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The James Altucher Show: Episode Summary
Episode Title
Wisdom Takes Work: Ryan Holiday on What AI Can’t Teach You
Episode Overview In this episode, James Altucher engages in a profound discussion with bestselling author and Stoic philosopher Ryan Holiday about his latest book, *Wisdom Takes Work*. This book marks the fourth in a series exploring Stoic virtues, focusing on the nature of wisdom as a continuous practice rather than a static trait.
Key Themes Discussed
The Nature of Wisdom
- Wisdom as a Practice: Wisdom is described not as something one possesses but as a practice involving humility, curiosity, and experiential learning.
- Asking Better Questions: The emphasis is placed on the importance of asking insightful questions and learning from experiences.
The Role of AI
- Limits of AI: Ryan argues that while AI excels in knowledge acquisition, it lacks the capacity for wisdom. AI can find and summarize facts but cannot engage in deeper understanding or moral judgment.
- Human Judgment: AI's inability to ask the right questions or acknowledge its limitations stands in contrast to the human capacity for discernment and critical thinking.
Experiential Learning
- Learning Through Doing: The conversation stresses the importance of experiential learning, emphasizing that wisdom often arises from engaging fully with challenges and life experiences.
- Historical Context: Ryan shares anecdotes from history and Stoicism to illustrate the timelessness of wisdom.
Practical Insights for Cultivating Wisdom
- Engage with History: Reading historical texts and biographies to understand different perspectives.
- Embrace Experience and Pain: Recognizing that growth often comes from facing adversity and stepping out of comfort zones.
- Seek Mentorship: Finding mentors who can guide and challenge one's thinking.
- Practice Open-Mindedness: Being willing to adapt and learn from new generations and ideas.
Timestamped Highlights
- [00:00] Introduction to the conversation about wisdom versus knowledge.
- [02:54] James shares his personal struggle with recognizing true wisdom.
- [05:37] Discussion on AI’s limitations in approaching wisdom.
- [08:57] The distinction between knowledge and wisdom.
- [16:10] The significance of humility in wisdom.
- [31:00] Debating if wisdom is innate or learned over time.
- [42:25] Practical ways to cultivate wisdom through reading, travel, and mentorship.
Conclusion Ryan Holiday's insights on wisdom as an ongoing practice resonate with the idea that true wisdom requires effort, humility, and a willingness to learn from both successes and failures. The episode emphasizes the importance of engaging with the world to foster wisdom, particularly in an age dominated by technology and rapid information dissemination.
Additional Resources
- Book: [Wisdom Takes Work by Ryan Holiday](https://www.amazon.com/gp/product/0593191730)
- Other works by Ryan Holiday on Stoic virtues:
- [Courage Is Calling](https://www.amazon.com/Courage-Calling-Fortune-Favors-Brave/dp/0593191676)
- [Discipline Is Destiny](https://www.amazon.com/Discipline-Destiny-Power-Self-Control-Virtues/dp/0593191692/)
- [Right Thing, Right Now](https://www.amazon.com/Right-Thing-Now-Values-Character/dp/0593191714/)
This episode serves as a reminder that cultivating wisdom is a journey that involves continuous learning, questioning, and personal growth.
Written by AI. May contain mistakes. Listen to the episode to check what was said.
Transcript
Automatic transcript. May contain errors.0:00Being an entrepreneur is a 24-7 job. And when you're hiring, you need a partner that works as hard as you do. That hiring partner is LinkedIn Jobs. When you clock out, LinkedIn clocks in. LinkedIn makes it easy to post your job for free, share with your network, get qualified candidates that you can manage all in one place. For one thing, you can post a job. LinkedIn's new feature can help you write job descriptions and then quickly get your job in front of the right people. You get qualified candidates. At the end of the day, the most important thing to your business is the quality of the candidates.
0:30And with LinkedIn, of course, you can feel confident that you're getting the best. Based on LinkedIn data, 72 % of small and medium businesses say using LinkedIn helps them find high-quality candidates. Find out why more than 2.5 million small businesses use LinkedIn for hiring today. Find your next great hire on LinkedIn. Post your job for free at linkedin.com slash altature. That's linkedin.com slash altature to post your job for free. Terms and conditions apply. What can 160 years of experience teach you about the future? When it comes to protecting what matters, Pacific Life provides life insurance, retirement income, and employee benefits for people and businesses building a more confident tomorrow.
1:15Strategies rooted in strength and backed by experience. Ask a financial professional how Pacific Life can help you today. Pacific Life Insurance Company, Omaha, Nebraska, and in New York. Pacific Life and Annuity, Phoenix, Arizona. Today on the James Altucher Show. I've worked in the AI space for 35 years in one way or the other. So I'm a huge proponent. But this is the one area where AI is a tool and not the leader, which is wisdom. AI is really good at knowledge. It's really good at helping you find knowledge. It can even give you knowledge. But it certainly can't give you wisdom. And doing something with knowledge as opposed to just memorizing it is the difference between accumulating facts, which I'll say is the AI world, and wisdom, which is the domain of humans.
2:06All of the virtues have to be seen as verbs and not nouns. Like, you don't have courage. You have to act with courage. Discipline is a thing that you do. Justice is a thing that you give, not a thing that you get. This isn't your average business podcast, and he's not your average host. This is the James Altucher Show.
2:38wisdom takes work this is the fourth book by ryan holliday about the various virtues of stoicism and wisdom is the most important of these virtues the other ones were he wrote books about courage temperance justice these were all great podcasts great books and i love talking to ryan about wisdom because i feel like so often i have felt that i've had wisdom and then realize oh no i'm the least wise person i know and so it was really interesting to read you know ryan's got a great style he has all these stories from history and his own life about wisdom that he that he puts in these books and also stories, of course, about the Stoics and how it relates to Stoicism, this ancient philosophy that really fits modern times in a very unique way.
3:30Always a pleasure to talk to Ryan about things above and beyond the book, like how we see wisdom in our lives and how to practice it and unexpected places to find it. So once again, I believe Ryan Holiday has probably been on the podcast more than anyone else, but each time it's a totally unique conversation, which I learned so much from. Hopefully you will as well. Here is Wisdom Takes Work with Ryan Holiday.
4:03It's funny, my agent and my editor practically dropped me over it. Like they did not want me to do this. But you know, you can't let these people dictate what you think is an important project. See, I think if you had done a physical book with Charlotte Woman, I would definitely know that it exists. and I had just zero idea that this happened. But that happens more and more. There's huge shows I've never even heard of. Yeah, I think content in general has become so fragmented. And like, you remember like 10, 15 years ago, if you made great content, everybody would know about it. Like you would be on Twitter, you would get a following on Twitter, people would read your content.
