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The Daily Stoic

The Stoic Skill AI Can’t Replace

27 May 2026

Transcription

Chapter 1: What insights do the Stoics offer about modern technology?

0.031 - 22.801 Ryan Holiday

Welcome to the Daily Stoic Podcast, designed to help bring those four key Stoic virtues, courage, discipline, justice, and wisdom into the real world. If you dropped one of the Stoics, you know, Marxist or Seneca or Epictetus or Cato into the modern world, they'd be shocked by a lot, right?

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23.602 - 41.396 Ryan Holiday

Culturally, they'd be shocked by the technology, cars and planes, the phones in our pockets, our instantaneous communication, how fast we can travel, the endless stream of news. I mean, I don't think they'd be shocked by the fact that society had changed and evolved. Like they understood a lot about change.

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41.796 - 68.429 Ryan Holiday

It's one of the fascinating themes in meditations, how often he returns to the idea of change, how inescapable something like change is. I guess I'm curious what they would think of artificial intelligence, right? What would they think of AI? Marcus Aurelius would be shocked to watch videos of himself generated by AI where he has a 12-pack. He's just absolutely shredded. I don't know.

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68.45 - 85.406 Ryan Holiday

It's an interesting question, right? What would they think of this tool? Obviously, I tell a story and... Wisdom that is sort of a fable about AI, the idea that technology can do your thinking for you, that there's some way to get wisdom other than a lot of work. I think they would obviously dispute that.

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85.446 - 106.582 Ryan Holiday

But this idea of wrestling with technological disruption, wrestling with change, wrestling with... The idea of magical solutions, you know, world changing innovations. What would the Stoics think about that? It's obviously something I think about. I think about it as a parent of young kids. I think about it as a person who runs a business. I think about it as a writer.

106.622 - 130.326 Ryan Holiday

I think about it as a person who has a question and wants an answer to that question. And, you know, I type it in and then I think about whether I can trust that answer. Anyways, I got asked to do this podcast a couple of weeks ago. It's called Beyond the Prompt. It's hosted by Henrik Werdelin. He was an entrepreneur and started a bunch of cool companies. And then Jeremy Utley,

130.373 - 148.496 Ryan Holiday

who's a lecturer at Stanford, who I actually know through RC Buford at the Spurs. And they asked me some of these questions, and I was sort of trying to think about what the Stoics would have to say here. And I thought it was interesting enough that I wanted to bring it to you. So you can listen to the whole podcast over on Beyond the Prompt. I'll link to that.

148.877 - 171.727 Ryan Holiday

But in the interim, here's just the Stoic parts. What I wanted to try to answer is like, How do we use these tools without being dependent on them? How do we stay disciplined in a world that I think is actually going to increase the amount of distractions being thrown at us? How do we separate what's true from what's false? What's bullshit, right?

172.288 - 188.469 Ryan Holiday

How do we not just keep, but sharpen our judgment, our character, our ability to think clearly? That's what I'm going to talk about here. So if you're wondering who those voices are, that's Henrik and Jeremy, but, um, What we're talking about is Stoics and AI, and I thought you would like this conversation.

Chapter 2: How would Stoics perceive artificial intelligence?

238.053 - 256.271 Ryan Holiday

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320.596 - 347.671 Ryan Holiday

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347.791 - 371.808 Ryan Holiday

And it's pretty remarkable, right? He's just over and over again, he's like, time is sort of racing past us and nothing is stable. And he says, like, when you're frightened of change, he says, you should remember that the status quo that you're trying to preserve was itself a product of change. He was like, you didn't exist. And then you came into existence. You yourself are a change.

372.188 - 397.407 Ryan Holiday

And just like you're no longer a 25 year old or a 15 year old or a 10 year old or a five year old or a fetus. Like we are ourselves always changing and evolving. And he's sort of trying to meditate on change. And one of my favorite little riffs he has is he says, it would take an idiot to feel distressed or indignant about change. He says, as if any of it lasts.

397.387 - 414.789 Ryan Holiday

It reminds me of an expression we have here in the South, which is, if you don't like the weather, just wait a minute, it'll change, right? And the idea that the things that we're stressed about, the things that we're, oh, I'm grappling with this, I'm trying to adjust, as if itself is stable and not going to change.

415.19 - 436.894 Ryan Holiday

Just a couple of years ago, we were wrestling with one version of AI, and now we're wrestling with another version of AI. And meanwhile, they're hard at work on another version that we can't even comprehend yet. And so there's a certain amount of presumptuousness and arrogance and sort of recency bias in how we react to what's happening around us. So I think that's one thing to focus on.

Chapter 3: What challenges do we face in navigating technological disruption?

469.434 - 489.73 Ryan Holiday

But some version of this has happened forever and always and always will. Continuously. Yeah. All of this is very precedented, right? The names and the dates and the people and the types of things are changing, but the change itself is ceaseless. So I think that's first and foremost. The second part that Stokes would have us think about is like, well, where did all that worry get people?

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489.71 - 511.111 Ryan Holiday

Did fretting about it and worrying about it and catastrophizing about it, did it help any of those people actually adjust to the changes that were in front of them? Did it arrest any of the change? And you might say, did it set any of those people up to take advantage of that change? Probably in some cases, but in most cases, also probably not.

