The Stoic Skill AI Can’t Replace

The more powerful our tools become, the more important our judgment becomes. In today’s episode, Ryan talks with Jeremy Utley and Henrik Werdelin, hosts of Beyond the Prompt https://www.youtube.com/watch?v=w-KmhckQkbU, about what the Stoics can teach us about AI, modern technology, and the skills we can’t afford to outsource. Beyond the Prompt is hosted by Henrik Werdelin https://www.beyondtheprompt.ai/henrik-werdelin, an entrepreneur known for co-founding BarkBox, prehype, and other startups, and Jeremy Utley https://www.beyondtheprompt.ai/jeremy-utley, a lecturer at Stanford and author of Ideaflow. 🎥 Watch the full episode on Beyond the Prompt's YouTube channel https://www.youtube.com/watch?v=w-KmhckQkbU: https://www.youtube.com/watch?v=w-KmhckQkbU 🎙️ Listen to the full episode on Apple Podcasts https://podcasts.apple.com/us/podcast/you-cant-outsource-wisdom-bestselling-author-ryan-holiday/id1721313249?i=1000767522225 and Spotify https://open.spotify.com/episode/5n2wqM22ABeK3RK8k8sSXJ 🎟️DAILY STOIC LIVE https://www.dailystoiclive.com/| Ryan Holiday is coming to a city near you https://www.dailystoiclive.com/! Grab tickets here https://www.dailystoiclive.com/ | https://www.dailystoiclive.com/ 🎙️AD-FREE https://dailystoic.supercast.com/| Support the podcast and go deeper into Stoicism by subscribing toThe Daily Stoic Premium https://dailystoic.supercast.com/ - unlock ad-free listening, early access, and bonus content:https://dailystoic.supercast.com/ 🎥 VIDEO EPISODES https://www.youtube.com/@DailyStoic/videos| Watch the video episodes onThe Daily Stoic YouTube channel https://www.youtube.com/@DailyStoic/videos:https://www.youtube.com/@DailyStoic/videos ✉️ FREE STOIC WISDOM https://dailystoic.com/dailyemail | Want Stoic wisdom delivered to your inbox daily? Sign up for the FREE Daily Stoic email athttps://dailystoic.com/dailyemail See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.

• 0:00Ryan 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.

• 0:15Ryan Holiday?

  If you dropped one of the Stoics, you know, Marcus really is or Seneca or Epictetus or Cato into the modern world, they'd be shocked by a lot, right? 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 and noise. 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. 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?

• 0:57Ryan Holiday?

  Marcus really is 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, it's an interesting question, right? What would they think of this? Obviously, I tell a story in 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, they would obviously dispute that. But, 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.

• 1:40Ryan Holiday?

  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. 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 gotta 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, started a bunch of cool companies. And then Jeremy Utley, who's a lecturer at Stanford, who I actually know through R.C. 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.

• 2:24Ryan Holiday?

  So you can listen to the whole podcast over on Beyond the Prompt. I'll link to that. 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 that's being thrown at us? How do we separate what's true from what's false? What's bullshit, right? 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 what we're talking about is Stoics and AI. And I thought you would like this conversation.

• 3:19Ryan Holiday?

  When you look at Mark Schuris' meditations, he probably talks about the theme of change and the pace of change more than just about anything else. 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. 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.

• 4:04Ryan Holiday?

  And he's sort of trying to meditate. On change and one of my favorite little riffs he has is he says, um, it would take an idiot to feel distressed or indignant about change. He says, as if any of it lasts. 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, that the things that were stressed about the things that were, oh, I'm grappling with this. I'm trying to adjust as if itself is stable and not going to change. 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

• 4:47Ryan Holiday?

  of presumptuousness and arrogance and sort of recency bias in, in how we react to what's happening around us. So I think that's, that's one thing to focus on.

