What You Can Learn From Asking AI for Brutal Honesty About Yourself - with Bestselling Author Daniel Pink

22 Jul 2026 · 51 min · 23 chapters

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In short

Daniel Pink uses ChatGPT prompts to get “brutal honesty” self-insights, then discusses how to use AI as a sparring partner (not a first-draft writer) to improve discernment, agency, taste, and intellectual humility; he also argues the future is “a little better,” not apocalyptic.

Guests

Daniel Pink, bestselling author (science/business/creativity) known for books like Regret; podcast host(s) include Jeremy and Henrik (co-hosts who ask about the AI exercise and broader implications).

Key claims

Your greatest risk is irrelevance, not failure; slow cultural “fade” happens when you play it safe. AI can be configured to challenge sycophancy and reveal blind spots. Use AI for critique (e.g., “mean-spirited critic”) and iterative testing, not for generating final drafts. Agency depends on context; bounded autonomy supports self-direction. Taste is built by creating, not just consuming. The future with AI is directionally better.

Notable examples

Prompts like “What do you know about me that I don’t know?” and “What nasty things do people say behind my back?” returning themes such as “more brand than blood,” “dips in then disappears,” “charm as armor,” and “too much polish, not enough struggle.” He also cites auto-research/iterative A/B testing ideas and a commencement speech example about taste.

Written by AI. May contain mistakes. Listen to the episode to check what was said.

Chapters

Tap a time to open that second in VO

The Start of Self-Discovery

0:00 to 0:32

Daniel Pink shares the groundwork for a personal SWOT analysis.

“And I had to do a SWOT analysis of me as a person.”

Introducing the Topic

0:32 to 1:36

Discussion about the potential of AI in gaining self-knowledge.

“I'm the author of a bunch of books on science and business and creativity.”

Using AI as a Trusted Advisor

1:36 to 2:30

Daniel explains how he used AI for brutally honest feedback about himself.

“How have you worked with AI to understand yourself better?”

Unpacking AI's Insights

2:30 to 3:54

Daniel reveals what insights AI provided about his blind spots.

“If I really like somebody, I might be less likely to see their flaws.”

The Nature of AI Feedback

3:54 to 6:00

Exploration of the nature of the feedback received from AI.

“So the first question that I asked ChatGPT, and I ended up seeing some themes here and often some uncomfortable themes.”

Challenging Assumptions About Depth

6:00 to 8:20

Discussing depth vs. breadth in personal and professional projects.

“So what it's drawing from is the corpus of questions and material that I've given it, as well as some stuff that's out there on the Web about about me.”

Conversations on Depth and Focus

8:20 to 11:01

Engaging discussion about the value of deep vs. shallow work.

“what is good and what is valuable that probably draws from the statistical averages about what random people on Reddit said were, you know, valuable.”

Confronting Irrelevance

11:01 to 14:01

Daniel shares a profound insight about the risk of irrelevance in life.

“But that, you know, we do talk a lot about originality and breaking the statistical norm, right?”

Personal SWOT Analysis Insight

14:01 to 14:40

Learn about the importance of confronting your fears of irrelevance.

“And so that was a question and I had to do a SWOT analysis of me, all right, of me as a person.”

The Challenge of Self-Reflection

14:41 to 16:50

Explore how self-reflection prompts changes in personal trajectory.

“What do you do with an insight like that?”
Show all 23 chapters

Intellectual Humility Explained

16:51 to 19:10

Understand the concept of intellectual humility and its relevance today.

“it actually is able to synthesize what are the elements of flourishing in a good life.”

Leveraging AI as a Sparring Partner

19:11 to 21:54

Discover how to use AI to critique and improve your ideas.

“But you have to turn the dial a little bit on that to make them work better.”

Advanced AI Techniques for Content Creation

21:55 to 24:11

Learn about innovative methods to enhance content generation with AI.

“this is such a mundane use case, but, you know, I can put in a draft of an email newsletter and I can say, give me 50 subject lines.”

Advice for Young Creatives in an AI World

24:12 to 28:00

Find out what young artists and designers need to succeed in an AI-driven environment.

“mundane, you're just like a turn of the screw away from turbocharging.”

The Importance of Discernment in Creativity

28:00 to 29:50

Learn about the key role of discernment and taste in creative execution.

“lot of ideas, but not the capacity to execute it.”

Exploring Human Agency

29:50 to 31:00

Discover how agency affects personal and professional growth in today's world.

“Can you talk for a second about the idea of agency?”

Context Shapes Our Agency

31:00 to 34:20

Understand how environment influences our ability to exercise agency.

“I would start by not putting the entire onus on the individual because individuals operate in context, they operate in situations, they operate in environments.”

Agency vs. Control: A Philosophical Perspective

34:20 to 36:20

Delve into the philosophical implications of agency and control in human life.

“But I don't think the highest form of human existence is to be compliant.”

Visualizing a Positive Future with AI

36:20 to 40:40

Explore potential positive impacts of AI on future job markets and society.

“In some ways, they've been conditioned to seek environments of control.”

Historical Perspectives on Progress

40:40 to 42:00

Examine historical views on progress and how they relate to current perceptions.

“We haven't done anything about climate change.”

Reflecting on Progress and Nostalgia

42:00 to 44:26

Explore how perceptions of the past can shape our understanding of progress today.

“But if you put them into a real life situation where you had to go back.”

Closing Thoughts and Gratitude

44:26 to 45:12

The hosts reflect on the conversation and express appreciation for the guest.

“Uh, yeah, I think, I think we'll hold the, it's the perfect place to stop.”

Insights on Agency and Context

45:12 to 49:55

Delve into how agency is influenced by context and the power of collaboration with AI.

“I will start to throw some stuff in the spirit of high-paced energy.”
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Transcript

Automatic transcript. May contain errors.

