Transcript of 685: David Epstein - The Freedom Trap, Narrative Values, General Magic, The Nobel Prize Winner Who Simplified Everything, Wearing the Same Thing Everyday, and Why Constraints Are the Secret to Your Best Work New

My next book, The Price of Becoming, will be out in a few months, available for preorder right now at learningleader.com. But in the meantime, I've been sending it to authors that I really look up to. A lot of them have been on this podcast. One of them is Daniel Pink, bestselling author of To Sell Is Human, Drive, Win, The Power of Regret, and many others. Just asked him what he thought, asked him if he'd write a blurb, an endorsement for the book, maybe one that I would put on the COVID And this is what he sent back to me. Dan Pink says, The Price of Becoming refuses to sell you a shortcut. Instead, Ryan shows how small daily deposits—100 shots, 500 words, a single tough conversation—compound into something that looks like an overnight success to anyone who wasn't paying attention. This is a clear-eyed, Powerful book. I'm super grateful for people like Dan Pink to have read it and shared his thoughts. I would love it if you would go to learningleader.com and preorder the book right now, or just go straight to Amazon and preorder The Price of Becoming. Thank you so much. Welcome to The Learning Leader Show presented by Insight Global.

I am your host, Ryan Hawk.

Thank you so much for being here.

Go to learningleader.com for show notes of this and all podcast episodes. Go to learningleader.com. Now on to tonight's featured leader. David Epstein is the author of The Sports Gene and Range, which spent years on the New York Times bestseller list. Before writing books, he was an investigative reporter at ProPublica and a senior writer at Sports Illustrated. Illustrated. His new book is called Inside the Box: How Constraints Make Us Better. During our conversation, we discussed why leaders should be regularly teaching others, then the problem with too much autonomy and how David learned this the hard way, then why the phrase how you do everything is how you do anything is completely wrong. We talk about that and so much more. Ladies and gentlemen, please enjoy my conversation with David Epstein.

David, man, it is awesome to have you back on the Learning Leaders Show. Welcome.

Thanks so much for having me again. It's a pleasure to be back. Wish I wrote books more often so I could come more often.

Hey, we don't have to wait for a book next time. All right. Okay. It's funny, you know, speaking of books, so I sent my recent my book that's not out yet, comes out in July, to 50 people and a handful of those people to get book blurbs. The other people, I sent it back to give me feedback. And you gave me one of the most valuable pieces of feedback just this week. You pointed out a factual error, not a typo or anything like that. Those are easy to find, but a factual error and made me completely rethink it and then change it. And it's being updated as we speak. So that's one of the most kind and generous things that a person could do. And I didn't ask you for that. I just asked you for a blurb, and yet you went above and beyond. So I just wanted to publicly say thank you for that. That was super, super kind of you to do.

I really appreciate that. I feared that I was causing a little bit of a hassle or being, you know, like you asked for a blurb and I was like, you know, I think this thing might not be right, but I thought since I saw it, I should draw your attention to it. But that's very kind of you to say and acknowledge.

Well, not to harp on this too much, but the easier move in a situation like that is just to let it go. That's the easier thing to do. The kind move, what great leaders actually do, David, in this case is they're willing to point it out and maybe cause some friction because you care more about me or how it's going to be perceived if I have an error in my book. And so I think that is really cool. It actually inspires me to want to be more like that. So I think it's worth it from a leadership perspective to point that out, to say, 50 other people have it right now. Nobody else has mentioned that, including ones who are proofreading it. So it's really cool. I appreciate that.

And I'm, I'm a fastidious fact checker and I just thought about what I would want in that situation. But I'm also the type of guy who, if somebody has something in their teeth, I'm, I'm like, okay to point it out cuz I think it's helping them. And you know, you just, you just have to do it in a polite way and then I think it's, it's, it's fine. Yeah, absolutely.

Let's get on to your book, Inside the Box, the newest one. And your dedication says 4A. I noticed there's actually a restraint in the dedication. It's like an act of constraint. It flows with the book. Is that on purpose?

Yeah, kind of, but also it's the first initial of my son's name and I just talked to him about it and we talked about it and he thought that would be cool. And so if he thought it would be cool, I thought it would be cool. So that's what we went with. Why not the whole name? We were just talking about it together and, and he thought it would be neat. So it was really just because to be sort of a fun inside little secret with my son, basically.

It's funny, Morgan Housel had a funny inside secret with his sister on his dedication too. And I, I love digging into those stories that we're all humans and we want to do cool little things for the people that we love with the, with certain parts of our book. So really, really cool, man.

Yeah, because it's like there's only one person who's gonna care about, or like two people that are gonna care about that dedication, me and him. So it's like. The one part of the book where I don't think about the audience. It's just for us. I love it. You know, my first book, The Sports Gene, I dedicated it to my wife and I called her my own very own MC1R gene mutant because that's the gene mutation that gives you red hair. And so I've got a lot of questions about that. So I try to use the dedications for— that's like the one spot where I'm just like something fun for me, you know, and one of my loved ones basically. Love it. Love it.

Let's, um, let's talk about your second book for a second. So. Range comes out and it's mega viral, right? It's everywhere. It still is to this day. It kind of created freedom for you to do whatever you want, which is cool. It's what we all think and it's what we all want. Yeah. But there's a question that you ask yourself, what are you optimizing for? And the answer that you came up with was autonomy.

Yeah. At the time. At the time.

Can you walk me through that whole situation with Range?

Optimizing for autonomy and how that made you feel.

In the late stages of writing Range, up until the late stages, I had a normal job. I was working as a more traditional investigative reporter. Like, I was writing about drug cartels and stuff like that. And I realized I wasn't going to be able to finish Range if I was staying in that job, which I loved, but I wasn't going to finish. So I left to finish, thinking maybe I'd go back. Didn't really know. Then the book comes out and does a lot better than I expected. And that allowed me to do this thing that every writer that I had known for years wanted to do, which is go on your own and do your own thing, have control of every topic you write about and the length you write to, and, you know, not being edited, all that stuff. So I was at this writer's retreat and, and there was a question we all had to answer, which was, what are you optimizing for this year? And that's when I said autonomy. And I, I set about just individualizing my whole life. I didn't write about anything that anybody else assigned me, only me.