• 4:57Speaker 01

  Does that, does that mean that concern is almost just normalized? Is just to, just to put a word on it. It's like, it's perfectly normal to be concerned. And now in this moment where maybe AI is kind of hyper present in the media and such, it's just, that's what people latch that this feeling of general existential concern. They go, well, now I have a name for it. It's AI.

• 5:17Ryan Holiday?

  Yes. I, I think that's right. I think first off, it would be like, okay, um, is it common to be concerned and worried? Yes. Like we go, this is unprecedented, as if in fact it, it's never happened before, but some version of this has happened forever and always and always will.

• 5:33Speaker 01

  Continuously. Yeah.

• 5:35Ryan Holiday?

  All of this is very precedented, right? The names and the dates and the people and the types of things are changing, but, but the change itself is, is ceaseless. So I think that's first and foremost. The second part the Stoics would have us think about is like, well, where did all that worry get people? 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, you might say like, did it set any of those people up to take advantage of that change? Probably in some cases, but in, in most cases also probably not. And so I think what, what Stoicism is trying to be, and sometimes people mistake it for kind

• 6:16Ryan Holiday?

  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 Schurio's in Meditations talks about being like the rock that the waves crash over. And eventually the sea falls still around. 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.

• 6:52Speaker 02

  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,

• 7:06Ryan Holiday?

  That's true. They're stateless in a sense. Yeah, that's a good point. 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, my boys the other day. We were walking back from breakfast and, and we, 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. And so we take a picture of it and we asked chat GPT, what, 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, uh, no, it's definitely a quarter. And it goes, I, you know, I could see why you would think that it's a quarter, but it's in fact a penny.

• 7:49Ryan Holiday?

  And I go, look, man, it's a fucking quarter. 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. Okay, it is a quarter, you know? And then, and then it's like, uh, that's a, that's a 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. It's, it said some other person. Finally, I was like, just give me a list of all the women who have ever been on commemorative quarters. And then I scrolled through, I figured out who it was. But the, the interesting thing to me is, is like, I was getting frustrated, having been bullshitted like so many times in a row. But it not only didn't pick up on any of my frustration because it's not a person.

• 8:32Ryan Holiday?

  Like if I was talking to an actual human assistant, this Change would have been getting heated. But also just the confidence and the shamelessness with which it gave me the wrong answer every time. Like a fresh slate, right?

• 8:46Speaker 02

  Did you see the, did you see the meme where, a meme where uh, somebody asks an AI where the wives ask the husband. So did you get the breakfast done for our kids? And he goes like, sure. And she walks in the kitchen, there's nothing there. She goes like, but you haven't made anything. Oh, my bad. I missed, I made a mistake.

• 9:03Ryan Holiday?

  Exactly. And, and like, um, the way it senses our emotions in that it's like, oh, you want to be congratulated for proving me wrong. And, 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.

• 9:29Speaker 01

  Okay, so one, 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.

• 9:38Ryan Holiday?

  Yeah.

• 9:38Speaker 01

  Just tell us, why is that so important right now?

• 9:41Ryan Holiday?

  Well, I, I actually use that quote. It's part of a larger story that he tells. And I, I talked about it at length in, in the book I just did on wisdom. He was talking about this wealthy Roman who wanted to seem smart. So instead of, you know, doing the reading or going to school or getting tutors. He hires a, a collection of wealthy slaves. And in Rome, often slaves were captured from other countries, you know, smart people. And then they were used as tutors. So most wealthy Romans would have, would have had slaves as their teachers or freed slaves as their teachers. So anyways, he hires these educated slaves. 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.

• 10:26Ryan Holiday?

  Or he would have them feed him answers like at dinner parties and stuff. And so finally, uh, you know, he kind of thinks he's getting away with it. And a friend comes up to him and he says, you know, I noticed, you know, you're so smart. You've been entertaining this all at this, at this dinner party. He says, um, well, uh, have you ever thought about taking up wrestling? Uh, 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. And, and his point was you just can't have people do this stuff for you. You think, you think you can outsource wisdom, but you can't outsource wisdom, just as you can't outsource exercise.