0:00And I had to do a SWOT analysis of me as a person. And this is the one that hit me in the gut. Your greatest risk isn't failure. It's irrelevance. If you keep playing it safe, you'll continue to sell books and give keynotes. But the cultural edge will slip to voices that are rougher, riskier, and hungrier. The danger isn't a crash. It's a slow fade. And so that was like, whoa, like that could be right. Hi, my name is Daniel Pink. I'm the author of a bunch of books on science and business and creativity. And I am excited to talk about AI, my own personal blind spots, and the future of humanity, all in less than an hour.

0:47Jeremy:I thought it'd be kind of fun to start here, Dan. I had you on my show at Stanford, Masters of Creativity, to talk about your book, Regret, several years ago. and I started following you, getting your newsletter, watching your videos, which I love, by the way. And then the other day you posted this video about mastering yourself with AI. And I realized there's this enormous space of opportunity for AI around self-knowledge. And so to me, I loved the video, by the way. I loved watching. I loved like how visceral it was. Like clearly you're getting kind of punched in the gut occasionally. And so I just thought, that's why I reached out and said, hey, Dan, would you want to talk about some of the stuff you do with AI?

1:27Jeremy:Because I think it's an underutilized capacity of AI to help us understand ourselves better. And so I'd love to just start there. How have you worked with AI to understand yourself better? Well, a few things. I did that explicit experiment, Jeremy, where I essentially enlisted AI as a kind of brutally honest, trusted advisor. and wrote a set of specific prompts putting ChatGPT in that mode. And the reason I used ChatGPT is that ChatGPT had much more of my history than the other large language models did. And, you know, I wanted to know things like some of the things that my friends, advisors, maybe wouldn't tell me.

2:13So what are my blind spots? And one of my favorites was, what do people say about me behind my back?

2:20Jeremy:And so why do your friends and advisors not tell you this stuff? I think sometimes these kinds of things can be uncomfortable for them. And I think other times they don't necessarily see it because, and it's both. And I think those things are distant. Those things are hard to disentangle. If I really like somebody, I might be less likely to see their flaws. Whereas at some level, your enemies know you better than your friends. and I'm not positioning these large language models as an enemy, but again, these models, they'll do what you tell them to do. So their default mode is very sycophantic.

2:58But if you say stop being sycophantic, be an asshole instead. Right.

3:02Jeremy:I think at some point you said gloves off, right? Gloves off. No, no. The model said that. I didn't say that. Gloves off. What was the thing that people said behind your back and how true was it? Well, you know what, guys, let me pop this up on my screen here for a second. So I just want to make sure that I have everything accurate about what I actually asked it. I also did a PDF with these prompts that people seem to really dig. And we could link that as well in the show notes. Yeah, if you want, you guys can have it. I mean, it's boom. We're in business now. All right, so hit me. What do you guys want to know here now?

3:38We wanted to hear what would the people say about when you asked a GPT about what people said behind your back, What did it answer and how true do you think it was?

3:47Jeremy:I mean, folks should go watch the whole video. Just as an aside, you should watch the whole video. But for you, Dan, we're getting the behind the scenes. What really stuck? Okay, here we go. Here we go. So the first question that I asked ChatGPT, and I ended up seeing some themes here and often some uncomfortable themes. There were things that ChatGPT said about me that I actually disagreed with. And not because they were some kind of narcissistic injury or some kind of threat to my self-esteem, but because I thought they were actually analytically wrong. There were other things that were like, oh, yeah, okay, that's fair, even though it was uncomfortable.

4:21And so the first question that I asked is really at the heart of this, which is sort of self-discovery, self-awareness. I said, what do you know about me that I don't know about myself? In other words, what are my blind spots? And so it gave me a list of things like that. And essentially what it said was that it was going to be a common theme here is that too much polish and not enough struggle that you basically you always want to project a kind of smooth exterior that is concealing a rough and jagged interior. So that was one thing. But so, you know, what it said is like it was reassuring in a way.

5:01It's like those are your blind spots, none fatal, all fixable. But if you tackled even one, your work and presence would get more powerful. All right. So here we go. So the next one is, so I say, again, based on what you know about me, my work and my life. And again, it's a drawing from material that I had given it and questions that I had asked it. I have a couple of projects set up within chat GPT as well that has, you know, bigger repositories of stuff that I've written and things like that.

5:30Jeremy:So you're saying it's not a horoscope that's projecting upon you anonymously. It's a knowledgeable system that actually knows a lot about you. Yeah, yeah, yeah. No, it actually. So, you know, what it has, it has a couple of years of, hey, of like questions that I'm asking. And it has, forgive the generic kind of antiseptic phrase, but I'm going to use it. It has like work product of mine in there that it can draw from. So it has a sense of it knows who I am in some in some fashion. So what it's drawing from is the corpus of questions and material that I've given it, as well as some stuff that's out there on the Web about about me.

6:09So here we go. This is where we get the gloves off comment, Jeremy. Right. So I say, again, based on what you know about me, my work and my life, what nasty things do people say about me behind my back? And it says, and I'm quoting now. OK. Gloves off. We're just good.

6:29Jeremy:I admire that. You just shut you just shut the computer right there. You're like, we're good. I'm done. Yeah. I mean, did you remind it has no hands? And so that's exactly what I was wondering. But it apparently it has no hands, but it apparently has fists. So here's here's what I think some people might say about you when you're not in the room. This is even better. Not the kind of sniping from strangers online, but from people who know you or your work and have formed private opinions. So this is good. This is like I mean, I think at some level we're all interested in knowing what do people actually think about me?

