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The Jordan Harbinger Show

1258: Ryan Holiday | Wisdom Takes Work

16 Dec 2025

Transcription

Chapter 1: What is the main topic discussed in this episode?

0.031 - 22.53 Jordan Harbinger

Soft gifts. Hard gifts. Long gifts. Colorful gifts. Coming up next on the Jordan Harbinger Show.

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22.75 - 41.499 Ryan Holiday

You read a lot about America. You spend a lot of time in America. You're like, Americans do this. You know, Americans f***ed this up. This is the importance of both travel and the study of history. is because you read about Rome and Sparta and Athens and you go, oh, wait, every country does this stuff. Every country is bad.

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Chapter 2: How does Ryan Holiday define wisdom in relation to knowledge?

41.64 - 49.495 Ryan Holiday

Every country has shameful secrets. Every country has weird, hilarious quirks. Every country has practices that make no sense.

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53.153 - 65.068 Jordan Harbinger

Welcome to the show. I'm Jordan Harbinger. On the Jordan Harbinger Show, we decode the stories, secrets, and skills of the world's most fascinating people and turn their wisdom into practical advice that you can use to impact your own life and those around you.

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65.088 - 79.205 Jordan Harbinger

Our mission is to help you become a better informed, more critical thinker through long-form conversations with a variety of amazing folks from spies to CEOs, athletes, authors, thinkers, and performers. even the occasional rocket scientist, war correspondent, or real-life pirate.

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79.545 - 95.424 Jordan Harbinger

And if you're new to the show or you want to tell your friends about the show, and I always appreciate it when you do that, I suggest our episode starter packs. These are collections of our favorite episodes on topics like persuasion and negotiation, psychology, geopolitics, disinformation, China, North Korea, social engineering, crime and cults, and more.

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Chapter 3: What role does reading play in personal development according to Ryan Holiday?

95.704 - 113.507 Jordan Harbinger

That'll help new listeners get a taste of everything we do here on the show. Just visit jordanharbinger.com slash start or search for us in your Spotify app to get started. Today on the show, we're diving into something that sounds simple but has ruined lives since people were wearing togas and debating geometry for fun. Virtue. The four virtues, actually.

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113.567 - 129.818 Jordan Harbinger

According to our returning guest and resident Stoic and Chief Ryan Holiday, virtue isn't something you have, it is something you do, which frankly sounds a little bit like a personal attack. Today we're focusing on wisdom. Hard-won experience, and no, there are no cheat codes. Today we'll get into why wisdom isn't the same thing as knowledge.

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130.118 - 145.293 Jordan Harbinger

It's the act of applying knowledge consistently, not just once when somebody's watching. We'll talk about reading books as a superpower and kind of a scam that I built my entire business around. how the greats used silence, note-taking, and systems instead of ego, and why fools are seldom humble.

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Chapter 4: How does the Dunning-Kruger effect relate to wisdom and humility?

145.634 - 166.388 Jordan Harbinger

We'll talk Montaigne, Machiavelli, social skills, why ancient education required both literacy and physical prowess, and why Ryan dropped out of college yet somehow cranked out a small library of bestsellers while his parents waited patiently for him to get a real job. All that and a whole lot more on this episode of The Jordan Harbinger Show here with my good friend Ryan Holiday. Here we go.

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168.038 - 169.901 Jordan Harbinger

How's the book doing? Is it out already?

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170.161 - 188.73 Ryan Holiday

Yeah, it came out last Tuesday. Yeah. How's it doing? I think good. And I'm trying not to check. Are you able to do that? They told me how it came out on the bestseller list, which was good, but I haven't like, I can say this honestly, I have not checked Amazon a single time. I have no idea what the rank is. I have no idea what the reviews are. It's actually weird.

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188.75 - 191.795 Ryan Holiday

Like I've tried to get better at not paying attention to that stuff.

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Chapter 5: What is the impact of ego on the pursuit of wisdom?

192.335 - 211.884 Ryan Holiday

And it's generally made me happier. And I think generally made me better at doing the important part, which is the writing. But there is something a little weird about it. It's not that I don't know. It just feels a bit anticlimactic. It did come out, right? I just want to make sure that the copies arrived to people.

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211.924 - 227.886 Ryan Holiday

I don't need you to tell me how you liked it, but I just want to make sure that I'm not missing something that went horribly wrong. And the reason the silence isn't because I'm keeping healthy boundaries, the silence might be because they're all stuck in a factory somewhere.

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227.906 - 242.723 Jordan Harbinger

For people who just chimed in on this, and we're talking about the book release and the book ranking, I feel like for me, it would just be very hard to work on something for years, release that thing, and then be like, I don't want to look at it. I'm getting deja vu.

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242.743 - 250.172 Jordan Harbinger

Maybe we've talked about this before, but this is how I think like Johnny Depp and some other actors, they never watched a movie that they're in. They just won't do it.

