Two Percent with Michael Easter
Why More Freedom Is Making You Miserable | David Epstein on Constraints
07 May 2026
Chapter 1: What is the main argument of David Epstein's book Inside the Box?
Welcome to 2%. I'm your host, Michael Easter. This is a podcast where we talk about improving your performance. I am an author, and today I am extremely pleased to bring on a fellow author whose work I very much admire. We're going to be talking to David Epstein. So David started as a sports reporter, specifically in the realm of the science of sports at Sports Illustrated.
Now, he became famous there and had a big moment of attention when he broke the A-Rod steroid scandal. So if you are a New York Yankees fan, you probably hate the guy already.
But please bear with me, because this guy is a very, very fascinating thinker who can tell us a lot about improving our work life, improving our performance in the gym and on the road if we're a runner, and just improving our thinking across the board in a way that we can live better. And David has a new book, which we are going to be diving into today.
It is called Inside the Box, How Constraints Make Us Better. And it argues that even though we often do not like constraints and we want as much freedom as possible, he argues that constraints are actually what lead us into better outcomes at work, better outcomes in our wellness, better outcomes across the board. Let's get into it. David Epstein, thanks for coming on the show, man.
It is my absolute pleasure. So the new book, Inside the Box, looks at the idea of how constraints can actually be beneficial. And there's one story that I loved that you opened the book with. It's about this company called General Magic.
Yeah. Well, so they have the people who designed the original Mac. You know, it's... The company was so visionary.
They're envisioning the iPhone.
Basically the iPhone. Yeah. And this was in the late 80s, early 90s? The CEO has a notebook. His name is Mark Peratt. In 1989, where he sketches a thin glass rectangle with no protruding buttons and a touchscreen where you can download apps and it'll be a phone and a computer. 1989, only 15% of Americans had computers and the internet didn't exist.
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Chapter 2: How did General Magic's approach to freedom lead to its downfall?
He saw all of this stuff. Like he envisioned a virtual meeting space where different devices could connect. And they called it the cloud in 1990. Like they were ahead. And again, they had the designers, the original Mac.
It was so, everything was so alluring, their vision, their talent, that Goldman Sachs actually took them public in the first so-called concept IPO, where they went public with an idea.
Nothing to actually sell. Just like, hey, check out this idea. Let's roll.
I mean, they had an idea. They had the idea plus the talent plus a 17-member, what they called the alliance, which was... basically other companies that had invested in them. So this was 17 companies from around the world. It was the largest consortium of international businesses in American business history. Each had given millions of dollars in investment and were going to be part of the team.
And these are like Apple, like these are giant, they're like Sony, right? There's all kinds of crazy names.
Apple, Sony, Panasonic, you know, AT&T, like all the, it was actually, they covered so much of the communications technology world that their meetings had to begin with an antitrust lawyer listing all the topics they weren't allowed to discuss. in their meetings because they covered everything. And they have this vision. So Mark Peratt, the CEO, he raises all this money early.
The stock price doubles on the first day. It's a Wall Street darling. And he says his goal in raising all that money so quickly was to create what he called heaven for engineers, where they could play and create and be limited only by their imaginations. As he said, what more could anyone else ask for?
And I think the answer in retrospect turned out to be a little less freedom because they could do anything. So they did do anything. Everyone who had a good idea, they did it. Like they built and built. They had no clear, they defined our customer as Joe Sixpack, which is very vague.
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Chapter 3: What lessons can we learn from Pixar's success compared to General Magic?
So after a few years of missed deadlines, they turned around and realized nobody knew the guy or what they were building from or what problem they were solving.
Joe Sixpack as in like beer?
Yeah.
Yeah, yeah. It's like saying Joe Schmo, you know, like random guy. So they didn't take any time to define their actual customer. So they ended up building for each other. And the project just grew and grew and grew. They couldn't ever decide what not to do. And so it ends up being this huge disaster. They end up selling 3,000 units of their personal communicator.