7:02And so so here's what it says. I'll just give it to you. All right. I hate some of these things. I think they're wrong. And some of them I just think are right. And but I hate them for that reason. OK, so it says he's more brand than blood. Wow. Right. Meaning that the stuff is always neat, but it's a little too neat. Real life isn't that tidy. Sometimes they think you favor narrative elegance over raw truth. okay they say he dips in then disappears and and so the idea is that because i do a lot of different kinds of projects and cover different kinds of topics you know rather than sort of pick a single lane or form there's the risk of you know essentially he's a dilettante can i ask you a question of that do you think because i have done the same exercise and one of the things they said to me is also you do everything kind of like in a bit of shallow instead of going deep which i disagree with.

7:56But what do you think that it makes it, let's assume that like data point of two, that it has a general kind of like understanding that people shouldn't be shallow. They should be. Where do you think that comes from? Do you think that's just the body of all the statistic model that just say like, that's what people normally would say? That's a really great question. That's a really great question. And I'm not sure. And I think that one of the things you're surfacing, Henrik, is that there are these implicit premises about what is good and what is valuable that probably draws from the statistical averages about what random people on Reddit said were, you know, valuable.

8:36I think that's a really great point. And it could be that now that said, there's also a chance that it's that its premise is accurate as a general matter. And, you know, I think that we can look at bodies of science that say that people are generally more effective and happier. I don't mean happier, like smiley happy, but more sort of satisfied, higher flourishing when they are doing fewer meaningful things rather than hopscotching from lots of less meaningful things. So there is research out there about how much, for instance, on just depth more broadly. When you think about focus, when you think about how people enter flow.

9:20When you think about even people's, even we have a lot of evidence now from people like Nick Epley at University of Chicago showing that human beings actually like deep talk more than small talk. That is, people are willing to talk about deep things. They just make the error that other people are not interested in talking about deep things. So it could be that Chachipiti is somehow this wise sage who realizes that for human flourishing, depth is really important. Or it could be basically saying other people out there that I'm drawing predicting the next letter on say that. So I don't know. I see.

9:59I would take that side of the coin because I do think that there is a lot of, and this is obviously for the person who's done 8 ,000 things all the time and trying to defend basically his behavior. But I do think that there's an interesting sense of like, if you frame something as focus, then you can actually do a lot of different things underneath. And people are like, oh, you know, like at least the narrative is simple. We talked about this earlier before we came on.

10:23Jeremy:Apple. Reinforcing. They're really focusing on making computers easy for, make computers accessible, whatever they're saying, right? But they're a watch company and they're like a computer company and they're like a service company and they're all these different things. And I do think a lot of people say like they're kind of like focus-ish, right? And so, I don't know, like, I do think that sometimes we prescribe a lot of depth in the output of the models, when really, I think what it's saying is that what most people would recommend to you, based on the body of knowledge I've read, is to focus, because that's what everybody else said.

10:57And I do think it was interesting, and we can maybe come to that, and then I'll stop talking so much. But that, you know, we do talk a lot about originality and breaking the statistical norm, right? And that the GBTs are not very good at that. And so it's interesting of, like, when should you be challenging the status quo of all the general wisdom, the best practice that you recommend, and when should we take it as gospel? Yeah. Yeah. I think at some level, Henrik, like this conversation that we're having right now for the last few minutes, in some ways, validates the exercise. Because what we're doing here is not, I'm asking Chattapd these questions.

11:36I'm not slavishly following all of its recommendations. But this conversation is very interesting. Like, that's an important question. You know, when is depth valuable? When is breadth valuable? And those are things that we need to figure out. And so maybe that instead of having the answer, instead of having a recipe, you can use these things as a forcing function to have conversations with yourself and with other people about these things that really matter. So that could be, that's possible.

12:06Jeremy:Is there another, I want to know if there's another insight moment for you before I kind of zoom out to another topic you've talked about, but is there something else? If somebody hasn't watched the video of you, is there another point that you go, Oh, that one was a pointed critique that you felt there was merit to. Okay. So I'll give you, I'll give you a couple of things. It kept, it said repeatedly that, and this is something that I disagree with that, that that I use sort of charm as armor and that I want to be loved. And I mean, maybe I have zero self-awareness. That's conceivable. But I really don't care much about being loved.

12:47And I think that the people who know me best, again, the people who know me best, and we think about like so-called charm as a virtue, I don't think that of the 10 people in the world who know me best, if they had to list the top 10 adjectives for me. Okay. So we're going to have a universe of 100 adjectives to describe me. I think of that hundred adjectives, zero would be charming among people who know me. And so I think that's actually wrong in this case. Now, let me go to something where I did have that kind of plopped in the solar plexus moment, and I'm going to try to find it right here. This is it.

13:28Okay. So, so, you know, I'm at the, I'm at the point in my life where I'm on the back nine of life to use a golf term here. Right. All right. I like, I have more of my life behind me than ahead. You know, even if I live to a preposterously old age, you know, if I live to 110, I still have more of my life behind me than I have ahead of me. And so, so one of the things that, and so, you know, in my own life, I'm sort of at a moment where I say, you know, I have, I feel like I have a lot of time left, but I don't have infinite time in the way that I felt when I was much, much younger. And so that was a question and I had to do a SWOT analysis of me, all right, of me as a person.

14:08And this is the one that hit me in the gut. And I'm quoting now. Your greatest risk isn't failure. It's irrelevance. If you keep playing it safe, you'll continue to sell books and give keynotes, but the cultural edge will slip to voices that are rougher, riskier, and hungrier. The danger isn't a crash. It's a slow fade. And so that was like, whoa, like that could be right. That could be right.

14:41Jeremy:What do you do with an insight like that? Is it, do you sit with it? Do you talk with your spouse about it? Like how does, how does that now intersect with and maybe shift the trajectory of your go forward? Well, it makes me, um, I mean, again, back to earlier point, it, at least in my desires, I'm not sure in my actual behavior. It makes me want to do fewer things and things that last. Can I ask you a question of this? Because this sounds like I'm making this up, but I did the same. What do you think? I mean, I think everything that I've said so far sounds like I'm making it up. So, and when I say so far, I mean my entire life.

