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 to read, you know, his dialogues, um, he's it would be better to have a d it would be ideal to have a dialogue with someone as wise or, you know, approaching the wisdom of Socrates. And and as it happens, a a cynic philosopher named is walking by at this very moment. And the the book seller simply raises his hand and points at him. And Zeno becomes a student ofrates and uh and his wife. uh just to just to give credit to uh the female philosophers of the ancient world.

His wife has a very difficult to pronounce name so I won't embarrass myself uh but she was not a nameless individual. Um but the point is this sort of philosophical team of Catis and his wife are the foremost philosophical influences of of Zeno's uh uh uh life and and you know uh creates nickname in Athens was the door opener which I think is such a great way of expressing what what the best teachers do. They they not only open doors they they open doors to rooms we didn't even know existed.

And so yeah, who is who is your teacher uh on your journey? I I I do I talk in the book both about teachers and mentors. Can you draw, you know, a a clear line between one or the other? I I don't know where one begins and the other ends exactly, but you know, who are you learning from? Who who's at whose feet are you studying at? I I think obviously there there are some people who are totally self-taught totally self-taught totally self-taught um who who find you know they learn by experience and and and books exclusively.

But I think that is a um that is that is more the exception than than the rule. You've got to find the people who you can ask a million questions to. 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. I mean, it feels to me like there are many options here, many sort of 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 sure sure sure dead or alive like the dead people that you've we talked about earlier or live people who are podcasters or authors uh uh and giving speeches uh that you can attend.

So there's that um and you do your best to get close to them um if if if that's within your uh uh if that's within the realm of possibility. But then there are also like people in your life who um are never going to be on Mike on a podcast but are just naturally wise to experience your grandmother. Um people you know some teacher you had in high school that you reconnect with etc. it's a boss or uh 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 uh progress.

progress. progress. Yeah. Look, uh I think uh there's a lot of things that you can learn from people telling you, you know, that that that's uh yeah, 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. Um and and there's some things that need to be tailored exactly to you. Um, I I talk a lot in the book about Montaigne, the the the French thinker.

You know, 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. Um, but but this teacher understands that even the curriculum in class and the assigned reading is not going to be everything that Montaigne needs. And so they they work out this this agreement uh that he gives him access, you know, books being rarer in in these days, the the printing press being a relatively recent in invention.

Um that that he's allowed to raid his teacher's bookshelf, you know, and we can imagine the teacher also picking out some specific titles and going, "Hey, I need you to read this one." Um, I I'm I'm writing right now about about Admiral James Stockdale, who's one of the few sort of modern proponents of of stoicism, and I'm just getting to the point right now where he's at Stanford, he's getting a graduate degree, and 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 Rinlander, who um who begins to to sort of do a series of extracurricular assignments.

for him books that he has to read and then Stockdale comes and and um they they they do they schedule one hour a week for discussion where they just talk about these books. I think most of us um and if not uh then I think we should all count ourselves as as incredibly fortunate to have this have you know one of those kind of intellectual relationships in our life. Someone further ahead than us we admire someone who possesses some some amount of wisdom who's who who sort of charts out a course of study or experiences for us and we either listen to them or we don't.

Uh, but when we look back, we go, I wouldn't have gotten where I am without that kind of one- on-one instruction. instruction. 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 [ __ ] you should avoid, the sirens, the perilous rocks uh of which you must uh beware. Um so let me before I get into the specific sirens, sirens, sirens, why dedicate a whole section of the book to the stuff you must avoid on the path toward wisdom? Well, I thought, you know, if if you if we think that wisdom is simply the acquisition of knowledge and experience and experience and experience um and you know, teachings and advice, um we're obviously missing something because you can you can learn a whole lot, but if you don't remove certain tendencies, if you don't avoid certain pitfalls, pitfalls, pitfalls, um you can end up being uh you know, uh something that I think appears in most of the different philosophical and spiritual traditions which is you know the intelligent fool right you can have all the knowledge in the world but be stupid at some level and so I I I 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 right like um there's the learning and then there's uh I don't know about you there the first time you 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 uh you know these these sort of timeless traps or blind spots that all of us have. And so, uh, I I wanted to spend a lot of time on that because I I I think, you know, um, that's probably what causes most of the suffering and the evil in the world is not, you know, it's not ignorance per se. It's uh, it's something different. Okay. So, under sirens in this section where we're talking not so much about commission, commission, but omission.