4:42But now if you make great content, usually it's very niche driven. Your niche, your subculture might know about it, but nobody else will know about it. Well, the interesting thing is, yeah, it might be much less popular, but the economics of it might be much better. There are sub-stacks that are actually providing decent livings for people that I've never heard of. I never see any of their writing because it doesn't get spread around, and yet they might actually be financially thriving in a way that they weren't 10 or 15 years ago. So it's like the economics are better, but their reach is smaller.
5:18Well, this is an interesting thing because, and this relates to your book, this relates to the idea of wisdom, which is that I don't think, and by the way, I'm the biggest proponent of AI. I love AI. I think people are only just now seeing the potential of it. I've worked in the AI space for 35 years in one way or the other. So I'm a huge proponent, but this is the one area where AI is a tool and not the leader, which is wisdom. AI can only learn from the past. And it's great at summarizing and it's great at communicating the past. And it's great at coming up with new ways of presenting things from the past.
5:58But it's not going to operate from first principles and come up with ideas that are hard to define as wisdom. Wisdom is a hard metric to say, yes, this is wisdom, this isn't wisdom. And I think when there's hard metrics, AI has problems. AI is really good at knowledge. It's really good at helping you find knowledge. It can even give you knowledge, but it certainly can't give you wisdom. What I think is really interesting about AI is obviously I use it as well. I think anyone that sort of instinctively rejects new tools or technologies without actually having messed with them, that's a form of anti-wisdom.
6:34Like, oh no, I know the best way to do things. I don't even want to try. I hate that attitude. But I do find that if I don't actually, if I don't know what I'm looking for and I don't have a good sense of like what, like a ballpark sense of right and wrong, not morally, but there's like correct and incorrect, AI is a really dangerous tool to mess with or a really unreliable tool to mess with. But if I'm trying to track something down that I know exists, it can be extremely helpful. Does that make sense? Like if I've read a book and there's something in that book that I can't quite remember, but I need help nailing down AI is great.
7:14But if I actually asked it to like teach me what's in a book, I find that it does a very poor job. Yeah, it does a very poor job. And why and why is that? Why are why are the summaries that AI does basically at a first grade level? And I mean that very seriously, like there's the Fisher Kincaid score, which tells you, given a piece of writing, what grade level it is. And kind of the ideal is fifth or sixth grade, actually. Ernest Hemingway's Old Man and the Sea was at a fifth grade or sixth grade level. And then you understand it. 12th grade level's too hard usually for people to understand. But AI does a first grade level job of explanation, and that's never good enough.
7:50Well, look, the facts of the Old Man and the Sea are not what makes it a powerful and important piece of literature, right? It's stylistically, obviously, brilliant as well. But it's the showing, not the telling, that makes literature what it is. And so, you know, a summary of a book of philosophy or a summary of a historical era is not really the point. It's immersing yourself in it for an extended period of time. It's the actual coming to know it on a deeper and more profound level that is the sort of whole point. There's a story I tell actually in the beginning of the wisdom book that I think sort of illustrates this point.
8:33And I think it goes to the idea of how timeless this is. You know, Seneca tells this story 2 ,000 years ago about this wealthy Roman who wants to seem really smart. So he purchases these really smart slaves. Each one's like an expert in a different Greek writer or poet. They just whisper in his ears all the things that he needs to know to sound smart at a party. And then one of the people comes up to him and says, you you know, you're so smart. Have you thought about becoming a wrestler? This is a guy who sees through the act that the guy is trying to pull off. The guy goes, why would I be a wrestler?
9:05You know, I'm an old man. And he says, yeah, but your slaves are still young. His point is you really can't have anyone do this for you. The knowledge of that poetry or that literature, it's not the recall that's important. It's not the memorization that's important. It's actually the process of engaging with it over a long period of time. That's like the whole point. And so when I say wisdom takes work, I really do actually mean that like the work is the important part and the wisdom is the byproduct of that work. Like I'm doing this right now. Like I'm writing a book right now and I'm working with a research assistant, but I'm finding that I still have to do the vast majority of the reading and the thinking and the spending time with the materials or else I can't just read summaries from someone else.
9:55I don't know and feel it deeply enough to really do the work. Yeah, and I feel like this is a theme throughout the book that the verb do is really important, to do something. Like when you talk about this even early on with Montaigne, how so many of his peers in school would just read and then be tested on the knowledge and have perfect answers, but you could be asked questions. how would you use this knowledge? And doing something with knowledge as opposed to just memorizing it is the difference between accumulating facts, which I'll say is the AI world, and wisdom, which is the domain of humans.
10:38Humans will have wisdom. And just to relate this back to the Substack aspect, people are making money now by basically providing subscription access to their wisdom in certain niches, wisdom that the AI cannot get, which is why I'm willing to pay for someone's knowledge, usually earned through experience, or either experience or passion. So passion, when you said immersion, it's another way of saying passion. Someone has to be passionate enough to be immersed in the crevices and the nuances of a subculture. That's exactly right. I think all the virtues, this is a point that goes back to Aristotle, all of the virtues have to be seen as verbs and not nouns.
11:18You don't have courage. You Discipline is a thing that you do. Justice is a thing that you give, not a thing that you get, right? And then wisdom too, it's not this like, oh, you're old, therefore you have wisdom, right? Like wisdom is a methodology, a process. The byproduct is that you have perspective and you kind of have a sense of how things go. I'll give you an example on this book I'm working on now. What's the topic of the book? I'm writing a biography of Admiral Stockdale right now. And so one of the sections, I needed to talk about how many graduates of the Naval Academy had died in the Second World War.
11:58And so I asked Chachi Biti, like whatever the latest one was, this was a couple months ago. But I said, you know, how many graduates of the Naval Academy died in World War II? And it goes, okay, let me tell you and I'll show you my work. And it says, okay, so the death rate of service members from the Academy during the Second World War was 7%. And then it said roughly 7 ,500 people graduated from the academy between 1940 and 1945. Therefore, you know, 7 ,500 times 7%, it was like 400 and something. And I was like, you know, look, I appreciate you showing me your work, but your work is bullshit.
12:35Like, you just multiplied two totally unrelated variables. Right. The 7 % of service members who died in the war has no bearing on the fact that 7 ,500 graduates graduated between 1940 and 1945. In fact, I think like 70 classes, and this is another statistic I already know, something like 70 classes had served in the war in some capacity. Like it was a huge number. 70 is too big. It was a very large number, right? It's at least going to be 30 or 40. Yeah, exactly. It was an extremely large number, right? A bunch of people were born in the 1800s, served in World War II, right? So I knew these numbers were, you know, I knew this math was totally wrong.
13:19By the way, I also didn't ask it to estimate. I told it to tell me exactly how many, because this is a statistic. And not only do I know it's a statistic, it knows it's a statistic, or it couldn't have told me 7 % of service members from the academy had died in the war. So it actually took a number that if it traced it back, it would have found the actual number. And then it did this weird calculation, right? I know this is a fact because this would be in the records of the VA, right? Like the Department of Defense would have records of how many people. And then you want to know how I solved this problem?