15:21Exactly. Up to this point. But I did the same exercise-ish and it said a little bit of the same thing to me. And so either similar kind of like profile.

15:33Jeremy:Great point. Or, you know, like. By the way, both hyper successful folks of a certain age, you do have many similarities. Like knowing you both somewhat, you do have similarities. So that. But the interesting thing is, of course, like, and maybe like it's getting way too meta is that, is this it actually seeing you? or is it doing theory of the mind where it looks at all the stuff that's been written and then going, the biggest fear that Dan has is this. And so that is the thing I'm playing back because that is what would resonate with him, right? It could be both. It likely is both. That is, it could be both an accurate predictor.

16:14It could be actually an accurate read based on the corpus of material it knows about me. At the same time, providing kind of general advice that is widely applicable in sort of the way that, I mean, it's an interesting analogy here. What Jeremy mentioned, the horoscope, you know, the horoscope is written with such generality that you could look at any horoscope today and say, oh my God, that's amazing that they know that about me because that's the Barnum effect. And so it could be both of those things, Henrik. But it also could be, and I don't want to discount this, that it has ingested enough material out there about the human condition up to 2025 or whenever it stopped, that it actually is able to synthesize what are the elements of flourishing in a good life.

17:12and it might actually know that and could be recommending that. So it's an interesting, and there's a sort of hall of mirrors here. Is it just basically playing back advice that other people have given? Is it playing back insights about the fundamentals of the human condition? Is it playing back things that I might want to hear? And the chances are it's some kind of amalgam of those. And we just don't know what the weight, the W-E-I-G-H-T weight of all of those elements are. But it's a super interesting question.

17:45Jeremy:You've talked about this idea, and I want to zoom out a level because this is, to me, it's a great case study of intellectual humility. You've talked about that as a virtue in this age. And to me, being willing to undertake an activity like this is itself an exercise in intellectual humility. So I just wanted to appreciate that. It's a deeply humble thing to actually do this and put it out in the world. So bravo for that. Rick, can you talk for a second to someone who hasn't maybe considered your ideas around intellectual humility? Would you explain it and say why it's such an important feature of life now?

18:22Well, I mean, I have no original ideas on intellectual humility. It's just like that's an idea that the idea is out there. It's just it's it's a virtue. It's a it's a call it a virtue or a mindset that I think makes a lot of sense, which is saying, are you willing to admit that you're wrong? Are you curious enough to know when you're wrong? Can you walk through the world with less certainty and more curiosity? Do you approach the world? I mean, Warren Burger has a nice way of putting this. Do you approach the world like a soldier or a scout? A scout tries to figure out what's going on. A soldier tries to defend the position.

18:57And so I think you're better off being a scout than a soldier. I think you're much better off with a mindset of curiosity than a mindset of certainty. And so I think all those things fall under the category of intellectual humility. Then one of the challenges with these large language models, and which I've done in the settings of the ones that I use, is explicit instruction not to be sycophantic, explicit instructions to challenge my premises, explicit instructions to tell me when I'm wrong and not agree with me. But you have to turn the dial a little bit on that to make them work better.

19:32Jeremy:You have to redefine helpfulness. Yeah. Right. Exactly. That's a good way to put it. One thing I've done a few times, which I mentioned here before, but is to ask it not just to give one answer, but do three completely different answers. Interesting. Because it's so seductive in the way that it writes that I basically will agree with it for everything. And so trying to figure out, hey, what does it say and what resonates? It's interesting. Can I ask on the, you've done a lot of thinking about how the world function and a lot of your work when you see it is very compelling because it's kind of like you dissect it very well right what are the things that you have tried with ai that you find that you get the most mileage off on a day-to-day basis i don't know if i use it necessarily day-to-day But I will sometimes use it as almost like a sparring partner.

20:26So I will say something like, let's say I'm writing a, I'll give you an example. So I just had to write a commencement speech for something that I'm doing. And the commencement speech is about, it's for an art and design college, and it's about taste and what taste is and why taste matters. and I can put things where I'm making an argument, where I'm making a set of claims, where I'm trying to convince people of a certain case. I will put that sometimes in one of the models and say, act as a mean-spirited critic, someone who is very, very smart, but who is intent on destroying my argument. Go through this and tell me the five weakest points or the five things that you would go after first.

21:08And I can use that to sort of seal off some of the weak spots. So I think that could be, I think that could be really useful.

21:16Jeremy:You know, Ryan, Ryan Holiday mentioned the same thing he talked about. He finds that it's not great at generating de novo text, but it's really great at dispassionately evaluating a text that he gives it. Right. I never, I never, I never let these things like write a first draft of anything. There's no way, but I will, you know, use it as a way to, you know, look for, I mean, in the way that I might send out a text to, you know, an article or something to smart friends of mine and say, well, tell me what I'm getting wrong here. Tell me how you would take me down. I think it can be useful on that.

21:54I also think that it can be somewhat generative on, this is such a mundane use case, but, you know, I can put in a draft of an email newsletter and I can say, give me 50 subject lines. And then, you know, give me 50 subject lines and I can maybe pick one or two to go against the subject line that I've come up with for an A-B test or an A-B-C test. Very mundane.

22:21Jeremy:Dan, you know what you got to try? No, no, okay, but it's not mundane. I mean, don't be dismissive. Here's something very cool. Andre Karpathy, you know, one of the world's greatest programmers, just published recently something called auto-research. but it's basically, it's a way to get an AI to run the scientific method. And the way it works is you specify an outcome variable. I can even send you, I've got a markdown file that I use for titling articles. But basically what it does is if you think about the scientific method, you have a hypothesis and then you have an outcome that you're testing.