I made my schedule totally individualized, and that's what I thought I wanted. And, you know, fast forward a year or so later, I learned there is such a thing as too much autonomy. I really missed the structure of a specific workday, of sometimes having other, other people asking you to do things or solve certain problems. So it's clear what you should be doing. The deadlines, the sometimes the annoyances of scheduling with other people, right? Where I had individualized my schedule so much that I was, I was never inconveniencing myself, but it meant that I wasn't really connecting with other people in the way that I was used to. And so this total freedom that I thought I wanted ended up feeling terrible, basically. And I've been reeling it backwards. So when I was in this phase, so one of the things when I had this total freedom where I said, gosh, books are so consuming, it's so hard. It takes up so much of my life and energy that I'm not writing another one unless I find the perfect topic. So I start dipping my toes into all these topics and I like it. I'm finding several things fascinating, but none's perfect.

And so, like, picture me, I'm basically like on a dating app, but I'm going for book topics. I'm just like swiping and swiping. I couldn't pick anything. Like I kept thinking, is there something a little better? And then I read this quote by Mihaly Csikszentmihalyi, the psychologist who coined the term flow for the feeling of immersion in an activity. And he's talking about marriage, but you could sub it for any other word. It wouldn't matter. And basically he says the great thing about being committed by your own choice is that you can stop wondering how to live and start living. Like it frees up this energy to actually do the thing. And I was like, man, this is what I'm doing with my topics. I'm just like wondering what's around the corner. That day I said, I'm really interested in constraints. I need some myself. I'm writing a book proposal on this. And of course, 2 weeks later, I was 10 times more interested in it because I decided to dive into it. And so that was the start of this process of me reeling back some of this excessive autonomy where, you know, I joined the board of a nonprofit in my community.

I started going to dance meetups so I could have embodied experience with strangers. All these things that kind of started adding structure back to my life. Even in my workday, I borrowed from a character in the book, one of the greatest living writers. She lights a candle to start her workday and blows it out to finish the workday and closes the door. And since I work at home, I would never shut down my workday. So I stole that from her. I use an electric candle though, because I have too much paper in my office. But, you know, and now that I mention it, I like my neighbor Cal Newport, the author of Deep Work and Slow Productivity. He'll, at the end of his workday, he does like a compute— he's a computer science professor— he'll say, system shutting down. You know, it seems silly, But when you have all that freedom, you actually need something to close the workday so that just like an athlete in training, you can recover and be ready for the next hard bout the next day and to be there for your family and all those kinds of things.

It's funny, I think I want to have my calendar completely open. No meetings, no structure, nothing. I think that. But then when I go back and analyze a month and I look at my calendar, I'm actually not that productive on those days. Yeah, I'm almost more productive when I have to squeeze in some stuff in between Zooms or in between other things, or I have a deadline.

It's weird. And your book kind of helped me understand that a little bit better.

Can you tell me more about the science of—

we think we want this thing of a wide open day and no meetings. Oh, this is going to be great.

And then before you know it, it's 2:00.

It's like, what did I even do? Yeah, so there's all this research on what cognitive psychologists call the path of least resistance. Basically, I love the way cognitive scientist Daniel Willingham puts it, where he says you may think your brain is made for thinking, but it's not. It's made for preventing you from having to think whenever possible, because thinking is energetically costly. And so when things are too open, all you'll do is what's convenient. Basically, your brain will be lazy. Yeah, because that's, that's what it wants to do. And so if your time is unstructured, your tasks are unstructured, what people typically end up doing is doing things that are easy. There's actually a finding in psychology called the mere urgency effect, where if things are too open, people will start doing things that seem like they, they're kind of urgent, like they have a deadline, even if they're unimportant. So when you're too unstructured, you'll start doing a bunch of stuff. But with no relation to its importance, just to have like checked off doing something. And so I think the typical pattern is when people— not that you shouldn't have slack time in your work at some points, right?

Because that's, that's a whole different topic. But when it's too free-flowing, people end up doing huge volumes of low-value stuff. And then it's only when they really see the deadline or some pressing need for those bigger things where they— now it's time to like really focus on that, basically. And so you want to be more proactively structured if you don't want to end up falling prey to all these cognitive biases where you'll busy yourself with relatively low-value work if you don't structure your time.

How do you do it? How do you structure your days now?

When I was in the book writing mode, which is most of what I've been to up until just now, basically, there are a few things I did. One, I would batch a lot of my work. So a lot of the research that went into Chapter 9, Gloria Mark's work on Attention Span. One of my main takeaways from that was that you should be batching your work so that you're monotasking in a given hour, say, during your day. So she found that people at work check email on average 77 times a day, and you can do all your email, you know. I'm not saying you don't need a lot of time for email. The way that people are usually doing that is they're toggling all the time between email and something else, and when you do that, one, it lowers your productivity. And now we know it, like, from physiological markers, it massively increases your stress. And there's some evidence that it might affect your immune function even. So you don't want to be doing that toggling all the time. And so if you can batch and separate that email into maybe 2 blocks during the day, you know, one in the morning and one in the afternoon— maybe that's not realistic for everybody, but maybe you can even start with a half hour of doing it and then a half hour of doing something else where you're not toggling.

So that's an important thing for me is batching. And when I was writing the book, this isn't right for everybody, but I wasn't looking at my email until my important work for the day was done. I used to start in my inbox. After reading her research, I never start in my inbox because of something called the Zeigarnik effect, where an unfinished task leaves like an open loop in your brain, basically, where it's taking up some of your working memory. And your inbox, right, is a never-ending, like, Zagarnik effect engine. And so I wouldn't open my email until really the end of the workday. Now, I'm working independently. That might not work for everybody. But I think most people can start the day with at least a little bit of what their important work is before they go into that, that inbox and captures their attention. So that's part of the way I structure it. And then I would, I end the workday like when my son comes in from school. I used to work like all through the night and all this stuff, and I actually don't think it made me better. I now think of it much more like a nap.