Yeah. Um, one of the entries is is called empty the cup. Yeah. Yeah. Yeah. What does that mean? Well, this is the famous Zen story of the the teacher and the student sitting down for tea and the the teacher goes to to fill the cup and uh and it overflows and he says, you know, our our mind is like this cup. If it's not empty, um, you know, it can't take any knowledge in. And so I I I wanted to talk about, you know, uh, a couple things there.

one, ego being a thing that often fills our cup and prevents us from learning. And then also, um, you know, the biases and the prejudices or the habits or the preconceived notions, whatever you want to call them, that that while perhaps they don't uh fill the cup exactly, what they tend to do is um poison or taint whatever you put in the cup. And so, um, the the idea of sort of clearing the mind, uh, understanding what we're bringing to things and trying to empty that out as much as possible to me is seems like an essential part of this sort of wisdom journey.

What are your modalities for doing that? Yeah, it's a good question. I I mean, to me, journaling is a big one. Um uh uh I tend to um I tend to like uh I think like stoic philosophy is this idea of sort of pausing and reflecting. So I I try to go okay I have this opinion I have this um this 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 our um 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 is I think one of the more essential parts of it. And and I think ego is one of the ones that I'm always trying to to check for. My view is sort of ego is the root of most of the um most of the big failures and and and conflicts of of the world and and whenever we can ask ourselves hey am I acting out of ego here uh where where is my ego distorting what I'm seeing and feeling and experiencing and how can I remove that from the equation you know the the better we're going to do and do and do and and by ego and I know you wrote a a whole book about the ego but and so I'm going to be annoying and ask Another definitional question or do you mean just like a an inflated sense of of the self?

self? self? Yeah. Not not the Freudian ego exactly, but that that sort of colloquial ego, you know, uh what whatever whatever is uh you know, Donald Trump being the embodiment of that ego probably, right? That just the the um the the sort of narcissism and inflated sense of worth. you said uh as you said the the maybe another less you know sort of uh uh triggering way to think about is like your identity as a person right um 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 um you know a totally innocent remark or something that has absolutely nothing to do with you you you know, that that's where ego gets in the way.

In recovery, they sometimes talk about ego as as as um being a conscious separation from I think that's an interesting definition. Like it's it's something that's getting in between you and whatever is happening. Actually, the 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. um you know it just it's just something that's like pushing away this because it threatens the identity or your sense of self. Yeah, it's actually quite profound.

Um I 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 on to something there. And that sense of separation, I mean, that goes really deep. Like we 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. We are inextricably inter. We're we're you are created entirely from non Ryan stuff. Yeah. Yeah. Yeah. Um and uh and yet you feel very much like Ryan.

And so, how can you not let that sense of Ryan, which is is true on some level, if you look in the mirror, you you'll see Ryan, but on some deep level is actually an illusion. How can you not let that separation [ __ ] up your decisions? Well, and here's where I I experience it quite practically, right? like the 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 but it has to resonate with other people, right? Like the the CEO is is making something of value that other people will willingly exchange time and money for, right? The politician has to be the representative of the people. Has to like the people. Has to 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 um professionally and personally and personally and personally is is by definition not about us. And so that's where ego really gets in the way of what you're you're trying to do or 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, you know, the sirens, the dangerous stuff on the path to wisdom. Uh there's another little chapter here called don't be a know-it-all.

Yeah, Epic Jetus's uh line was uh remember it is impossible to learn that which you think you already know. And 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 the irony of humility is that it actually makes you smarter. You know, we've been talking about the Oracle of Deli.

Um at some point, Athens dispatches someone to the uh to the Oracle. And 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?" uh you know uh in in the ancient world like it it it it occurred to me that that part of the function of the oracle must have been as a cooling off mechanism like uh it it's going to take them a a week or two or a month by by foot to travel like a week or two by boat or a month or two by by by foot to get there.

like it must have functioned as as the the founders supposedly said the Senate was supposed to as the the the saucer that that cools the cup. Um but but um at some point Athens dispatches uh dispatches uh dispatches uh uh a messenger to the to the oracle to ask you know is there anyone wiser than Socrates? And the answer comes back no one is wiser than Socrates. And this is all quite baffling to 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 his interest in asking questions instead of providing answers, that is in fact the source of whatever wisdom he he does possess. And so um if if we can understand that um the more we focus on what we don't know, the more we will come to know and the less we sort of reflect in glory in all that we have learned. Um the the the the better we're going to be. Didn't stop Socrates from getting himself killed.

himself killed. himself killed. It's true. Maybe that was that that was him uh him him being a little proud of himself. Have you, this is a total digression, but I just read this novel about the a set in the ancient world set in Syracuse uh called Glorious Exploits. Have you read it? Who's it by? It's by a firsttime Irish novelist whose name is Evading Me now, but we'll I will put it in the show notes. Uh my friend Zev recommended this book. It's very funny. Um, and uh, but it was it to me why it's coming to mind right now is it it gave me this feeling that listening to you gives me too, which is just a a cintillaa of a taste of what it must have been like to live at that time.