13:56It's pretty not multi-billion dollar data centers and all this advanced computing. There's a plaque at the Naval Academy that lists every person from the academy who died in the war. And I just counted the names on the plaque, right? Like I found a picture of the plaque and then I counted the names. And so it's not just like sometimes it's bad at solving things. Like sometimes it's so smart. And I think this is true. Sometimes it's sort of dispensation to calculate things or use this computing power it has actually overshoots and misses somewhat lower tech solutions to straightforward problems.
14:42Yeah, and it's interesting because I feel like there's two categories of people around the so-called wisdom or knowledge of AI, which is there's the category that says AI is bad. It's ultimately going to veer in this evil direction. It's going to take all the jobs. It's not going to give us good guidance and we're going to rely too much on it. So there's that category. Then there's the category of people who 100 % believe AI is going to solve everything. And neither category is correct. Just like the computer is a tool. Yes, the computer can do things that humans can never, ever do and will never be able to do, but it's just a tool.
15:17It's not going to run the world. We're going to run the world using them, but in this case, you had to use your own common sense to do something that the AI would never do. And you mentioned throughout the book too, there's various, it's hard to define wisdom because wisdom's almost like a recursive definition. Like, you know, wisdom is for people who say they're not wise. is the sort of definition of wisdom. Going back to Socrates, yeah. You know, you say that, you know, basically you kind of have to admit that you don't know everything in order to have the opportunity to know everything and in order to have the opportunity to be wise.
15:53And I think that's a theme throughout the book as well. Well, and look, it just - And AI thinks it knows everything. It just doesn't even know to not know everything. I was just going to say, that's actually where AI is particularly bad is obviously I've used it to do lots of different queries over the last couple of years, it has never once said it doesn't know the answer. It's given me a lot of really shitty answers. It has never once given me the answer. And almost never does it ask for more information that would help it get better answers, right? So this is ironically a very human thing, which is our sense of knowing or our confidence that we can figure stuff out actually makes things much harder for us.
16:35The ability to say, I don't know, or that I'm confused, or to come back and request better specifications or more details or some context actually helps us do what we do. The thing about wisdom is that I think it's hard exactly to define. It's sort of a, you know it when you see it. It tends to be obvious in other people. It shouldn't be so obvious in yourself. Like if you confidently think you have wisdom, that's alarming. and then there is no one who is so wise that they can't learn more. That is, I think, something we should all be able to agree on. Even the wisest person has wisdom left for them to learn even if that wisdom is just knowing more about themselves, right?
17:21Because how many really smart, even wise people would we say are truly self-aware? Not many. Yeah. And look, not anybody in every situation is self-aware. Basically, all people are not self-aware in some situations. And I think that's your point, is that almost a prerequisite to learning something new is being able to admit, oh, I'm not smart or knowledgeable or wise in this area. And one thing I've noticed, how old are your kids right now? My oldest is about to turn nine, and then my youngest is six. by the way that's the best ages from like six to 12 are like by far the best ages but i'm also realizing that above 20 starts to get to be the best ages again sure and my kids are in their 20s and sometimes i find myself arguing in the mood about things and then they argue back and then i'm defending and and but at some point always in these arguments i realize you know i actually know jack shit about what i'm talking about right now like and that's only been something that's happened recently, maybe because my kids are of age where they can argue with me like this.
18:28But like so many times I realized, oh, I'm arguing about something I really don't know anything at all about. I don't even know if the facts I'm saying are actual facts. I'm not saying this is wisdom or not, but I think becoming aware of when you don't know something is become, this is only true for me in like the last five years. This is like a key aspect to my own growth. Yeah. Well, my favorite line from Epictetus is it's impossible to learn that which you think you already know. So ego is this sort of real antidote to wisdom because it prevents us from knowing things. But yeah, I think weirdly though, the more you know, the less attached you should become to the idea that you know, and the more you're comfortable with letting other people think they know.
19:13Like there's this great Tom Segura bit that I think about all the time. And he said, you know, that since he became a parent, he just doesn't have time to argue with people anymore. So someone comes up and tells him stuff. He's like, sure, you're right. You know, like, and to me, that's actually, you know, someone might go, oh, that person's weak willed or stupid that they're just like accepting all these things that other people tell them. I think there's actually quite a bit of wisdom in that because you realize what's actually valuable is your time and your peace of mind. And so you're much less insistent in having stupid fights with people about things that don't matter and that you don't care about.
19:49And again, this This is actually something that Stokes talk about. That one of the signs of approaching wisdom is that you just get in fewer arguments. Not because you're right all the time, but you just don't give a shit about being right. That reminds me of all these memes on the internet. It's a picture of a guy driving home from a date and he's thinking that date didn't go well at all, but at least now she knows that rent control is evil. Yes. Or just those videos of dudes forcefully explaining things to women. And the woman is not just physically threatened, but so profoundly uninterested in what the person has to say, but he needs to say it.
20:30I think that is, as you get older and you get a little bit more confident in yourself, you just cringe at that because you know all the times you have been that person who just needed somebody else. It's not that you needed them to know something. It's that you needed them to know that you knew something. And that is, you know, about as foolish as it gets. Well, how much of wisdom then do you think is a function of age? Because, you know, obviously we have much more experience as we get older and we're able to process that versus younger people. But even the brain, you know, Arthur Brooks points is how the brain changes so that your raw ability to just calculate is gone, but you have this wisdom, supposedly.
21:15Hopefully. Yeah, hopefully that's the thing. Yeah. I mean, look, I think there's a lot of stupid old people too. So I think it is necessary, but not sufficient for wisdom, right? There's a Churchill line that I think about that I think captures a lot of people's lives, young and old, but he was talking about Chamberlain and he said, whenever Chamberlain stumbled over the truth, he picked himself up and carried on as if nothing had happened. And I think a lot of people go through life that way, which is that they have experiences. They are being exposed to the things that time and age expose you to.
21:55But because they think they already know, or because they're too self-conscious, or because they're too dense, or whatever it is, they don't learn the lesson. They just carry on. Then they learn the lesson. They get taught the lesson again and again and again and again. And so I think there are some things that only time and experience can teach you. But just because time and experience are saying them to you doesn't mean that you have to hear them. And you point out in the book the importance of having an open mind. And I think all of us feel like we're open-minded. I feel like a symptom of non-wisdom is when you're trying desperately to hold on to some structure or idea you believed in that you just don't want to let go of.
22:37Like, so you give the example of Louis Agassi's who's arguing against Darwin, and he just won't accept. There's really no facts in the argument. Like, it's very hard to prove these ideas in evolution. But Louis Agassiz is so kind of genius guy, right? He's at Harvard, you know, presumably had many accolades in his youth for being smart and wise or whatever. But ultimately, he succumbs to this inability to accept change and Darwin's new ideas. I think you see this a lot with really smart academics. is that it's not even just that like, hey, I'm set in my ways. It's like there's an element of professional jealousy or grievance.