I mean, I was a competitive 800-meter runner, and you know that you have to program rest just as assiduously as you have to program training. And I now realize that's true for writing too. And so this book, my previous two books, I turned in at 5 PM on the day in the contract. This one I finished early, and I just sat on it for a few weeks. I'm like, Does anybody turn in books? I don't even know what to do. And then I sent it in. But I think focusing and then resting, along with some other constraints that I implemented in my process, actually made me way more efficient.

I think it was Michael Easter. Stress plus rest equals growth.

Brad Stone and Steve Magnus are on that all the time. Yeah, yeah, absolutely.

That feels like what you're talking about. So stress, like go hard, plus rest. Is what equals the growth, or in your case, what equals productivity. Getting the work done in a little bit more structure in your day seems to be helpful. What about for the person who does have lots of meetings, the corporate America leader? So it's not too much free time, but how are they still productive in between all of these meetings that they need to go to, or at least they think they need to go to?

Yeah, I mean, attempt to schedule some blocks where you have focused work. I, I was talking to— I did a I was interviewing recently Ryan Poles, the general manager who turned the Chicago Bears around. And like, he's kind of obsessed with constraints now. So he's starting to see it like, he read an advanced copy of the book and I now see it showing up. He'll like text me laughing whenever he gets a constraints quote now. Because he came into a team that was a teardown and didn't have much to work with. And so they really built a lot of their systems around constraints. And he'll talk about in his own work, he has to schedule time just for thinking. Every day. And he said, that sounds silly. That should be the thing you just fit in between stuff. But if you don't schedule it, it does not happen. And GMs, for anyone who knows pro sports GMs, they are absolute workaholics. Like, they could be working every second of the day. And so for someone like that to say, I schedule in just thinking time, and I think he has 2 blocks a day, if I recall, where he schedules just thinking time.

These don't have to be super long. but sometime where you slow down, what's the priority work to do here? What's the thing I can focus on? And, and you just get a little bit of thinking time. So scheduling that in as if it's as important as those meetings, because it is, we just don't usually schedule it. Overall, the extent to which you can monotask through the course of the day, it seems inefficient, right? You feel like you have to monotask, but again, Gloria Mark's work shows that If you can break these things up into blocks of monotasking instead of multitasking, you actually will end up with more done overall. But it makes people feel bad because they have to delay certain things at least a few hours.

I love reading about Daniel Kahneman and your relationship with him. You had a lunch and he said— did I get this right? That he, like, Thinking Fast and Slow is, you know, a classic, that he was miserable writing it.

Yeah.

And because of that, he co-authored his next book. Can you get into your lunch with him, what you've learned from him, and how maybe it's impacted you as a writer and as a leader?

Before I was a writer, I was trained to be a scientist. I kind of obsess over misuses of data, and I was giving a talk at some event about some misuses of data, and I didn't know he was in the audience, but someone after the talk said, oh, Danny Kahneman would like your email address. Like, sweet! Because I'd read a bunch of his papers and everything. It was like 6 months later, he emails me and it's like, Do you want to get lunch tomorrow? Like, I'm there. Yeah. And as we were talking, well, two things. First, I brought this paper that I wanted to ask him about called On the Psychology of Prediction, and he said it was his favorite paper that he'd ever written, so I had him sign it. Um, and I now have that framed, but I was confused at the time where I was reading a lot of expertise research, some of which showed that people got better with like very narrowly focused practice and specialization, and some that showed that not only did they not get better, they got more confident, but not better, which is a really bad combination.

And he said, oh, and I was telling him which papers I was reading. And he said, oh, oh, yeah, no, I know the answer to that. It depends on the characteristics of the domain. You need to go read this research on kind versus wicked learning environments. And in the kind environments where work is more repetitive and feedback is quick and accurate and work next year will look like work last year, that's where this really narrowly focused training excels. But in the wicked learning environments where Things are always changing. Feedback could be delayed or inaccurate. Work next year might not look like work last year. That's where you act— often see narrowly focused practice making people more confident but not better. And that ended up becoming the frame for a lot of Range, basically, that people with this broader toolbox were better equipped for adapting in a fast-changing work world. And so we talked about that and it ended up becoming very important for the book. But then we just got into talking about books and writing. And of course I'm like praising Thinking Fast and Slow, you know, like it's a, the book's amazing. If you take out the chapter on priming, there's none of that work replicated.

But he said, never again, never again. Like, really? And he was saying it was horrible. He said it was the worst few years of his life because it was so isolating. Like, he was used to working with a partner or multiple partner and colleagues, and he felt so isolated. So he said he'd never write a book again, or if he did, he would write it with somebody else. And that's in fact what he did. And I get what he's saying. It is lonely. Yeah, to be honest, going forward, I mean, I think for the next few years I'm going to make sure I'm doing work that involves other people. Really? Like what? Yeah. Don't totally know, but I've started making videos recently, so there are some regular faces that I'm working with doing that, like on YouTube and Instagram. And already I'm enjoying that switch to having people that I'm talking about ideas with on some regular cadence. Yeah, so I don't know what's next because after every book I say never again. And I mean it every time. Although this time I will say my process was so much better. Look, I think one of the motivations for writing Inside the Box was that I was terrible at putting constraints around my own work.

For my first two books, so it was a me search, right? It was a lot of me search in this book, not just research. And I was terrible at putting constraints around my first book, so I wrote 150% the length of a book to get my first two books and then had to cut back. I cut a trip to Arctic Sweden for my first book. Had I planned better ahead of time, I would have realized that it wasn't going to work out right. And having a kid and other responsibilities, I'm just like, I can't do that. I can't be taking trips to Arctic Sweden that don't count for the book, you know? And so this time around, I had a different process where because I don't, I don't write for the first year of a book project. No writing, just research. And after doing that this time around, I made on one page and one page only, like an architectural outline of how the book would look. So I'd never done that before. Actually, this is it right here. As you can see, I wrote as small as possible to try to like defeat my own system.