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250.473 - 259.797 Ryan Holiday

So this is a little different. I definitely don't like to watch videos of myself on stage. I would never watch movies that I was in because I would be mortified.

Chapter 6: How can we treat learning as a lifelong practice?

260.138 - 283.556 Ryan Holiday

I don't like that kind of performance. That's not my jam, right? I have no problem... going over something I've written and I look at the book proudly. It's just to me when Johnny Depp's or, you know, and he's a problematic figure. But when you take any sort of performer and they're like, I don't like to listen to what I do or I don't like to watch what I do, that I understand.

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283.616 - 305.964 Ryan Holiday

That's like this weird, uncomfortable thing. To me, though, the more dangerous thing is if you love the sound of the applause. whether you like to watch your work or not, is secondary to, I think, a more insidious form of ego narcissism, which is like you're sitting in the audience and you're just like soaking up the adoration, like, look how great I am.

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306.385 - 323.35 Ryan Holiday

So for me, it's not that I'm like done with the book because it's out. It's more like I tried to take all my winnings off the table before it came out. in that I enjoyed working on it, and I think I did my best work, and I think I said what I wanted to say.

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Chapter 7: What systems do successful people use to retain knowledge?

323.39 - 341.562 Ryan Holiday

And then I think I did everything that I can do from a marketing and promotion standpoint, which is important too. I'm not just some pure creative who's just, well, I hope it comes out. I obviously... I'm doing a podcast right now with you. I care about telling people about it and I want them to read it.

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342.123 - 371.908 Ryan Holiday

I think I've just learned that it's not healthy to spend, this is the culmination of six years of work for me, that I'm going to spend six years working on this series and then somebody who got a free copy of from the publisher Amazon write some shitty review missing the entire point of the book and that's the first thing that pops up the day it comes out and because I'm frantically refreshing

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371.888 - 394.072 Ryan Holiday

The whole experience is now tainted in some way. And I've had that experience before. Sure. Because I was setting myself up to be exposed to it. And I just decided, hey, like, this is not the best use. And then the weird quirk of publishing, I guess this is most art. There is a huge lag between finishing something and it coming out.

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394.653 - 415.227 Ryan Holiday

And so what I try to do is always be in the middle of the next thing. And then what that does is it actually means that there's a real cost to getting obsessed with how the thing that just came out is doing because what it's taking away from is what I should be doing now. I see.

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415.207 - 416.188 Jordan Harbinger

Yeah, that's interesting.

Chapter 8: How do we balance feedback and criticism in personal growth?

416.228 - 433.286 Jordan Harbinger

I hadn't thought about that. As someone who's never written a book, I mean, podcasts are different, right? Because some people will like an episode, and if people are like, I hated that episode, I don't really care. I mean, I care in that I want to create good things for my audience, but any episode I create, someone will hate it for some reason. Sometimes it's a good reason.

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433.686 - 448.024 Jordan Harbinger

Like, wow, Jordan was sick, and he just wasn't on his game, and this isn't his best work. Other times it's like, I hated the fact that this guest's voice sounded this way. And I'm like... Who cares? Right. I just but if it's a book, there's just so much more work that goes into it.

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448.344 - 461.565 Ryan Holiday

You also have another one coming two days later. Yeah, it's like a train. You know, it's like this is when it comes in and it comes out. This is what it does. So there is something about a release or a launch that is different. It's higher stakes.

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461.545 - 485.126 Ryan Holiday

But I do imagine that when you're looking at the Spotify comments on the bottom of the episode, very rarely are you getting constructive, informative feedback from that. Feedback is essential and criticism is important. But like somebody firing off an email or posting a comment, that's not what you let in if you're trying to get better.

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485.186 - 491.552 Ryan Holiday

That's what you let in if you either want to fill up your ego or you want to feel like a piece of shit.

491.532 - 504.355 Jordan Harbinger

Yeah, that's interesting. I have more questions about critics later, but I want to jump into the content of the book because there's so much here. I have to admit, whenever I read your books, I'm always like, okay, I'm probably going to understand like two thirds of it.

504.555 - 520.963 Jordan Harbinger

One third of it is going to go over my head or be like so in the weeds on something historical that I'm not going to really apply that or have many notes for it. This book, I really enjoyed it because I was like, oh, wisdom, like This sounds deep. I don't know if I'm in the mood for this, but I plowed through it in one sitting, which is a good sign. Oh, well, thank you.

520.983 - 524.608 Jordan Harbinger

And you didn't invent wisdom, but you wrote a good book about it. So I'll give you that.

524.969 - 544.978 Ryan Holiday

Well, I will say one thing. This is feedback. One thing, as obviously I've done a lot of podcasts over the years, you are one of the only shows that you can count on for sure to have actually read the thing as opposed to, you know, they're just riffing from the back cover, having been briefed on who the guest is a few minutes before they go on.

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