23:18So I think a big part of it is it's like, wait, no, no, I'm the smartest biologist and naturalist in the world. How can this guy across the Atlantic have upended everything that I was supposed to matter about? So I think psychoanalyzing him a little bit, I think part of it was just resistance to ceding the top of the field to someone else or to a new school of thought. And I think we see this quite often where it's a lowercase c conservatism. So not political, but just in the sense of like, well, I just don't want, I don't want to have to change my worldview in which I'm no longer the preeminent or the dominant or the main guy.
24:02And so I'm not only not going to accept it, I'm going to actively resist it because there's like an energy and an excitement to being sort of the dissenter against it. Yeah. And also, like you say, this inability to seed that a next generation is coming. And I think a key part of wisdom must be able to take on a new role in your own life where you enjoy to see the next generation surpass you. Like it's not just like accepting it, but enjoying it and learning from it. Like again, being open to learning new things, even after everyone's already told you you're the smartest in the world. Yeah. I was actually talking to this woman.
24:44I know she's 95 and I was complimenting her that she, it's not that she was still young and then sense that she was active, but she was like still interested in like new things that were happening. You know, like she's not just watching the news all day being angry. She was aware of what was happening culturally and curious about it, right? And I think that's wisdom. Not needing for everything to stay the same and for your role in them to stay the same. There's kind of a fragility there that I think is quite understandable. I mean, it would be hard at 90 years old or 80 years old or even 50 years old if you were used to sort of driving things to have to accept that the game has changed or the situation has changed or the world has changed.
25:27and the way that it once was is not how it is anymore, that can be really challenging for people. I mean, maybe accepting change is a key aspect of wisdom. A lot of times you get into something, you get into a situation and you think it must be this way always. Like whether it's a marriage or a business partnership, a friendship or some, I think about this, this happens a lot in business. Like, okay, we're doing this, It's got to work or else. But being able to be flexible and change, transform your ideas, transform your partnerships, and doing it in a way that's congenial to everybody and doesn't involve lawsuits and stuff.
26:08I think this is a key aspect of wisdom too, like just personal relationships. Totally. I mean, look, somebody came of age when the sort of business culture was X. Well, now business culture is Y. you know and your insistence on well that's not the way we used to do it is kind of pathetic i think the irony that the stoics would point out is like whatever the status quo that you're trying to preserve is it hasn't always been that way right like if you study history even a little bit you realize this thing that we're assuming is normal actually was transgressive and new not very long ago. And there was something transgressive and new behind that and transgressive and new behind that.
26:52The thing that we're trying to protect from change was itself a product of change not that long ago. And so, yeah, I think wisdom understands that larger perspective. It subtracts your identity out of it. So it just says, hey, these are the ways that things come in and none of them are good or bad. They're just different environments that you have to figure out how to adjust and thrive in. Some might be preferable to certain strengths or certain personality types or advantages, but you figure it out. And that's what life is about. Take a quick break. If you like this episode, I'd really, really appreciate it.
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27:38It means so much to me. Please share it with your friends and subscribe to the podcast. Email me at Alcantra at gmail.com and tell me why you subscribed. Thanks.
27:55So I have started many companies. Some did well, some did not do as well. I've also run many companies. I've advised many companies and I've been involved in all aspects of the hiring process, whether sometimes I would have to hire a CEO, but sometimes software developers, sometimes designers, sometimes head of sales or business development. I've been involved in basically every aspect of running a business and hiring is maybe the most important thing you could do when you start a business. So I'm going to give you one piece of advice and it's related to what I'm talking about here. You know, I used to think I was frugal because I would try to find employees as cheaply as possible.
28:34You know, someone young, just starting out, whatever. But what I've learned is you do so much better as a business finding the best person in your field. If you want a head of sales, find the best head of sales. If you want a software developer, hire the best software developer. It ultimately will save you money, but it'll also save you so much time, so much aggravation, so much anxiety. These are all things you need to preserve. It's really important to hire correctly. When you're running a business, your mind is on your business 24 hours a day, seven days a week. That's the problem with being an entrepreneur is you never leave the work at the office.
29:10So when you're hiring, you need a partner that works just as hard as you do. I have found that a great hiring partner is LinkedIn jobs. When you clock out, LinkedIn clocks in. LinkedIn makes it easy to post your job for free, share with your network, get qualified candidates that you can manage all in one place. And I find this is such a great platform to find people for your job because millions of people are on LinkedIn, millions of qualified people. Here's how it works. You post your job. LinkedIn's new feature helps you write job descriptions and then quickly get your job in front of the right people.
29:43Post your job for free or you pay to promote it. Promoted jobs get three times more qualified candidates. You get qualified candidates. At the end of the day, this is the most important thing to your business is the quality of those candidates. Based on LinkedIn data, 72 % of small and medium businesses using LinkedIn say that LinkedIn helps them find high quality candidates. That's good information. You share with your network. So when you're on LinkedIn, your whole business network knows you're hiring. So find out now why more than 2.5 million small businesses use LinkedIn for hiring today. Find your next great hire on LinkedIn.
30:17You can post your job for free at linkedin.com slash altature. That's linkedin.com slash altature to post your job for free. Terms and conditions apply.
30:55and then quickly get your job in front of the right people. You get qualified candidates at the end of the day. The most important thing to your business is the quality of the candidates. And with LinkedIn, of course, you can feel confident that you're getting the best. Based on LinkedIn data, 72 % of small and medium businesses say using LinkedIn helps them find high quality candidates. Find out why more than 2.5 million small businesses use LinkedIn for hiring today. Find your next great hire on LinkedIn. post your job for free at linkedin.com slash altature that's linkedin.com slash altature to post your job for free terms and conditions apply i wonder how much wisdom is a talent in the sense that like so i was once talking to eric adams who for better for worse became mayor of new york city and look whether or not he did a good job or a bad job who knows there's been a lot of good mayors of new york and a lot of bad mayors and he saw new york through a difficult time obviously now he's going to be gone this is before he was mayor i was having this conversation with him he was telling me how when he was like 12 or 13 i forget the exact age 13 14 he and his brother got severely beaten by the police and probably you know the implication was some it was there was some racial issue to it and they were both around the same age he and his brother but they both reacted very differently his brother went off to whatever he didn't describe specifically, but up to no good.
32:20And Eric went on to become a very successful leader of Brooklyn. He became also successful. He became a policeman afterwards and became an advocate for getting rid of corruption in the police. So he was very much not liked in the police because he was policeman against all the corruption. Then he became a very successful leader of Brooklyn, then mayor of New York. And how does one person, same background, same upbringing, similar genes. One person goes one way after a horrific event and another person goes another way. And I now argue in your book, Abraham Lincoln, you talk about in this book and many other books, he comes out of the worst conditions.