I think that's insane. And if it's not on that page, it is not in the book. And I think that made it more coherent. It also allowed me to see kind of ahead. So the book's 20% shorter than my other two. I think it's much tighter writing. I was so much more efficient that I don't feel nearly as burned out because I didn't write a book and a half to get one book. So a lot of this was very much about constraining myself and making sure I had a clear, like anyone making a product, what's the problem I'm trying to solve here with this thing that I'm doing? And it's the fact that we overvalue freedom and undervalue useful constraints. And, and I wanted to make that clear.

I just thought of this. Range is one of the few books that again went mega viral. Have you talked to Morgan Housel or James Clear about the next book after writing a mega viral book? I mean, Morgan's done it a couple times. James is, is still waiting or working on it. Have you talked to those guys about that?

No, I mean, I've talked, I've only met Morgan briefly. James is a friend. Yeah. A little bit. I've talked to him about that, but not a lot. I have talked to Malcolm Gladwell, who's a close friend, about things like that. You know, do you ever, we would talk while we're running, we're both competitive runners. I would ask him, do you ever worry about like competing with your former self? His answer was delightful, but not that useful to me because it was basically No, I think he— I think what he literally said was, oh no, I don't have any of your Jewish neuroticism. I have a Jamaican's joie de vivre and a British stiff upper lip or something like that. He's part British, part Jamaican, his parents. So he said something like that. So he just said no, he doesn't have that, which was cool, which was cool. But it is tricky, you know, it can be a little paralyzing. I remember even after my first book, The Sports Gene, which was still a bestseller but not in the way that Range was. And immediately the pressure was to write The Sports Gene 2. Yeah. I just didn't want to do that.

I mean, I was burned out from doing it. That book addressed a lot of my own questions I found the most fascinating about sports. And so I almost caved to that pressure, but I didn't. And that meant it took me a lot longer to get to my second book, right? It was 6 years between books. But I also think I was much better for it. But it was a challenge. It was a challenge. I mean, I had to part ways with my agent because we didn't see eye to eye. So yeah, it's tough. Do you have any advice? Because I'm all ears.

I mean, I would love to have this problem, David. So I think a lot of people would, and most people in the world do not know. And Morgan's approach— I asked him the same thing— seemed to be like, look, is it weird that The Psychology of Money is going to be the biggest-selling book I ever have? Yeah, I guess. But I'm just going to keep writing. I'm just going to keep going and keep moving forward knowing that The next one probably will not sell as much. And in his case, the next two have not sold as much. They're still amazing books, but they just haven't sold as much. They haven't caught fire like that. It just seems like almost divorcing yourself of the results. You're proud of the work. The book is awesome. I mean, it's really, really good. You know this, you worked like crazy on it. The research, the storytelling. At this point, you're gonna work really, really hard to seed the market and sell a lot of 'em, but then it's out of your control after that, you know. It's almost like you have to be okay with whatever happens. That's right.

And you touched on a few important things actually that I want to highlight. One is a lot is out of your control. Again, with my first book, I remember a colleague at Sports Illustrated told me— well, at that point I thought it was just my side passion project. I wasn't even really— it was stuff that I had pitched to Sports Illustrated and hadn't been able to get in. So, and I remember a colleague telling me, because the book's about genetics and athleticism, and he said You know, if a book about genetics and vampires comes out the same day, you're screwed and there's nothing you can do about it. And he was right. You know, a lot's out of your control. And to Morgan's point, I think the one thing I will say with Inside the Box was when I transitioned out of science into writing, for a while I was saying, this is something I'm doing for a specific purpose. I had specific topics I wanted to write about. Then I'll get back to this other stuff. But somewhere along the road that changed and I very strongly identify as a writer now, as like a craftsman, and look at other people's craft.

And I've taken, you know, fiction writing courses just to learn about craft and things like that. And so with this book, this structural experiment where I made the architecture ahead of time and drew the introductory story back every 3 chapters to highlight a new layer of constraints that led to a world-changing breakthrough. That was a new structural experiment for me. And I found it so engaging. I think it worked, but that will be for other people to judge. But I found it so engaging because I like to start a book project that in order to finish it, I don't presently have the skills that I will need to have to bring it to fruition. I want it to force me because I can't learn as ferociously when I'm not writing a book. There's just like something about that constraint that forces me to learn in a way with like a velocity that I just can't otherwise. And I'm naturally kind of shy and it forces me to just talk to everybody in the world that might know anything about what I'm talking about. And so I found this, the writing experiment so engaging that there was so much along the way where I was like, this is a really worthwhile thing to be doing.

I'm really glad I'm doing this experiment. I think I'm getting better at my craft. So to some degree, that made me feel, if it doesn't work as well commercially, this was a worthwhile thing to do anyway. And so I think that's been really helpful. Isn't it cool to see?

I found one of maybe the greatest tools for learning in the world is to teach. And writing is definitely a form of teaching. Getting up and speaking about it in front of a group is teaching. Actually going to a university and guest lecturing is teaching. I just find when I am put in the position to, quote, teach, it is such an amazing learning. I even wrote that, I think in my next book, I said, this book's for me. This is for me first and foremost, because I wanted to learn more about the power of compounding. I want to learn more about excellence. I want to learn more. Yeah, exactly. Research, man. And I certainly hope it helps other people, but it started out of my own desire to aggressively chase down my curiosity with great rigor. Yeah. And this is what's come out of it. And so at that point, Yeah, I'm gonna try to sell like crazy, just like you are. And then after that though, it's still a win. It's a big win because I learned so much in the process. I think that applies though, and I'd love to hear your thoughts on this idea of why leaders should regularly put themselves in the position of being a teacher because it's such a great tool to learn.