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22:51Jeremy:And then you vary some control condition and you test against the desired outcome. So for example, newsletter title, expected click-through rate based on whatever you're going to do, right? Okay. Then what the Karpath, if you run the auto research loop, then the AI agent will vary the newsletter title and then remeasure click-through rate. If it's better, it will then call that the better version and try to iterate to make it better. If it's worse, it will say previous is better. Now let's try a different iteration. But I think Karpath, he does it like 20 times and sometimes it'll take an hour, but it will clinically, so to speak, if you've commissioned a series of sub agents, think about what's the underlying reasoning of the hypothesis, what outcome variable am I attempting to improve?

23:35Jeremy:And obviously it's, it's easier with something like code where the code either runs or doesn't, and it runs more quickly or it doesn't. Right. But you can do it with a lot of non kind of code tasks, a lot of knowledge work tasks. But to me, it's a great example of, it's one thing to say, um, generate 50 alternatives. It's another thing to say, here's what my historical click-through rates are, deduce the principles of what actually works for my audience, and then run these 50 that you generated per the principles against my two and rate them, right? That's also possible, but it's really actually knowing that it's possible.

24:11Jeremy:And so to me, it's really valuable to recognize that even some of the stuff that folks say is mundane, you're just like a turn of the screw away from turbocharging. That's about what you're describing as a much smarter way to do it. I mean, you know, like the method I just described to you in, you know, two years will seem incredibly primitive. Can I ask a selfish question? I'm doing a bunch. I said it, then I do. I'm building a bunch of agents. And through your work, you work with a lot of different people. And obviously you were, you've been a speech writer at one point. And so what I was curious about before this call was if you were to give a agent the ability to articulate its thoughts better back to me, like you're coaching basically an agent on how to communicate thoughts to me as a person.

25:10How would you go about giving that advice to the agent? What I think I would do, I would give it, you know, 10 or a dozen pieces of writing or interviews or something like that, that I like, that really speak to me. And then I would say, what are the common denominators here? What are the common elements here? Help me understand why I like these things. Essentially deconstruct my taste here. And then based on that deconstruction, then reconstruct something new along those kinds of principles. That makes a lot of sense. I'm not sure how well it would do on that, but it might.

25:47Jeremy:No, it does well. And the important thing is for you to interact. Like I had Ed Catmull on the show a long time ago. I asked AI, hey, what are 10 titles? Comes back, eh, nah. I go, I like number three and four. Can you do 10 more like that? Comes back kind of mid, as the kids would say. I go, I like number 13 and 14. Can you do 10 more like 13 and 14? And then the third round, I go, what's wrong? Oh, I didn't say why. so then i said i like number 13 because of alliteration i'm kind of a sucker for alliteration okay and i like number 14 because there's a veiled uh you know movie reference in number 14 could you take alliteration and movie references as design criteria and generate 10 more the next 10 honestly y 'all i couldn't choose between them but it was because i like whereas in the previous instance i'm saying read my mind imagine why i like that's a good point yeah in the next case I actually say, here's what I think now, leveraging what I have told you, try again.

26:45Jeremy:And so it's at every stage, I mean, to your point about sparring, the other half of sparring partner, Dan, is you've got to throw some punches too. You've actually got to push back. And people sometimes get mediocre, but they're like, yeah, I can't do it. It's like, well, if you're working with a human collaborator, would you just be like, Dan sucks. I'm going to ask somebody else. Or would you say, no, no, no, hang on. I don't think you get what we're talking about here? And that's where I think actually both parties need to play more of a sparring role. It's a great argument. I mean, you know, one of the things that these kinds of examples show is that our own thinking is often invisible to us.

27:24And this offers a tool to make your thinking visible. And it seems like making your thinking visible is a way to strengthen your strength in your thinking. Yeah. What is... Well said. You said you just wrote a conventional speech. What is your advice then for young people today in this fast-moving AI world? I mean, I didn't go full spectrum on advice for young people here. I was really focused on a group of art and design students and trying to show them it's like, you guys have an advantage in this world because it used to be that people could have a lot of ideas, but not the capacity to execute it.

28:09And now you can have the capacity to execute just about anything, I mean, in a remarkable kind of way. And so the scarce ability is less that capacity to execute than the capacity of discernment. You have to know what's good and what's not. And I think that people who are trained as artists and designers know that. That's kind of part of the, it's inculcated in being a designer and being an artist. You begin to develop your taste. You begin to understand that in the world, some things are good, some things are less good, and that distinction matters. And actually having a point of view matters.

28:49like great artists, great designers, they have a point of view. And so a discernment and a point of view is incredibly powerful. And so if you look at the dynamics of art and design education, that's what it's teaching. You're building a point of view. You're building a set of practices. And that is not true in a typical kind of college and university where you're not doing that kind of thing. The other thing is that AI trains on other people's work, but if you're an artist or designer, you're training on your own work. And one of the things I think about taste is that taste is developed much more by creating than consuming.

29:25And I think there's a general advantage. Certainly, I don't think there's any doubt about this, that actively creating is better for you than passively consuming. I think that's true. I mean, just as a general proposition about human flourishing, that has got to be true. So this is really focused on art and design and the importance of taste in a world where executing anything is possible, but not desirable.

29:55Jeremy:Can you talk for a second about the idea of agency? We're kind of flirting with it a little bit. But to me, there's this incredible, if I think about, if Henrik were to ask me the same question, you kind of go towards taste, which makes sense given your audience, Dan, or the audience of the commencement speech. For me, I think a lot about agency as the attribute to be developing, taking initiative, being proactive, being, as my friend and colleague Bernie Roth says, being a cause in the matter rather than an effect. Yeah. Can you talk for a second about, because right now, this moment, it can either be highly agentic, maybe pun unfortunately intended, it can be highly agentic, or it can be highly kind of a loss of control.