• 11:08Ryan Holiday?

  Because the point is, is that it's a byproduct of the work that you do, not a thing that, that you're a conduit for.

• 11:16Speaker 02

  But do you think that is the same thing for technology? I mean, like you can still be smart and use your GPS. You know, there is, 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.

• 11:32Ryan Holiday?

  I, 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, I've certainly surrendered whatever ability I had to navigate before GPS. Uh, not that it was particularly impressive, almost entirely to, to my phone. But I can't call myself a navigator and I wouldn't consider myself good at navigating just because I rarely get lost. Right? 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 know, you can have access to lots of information. It's not quite the same thing as being wise or, or, or even smart.

• 12:14Ryan Holiday?

  And so to me, it's, um, 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.

• 12:27Speaker 01

  The person who could write that essay.

• 12:29Ryan Holiday?

  Exactly.

• 12:30Speaker 01

  Circling back to the beginning of this conversation, we talked about how the Stoics took change as a given, change as a constant. Recognizing that folks right now tend to think we're in a moment of particular change, are there any mindsets or behaviors, rituals, routines, et cetera, that you would recommend, inspired by the Stoics, in terms of how to successfully navigate change? How do we do it? What are the things that we can implement in our lives that the Stoics have known?

• 13:00Ryan Holiday?

  Well, so the basic idea in Stoic philosophy is we don't control what's happening, but we control how we respond to what happens. And so the idea for the Stoics, it wasn't like, hey, these are the things you have to do. This is how you're successful. Instead, what they tried to be is really adaptable and adjustable to circumstances. That's what Epictetus said he was trying to teach his students, was to teach them to be able to be the kind of person that whatever happens, they could say, oh, that's just what I was looking for, or, oh, I can work with that. And so I think, you know, thinking again about what are the sort of meta skills? What are the things that aren't going to change? What are the things that are going to remain valuable?

• 13:42Ryan Holiday?

  You know, even if some of these trend lines continue, that's kind of where I would go as a person, is like, hey, what are the kinds of things that throughout historical moments, throughout moments of flux and change, have sort of remained unchanged? And that's probably the kind of, you know, investment I would make.

• 14:03Speaker 02

  If I can make an add-on to that question?

• 14:05Ryan Holiday?

  Yeah.

• 14:06Speaker 02

  If it is about, you know, basically saying, there's things I control and there's things that I don't control, and what I can change is how I kind of deal with it. But increasingly, isn't AI, it gives you control of a lot, right? Like, suddenly, you can write the legal brief without being a lawyer, you can ship an app without being an engineer. And so, the nicety of being able to say, I am not in control of all this, so therefore I just have to deal with my own emotions. Is that being kind of like degraded now that you are in much more control?

• 14:40Speaker 01

  You mean almost evasive or like burying your head in the sand? Is that what you're getting at?

• 14:44Ryan Holiday?

  I don't think the Stoics are saying, hey, just focus on your emotions. Nothing is in your control. I think when you look at the lives of who the Stoics were from, from, you know, emperors to generals and entrepreneurs and executives, all these people throughout history, they're always high agency people. And so I think, you know, seizing the, the increased amount of agency that certain technology might offer us doesn't strike me as outside the bounds of Stoicism. I think what they mean is like, hey, um, you don't control whether you're living in the middle of an AI revolution or not. You do control how you respond to that revolution, whether you decide to learn about it or not, what, how you deploy it inside your business or your life or not.

• 15:27Ryan Holiday?

  You decide whether you despair and give up and go, everything's pointless. We're all going to be replaced or not. And so to me, that's what the idea means. It's like, most of the macro trends in the world are not up to us, you know, including the weather and the economy and the political situation. We can have little bits of influence here or there on some of those things. But for the most part, the larger macro world is not up to us, but our sort of our inner emotions, our actions, our decisions, our, our priorities. These are all things that are up to us.