32:57Many people come out not Abraham Lincoln and he comes out Abraham Lincoln. What's the difference? Well, I think that's a great question is what lesson are you going to learn from this? Right. And I was just thinking about Lincoln, as you said this, there's a version when life kicks the shit out of you, when you come from nothing, it's hard. You're having to fight to survive. The world is indifferent to you. There's a version of Abraham Lincoln's life where he becomes a self-made lawyer, and then he owns a bunch of slaves who work his plantation, and that's the source of his wealth and success.
33:35One of the reasons he was so sympathetic to slavery, he said, was that he had grown up a slave. Like his father had worked him in the fields and beaten him and seen him as an extension of himself. And so you could just as easily, though, see not taking empathy out of that, but as a this is how the world works, right? Somebody, the person who is hazing you at your new job or the school you just started at almost certainly was hazed, right? And so that's often how cycles go. And so the question is like, what lesson are you going to take from this experience, the right one or the wrong one? And I do think oftentimes there is a right one and a wrong one.
34:16And yeah, maybe the sort of swing vote there is wisdom. But then how do you develop it that young? Like, that was why I'm asking, is it a talent to be wise? Well, I think it's a talent. I often think it's a result of the influences that you have, right? And I think one of the reasons that, like, look, maybe you have perfect parents and you're surrounded by all the right people who are able to inject right at the right moment that little bit of wisdom or guidance that you need that helps you go the right way instead of the wrong way. Hopefully you're lucky and that's who you were born with, right?
34:52But if you weren't, now it's kind of a roll of the dice. And I think what happens for someone like Lincoln is he has a bunch of parents other than his father, right? And that is the books that he was eagerly digesting. And people knew that if there was a book within a two-day walk of the Lincoln cabin, Lincoln was going to come and get it and read it. We can trace many of the beliefs that he had down not just to books generally, but to these specific kind of school books that were called readers back then And it would kind of just be like a greatest hits book of quotes and passages from poetry and stories from history.
35:34Like a bunch of Lincoln's beliefs can be traced back to like very specific books that we know he read as a kid in his log cabin. And so, I mean, I think obviously I learned some stuff from my parents. But one of the reasons that I think I went the right way when different juncture points in my life is that I'd been exposed to these great ideas in books, like some of the wisest men and women that had ever lived, some of the most impressive people that ever lived. I was able to access their wisdom and perspective at a very early age. And so when I had experiences or pivot points in my life, I wasn't just trusting my own gut and I wasn't just relying on my dad or my mom's advice, but I was able to think about what Lincoln had done and all these other people.
36:23That is really what the power of books allow us to do, to have more than one life of experience to draw from. So now, and I don't know what the stats are, if people are reading more every year than the year before, it almost doesn't matter to me because I sort of feel like people are probably reading less. Now, maybe the stats are people are reading more books, but they might, I don't know, maybe they're romance novels. It just seems to me like it's natural if you have ai and and non-stop inundation of text from from twitter and other places you would read less books so what's going to happen to the next generation which are they not going to have the opportunity to read about lincoln and i already noticed this by the way that young people have much less knowledge of the history of the areas even areas that they love than people our age.
37:14No, I think about this with my kids because I get it. It's like I'm trying to tell them some story from history. It's just not as interesting as a Mr. Beast video. That video, in the same way that broccoli is just not as good as some genetically engineered for taste bag of Doritos. This is not a fair fight. And so, yeah, I think that's a huge problem. At the same time, you think about it historically, books have stood up pretty well over 3 ,000-ish years. So I think things come and go from ways. That is one thing you have a sense of in history, is just how many moments everyone was despairing over the loss of this or that.
37:59And when you zoom out long enough, things stay relatively stable, or there's some new equilibrium that gets reached. So I just try to think about like with my kids, at least there's like, you know, like audio books are a thing that we couldn't listen to in the car when I was a kid because like it didn't exist, you know? And then later in my early adulthood, it was hugely inconvenient because if you wanted to listen to a 300 page book, it was like 12 CDs or something. And now it's just like, I can just pull it up on my phone. Or I can do voice-to-text articles that I want them to hear. So I just try to actively counteract whatever this sort of impulse of culture is.
38:48And then try to use the new technologies, whether we're talking about AI or whatever, and go, okay, how do we use this to increase? Like if we just read a book, we just talked about something, and now we have questions. Let's get in a debate or a discussion with ChatGPT about it and see if we agree with their take or not. And then I'm also teaching them how to use the tools at the same time. Yeah, it's interesting because at the same time, the evidence might suggest to them that the tools we have available, like the Mr. V's video versus reading about Lincoln, are better for them. Because guess what?
39:26In almost every era of life, the new generation is better and smarter than us. Yeah. If you look at any TikTok video, they obviously play musical instruments far better than any. So many kids play the piano better than the best pianists of the 20th century ever could have possibly imagined. Like somehow or other, they are getting wisdom from the tools in front of them, even if it's not the wisdom the way we might have gotten it. Like they're getting knowledge, wisdom, skills that far surpass us. Just seems to me. Yeah, and what I try to do is like, okay, so you just watch this Mr. Beast video where he travels here.
40:05Like, let's go there. You know, like whenever my kids are expressing an interest in something instead of judging it or shutting it down, I want to go towards that. Because to me, not only is that a source of connection, but again, I want to teach them this meta skill of like curiosity is the beginning of a conversation or it's the beginning of a process and you don't know where it's going to end up, but it could change your life. Well, that leads into my next thing, which is that let's say you're listening to this podcast or video or however you listen to this. Everybody thinks they're wise. I think I'm wise.
40:41You think you're wise. We all think we're wise. But setting that aside for a second, how can we practice wisdom, whether you're five years old or 95 years old? How can I myself practice having more wisdom? Well, you know, just to go to what we were just talking about, but it just occurred to me, I was driving my boys to school this morning and my son goes, I want to listen to a podcast about the history of Disneyland. Now that's like not something I'm interested in at all, but I was like, fuck yeah, dude, you know, like let's figure this out. And not only are we listening to it, but we're critiquing the podcast of the, you know, it's like, who's making a, whatever the first one I pull up on Spotify is not necessarily going to be of the highest quality.
41:22So we're not just listening to it and thinking about what we can learn and maybe there's books or whatever, but we're also like, hey, what do we like about this? What do we dislike about this? And so I think understanding that knowledge is this conversation, like that's what they often call philosophy, the great conversation, that it's this sort of thing that goes back, that you're kind of arguing and discussing and debating with Socrates and Aristotle and Plato and Marcus Rius and Seneca, that that's like a big part of it. I like that a lot. But I guess when I tried to build the book around was this idea that there's a handful of just basic skills that if you can pick up, you're going to accumulate wisdom over time.