Yeah. And by the way, since you're highlighting the me search point too, that's another thing that made this book project worthwhile to me no matter what happened is I needed to get better at this. I often felt overwhelmed. I often felt, you know, too much choice, too much decisions, not enough structure. In the age of AI, I find the tools fascinating and they allow me to do more. I also find it even more overwhelming than the world before, right? So I was looking for the antidote myself. And so the book has improved my life for sure. In terms of teaching, there's actually a quote in Inside the Box from Seneca, the famous Stoic philosopher, docendo discamus. In Latin, which means by teaching we learn. So that's an, a quote from an ancient philosopher, but it's now been backed up by modern science, which has found that if people think they're going to have to teach certain material, they organize it more coherently in their own mind. Like they start pulling out main ideas and attaching different ideas together. And in what's called the brain semantic network, how you connect ideas together. And it seems like you should always do this when you're trying to assimilate information.

But the fact is, like many good constraints, if you're not being forced to teach it, you just don't do it. It's very difficult to do that. Teaching it is even better. But in these studies, just making someone think they're going to have to teach it makes them learn it in this much more coherent way where they can use the knowledge, they remember the knowledge better. So it's like forcing someone to consume information through that frame of I'm going to have to teach this just activates a different network in the brain. That makes you learn in a, a much more durable and flexible way. So the teaching is for the teacher often. So I think it's something that we should all do really frequently. I don't know if you find this, but when I'm working on my book ideas, talking them off of people is one of the most important things I do in the process. That teaches me where I don't know what I'm talking about, where I have holes, you know, how to make the argument, what ideas are connected, all those sorts of things.

One of the questions I ask every leader I work with, when's the next training you're leading? When's the next paper you're publishing or you're going to post or you're going to share with your team? So it's whether it's getting those messy thoughts out of your head onto the page from a writing perspective, again, teaching or standing up in front of a group of people who are very valuable to you because they work within your company and you're tasked with teaching them something. You are gonna benefit as much or more than anybody. Yeah. So I think that's a, a great prompt or great thing for a leader to say, I don't have time for that. Are you kidding me? You don't have time to get better. You don't have time to help other people. You don't have time to get really, really clear on what you believe, what you think. You're out of your mind. Of course you have time for that. That's like the most important thing to do. So it's definitely something I push on people, but they don't always love to hear that because it takes time. It takes effort to organize those thoughts, to get really clear.

But I think it's super valuable and important for us to do on a regular basis.

Totally. The Kendo Disk moves for the win, but it's a desirable difficulty, right? There's this whole area of cognitive psychology about desirable difficulties, things that often slow learning down, make it more frustrating in the short term, things that are inconvenient. And the fact is, those are the best ways to learn. But again, going back to our brains will prevent us from thinking hard if we ever have to. I think that's why you need things like constraints, or you need the the directive to, you're going to teach this. It would be wonderful if we could just flip it on and say, I'm going to learn this really well now, but it just doesn't work that way. So I think we need to embrace these desirable difficulties and they're called desirable difficulties for a reason because they're difficult but desirable in the long term.

You, um, came across some philosophers, Susan Wolf and Todd May, this concept of narrative values, the recurring themes that give like a coherence to a life. Can you tell me more about what you learned from Susan Wolf and Todd May and this idea of narrative values, as well as what you've identified are yours?

That's so interesting because I have not done a ton of podcasts, but I was wondering if I would ever be asked about this because it's, it's late in the book. It's sort of more conceptual. One of my favorite parts. Interesting. Interesting. I, I will say in all my books, the things that I predict will be the most interesting to people, I must have an okay radar because the books overall have worked. But within the book, I'm terrible at predicting what other people will find.

What did you think of this one? Interesting. Of this specific part, this idea of narrative values. Oh, I loved it.

And but one of the reasons it's later in the book is because it's, it's sort of more abstract and conceptual and personal. So I'm like, this is for people who got this far. You know, they, they got through chapter 1 that talks about like the most important company nobody's ever heard of. This stuff is if they're, if they're really with me on this journey in a more personal way. And the narrative values you're referring to, so this is a part, you know, in the last part of the last chapter where I'm talking about things like how constraints can help make a life more coherent. Because we know it's really important for well-being to have a coherent life story. These two philosophers you mentioned write about meaning, how to find meaning in life. And Susan Wolf said, well, meaning comes from subjective attraction to something that is objectively attractive, meaning that you are personally drawn to something that has objective value. But then the question is like, what is objective value? And Todd May says it comes from narrative values, and those are qualities that are prized across all cultures. These could be things like loyalty, heroism, hospitality, caring, love.

And so he advocates identifying those values, certain, you know, kind of universally respected values in your own life story and telling them through your story. And it's also a way to consolidate your caring where there's so much stuff you could care about in the world, it's overwhelming. But if you can kind of pick out certain clear values, that helps you feel agency, it helps you feel more coherent. And so for me, I went and looked back in my life and some of the ones I identified were curiosity. And open-mindedness and diligence and resilience. Now that I've started telling my story in that way, it shows up everywhere. I'm like, of course I did this because that's my value. But going forward, I realized I also wanted some things in my story that I didn't have. So I identified forgiveness in particular because that has not been a strong suit for me. I don't know why. I have no trauma in my life that I can point to why I've been like, bad at grudges, like why I've held grudges for things I don't know why. But as I write in the book, when I was at Sports Illustrated, I wrote about this guy named Ben Helfgott, who was the only living Olympian to have survived a concentration camp, two-time British weightlifting champ.

You know, almost everybody in his family and extended family was killed in the Holocaust. He became the head basically of this group called the Boys, these kids who were orphaned in Poland and brought to England. And kind of resocialized. And he just preached forgiveness all the time. Like, he would tell these guys, you have to go back to Poland or Germany or wherever and rebuild bridges. The people today aren't responsible. Like, we have to rebuild. And when I would see what he was doing, these like petty grudges that I'm holding are nothing compared to what this guy has forgiven. And I want to be like that, because you're just— you're poisoning yourself, right? When you hold these grudges, like feeding yourself your own poison. And so I decided that I wanted forgiveness to become one of my narrative values. So I had these ones that already come easily to me, that give me a coherent life story. And then I chose one out of all the things that I see that I wish would be better in the world, that I'd like to work on. You can't do them all. And so I wanted to pick this one value to sort of add to my, my holster of, of themes in my story going forward.