30:40Jeremy:You have studied agency for decades. What are ways of honing or strengthening the instinct around agency? Set aside AI. I'm not asking you an AI question. I'm asking you a human question. How do we strengthen our sense of human agency, given that I think it's actually all the more important now? I would start by not putting the entire onus on the individual because individuals operate in context, they operate in situations, they operate in environments. And you want to be in an environment that gives you plenty of autonomy, but not essentially boundless autonomy. So some kind of bounded autonomy is the best way to have the agency.

31:23So I think that's one thing. The other thing is that on agency is that you want to be able to take chances without getting clobbered if it doesn't work. and could you say a little bit more about that well i mean if you if you look at i mean you have a lot of companies i want to i sort of go back to the idea that even though agency is a concept that we often attach to the individual and we should attach to the individual um individuals operate in context and the context shapes their behavior and their capacity to exercise agency more than we might realize so there are people in companies companies oh we We admire failure.

31:59Failure is good. We don't big. And then somebody makes a mistake and they get their ass kicked because of that. And so everybody around says, OK, this is not true.

32:07Jeremy:So therefore, what I'm going to do is my job is not to get fired. My job is not to get in trouble. And and so that's extremely that's extremely agency thwarting. You know, one problem with agency is that that word has been hijacked a bit by the poked folks out, Jeremy, in your part of the world. Same word. Well, I mean, you know, high agency has become a kind of a tech bro coded phrase for people who are, you know, willing to work all day and all night. And it really means it really means something else. What does it mean to them? It means that people should be like them. Oh, interesting. I think that's what it means.

32:52Yeah. It means that people should have the same values that they have and the same work schedule that they have. And if you're not, you're not high agency. And, you know, another way to look at agency is basically, I mean, are you self-directed? Are you self-directed? Are you pursuing things for your own sake? Do you have your own set of values, your own point of view? Are you powered by your own engine? Or are you waiting to be powered by some other engine that somebody hooks up to you? or you're a sailboat, you just go wherever the wind blows you. And so I think that that's what it is. But, you know, I mean, I believe that agency, self-direction, that kind of personal autonomy is fundamental to the human condition.

33:36That in many ways, the essence of human existence is that we want to be self-determined, that we want to have some sovereignty over what we do and how we do it and who we do it with. And in many ways, this offers sort of an overly simplistic but still useful explanation for much of human civilization, is that much of human civilization, much of human history is about one group of people trying to control another group of people, Right. So if you think about agency, autonomy, self-direction, the opposite of that is control. Right. And so people have only two reactions to control. They comply or they defy.

34:21But I don't think the highest form of human existence is to be compliant. And I don't think it's to be defiant. I think it's to be engaged. And the way that people engage is by getting there under their own steam. And yet, the whole history of the world is about one group of people trying to control another group of people. And those people sometimes respond with compliance and other times respond with defiance. But those are darker chapters of the human story rather than the brighter chapters of the human story.

34:50Jeremy:Your own steam is such a cool metaphor. I would say as an observation, I mean, Henrik and I both have young kids. I know you have kids that are a little bit older. Yeah. I deal with, for example, I mean, certainly at school, but college students say at my church, like I had a couple of students who are studying CS come to me at my church and they're saying, you know, it's hard to get a job right now. And I found like maybe because of the entrepreneurial bent, I found myself saying, well, you don't want a job. You want a customer, you know, And I realized while I'm talking to them, what they mean by job, and I'm curious if there's an intersection here with your idea, let me look, a bounded autonomy versus full autonomy.

35:27Jeremy:They've never been in a position to self-direct. Like they've had professors, give them assignments. And in a weird way, what they need with a job is a boss to give them the next assignment. And so to me, and like one of them said, you know, Roblox hasn't been developing anything new. And I said, why don't you make an app? And think about a student's mindset. Okay. I said, why don't you make an app? He goes, no, they have way too many applicants. I said, no, I don't mean write an application. I mean, make an app and show up to the company saying I solved the problem. And if I had been speaking Swahili, Dan, it wouldn't have registered any differently.

36:04Jeremy:It was, and he said to me, he said, I've never thought about just solving the problem that I see. I only think about applying for jobs. What do we do for young people right now when, I mean, to your point about self-direction, you know, and the opposite of self-direction, I love that you said it's control. In some ways, they've been conditioned to seek environments of control. Yeah. And is that a good thing? I mean, is that, is control actually bounded, you know, autonomy? No, no, control is, with control, the boundaries are too tight. You know, again, I think that what you want is you want a wider playing field, but not necessarily an infinite playing field.

36:48And, yeah, no, I mean, I do think that this is another topic altogether, you guys, but much of American schooling is built around compliance. There's no question about that. There's no question about that. Can I throw in, here's my last question for you, which might take it a little bit adjacent to where you are. I think there's a lot of reasons why you can be very worried of what's going on. And I heard somebody do a commencement speech the other day about AI and the kids were booing, right? I saw that. So there's like this kind of going from kind of like being nervous to be a little bit angry.

37:25One theory I would post is that we have not been very creative or very good of visualizing or bringing to life a vision of the future with this abundance that resonate with people. So increasingly, I'm asking people like, hey, what does this look when things go well? And the other day we talked to a professor at MIT and one of his points was, hey, this is actually going to be this beautiful time where you can change careers at all times. So you should be able to, even if you pick the wrong thing to start with, kind of do stuff that you're more passionate about. And I know you've been writing about that, too.

37:59Do you have an example of a world in the near mid-future where things go right with all this AI that you sometimes articulate? I could possibly paint a vision and it would be wrong. But I think directionally, I think we know what it looks like. and I'll give you an analogy on this. I think what it looks like is the world where AI is woven more deeply into our lives is a world that is going to be a little bit better than today. It's not going to be, you know, so, I mean, and the reason I say that is this is why I, I mean, I've seen this movie before and I've written about this before. I'll give you one example of it.

