Why Too Much Freedom Is the Enemy of Success

In the following excerpt, Derek talks to David Epstein about the genesis of his book Inside the Box. 

Derek Thompson: So I want to go back to 2019. Your book Range comes out. It’s a super-massive bestseller. Take me back to May 2019. Remind us, what was Range about? And in the aftermath of a book like that, how do you find your next project?

David Epstein: Yeah, it was about the benefits of having broad experiences and a broad toolbox in an increasingly specialized world, and it made the argument that that’s increasingly important as the world changes really rapidly and people need to be adaptable. And as you alluded, it found a wider audience than I myself expected. It was also so much work and I felt like I needed to live up to it again after that, and I decided I was only going to write another book if I could find the perfect topic. And so over the course of about the next two years or so, I started dabbling in a whole bunch of different topics, because I never have a problem finding enough things to be interested in. Like for you, I think our problem is what do you execute on? Not, like, how many things are you interested in?

And I found a lot of things that were interesting, but I could not find anything that was perfect. And then I was reading some work by Mihaly Csikszentmihalyi, the psychologist who’s most known for coining the term “flow” to describe the feeling of immersion in an activity. And he has this quote where he’s talking about marriage—but I think it could be applied to anything—where he basically says, the great thing about being committed, if you commit by your choice, is that you free up all this energy for living instead of wondering how to live. So you can get busy living instead of wondering what’s around the corner.

Thompson: I actually have the Csikszentmihalyi quote right here in front of me.

Epstein: OK, yeah.

Thompson: May I read it—

Epstein: Yeah, please.

Thompson: Before turning things back over to you?

Epstein: Yeah, yeah.

Thompson: “By making up one’s mind to invest psychic energy in a marriage, regardless of any problems, obstacles, or more attractive options that may come along later, one is freed of the constant pressure of trying to maximize emotional returns. Having made the commitment and having made it willingly, instead of being compelled by tradition, a person no longer needs to worry whether she has made the right choice or whether the grass might be greener somewhere else. As a result, a great deal of energy gets freed up for living instead of being spent on wondering about how to live.” And later in that passage, he says, “Limitations are liberating.”

Epstein: Yeah. And this hit me in the face like a kick with a golf shoe. And I said, “Oh my gosh, this is what I’m doing with topics. I’m finding really fascinating stuff, but I’m swiping right.” Is that, I’ve never been on dating apps—

Thompson: No, you were swiping left because you were rejecting, swiping right—

Epstein: I was swiping left.

Thompson: Is accepting.

Epstein: Well, no, no, I wasn’t totally rejecting. I was keeping them in the hopper, but then like, “But what else is there?”

Thompson: Oh, I see, OK. Got it.

Epstein: So keeping a lot of things open.

Thompson: I’ll accept the right swipe.

Epstein: And as soon as I read that quote—one of the topics I was interested in was useful constraints. I said, “I’m writing a proposal on that tomorrow.” And naturally, by two weeks later of research, I was 10 times as fascinated, and that was the beginning of this book.

Thompson: So I want to put these two projects next to each other, Range and your new book, Inside the Box. So Range essentially argues that we need to reject the pressure to specialize and be generalists. And Inside the Box, you’re arguing that we need to reject the allure of freedom and design constraints on our lives. Does this amount to you changing your mind? Is it hypocrisy, or is there a subtle nuance here, in which it can simultaneously be true that the world is pushing us to both specialize and want too much freedom?

Epstein: Yeah. And I don’t even think it’s that subtle. I mean, to me it was a natural next question and became more natural as lots of readers asked me versions of the same question, which was: “OK, I actually have these broad experiences. I have wide-ranging curiosity. I have tons of ideas, but I don’t know what to do.” And so it felt like this natural next question of, OK, at some point you have to focus that into doing something, into achievement, into satisfaction, all those things. And I count myself among those people that was struggling with this. I was training to be a scientist in my first life, then I became a writer. I had this very broad background, but I did have a challenge drawing boundaries around my projects. In fact, with my first two books, I wrote 150 percent the length of a book and had to cut back to get a book.

I cut a trip to arctic Sweden for my first book that, had I drawn better boundaries around the project, I would’ve seen wasn’t going to work. Then when I became a parent, I was like, “I can’t be writing a book and a half to get a book.” I realized there’s a hefty dose of me-search in this book, that I stunk at putting useful boundaries around my work and wanted to get better at that. So it really changed my writing process a lot, but that’s a whole other thing.

Thompson: There’s several themes from this book that I think are worth a deep dive. And the first that I want to discuss is this idea that individuals and organizations with ultimate freedom and few constraints often struggle and fail. And the canonical example from your book is this company called General Magic.

Epstein: Yeah.

Thompson: What was General Magic?

Epstein: Most important company nobody’s ever heard of.

Thompson: That’s exactly right.

Epstein: Most important because of the people who came out of it. So this was a company, it was the first so-called concept IPO, where their vision, talent was so alluring, Goldman Sachs took them public with an idea, not with a product, in the mid-’90s. So starting in the late ’80s, really, this company was essentially building the iPhone before the internet. And it was founded by two of the original designers of the Apple Macintosh, and then a third Apple employee whose job was seeing the future of technology. And by the way, I got to give you his PhD dissertation, this guy, Marc Porat, 1976 at Stanford. He coins the term “information economy” on the first page. Reading this thing is eerie as hell.

He saw the next half century of technological change, not just the promise, but problems with misinformation, inequality, all this kind of stuff. So he’s the visionary CEO. In 1989, he’s sketching a thin glass rectangle with no protruding buttons and a touch screen that has rectangular apps on it. And so their vision is obviously correct. Money absolutely pours in. International partners pour in. So many international partners, their meetings have to start with an antitrust lawyer listing all the things they’re not allowed to talk about.

And in building these personal communicators, they get to work, there’s huge amounts of innovation, but they have so much talent and so many resources, they can do anything. And so they do do anything. Every good idea they have, someone starts doing it, right? They don’t define a clear user. They call their user Joe Six-Pack, so they don’t really know. And they realize nobody’s really met the guy after missing a few years of deadlines. And so the project grows and grows and grows. And the CEO, Marc Porat, says, “Well, I raised so much money to create heaven for engineers, where they were unlimited, limited only by the things they could imagine. What more could anyone ask for?” And I think the obvious answer became less freedom. I interviewed dozens of former employees there, and the refrain was “We just couldn’t figure out what not to do.”

So I think there was one emblematic interview with this engineer named Steve Pearlman. So the thing comes out. It’s a total disaster. The stock price doubles on the first day; two years later, the company’s basically worthless. Because when the communicator comes out, it’s like, it’s a 200-page manual, it’s so many features, nobody really understands how to use it. So Pearlman’s supposed to create the calendar function for this thing, and he writes it from 1904 to 2096 and checks it in, done.

This excerpt has been edited and condensed.

Host: Derek Thompson
Guest: David Epstein
Producer: Devon Baroldi
Additional Production Support: Ben Glicksman