Well, the reason the reason I ask is like the best book that I read this year, by the way, talking about speaking of the speaking to the dead, uh, I I find that that often like my favorite book of the year is like never published in that year that I'm reading it. It's often like some 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. Um, but I I I read this book, The Last of the Wine by Mary Renault, which is a novel about um basically Pericle in Athens.

Uh Socrates is one of the main characters and it was like hugely popular many many years ago. And it it was the same thing when you when you it's so easy to think about these historical figures as like like you know you think of Socrates walking around Athens in 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.

Um and and then he lives through a time called the 30 tilents and then you know later he's put to death. Like he lived in this incredibly fitful uncertain chaotic like uh stressful time and you know we just 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 gonna [ __ ] it all up.

And it's like that's what they felt like. Montaigne lived through the Reformation and the Counterreformation like Counterreformation like Counterreformation like his his whole period of like retreating to his study to think about things like that wasn't a a voluntary choice. He was worried about being burned at the stake and that's why he retires from public life. life. life. So just to pick up on that, the the what you said about Socrates and the Athenians losing wars. The this book Glorious Exploits is set in um I said Syracuse um and I didn't know until I read the book that Syracuse was on Sicily.

The Athenians had invaded at this at the point in this that where this book takes place and had lost and they were keeping a bunch of the PS, the prisoners of war in the bottom of a quarry. quarry. quarry. Yes. Yes. Yes. Um and uh some locals got this mad cap idea to put on an Athenian play using the Athenian prisoners and uh hilarity ensues. Well, so so so two things related to that, right? That about how interconnected all this stuff was. That failed flawed invasion is led by Alcabites, who's Socrates's student protege, who's like your classic example of a brilliant, egotistical, brilliant, egotistical, brilliant, egotistical, narcissistic narcissistic narcissistic fool, right?

Um and uh yeah that that th those prisoners because because the Athenians get like absolutely uh decimated uh just went through they were basically like worked to death in these horrible camps. It it it's it it was uh it and they almost all died. It was brutal. Uh but I didn't know about this novel and now I'm very excited to read it. listeners should know that uh Ryan is the proprietor of a bookstore. If you find yourself in uh Austin, Texan, Austin, Texas, or the Environs, you should go check out his bookstore, which is called is called is called the Painted Porch.

Uh just to make it all full circle, that's where Zeno sets up in the Agora. It's the Stoaile or the painted porch is where he uh begins to host his philosophical discussions. Uh so that's where the name comes from. Let's keep going with some of the sirens. sirens. sirens. Yeah. Yeah. Yeah. Um this is more of a commission than omission, but but um it's uh I think worth talking about. Uh seek criticism. Problem with success is that uh the stakes become ever higher and the your access to accurate information, feedback and criticism uh is less and less.

like I I I've I've thought about this practically uh on on this very book. Um I sent in the first draft of it and my publisher was like, "Sounds good." Uh you know, I 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. It's definitely not. There is no way that it was right." And and so like I had this it's funny earlier in my career uh both out of ego and then also you know as you're sort of fighting to to 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 with feedback and then the irony is once you succeed at some level um that goes away and that's actually not a a privilege.

It's a kind of a curse. And so, you know, I ended up having to uh do quite a bit of work to get the feedback and criticism that I needed to get the book where I I think it ultimately needed to end up. And and obviously, you know, this is a minor example, but you can imagine, you know, the president doesn't get uh many people telling him that uh that that that they're they're not doing a good job. There's a a story that Gerald Ford, speaking of presidents, Gerald Ford was fond of this story about Abraham Lincoln when he was inspecting the the defenses around um around uh you know the Union lines.

He he's obviously so tall uh that a that a Confederate uh uh sharpshooter uh takes a shot at Lincoln and just barely misses. And a and a and a Union soldier, you know, petrified, he 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. Uh and and that that is uh you know not just it's let's say less uh a risk in a democracy where you have freedom of speech but you can imagine not many people uh are able to tell Vladimir Putin that he's [ __ ] up this Ukraine thing and that he made a colossal mistake and needs to back out, right?

like dictators uh you know presidents uh celebrities you know CEOs etc um 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 a board of adviserss if if you don't cultivate that you're uh you're not just going to stop getting better you're going to start getting worse. See it in Kim Jong-un's fashion choices. Um, Um, Um, yeah.