I love it. Curiosity, diligence, open-mindedness, and adding forgiveness as kind of an aspirational value. So I go back and forth on this one element. I'm, I'm just gonna drill down on, on this forgiveness for a second because, you know, your background's in studying athletes and greatness. There are stories of Tom Brady, Michael Jordan, others where they, they definitely held grudges and they've got a huge chip on their shoulder and sometimes they even make it up in Michael Jordan's case, which I'm sure you've seen all about, right? Yeah. And I have friends that I work with that are leaders where they openly ask questions like, what's the chip on your shoulder? Or what grudge do you hold? Who are you striving to prove wrong? And they kind of like it because maybe it'll be a motivating factor and that'll help their company.

And so I go back and forth on this because I, David, I am very motivated to prove my supporters right.

Yeah. I feel very lucky to have great support, great loving parents, brothers, my wife, my family, amazing friends. and I just so badly want to say you were right for believing in me and let me go out and prove that right. Way more than the people who have not believed in me or said mean things.

You know what I mean?

And so I don't know, I go back and forth. What do you think when it comes like motivation and excellence and winning and doing big things when it comes to chips on your shoulder versus proving people right? Yeah.

I mean, it's interesting, like you mentioned Michael Jordan, he was, redressing made-up grievances. Yeah, in many cases.

The Bradford Smith, remember? Like, yeah, made stuff up.

I mean, I have found that to be powerful for me sometimes, that prove people wrong, as they say, you know, as I think Josh Wolfe says, chips on shoulders put chips in pockets. Yep. And I think there's some truth to that, but I think that can be separated from a kind of forgiveness. I think you can want to prove people wrong or prove people right without harboring a personal feeling of having been wronged in some way that can't be recovered. Because otherwise, I think it just, you're like harming yourself over the long term. So I think it can be separate. Like, I think you can still want to prove people wrong. I mean, I want that all the time to prove people wrong.

Do you have a lot of doubters or haters?

Probably some fake ones, but also like, if I'm being honest, you know, so I just started making long-form videos that I started posting online. And anytime I do anything like that, it's a different audience. And so a huge amount of the commentary is nasty comments about my last name, you know. Oh God, I never thought of that. Wow. It's never going to work. And I'm, and I'm shadow banned. That's the thing. When I just, I just posted a video that's taking off kind of, but, and all the comments are just about, oh, you're shadow banned because of your name. Like, if I'm shadow banned, how did you and your 50,000 friends get here? You know? But yeah, that motivates me a little, but I don't, I don't, I'm not mad at those people. I don't care. I wish they'd be a little more creative with their jokes. Like I want to laugh, but it is sort of like, I'm going to show you, but I don't actually have any animosity for them, you know, it's just like you want to prove them wrong. Yeah.

I mean, it's a reflection of them, not you talking about this book. You said there's a thinker who's really influenced this one. It's a guy named Herbert Simon. I had not heard of him. What is it about him that has influenced you so much? Yeah, by the way, can I just say I'm really enjoying this interview.

You're asking me all kinds of things that nobody's asked me about. I've digressed into some things that I hope I didn't go too far off because I have a digressive brain, but yeah, I'm quite enjoying this conversation. Herbert Simon, yeah, definitely the most. His thinking is behind so many pages in this, in Inside the Box, where he was trained as a political scientist, but he won the highest award in computer science, the the Turing Award for— because he did the first AI demonstration ever. He won the highest award in psychology. He's one of the founders of cognitive psychology. So meaning not like therapy, but like how our brains solve problems. And for good measure, he won the Nobel Prize in economics. One of his quotes serves as the epigraph of the book. It is a myth widely believed, but not less mythical for that, that people are most creative when they are most free. And so much of his work is about constraints, both in how important they are for people in problem solving, like to cut down problems, what he called the problem space, to make problems manageable. And also just personally. So he coined this term satisficing in his most famous work.

It's a combination of satisfy and suffice. And it means basically having good enough decision rules. And he contrasted that, well, what has been contrasted to by people who followed up on his work is, is maximizing. Maximizing, maybe we would call it optimizing now in optimizer culture. And it turns out from a mountain of psychological research that it is almost always bad to be a maximizer, someone who is trying to get the perfect choice in every decision. Maximizers are less happy with their decisions. They're less happy with their lives. They're more prone to regret. There's not much evidence they actually make better decisions most of the time. Whereas satisficers will tend to have, whether they do it explicitly or not, good enough rules. And once good enough is exceeded, you may go to outstanding. But once good enough succeeded, you can accept it and move on. And I think this is an incredibly important tool for life today, where we have so much choice, right? Consumer choice has multiplied by 100 million fold compared to before the Industrial Revolution. Wealth has only multiplied 400-fold. So it's a massive increase in choice. There are evidence from surveys now that these maximizing tendencies are on the rise, probably because you can do so much comparison online of what you could be doing or what you could be buying or who you could be, that it's leading people to have more maximizing tendencies.

And those are really, really bad for well-being. So Simon was a proactive satisficer. He said you need 3 sets of clothing, one on your back, one in the wash, and next one ready to wear. And he just simplified all the decisions in his life so that he could save cognitive bandwidth for the really important ones. And reading about his life, you'd almost think, hey, here's a guy who has low expectations. Like, he would be terrible in optimizing influencer culture because he was always settling for good enough. He famously said, the perfect is the enemy of the good. So you might say this guy just has low expectations. If he hadn't won the highest possible awards in economics, computer science, and psychology. And so his thinking just about how important constraints are both for human problem solving and for well-being kind of pervade the book. He really introduced him at length in the last chapter, but his work is sprinkled throughout.