When it comes out, it has so many features that the battery life's terrible. The user experience is choppy. It's expensive. It's confusing. But there was one... that I think kind of encapsulated their problems. And it was this guy, this engineer named Steve Perlman, whose job was to create a calendar function for their operating system.
And so he creates it to run from 1904 to 2096 and checks it in and is like, all right, I'm done. And then one of the managers comes to him and says, look, somebody might build apps that go way back in history or way into the future. You have to make it longer than that. So he opens it up again. He goes back to year one. Fine, thinks he's done.
Then another team comes to him and says, look, why are you starting with that arbitrary religious context? You should go back to the beginning of astronomical time. So he builds the calendar app From the beginning of the universe, way into the future. And as he said, if he had stuck from 1904 to 2096, it would have been four lines of code and he could have moved on.
And instead it dragged on for months.
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Chapter 4: How does the Green Eggs and Ham Effect relate to creativity?
And this is how everything worked there because they didn't put boundaries in place. Everything grew and grew and grew until it just totally collapsed under its own weight.
So this becomes this like big metaphor for the book. We often think that freedom is like the most desirable thing. For creatives, for businesses, it's like you just take some smart people, you let them figure it out, they'll do it.
But this becomes this great metaphor for the fact that even when you have the greatest teams ever, you need some sort of boundaries because without boundaries, things just turn into chaos.
Totally. And in fact, in one way, I would say that General Magic was actually a success, which is it's so traumatized in a business sense. Some of the people that were there, especially some of the younger employees, that they learned all these lessons about the importance of constraints that they then took
in their next stops in their careers and did things like led Google Maps and built the Apple Watch, co-founded Android, LinkedIn, eBay, you know, all these other companies that you've heard of. Or the guy who became an absolute zealot for constraints, a guy named Tony Fidel, who General Magic was his first job out of college and these were his heroes.
And so he was just devastated when the company collapsed. I was actually connected with him by the famous venture capitalist, Bill Gurley, who's like famously invested in Uber and Zillow. I told him I was interested in constraints and Bill said, oh, we have a saying in venture, more startups die of indigestion than starvation, like too much, not too little.
He said, you got to talk to my friend, Tony. So he connects me to Tony Fidel. The first time I talked to him, he's like yelling at me. If you don't have constraints, make up constraints. He's like a very intense guy. And he went on to lead the design of the iPod.
And when he showed Steve Jobs a styrofoam model in March of 2001, got the green light and said, we are shipping by Christmas, gave like 10 weeks for the first design and then stop and collect your lessons and go on. And it forced the team to think creatively and repurpose technology.
So the famous scroll wheel is something that they basically repurposed from a Danish cordless phone because they were saying, look, we can't build everything from scratch like they had done at General Magic. Then Fidel goes on and he co-founds Nest, the smart thermostat company. where he forces the company to work inside a literal box.
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Chapter 5: What are the psychological reasons behind the need for constraints?
I think the typical point of view would be constraints are going to constrain creativity, right? And so when you have these products like the iPod, the first iPod, the Nest, you're like, wow, that must have taken a lot of creativity, a lot of thought and just kind of figuring things out. But you also write about this idea called, is it the green eggs and ham effect?
Where having constraints can actually enhance creativity because, well, I'll let you explain it.
You know, it reliably does. In fact, there was just this, I cite this recent survey by psychologists around the world of known creativity myths, things that we know from psychological research are not true. And the second most popular one is that people are most creative when they're most free. And as you mentioned, psychologists know this isn't true.
There's actually something called the Green Eggs and Ham Effect, which is named for the fact that Theodore Geisel, a.k.a. Dr. Seuss, wrote Green Eggs and Ham on a bet that he couldn't write a book using only 50 words. And it forced him to experiment with rhythm because he couldn't use vocabulary.
Even before Green Eggs and Ham, he had been given the task to write a children's book using only 200 words from a kid's vocabulary list. And at first, he starts looking at the list. He starts complaining to his wife. He says, there are no adjectives.