42:04Asking questions is one. Reading is one. Obviously, travel is a big one. Studying history is a big one. Mentors and apprenticeships, that's a big one. And people might go, oh, that's so basic. Everyone knows that. But I mean, to go to your point about statistics, most people don't read, right? Most people don't have a mentor. Most people stop going to school as soon as they graduate from high school or college. These are like little decisions that if you make and you practice them over the course of a life, you will get very far. And I think this is important. Again, wisdom isn't something you arrive at.
42:42If you start walking towards the horizon, you will never reach it, right? Because it doesn't actually exist. You're never going to touch it. However, you walk for an hour, then you look back behind you, you will have covered a significant amount of ground. You will know, you can objectively see that you are further along than when you started. You're never going to arrive, but you've covered distance. And so if you can pick up these kind of basic practices, and you can do them day in and day out, or week in or week out, you're going to end up somewhere very far from where you started. And by the way, we're all lucky in that we've started much further along than the generation before, and the generation before and the generation before.
43:24Why do you say that? Because we have more books and information we have access to? I just mean, sometimes you read some of the stuff from the ancient philosophers and you go, oh, the reason we think this person's so smart is literally no one had ever thought of this before. But like, we know a little bit. Our baseline of knowledge is high. It's like the standing on shoulders of giants thing. Right. By the way, I love that question your kid asked. Can we listen to a podcast on the history of Disneyland? Because instead of just saying, so obviously he loves Disneyland. You've probably taken him there.
43:57You've had a fun time. But now he wants to know the history of it. And the history of it, by the way, is dark. Walt Disney wants to create this utopia. And it's both dark and playful, but it's got to be fun for kids. And so understanding kind of the deeper philosophies behind the creation of Disneyland. And also there's Disney's both failure and success as a businessman. His first one or two companies ended in bankruptcy, but he had this vision, he had this belief in animation and so on. Like that story is an intricate, complicated, nuanced story with a lot of questions about the philosophy and so on.
44:36So this is a great topic, by the way. Yeah. It's like, look, when you read history or biography, you pick up a biography of Walt Disney. You're learning about this man, but you're also learning about the psychology of that man. You're learning about the era that he lived in. You're learning about all the people that intersected his life. You're learning about business. You're learning about art. You're learning about management. That's the other thing I would say. I don't talk about this in the book, but I do think people don't read enough history and they don't read enough biography. They read too much either contemporary stuff or they read too much secondary stuff and not enough kind of primary deep dives into topics and people that allow them to then go off in all these different directions.
45:24yeah yeah i i agree and i think there's one great benefit of youtube which is that if you're not a reader there's all sorts of analysis and synopses of different periods in history like i'm probably never going to read a book about world war one i have no interest in it but i also realized recently i have no clue what world war one was i have no clue you probably have read books about it and you know i have no clue why what world one was fought over you think of world war ii you can come up with various stories okay it was fought over to stop the holocaust from happening it was fought over because hitler was evil and was going to take over all europe and japan was going to take over all of asia so we were fighting this fascism i have no clue i have no story or narrative at all about world war one so i'm not going to read a book because i'm just not interested.
46:14But I would watch an hour-long video or even a 20-minute video just to get a sense of it and try to understand a little bit more. So there's other things now too. No, of course. You can go watch video of soldiers in World War I. That's incredible. The access that we now have to things, just basically every book that's ever been published is available. like every video that's ever been shot is available. And that's a pretty incredible gift. I mean, the curse is that it's impossible to make your way through all of it. But I just think as a general policy, when you have that sort of flicker of interest, do you have the skills to satiate it, right?
46:59Like I know, because I know you, I know there's a bunch of things that you've been vaguely interested in that you went and figured it out. you know, stand-up comedy, chess. You're like, oh, I'm interested in that. I want to know more. I want to give it a try. Like, it's easy to take for granted knowing how to do that. And then you meet people and you realize they don't even know where or how to start with something like that. And this is where the doing versus reading is really important. You could read 24 hours a day about stand-up comedy and watch every stand-up comedian and you'll become proficient in the way that an academic becomes proficient.
47:38But so you could argue, well, this comedian is different and this comedian has this point of view and these techniques are being used. You could say all these things, but doing something is really, really hard. Doing something hard is because it's painful. You have to have, I feel like there's an element of pain in wisdom because in order to avoid that pain, you got to do it again and again and again welcoming the pain and then somehow getting to the other side of it, which is, you know, I'm not just stand up comedy is actually the weirdest thing to say, oh, I experienced pain over humor, but whether it's becoming a success in business, whether it's writing a book, as you know, writing a book is a painful experience.
48:22You have to do something very unnatural. You have to sit down for a year or more and type, use the skill called typing, which didn't even exist 100 years ago. After the first half a million years of our species' existence, there was no such thing as typing. And it's painful. Nobody likes doing it. But you have to do it in order to really get the nuances and the subtleties, which I guess is part of the wisdom. Well, the subtitle of the book is Learn, Apply, Repeat, because I think these things are related. So you read about something. I was actually just reading this essay that David McCullough, the biographer, wrote.
48:56And he was talking about how he learned And the night that Truman became president, the night that FDR died, he's meeting with some senators and he gets this message that, you know, he's needed at the White House. They don't tell him, you know, what it is. And he has to go get his hat from his office and then head over to the White House. And he famously doesn't know why he's being called, but he feels like it's important and he just starts running. And so they know the exact way he ran to his office and then to the White House. Right. Right. And so McCullough doesn't just hear about this. He actually puts out a request to the Senate archive or something, and they allow him to retrace the steps where Truman goes.
49:39And he runs it. And he was talking about what he learned actually doing it. He was like, for instance, there's a lot more steps than I would have thought, like stairs. And he's like, it made me understand that Truman was in better shape than I would have guessed. Right. And you're like, oh, okay. So he had this little bit of knowledge and then he had to apply it. He had to go take it into the physical world. And what happened when he did that was he learned another bit of knowledge that informed what he wrote about. And then you could say that he probably also took from this, oh, it's not just enough to hear something.
50:18You have to go physically experience it where you can because it informs the writing. And then, you know, this getting meta on top of meta, I'm in the middle of this biography I'm writing. I'm like, oh shit, now I have to go physically do a lot more things than I was planning on physically doing for this book. But I think McCullough is probably right here. And there's going to be things that I can't learn from books that I'm going to have to go see firsthand. Well, and this is something, you know, I read Bob Carroll's autobiography on your recommendation, actually. It was one of the books you most recommended.
50:58The LBJ series? No, not the LBJ series. His memoir about writing. Oh, yeah. Yeah. That, for me, is his best book, actually. Of course. Like, I love the LBJ books. I love The Power Broker. But seeing his experiences writing The Power Broker and writing that. So in the book Working, he describes how he moved to LBJ's. He moved to Johnsonville. Yeah. Yeah. Which was like the tiniest town in the world. Everyone was like a cousin of each other. And then there's him in there. And through that, he gained so much knowledge about LBJ by doing. And again, it came from your recommendation. I wouldn't have known about the book otherwise.