So I really identify with this as well because I own 15 of these shirts and I wear this. I've worn this every day for the last 4 years and ate the same breakfast every day. I know this guy wore the same socks. He lived in the same house for 46 years, ate the same breakfast every every day. Some would say, God, dude, get a life. That's boring. Or whatever. To me, I don't know if I'm gonna act like the Barack Obama, I'm wearing the same suit so I don't have to spend mental bandwidth, but that's kind of where I read about it initially and thought, that's what I'm trying to do. That I never want to decide what I'm wearing ever. And I don't, I don't decide. I mean, I spend zero time. I never want to decide what I'm eating. I eat breakfast at usually around like 12 o'clock and it's the same eggs, fruit, and protein oatmeal like every day. And to me, like, it's— I love it. I think it's great. Do you subscribe to this?

What do you do? Yes. Choosing when to choose. You're choosing when to choose. And that's what you want to be doing because otherwise you're just making decisions all the time.

So many people make fun of me though when I go to like my daughter's soccer games or I go anywhere else, like, there's the black shirt again. Whatever. I'm like, why does it matter? Why do we care about this?

I don't understand. You know? Yeah. I get like, I have a t-shirt that I think fits me well. I'm like, then I'm going to have 8 of those in different colors. Yes. Yes. Why, why would you? Maybe. Yeah, because you want to choose when to choose. Like, if I were a fashion designer, I wouldn't do it that way, but I'm not. And so I want to choose when to choose and save my cognitive bandwidth for the things where I really want to expend my energy. And I think with so much choice, there's one study I cite in the book that shows that as consumer choices exploded, people are more likely to see all of their purchase decisions as expressions of their identity. It's like freighted with even more weight and stress and all this stuff. Like, don't do that to yourself. Where you can simplify, where you can get good enough. And this is, I should say, because I think I've had maximizing tendencies. So, one of the things that was really important for me, again, after Range, this thread keeps coming back of what do you do after you have a book that went well, but it's an interesting thread where, again, I didn't have a normal journalism job anymore.

And so I'm like, what do I do? Do I only write books now? That means everything has to be this huge project. So that's when I started a newsletter and the newsletter was basically a satisfying exercise for me. I was already knew a lot of Simon's work. So if a book has to be a 9 or 10, I said, if a newsletter post, once it hits 6.5, I'm sending it. Maybe it goes to 8, you know, but if I feel I've gotten to 6.5, I send it because there's always more stuff I want to add or more tweaking I want to do. So that became a, I'm not really selling people on my newsletter here very well, am I? But, um, but. That became a really useful, satisfying exercise for me because I was kind of getting stuck in a little bit of perfectionism syndrome. And so I think everybody should have those. And now I do. I start doing like beginner dance classes and stuff. I often choose to be a beginner at something to make sure that I'm having some satisfying in my life. And I think we all should, because it doesn't— it— we got to get over the idea that good enough means you have low standards.

It actually means that you're Saving your bandwidth for the most important things. And, and there's something I write about inside the box called Fredkin's paradox, which is this finding that we spend the most energy on the least important decisions because we agonize when the options are really similar. So either we're agonizing because they're similar, we can't tell the difference, but that either means they're so similar the difference doesn't matter much, or we, we can't tell the difference and so agonizing more isn't going to make a big deal anyway. And so you don't want to be falling prey to Fredkin's paradox. You have satisfying limits, good enough decision rules.

What do you think of the phrase, how you do anything is how you do everything?

I definitely don't subscribe to that overall. I would say overrated phrase because, look, thinking about us and our, our, uh, fashion taste, like, we wouldn't be very good writers, would we? Because we're mailing it in with our shirt selection. Let me—

can I just say it is so wrong? It's not even close to right. I, I mean, why do people keep saying this? There's no element of that that is correct. Maybe you could tell this has been a thing for me. I keep seeing it everywhere on Instagram. Everybody says it to me and I go, no, that's not right. Why are we saying that? That's not how we are.

You know, also it's insane because everybody is bad at some things. Yes. So of course, of course. And, and is entitled to be bad at some things. And so, you know, when we think about telling people to lean into their superpower, identify it, we are implying that a bunch of other things are not their superpower. Right? Yeah. And so to the extent that it means you should take risks or practice with something when you're training, that you should take it seriously. Yes. But otherwise, I think patently untrue. Like I said, otherwise you and I would be in trouble just based on our fashion choice alone.

I meant to bring this up earlier and I know we're running out of time, but I want to get into General Magic just because I love the documentary so much and you write about General Magic. Maybe for the business leader who is within corporate America trying to lead something that they have aggressive goals, they have a tough job. In General Magic, it's a little bit different than that because it's kind of a startup. They're trying to do something new that hadn't been done. They're way ahead of their time. What can we learn as leaders from the story about General Magic?

Yeah, as I say, most important company, uh, nobody's ever heard of. And they have a vision of the future of telecommunications. They're essentially building the iPhone starting in the late '80s. Before the internet even existed. They have designers of the original Mac. It's so alluring that Goldman Sachs takes them public in the first so-called concept IPO, meaning they didn't have a product. They went public with an idea. They build this huge consortium of international businesses, all this stuff. And they did have the right vision. Like, if you go back and look at what they were doing and read their documents, they saw what was coming. For the next generation, but it turned into a massive failure because they had so much talent, they had so many resources, they could do anything. And so they did do anything. Everything got bigger and bigger. So they're basically making this personal communicator and it's like every cool idea that an engineer has, they do it. Does it fit in? I don't know, but it's cool. So they do it. They never identified a clear customer. They called their customer Joe Sixpack. After a few years of missed deadlines, they realized nobody knew the guy who was that, so they didn't have a clear problem to solve.