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511.211 - 534.044 Ryan Holiday

And so I think what stoicism is trying to be, and sometimes people mistake it for kind of emotionlessness, I think a better way to describe it would be kind of an even keel, not getting too high or not getting too low. Mark Strelitz in Meditations talks about being like the rock that the waves crash over and eventually the sea falls still around.

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534.104 - 550.971 Ryan Holiday

It's actually similar to a thing that the Buddhists talk about, which is, you know, you take a cup of, say, water from the river. It looks clear in the river, then you grab it in a cup and you can't see through it. But if you let it settle for a second, you know, all the silt goes down to the bottom and then it becomes clear again.

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551.011 - 566.322 Jeremy Utley

Would you then argument that agents, AI agents are very historic? I guess they're always at the moment because they only respond to a prompt you have. And they are pretty even keel because they don't have emotions. I mean, that's true.

566.382 - 567.523 Henrik Werdelin

In a sense.

567.543 - 588.972 Ryan Holiday

Yeah. There is an emotionlessness to it. I mean, my favorite and also most exasperating part of AI is the complete shamelessness with which it will make mistakes. I was with my boys the other day, we were walking back from breakfast and they found this quarter on the ground and that they'd never seen a quarter like this. And I go, I wonder if it's like rare.

588.952 - 610.542 Ryan Holiday

And so we take a picture of it and we asked ChatGPT who was on the quarter. We hadn't recognized the person. And it promptly goes back, oh, you're not holding a quarter. That's actually a penny. And I go, no, it's definitely a quarter. And it goes, you know, I could see why you would think that it's a quarter, but it's in fact a penny. And I go, look, man, it's a fucking quarter.

610.562 - 630.939 Ryan Holiday

I don't know what to tell you. Like it says on the front, it's a quarter. And then it goes, oh, you're right to push back. OK, it is a quarter, you know, and then and then it's like that's that's Eleanor Roosevelt on the quarter. And I go, I'm pretty sure it's not Eleanor Roosevelt. You know, it doesn't look like her at all. Oh, you're right to push back. It's not Eleanor Roosevelt.

Chapter 4: How can we maintain discipline in a distraction-filled world?

682.152 - 708.48 Ryan Holiday

Exactly. And like the way it senses our emotions and that it's like, oh, you want to be congratulated for proving me wrong. And so so anyways, it is it's an interesting insight reflected back of human psychology, both like why we have things like shame and responsibility and accountability, but also how much our emotions can distract us from from the point as well.

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708.764 - 720.242 Henrik Werdelin

Okay, so one quote I want to give you here. You've written a lot about this. Seneca's quote, no man was ever wise by chance. Yeah. Just tell us, why is that so important right now?

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720.475 - 723.482 Ryan Holiday

Well, I actually use that quote.

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Chapter 5: What strategies help us distinguish truth from falsehood?

723.502 - 742.303 Ryan Holiday

It's part of a larger story that he tells. And I talked about it at length in the book I just did on wisdom. He was talking about this wealthy Roman who wanted to seem smart. So instead of doing the reading or going to school or getting tutors, he hires a collection of wealthy slaves.

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742.383 - 757.102 Ryan Holiday

And in Rome, often slaves were captured from other countries, sort of smart people, and then they were used as tutors. So most wealthy Romans would have had slaves as their teachers or freed slaves as their teachers. So anyways, he hires these educated slaves.

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Chapter 6: How do we sharpen our judgment and critical thinking skills?

757.142 - 775.887 Ryan Holiday

Instead of having them teach him, he just used them. So if he needed to say something smart, he would have them whisper it in his ear or he would have them feed him answers like at dinner parties and stuff. And so finally, you know, he kind of thinks he's getting away with it. And a friend comes up to him and says, you know, I noticed, you know, you're so smart.

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776.047 - 796.618 Ryan Holiday

You've been entertaining this all at this at this dinner party. He says, well, have you ever thought about taking up wrestling? That being obviously one of the other sort of dominant areas of ancient life, the sport of wrestling. And the man says, I'm old. I'm way too old to pick up wrestling. What are you talking about? And the guy says, ah, but your slaves are still young.

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796.598 - 815.044 Ryan Holiday

And his point was, you just can't have people do this stuff for you. You think you can outsource wisdom, but you can't outsource wisdom just as you can't outsource exercise. Because the point is that it's a byproduct of the work that you do, not a thing that you're a conduit for.

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815.145 - 831.027 Jeremy Utley

But do you think that is the same thing for technology? I mean, you can still be smart and use your GPS. There are some technologies that we've adopted that then have... meant that we'd lost the ability to do that thing, but we are probably not less smart of it.

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831.361 - 850.823 Ryan Holiday

I think that's a great point, right? They call this sort of cognitive offloading or cognitive surrender. And so there are some tasks that are not really worth doing that you can probably surrender. I've certainly surrendered whatever ability I had to navigate before GPS, not that it was particularly impressive, almost entirely to my phone.

851.404 - 873.705 Ryan Holiday

But I can't call myself a navigator and I wouldn't consider myself good at navigating just because I rarely get lost. Like that's a function of the GPS, not anything that I have. And I think wisdom is a good example of something that you can have access to lots of information. It's not quite the same thing as being wise or even smart.

873.825 - 886.676 Ryan Holiday

And so to me, it's like, look, you can have chat GPT write your essay. But the point was never to write the essay. The point was to be the person on the other side of writing the essay who has clarified their thinking.

886.696 - 887.777 Henrik Werdelin

The person who could.

887.757 - 888.94 Ryan Holiday

Exactly.

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