And this is why you read the comments on your on your videos, right? Thank you for putting my dumb behavior into the most positive light. Um, well, no, I I will say just one thing like 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 so that that is that is the art of it. Um, it's it's not what everyone thinks, but but how do you get it from the right people in the right way?

Part three in the book. So, we we we talked about the the fir we talked about the first two parts of the book, the training ground and then the sirens, the the stuff you should avoid on on route hopefully to wisdom. Uh, part three uh of the book um uh is called the apotheiois or the the touching of the divine. What does that mean and what's the relationship to wisdom? Yeah. So, what I ended up kind of doing in in each of the four books in this series is is you're kind of like there's like your beginner level, there's your intermediate level, and then there's there's your sort of advanced level.

There's some kind of transcendent level of each of these virtues, right? There's 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 who's willing to go to jail for an idea or or 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 there's the uh sort of foolishness and error that we try to to to avoid.

And then there is some level of kind of transcendent wisdom like like Gandhi's education is fascinating to me right uh he he has some ordinary schooling in in India then he goes to London for law school which is where he really becomes a a sort of a a critical thinker uh and and 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 in the law, right?

There's some other level of education and learning and insight and understanding that that he learns first in South Africa and both as a practicing lawyer and then as a fledgling activist and then later when he goes back to India. um you know so so my my point in the third part of the book is just like the the ideal like the the highest level of of of wisdom and and I talk a lot about Lincoln because Lincoln's fascinating in this regard you know he sort of mirrors all these different levels you know his 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 that he becomes the sort of Abraham Lincoln, the great man of history.

And and that education is what I'm 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 that you have a lot of recommendations, but let me throw a couple of of them at you and get you to hold forth. Um, one of them you've got a a chap a subchapter here or a chapter here under this um under this third part of the book called embrace the mystery.

What do you mean by that? Yeah, you know, uh before you know stuff, you think the world is very simple and then uh you study and you learn and it becomes a little bit more complex and then uh you study it more and more and it becomes simple again and then you study more and more and it becomes complex again. I I guess what I'm talking about and I talk about this a lot in in in part three of the book is the complexity and contradiction, the ineffibility of things like even the idea of wisdom.

Like I think I've gotten better at going like I actually don't know how to define wisdom exactly. I don't think and and perhaps the definition of it is actually not the important thing. So I just wanted to spend some time in the book, you know, talking about that ineffibility, that contradiction, that complexity. And and I think this is why often some of the the wisest people love fiction and poetry and the arts. There in a way almost a poem comes better to encapsulating the truth of something than you know uh a textbook can.

even though they're 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 it's very hard to achieve any kind of real or lasting wisdom uh without paying for it. You know, um as the the ancient said, we suffer into truth. Uh that was Escilis. Um, which by the way, uh, Robert, uh, Robert F. Kennedy, the first one, famously quotes this line to a a rockous crowd in Indianapolis the night that they all simultaneously learned that Martin Luther King Jr.

has been killed. Um he he was speaking of his own painful lessons from his brother's death. You know that you want to be angry, you want to rage, and then he just, you know, sort of where does violence in this way take you? And he he was just talking about about about the these these lessons that we have learned painfully over the our experience as a as a human race and then also individually in our own lives. And so, you know, 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, you know, the insight and the understanding and you can suffer and screw up and not take wisdom out of it. Uh, too, I guess. Uh, so that's kind of the choice that you have. you have. you have. 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.

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Um but moving along, there's another chapter here I want to hear you talk about uh which is called Grasp the Essence. The story I I tell in that chapter is about Lincoln writing the Gettysburg Address, which is word for word, poundforpound, word, poundforpound, word, poundforpound, one of the greatest things ever written in the English language and then also most impactful things ever written in the English language. And 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 he had experienced personally and then and then witnessed as he toured these battlefields and read the casualty counts.

You know what Lincoln is doing there is articulating fundamentally what America is, should be, and could be. And you know the fact that he does it in what like 260 some odd words is all the more remarkable when you when you learn and I didn't learn this in school that the that that he was not the main speaker of the day. Um Edward Everett was widely considered America's greatest ortor at that time and he spoke for two hours before Lincoln. the Gettysburg address was shorter than the than the invocation, the prayer that kicked off the events there at Gettysburg.

And so, uh, but but Everett, uh, tells Lincoln that either that that evening or the next day that that he came closer to expressing the essence of what what needed to be expressed in in two minutes than than Everett had done in in two hours. And and you know that that that was not a magic trick. That was uh an intellectual and personal and spiritual the culmination of an intellectual and spiritual journey that that that had gone back to, you know, Lincoln's earliest days. I'm going to expose my ignorance here because I 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 you're totally right. It it is it is uh it is in the second inaugural. But just to go to our point about expressing the essence, the idea if you've been to the Lincoln Memorial that his two greatest uh pieces of writing and 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 we think of him as a politician giving speeches, but these were meticulously crafted documents that oftentimes he just read.