When I was interviewing a lot of the people who worked there, they kept saying, we couldn't decide what not to do because there were no boundaries. I think a really telling interview was with a, an engineer there named Steve Perlman who was making a calendar function for this personal communicator. And he writes it to go from 1904 to 2096 and checks it in and thinks he's done. And then one of his That someone else comes to him and says, Steve, someone might write apps for historical stuff or way into the future. You gotta make this calendar bigger. So he writes it to go from year 1. And then he thinks he's done again. And then someone else comes to him and says, why are you starting with an arbitrary religious context? You should go back to the beginning of astronomical time. So he opens it up again and writes the calendar function going from the beginning of the universe. And as he said, if he'd left it at 1904 to 2096, it would have been 4 lines of code. but this was how everything operated at General Magic. They could do it, so they did do it.

And when the device came out, it didn't solve a clear customer problem, so nobody was sure it was for them. It had a 200-page manual. It had so many features that it was— battery life was terrible. User experience was choppy. They sold 3,000 units in the first 6 months, mostly to people who they knew. And meanwhile, people inside of General Magic who bit off much smaller chunks had success. So one low-level service engineer started a website called AuctionWeb that was facilitating auctions online. And he went to his bosses and said, look at this, this is doing one of the things we want. Do you want it? And they said no, you know, too small for them. He left and he changed the name to eBay. So that was Piero Midiar. He was a low-level service tech there. Another third-party app developer created an app called Graffiti where with strokes of a stylus would be turned into writing. And he said, when it was clear General Magic was going to fail, he took his app and said, I'm going to solve a clear customer problem. Busy professionals want their contacts and calendar on the go to sync with their computer.

And so he did just calendar, contacts, and a memo pad. And that was the Palm Pilot. In the same era, by doing way less, by doing something, not everything. And so General Magic became this kind of cautionary tale in the book where they could not draw boundaries. They had no constraints and it was a disaster. But people inside, I still think the company was a success in a different way where people inside the company learned such important lessons about constraints that they then took out of there and they made Android and the iPod and the Apple Watch, uh, and led Google Maps and founded LinkedIn, co-founded LinkedIn and, and eBay, obviously, and Nest. So Tony Fadell, who's an important character in the book, It was his first job out of college, so he was like deeply traumatized because these were his heroes. When I first interviewed him, by the way, Bill Gurley, the prominent venture capitalist, when I told him I was thinking about constraints, he said, we have a saying in venture, more startups dive into digestion than starvation. And he said, you got to talk to my friend Tony if you're interested in constraints.

So I called Tony Fadell, who is known as the Podfather, who's the lead designer of the iPod. He's a very energetic guy. He's almost yelling at me. He's like, if you don't have constraints, make up constraints. And he told me that when he co-founded Nest, the smart thermostat company, he made his team work inside a literal box where he made them prototype the box before they had the product because that was how it was going to look to the end user. And if it didn't fit on that box, it was not a priority for them. So as he told me, with these ultra-constraint-based things, it makes you think really hard. It slows you down, he said, but it forces that thinking. That's kind of the mindset shift that I hope this book engenders, is from seeing limits purely as obstacles to seeing them as opportunities to clarify priorities and launch into productive exploration. So good.

Hey, one more question before we run. This is a personal one. You're cool with it? Sure. It's one year from today. You're with the people that you love. And you're popping bottles, you got champagne everywhere, you're spraying it all over the place. I don't know if you drink champagne or not. Okay, go with me here. Okay. And drinking the metaphorical champagne, you're celebrating. What are you celebrating? A year from now?

Mm-hmm. Honestly, the first thing that comes to mind is my dad, I think, has made a lot of healthy life changes in recent years. You know, I was a, like a national level 800-meter runner and he'll send me his like very slow, you know, mile or 5K when he PRs. And I find it very exciting and very cool. And I wanted him to work out like this for years and years. And so I would love to be celebrating if he could get up to a 10K, say, PR. I think that would be fun. So I know I'm supposed to say something about my book and there's certainly things that I would celebrate. Like, would I love to have another number one New York Times bestseller? Absolutely. I would. But if I were popping champagne, I think it would be more likely to be about family stuff, probably.

God, that is so good. Thank you. It gives me chills thinking about that. We'll talk in a year. I want to hear about your dad. Okay. Uh, the book is called Inside the Box: How Constraints Make Us Better. Not surprisingly after Sports Gene and Range, but it's super useful. Storytelling's insane. It's so good. Thank you, man. And thank you for your kindness and generosity away from the recording. Because when you meet your, your heroes, your literary heroes, and they're even better, better humans, better people than they are as writers, man, it just makes you feel good about the world. I root so hard for you. Not that you need it, but I root so hard for you because you're just a great dude and I'm super appreciative for you, man.

I appreciate that. I need it. We all need it. And I really enjoyed this conversation.

Really. Thank you. Appreciate it, man. We'll talk soon. Thanks so much.

It is the end of the Podcast Club. Thank you for being a member of the End of the Podcast Club. If you are, send me a note, ryan@learningleader.com. Let me know what you learned from this great conversation with David Epstein. A few takeaways from my notes: identify your narrative values. Pick 3 to 5 qualities you want running through your life story. David's are curiosity, diligence, and courage. And then he added on forgiveness as an aspirational value. Pick whatever is true to you and let those values make decisions for you before you ever face the decision. So good. And then design a constraint you don't have. Create a deadline, a word limit, a candle you light at the start of the workday and blow out when you're done. Whatever it is, do not wait for structure to be imposed on you. Build it for yourself. Then think about General Magic. Do something, not everything. The General Magic engineers could build anything, so they built everything. Jeff Hawkins took one small piece and made the Palm Pilot. Another created eBay. The list of things you could do is so long, it's infinite, but you should create some constraints.

It's weird, it feels counterintuitive, but the constraints actually make you better. Once again, I would say thank you so much for continuing to spread the message and telling a friend or two, hey, you should listen to this episode of the The Learning Leader Show with David Epstein. I think he'll help you become a more effective leader because you continue to do that. And you also go to Spotify, Apple Podcasts, subscribe to the show, rate it, hopefully 5 stars, write a thoughtful review. By doing all of that, you are continually giving me the opportunity to do what I love on a daily basis. And for that, I will forever be grateful. Thank you so, so much. Talk to you soon. Can't wait.