51:35That book was such a great book about writing and about studying history and studying people. I really loved it. But you're going to have to do this when you write about Stockdale. What are you going to do? I know. No, I am. I've already done some of this stuff. But yeah, you're going to have to physically go and do the stuff. And it would be nice if there was a shortcut. And there are some things that can make it better. But for the most part, there's no substitute for doing the hard thing. And I think that's why we know who McCullough and Bob Caro and Walter Isaacson, another historian, that's why we know who they are.
52:10Because they've done this. They've written these books that have stood out among all the other books. There's tons of books about LBJ. tons of books about Truman, but these historians have stood out in some way because of these extra things. I'm just realizing now as I talk to you about it. So that's the way to stand out because no one else is going to run up and down the steps that Truman ran. They're just going to sit at home and ask AI, give me a bio of Truman. I'm going to rewrite it as a biography. Yes. No, no, that's exactly right. I think some of this stuff isn't explicit. He doesn't actually tell you that he did it, but you can feel it in the writing that there's just a level of authenticity and realism to it that I don't think you can get any other way, not accurately at least.
52:57Yeah. So that's interesting. So what made you decide Stockdale? Well, to go to the point about growing and trying hard things, my books are all different from each other, but especially these last four that I just did being part of a series, there was a formula and a style that I've gotten really good at and really comfortable with. And so I was just thinking, what's something I've never done before that I could try that even if I fail at, I will grow as a writer and as a person for having done. And I already, you know, I'm about maybe 30 % done with the first draft right now. I could quit right now and the project would be a huge success.
53:42Not like, it's not publishable, but like, I have gotten much better. I've learned a bunch of stuff. I've had to figure out a bunch of stuff. I've changed my process. I've had to read hundreds and hundreds of letters. I've never had to, I don't use letters in my books. On my book about Peter Thiel, I had to figure out how to digest a bunch of legal documents. Well, this is the first one where I've had to do interview transcripts. I've had to do my own interviews. and then I've had to process lots of sort of, we had to go through the archives. A bunch of his archives are at Stanford. And so we've just gone through hundreds, if not thousands of pages of letters and orders and all these things.
54:23So I struggled with how to make sense of it all and the depth that like this book, it's just gonna be longer and harder and different than anything I've done before. And so I'm having to challenge myself and I'm just genuinely loving it. yeah like when i think of you i think of like your biggest mentor obviously has been robert green author of 48 laws of power mastery seduction all these all these great brilliant books and a lot of your books have not the exact format i would say he's very different in some ways but a similar format where you have this theme and then historical stories and examples that ride through that theme and and also you've co-written books like your recent book with george raveling like just like Robert Greene with 50 Cent.
55:08So you've co-written books with others, but this is the first book. If you're writing this biography of Stockdale, I don't think Robert Greene has written a history or a biography of someone. No, and I'm having to find new mentors, right? Because obviously Robert's a great writer. He's taught me a lot. And if I had questions, he would be very helpful. There are things that I want to know how to do that he's not the right person for me to ask. And so not only am I sort of having to ask lots of questions to other people, I'm even looking for like a new, a different kind of editor. My editors at the imprint that I'm at, they don't specialize in this kind of book either.
55:48And so I'm having to kind of adjust my team and my sort of board of advisors, if you will, to be better suited for the type of thing I'm building here. Yeah, that's interesting. So what are you doing? Who's your mentors in this now? Well, I've been slowly interviewing. I interviewed Ron Chernow a couple months ago. I'm doing a thing with Doris Kearns Goodwin in California in February. I got to ask her some questions. I'm just asking questions from people. I'm obviously reading all of their books. And then I'm in the middle right now of vetting different. I'm bringing on an additional kind of editor or coach, as I was saying.
56:29I could figure it out on my own or I could try to get away with not having one. I want to bring on someone who's worked with a bunch of writers that I would say are a caliber above me so I can aspire to get where they are. Right now, I think you have the ideal life. You're living a couple of miles outside of Austin. You've got a bookstore. When I visited, there was a lot of people there. like it's a popular bookstore, even though it's like 30 miles outside of Austin, you do your podcast there. Then you've been, you've written these last, what is it now? Like eight books, nine, more than that, because you have kind of the summary books too.
57:09You have like 10 books or more on stoicism. And obviously you've achieved a lot of success as a writer. Would you say the success you've had as a writer is more or less than the ancillary success that came from writing about stoicism. So you asked to speak at a lot of places. You're probably a consultant for a lot of places. Which has actually generated more money? That's a good question. I don't know. Books have sold very well, something like 10 million copies now in 30 or something languages. So I could probably just live on that. I mean, I could definitely just live on the royalties at this point.
57:45But I kind of think about the books as being the entry point into the universe. and at the same time also funding other people to discover the work. So, you know, that's what we do on social media. That's what we do on the podcast. That's what we do on YouTube. So I kind of just think about it as this like universe of stuff. So my main thing is I like writing, like writing books. But to go to your point earlier, I understand that most of the population doesn't wake up and go, I want to read a bunch of books today, right? Like it just doesn't fit well in their life. And so I try to translate what I do into these other mediums just in the same way that the books get translated into other languages.
58:28So I kind of think about it as all like feeding into the same place. The nice part about speaking or consulting and other things is that a video is free for everyone. A speech is usually paid for by 0.0001 % of the population. that is, you know, like I spoke to this large company yesterday, this large parent company that is, you know, has, I don't know, let's say 100 ,000 employees. So I spoke to just 30 CEOs inside that parent company, right? And so obviously, they're able to pay a lot of money because, you know, they have billions of dollars in revenue. And that's able for me to fund a lot of the other stuff that I do because it allows me to give away a lot of stuff for free, I guess is what I'm saying.
59:19You don't really separate it out as sources of income. It's all part of the same machine. Yeah, it's the basic marketing funnel, which you know all about. The purpose of all of it is to make more stuff. I remember Casey Neistat said that to me once. He was like, we don't make stuff to make money. We make money to make stuff. That's what an artist does. And that's kind of how I think about it. I love that quote. And that quote is very Casey Neistat. Yes. And like, okay, so what, he's an interesting case is that I don't really hear as much about him now as I did 10 years ago. And obviously everyone's, including my own, like everyone's career arc is different.
59:54What's Casey doing now? He's been on my podcast twice, but not in the past 10 years. I was just in New York doing the launch of Wisdom and we went for a run across the Brooklyn Bridge at like six in the morning. It was lovely. It's interesting that you say you haven't heard from him in a while. I bet if you pulled up like his YouTube feed, you'd be like, wow, these things are doing more views than ever. Which is exactly, I think, the point that we opened with, which is like, it feels like the field is much, much bigger. So it's harder to keep track of everyone. But also the audience is much, much bigger.