He fished a a scrap of paper out of his pocket and read the Gettysburg address. Um but but the fact that those two speeches could fi could could fit on I think three tablets, you know, in the Lincoln Memorial is just a a magnificent statement of brevity and distillation. It's incred. 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 and I 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 that every sentence and phrase in the second inaugural has become a book title.

Um and you go yeah probably because like every phrase in it is is uh is perfect. Couple more questions for you before I let you go. There's a chapter here right at the end called pass the final test. Yeah, Yeah, Yeah, Cicero said that uh 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 So of all the things that I'm I'm writing about in the book, this is obviously the one I have the least experience in.

Uh and and I I have no idea whether I'm I'm right or not, but if if the dead can can teach us anything, I'm just trying to sort of channel what they have have spoken to us about. But the the idea being that that that all philosophy is is aimed at at at both living well and then ultimately dying well. I I wanted to talk about sort of some of the lessons that that death teaches us and then sort of how we orient ourselves. I I open the book with Montaigne and I end it with Montaigne.

Um he he he had written that um and he loved that line from Cicero, but he had written that that he he hopes death will find him planting cabbages. And what he meant was that he hoped death would would just find him in the course of a of an ordinary regular moment of life that he was living well. Um and I I think there's something kind of zen about that. It's kind of the perfect expression. Um but you know death is everpresent. The Stoics want us to remember that death isn't a thing that happens at the end.

That in fact death is happening now. So Senica would would say that actually I do have some familiarity with death because I've already died you know nearly 40 years. uh and and that 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, you know, a a fundamental piece of wisdom that that that can be lifechanging.

lifechanging. lifechanging. There's a final phrase I want to ask you about. Thou mayest. Oo, yes. Um, this is uh Steinbeck. Uh, have you read East of Eden? A long time ago. It is it is worth rereading because it is an incredible book. I I reread it early in the pandemic and um just a beautiful, magnificent kind of epic novel, which by the way has a lot of of stoicism in it. Lee, the um the the Chinese uh servant to the to the main family is is this philosopher who's always quoting Marcus Aurelius to the two boys.

Um in any case, uh Steinbeck writes this writes this writes this uh book about writing uh East of Eden and it's called Letters uh letters from a novel, I think. Um anyways he's talking to his editor and he says basically the the the fundamental premise of the book uh and he thinks this is his insight into the ancient traditions too is that um the the the commandments are not thou shalt not as in like you absolutely are not allowed to do these things but the but that thou mayest like that that you you have the choice not to and that who we are is ultimately about making this choice that that that free will is the essential part of the Christian tradition, part of the 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. Uh that there's a punishment uh for for for doing or not doing the right thing. He's saying that it's a choice and that this choice is the the thing uh that that that matters that says who we are. And and so I I I begin and end the series uh calling back to that story about the choice of Hercules which was so informative for Socrates and um a and then later for Zeno that the choice of Hercules being um this very idea that Hercules comes to the crossroads, the choice between virtue and vice and and the the the the path of vice he is told will be easy and straightforward and wonderful and pleasurable and all of these things and that and that the path to virtue will be hard and difficult and may not pay off and which one is he going to choose.

Um 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 uh crazy thing I was uh surprised to learn. Um, uh, John Adams thought that the choice of Hercules should be what's on the seal of the United States, United States, United States, not the the eagle. He thought the choice of Hercules was fundamentally what a country built around liberty was saying. That we're not 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 is is who you are. It's always great to talk to you. I'm gonna ask the two questions I always ask at the end of uh the show habitually. The first is, is there anything you were hoping that we would get to that we didn't get to? No, this is this is amazing. I I always love talking with you. I never have a good I I never have a good answer to that question. Also, like do you ever do people ever ask you like is there a question you wish I asked?

And I go I no I don't I don't I don't sit around waiting for for questions. That's that's uh Anyway, so now 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., etc. Please just step into the plug zone. Oh yeah. Well, well, ego wise, this one's much easier for me. Uh um so so the Stoic 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 uh anywhere. And then uh I'm probably best known uh for my book, The Daily Stoic. And then uh daily stoic.com, which is a a stoic inspired email every day. And then podcast and uh YouTube stuff. So that you can find uh daily stoic pretty much everywhere you would go. Ryan, thanks again for making time for this awesome. this awesome. this awesome. This is amazing. All right, hope to see you soon.