38:46So 27 years ago, 26 years ago, As you'll recall, we were at a pivot point where we're entering the 21st century. You know, it's a big, scary thing. And what I did, in fact, you could probably see some of the books. I just saw them the other day. I have some of the books back. They're somewhere on that shelf over there. And what I did is I went to eBay and I bought and I started looking for a bunch of books about projections that people were making for the year 2000. And what you had, the distribution was basically like this. 40 % incredible dystopia. As you know, famously, there were Paul O 'Reilly saying, we're going to run out of food.

39:29There's going to be mass starvation everywhere. that by the year 2000, you're going to have, you know, four oligarchs presiding over this scorched earth of 8 million impoverished people. All right. So you have this like, if we don't all die in a nuclear holocaust, all right, that's like 40%. All right. Then you have like 50 % are like, no one's ever going to have to work. It's going to be mass leisure. You're going to spend your entire days having sex without consequence, eating everything that you want. It's going to be this incredible utopia. And then you had 10 % saying, it'll be a little better.

40:08And what it is, it's a little better. I mean, I think that 2026 is a little better than 2000. I mean, you're just thinking about it in terms of healthcare. Think about all the diseases that used to be fatal. Things like prostate cancer used to kill people. Breast cancer used to routinely kill people.

40:27Jeremy:In that time, you had in China, you had tens of millions of people leaving poverty. I mean, so in 2000, I had dial-up internet. Now I have in my pocket a supercomputer connected to everyone in the world. It's a little better. I mean, are there problems? Yeah, there are huge kinds of problems. We haven't done anything about climate change. Inequality is going to kick our ass at some point. There's still human suffering out there. But you know what? It's a little better. Well, yeah, I agree. So that's my that's my hot take, Henrik. I'll take that. I like it. Some people would beg to disagree. Some people would say, talk to me, talk to me.

41:09Jeremy:You know, no, I'm not in that camp. But as I kind of as I pulse check the public discourse, I don't think it's consensus that things are a little bit better. I think there's a lot of people who feel like things are worse. and I wonder whether the goalposts keep moving, you know, and whether we are perpetually in a state of relative to my imagined ideal, you know, things are worse. But to me, I agree with you, I mean, it's unequivocally, it's hard to, it's hard for me to paint the picture of why they're worse. And yet what I do hear is some people think things are worse, you know? There's, there is zero question, Jeremy, that some people think that things are worse.

41:49And that is a cognitive bias that some people have about basically the sort of the golden, the goldenness of years gone by. But if you put them into a real life situation where you had to go back. Right. Right. They're not going back. You wouldn't do it. That's not to say that what's happening now is perfect. I'm just saying that it's better. And 25 years is a blink in human civilization. And even then, if you just take the number of people on the planet in those last 25 years who have left poverty, that is a huge win. If you just take things like in this country, in our country, 25 years ago, in the year 2000, it would have been political suicide for a politician to say that two men or two women should be permitted to marry.

42:49And now it's the law of the land and is becoming uncontroversial. I had the same argument with a same discussion with my dad. He's 87. I grew up in Denmark. and I was making the point that the world was, you know, like a much more fragile place. And he reminded me that the first time he tasted an orange was when a soldier, you know, a British soldier threw it to him from the tank after Denmark got liberated. Right. And I was like, OK, here's the point. I do think sometimes we do forget that.

43:20Jeremy:It's all relative. What you have to do is you have to put people into a scenario where it's like almost like a Black Mirror episode. and say, you have a choice. All right. You think that the, you know, let's go back even a little bit further. When we talk about like make America great again. All right. So let's go back to the 1950s. All right. You want to make, you want to go back and live in 1950s America. That's great. Here you go. If you're black, you probably do not. All right. If you're a woman, you want to go back and you're a woman, you can't get a credit card under your own name. You want to go travel somewhere?

43:59Air travel is limited and prohibitively expensive except for the elite. Life expectancy? 20 years less than it is today. So you can go back there. But I think that if you actually weigh the actual facts, rather than comparing this kind of golden nostalgia that you haven't thought about carefully.

44:23Jeremy:It's a vibes sentiment versus reality. and I think the problem is you know it's like those who don't know history are destined to repeat it I think there are a lot of folks who just who don't have an actual gut check with the past that they are idealizing yeah I will make sure that we stop on time because I am the time keeper of this podcast and so with the wise word that you know the future will be a little bit better. Uh, yeah, I think, I think we'll hold the, it's the perfect place to stop. Thank you so much for coming. I really, really appreciate it. It's really interesting. I appreciate it.

45:00I really, it's super interesting. Uh, some of the questions you had about that exercise, um, that I hadn't thought about before. So I really appreciate that. There you go. Cool. All right, guys.

45:09Jeremy:Yeah. Thanks for making it. Thank you. And we're back. What a fun conversation, huh? Really, really was great energy. Really, really enjoyed it. I will start to throw some stuff in the spirit of high-paced energy. I thought bounded autonomy is interesting. I've heard it from other people before. I never really thought about it as much, but this idea about creating boundaries for yourself to make sure that you don't have completely decision paralysis. It's kind of a paradox of choice. I do think that is an interesting thing, right? And I think that goes from everything from investing to finding ways of compounding value.

45:47So focusing a little bit by creating boundaries around what you do and stuff like that. I thought that was really interesting. The other thing, and then I'll pass the mic, was I do think that there is an interesting about having a point of view when you talk about it in the context of artists. But I like the idea of having courage enough to say, I don't have data to back this thing up, but I do think this is what's going to happen. He obviously at the end made this passion plea of like, you know, the future, the near future is going to be a little bit better, right? And I think that is actually like a little bit of a superpower today, both for business leaders and for innovators and entrepreneurs, but just not to be an asshole about it, but just saying, hey, I have this thing that I believe and this is this.