1:00:29So you could not be getting the same share of attention, but actually be doing better than you've ever done before. And so I think, as far as I know, is stuff is still crushing. It's great. I watch it when I can. But it's just not, like the internet is not this, small town that it was for a short period of time. Yeah. Well, look, Ryan Holiday, you know, I think this must be like the, at least the 15th or 16th time you've been on the podcast. Cause you, I know you were on the podcast for every single book ever since the beginning. And you've also come on a whole bunch of other times whenever we've just wanted to chat.
1:01:08Basically every time we wanted to have a conversation, I would say, let's just put it on the podcast. We very rarely had a conversation outside of the podcast. Well, I think that's a function of one, you having one of the longest running podcasts that I know about. Two, I've written way too many books. And then three, you've been very good to me and you've invited me on every time. So I appreciate that. But yeah, it's funny. It's like we have these hour, two hour conversations every year or two. And then I don't think we've ever just chatted on the phone. Yeah, we've had dinner once or twice. I think we've gone out a number of times, but yes, podcasts, I don't know about you, but they've replaced a chunk of like, let's grab coffee and catch up.
1:01:50I tend to find that happens over podcasts in a way that's good because you end up having really deep conversations that you might not have had in real life. If at the same time, there's probably personal stuff that doesn't get discussed because it's being recorded that it would be good to talk to people about that I don't probably do enough of. Yeah. Agreed for me as well. And maybe that'll change someday. Maybe we'll have to grab coffee and just like talk about bullshit stuff sometime. Yeah. Well, Ryan, wisdom takes work, learn, apply, repeat another great book in the series. And this is the end of the series of the four virtues.
1:02:30So I'm really looking forward to the Stockdale book. I've been curious about Stockdale, honestly, ever since probably about 1980. I was 12 years old and I read Jimmy Carter's autobiography. I think it was Why Not the Best. And that quote comes from Stockdale. So I've been curious about Stockdale ever since - No, no, that quote is from Admiral Rickover. Ah, my fault completely. But this is something, I mean, I vaguely knew about it, but what I'm writing about, Stockdale and Carter are at the Naval Academy at the same time. They're part of the, they're living in the dorms right next to each other.
1:03:05I didn't know that. So it's this interesting intersection of lives, which I've been fascinated to dive into. So how do I know about Stockdale? I guess he was Ross Perot's running mate, right? That's when he famously was introduced to the American public. Well, I mean, he was famously introduced to the American public as a POW when he won the Medal of Honor. But it was this kind of second act to his career and it went very badly. And I haven't gotten there yet, but it's an interesting wrinkle on this incredible life that then we sort of humiliate him on the public stage instead of venerating him the way that we should have.
1:03:44Well, look, I look forward to hearing more about him after I read the book and have you on the podcast again. Well, as soon as I finish it, I'll let you know. Thanks again, Ryan. Thanks for having me.
1:04:06This November, action is free on Pluto TV. Go on the run with Jack Reacher. Every suspect was a train killer. Then buckle up for Drive, World War Z. Every human being we save is one less fight. And Charlie's Angels. Damn, I hate to fly. Launch into sci-fi adventure with the fifth element and laugh through the mayhem in Tropic Thunder. What is going on here? All the thrills, all for free. Pluto TV. Stream now. Pay never.
From the publisher
A Note from James:
Wisdom Takes Work is Ryan Holiday’s fourth book exploring the Stoic virtues, and this time he’s taking on the big one — wisdom. His earlier books on courage, temperance, and justice were all great conversations, but this one hit me personally. I’ve often thought I had wisdom, only to realize later that I didn’t — or at least not as much as I thought.
Ryan’s writing blends ancient Stoic philosophy with modern life in a way that feels both practical and timeless. We talked about how wisdom isn’t something you possess; it’s something you practice. It’s not about having all the answers — it’s about asking better questions, learning through experience, and staying humble enough to admit what you don’t know. Ryan’s back on the show — probably more than any other guest — and each time, I walk away seeing the world differently.
Episode Description:
James sits down with bestselling author and Stoic philosopher Ryan Holiday to discuss Wisdom Takes Work, the newest addition to his series on the cardinal virtues. Together they unpack what “wisdom” really means — not as a static trait, but as an ongoing practice of curiosity, humility, and doing hard things.
The conversation ranges from the limits of AI (“great at knowledge, terrible at wisdom”) to the importance of reading history, counting names on a plaque instead of trusting bad data, and learning by doing. Ryan also shares new insights from his upcoming biography of Admiral James Stockdale, and how the act of challenging himself as a writer mirrors the Stoic pursuit of wisdom itself.
What You’ll Learn:
- Why wisdom isn’t about knowing — it’s about learning, questioning, and doing.
- How AI amplifies knowledge but can’t replace human judgment or discernment.
- Why experience, pain, and humility are necessary ingredients for growth.
- How Ryan’s research on Admiral Stockdale is changing his approach to writing and life.
- Practical ways to cultivate wisdom — from reading and travel to mentoring and open-mindedness.
Timestamped Chapters:
- [00:00] Introduction: The difference between knowledge and wisdom
- [02:54] A Note from James — Why wisdom is the hardest virtue
- [05:37] AI’s limits and the danger of overconfidence
- [08:57] “Wisdom takes work”: Stoic principles in action
- [11:35] The verbs of virtue — acting with courage, justice, and discipline
- [13:12] Ryan’s AI experiment and the Naval Academy plaque
- [16:10] Knowing what you don’t know — humility as wisdom
- [18:30] Parenting, ego, and learning to argue less
- [22:00] Why age doesn’t guarantee wisdom
- [25:10] The trap of resisting change and staying “the smartest person in the room”
- [27:00] Adapting to new generations and ideas
- [31:00] Is wisdom a talent or a learned skill?
- [34:00] How books and mentors shape a wise mind
- [37:00] Raising curious kids in the age of MrBeast and AI
- [40:20] Teaching curiosity and lifelong learning
- [42:25] Practicing wisdom: reading, travel, and mentorship
- [47:00] Learning by doing — the pain and reward of hard work
- [50:20] Writing, research, and the lesson of David McCullough
- [53:07] Why Ryan’s next book is his hardest yet — Admiral Stockdale’s story
- [55:50] Finding new mentors and growing past your comfort zone
- [57:14] Living the Stoic life — success, service, and perspective
Additional Resources:
- Ryan Holiday – Wisdom Takes Work
- Ryan Holiday’s other Stoic virtue books:
- Admiral James Stockdale – U.S. Naval Academy Biography
- Robert Caro – Working: Researching, Interviewing, Writing
- David McCullough – Truman and John Adams
- Ryan Holiday’s The Daily Stoic Podcast – Spotify
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