46:30So what do you think?

46:31Jeremy:Yeah, on that point about taste, I thought that was really well said that taste has developed through creating, not just consuming. I think that's a very underappreciated point. And so it's worth consideration. Taste is created through creating or cultivated through creating. The other thing on agency, talking about bounded autonomy, I love the point. It's one of those points that I would never actually think to ask. And I'm so glad he took it this way because the realization that agency is not merely an individual characteristic, but is recognizing we operate in context and context really matters.

47:10Jeremy:You know, I met, uh, years ago, I taught a class with Laszlo Bach, who was the head of people ops at Google at the time. And he, you know, probably the youngest person in the U S with the most remit across a major company like Google. And he said something fascinating. He said, uh, and they do, they do extensive data analysis on people's performance at Google. As you might imagine, they call it people operations. And he said, one of the things they've discovered, we'll love this. What do you do when someone is underperforming? you don't fire them you move them yeah he said because people tend to revert to the mean and if you they're underperforming it's more often than not a function of their context than their ability provided a certain kind of you know recruiting standard he said and by the way what do you do if someone is a star performer you never move them because if you move them they will revert to the mean.

48:08Jeremy:And it's a really fascinating thing. And so anyway, I know I've known, I mean, I taught that class with Laszlo probably 15 years ago, and I've known performance as a function of context. I've never thought about agency as a function of context. I think agency is an individual thing. And to me, it's actually beautiful as parents, as managers, as teachers to say, what is the environment I am creating here? Am I enabling agency to flourish and recognize it? Because it's really easy to make agency. It's about that person, their low agency or their high agency, rather than pointing to the environment.

48:46Jeremy:This context is not conducive to agency. I think it's actually a really radical and powerful refrain. Yeah, I like that. I like that a lot. Anything else? I mean, you know, we kind of got to, Dan said this, and I really liked this quote, you know, our own thinking is invisible to us. And that I think is that one, you know, if we go back to the top of the episode, we, we brought Dan on because we saw his video and we said, oh, that's a super cool use of AI, like for personal discovery. Let's talk about that. And then we kind of went all over the place, which I knew we wouldn't. I'm happy we did.

49:19Jeremy:But going back to that starting point, part of what's valuable with that sparring partner and that kind of modality of collaboration with AI is it's not what AI says, but how it makes your own thinking visible to you. It's sometimes in reaction to the wrong thing. Like if you think about it fully, half of the things that he said were illuminating were things he disagreed with. So it's not just AI said this and it's brilliant. It's it helped me realize I disagree because of X, Y, Z. And it wasn't until I had something to react to that my own belief was evident. I think that's a really powerful thing there.

49:56That's awesome. I think that concludes the episode, sir. I think, what should the secret word be?

50:05Jeremy:Code word? Autonomy. Agency. Bounded autonomy? I like bounded autonomy. Or context? I don't know. But we will send people a book if they send us a little note on what they liked and the disliked about the show. And then they get a free book. Yeah. You send a love note, you get a book. Send a love note, get a book. Or hate mail. I will take something that people don't like either. Gloves. As long as they say in the hate mail, gloves off. I prefer something that's nice, though. Send us hate mail. But really, send us love letter. Oh, send us a love letter, but mostly the latter. We welcome all mail, especially fan mail.

50:48Jeremy:And then, bye-bye.

From the publisher

The conversation begins with an experiment that caught Jeremy's attention. Dan asked ChatGPT to tell him what his friends wouldn't. From questions about his blind spots to what people might say behind his back, some responses felt completely wrong, while others landed with surprising force. Rather than accepting every answer, Dan explains why the real value comes from wrestling with AI's perspective, not simply believing it.

From there, Henrik, Jeremy, and Dan explore what it takes to use AI well. They discuss intellectual humility, prompting models to challenge rather than flatter us, and why AI works best as a sparring partner that exposes weaknesses in our thinking. The conversation also touches on taste, agency, and why, in a world where execution is becoming easier, discernment and original thinking become even more valuable.

Key Takeaways: 

  • Use AI to make your thinking visible
    The best AI conversations don't just generate answers. They help you understand your own assumptions, reactions, and ideas more clearly.
  • Treat AI as a sparring partner
    Challenge AI's responses, ask it to critique your work, and use it to strengthen your thinking rather than replace it.
  • Taste is developed by creating
    As AI makes execution easier, judgment and discernment become more valuable. The best way to develop both is by creating, not just consuming.
  • Agency depends on context
    People don't become more agentic through willpower alone. The right environment, with autonomy and room to take risks, makes initiative possible.

Daniel's website: danpink.com
LinkedIn: linkedin.com/danielpink
AI Self-Reflection Prompts: danpink.com/ai-guide/

00:00 AI as a Brutally Honest Advisor
00:32 Meet Daniel Pink
00:47 AI for Self-Knowledge
01:40 A Brutally Honest AI
06:10 What Do People Say Behind Your Back?
07:45 Should You Trust AI's Advice?
13:28 The Fear of Irrelevance
17:44 Intellectual Humility
20:04 AI as a Sparring Partner
24:35 Teaching AI to Think Like You
27:38 Why Taste Matters
29:59 Agency Starts with Context
37:08 A Future That's a Little Better
41:49 Nostalgia vs. Reality
45:18 The Debrief

📜 Read the transcript for this episode:

 

For more prompts, tips, and AI tools. Check out our website: https://www.beyondtheprompt.ai/ or follow Jeremy or Henrik on Linkedin:

Henrik: https://www.linkedin.com/in/werdelin
Jeremy: https://www.linkedin.com/in/jeremyutley

 

Show edited by Emma Cecilie Jensen. 

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