And then he says, I think in fine Seussian form, it's like trying to make a strudel with no strudels, which I think is hilarious because it's like he was the same guy in his personal life as his books. And then he just decides, throws his hands up and says, I'm just going to take the first two rhyming words on the list and make a book. And the first two rhyming words are cat and hat.
And that kind of changed children's literature forever. It gets to this idea that cognitive psychologists have really fleshed out now that, you know, as the cognitive scientist Daniel Willingham has put it, you may think your brain is made for thinking, but it's actually made to prevent you from having to think whenever possible because thinking is energetically costly.
And so if you're not forced, you'll just go down what cognitive psychologists call the path of least resistance, meaning you'll just reach for ideas that you've already used or that you've seen what's familiar, what's easy. And so unless, in many cases, unless the normal thing is actually blocked, it becomes incredibly hard and sometimes impossible to be creative.
Yeah, and that... That was one that, one, surprised me at first. And then two, I thought about my own work. And when I'm doing a book, like I was, I just finished this, a draft of another book. And as I was writing that, I would have sections where I'd be like, oh, this kind of worked before in my last work. And I'd start to do that and be like, yeah, but you can't do that same sort of thing.
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Chapter 6: How can identifying what to stop doing improve performance?
It was originally somewhat creative, but now that I'm doing it again, it no longer becomes creative.
Absolutely. I mean, to your point, we were talking before we started recording about my process a little bit for the book this time around. And this was the first time I ever created an architectural plan for how I was going to order the information before I started writing the book. A hefty portion of this book is me-search.
I was terrible at putting constraints in place and wanted to get better at it. That's often the case for a lot of the things I'm researching is I'm bad at it and want to get better. And so I wrote way over length in my previous two books and it just incredibly inefficient. So this time I made this one page outline. I forced myself to outline the whole book on one page.
As you can see, I ended up writing very, very small, my own attempt, my brain's attempt to defeat my own system. But if it's not on this page, it's not in the book. So this is the first time I wrote the length of a book to get a book. And the book is tighter than my others, about 20% shorter. But it also blocked the kind of...
Some of the methods that I was used to because I had never laid out a plan ahead of time where I wanted the beginning and the end of the book to kind of come full circle in a way that the other ones didn't. And so I think that was really helpful because especially and it's exactly what you're saying, like we've gotten competent at this thing.
which is great, but competency can also be a trap from getting better. It's like you end up lifting the same weights the same number of times every day, which means you may not get worse, but you're also not going to get better.
It's like putting bumpers up. If you don't have the bumpers, you're probably going to get it in the gutter sometimes. And I find that in my own writing where I will find a thread that I'm like, I don't know if it works for the book, but it's kind of interesting. And then I'm writing, you know, a thousand words on this.
And then I read it and I go, yeah, this is interesting, but what the hell does it have to do with this book I'm writing? Or if I could just keep down the lane, it would be a much more efficient process.
I have that problem in spades. I mean, I have a very... A psychologist I was interviewing once told me that I have a... What he called a flat associative hierarchy, which means that I see lots of disparate ideas as kind of connected. It's easy for me to connect them. And that can be nice because I maybe find things that aren't obvious to other people.
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Chapter 7: What strategies can help in making better decisions in life and work?
But it also means that I can be incredibly prone to doing what you're describing, which is going down these rabbit holes of things that I think are interesting. And they're really... Not that well connected in a way that will make sense to other people. And so I really need structure to kind of prevent myself from writing books that are just all over the place.
Yeah. What did reporting this book make you think about when people get too many resources? like specifically financial resources, it kind of made me think that a lot of times you find that people who sort of have it all almost have nothing because a sort of aimlessness sets in. It's like when you can have everything, why go after anything?
Yeah, I mean, I think it's, I actually don't think it's healthy for, as Jonathan Haidt told me in one of the interviews in the book, it's not healthy for anyone to have everything everywhere all the time. Um, and a lot of us, even if we're not rich are kind of in a situation like that in, in the digital world now.
Um, and so I think when it comes to businesses, there are a bunch of, you know, there are examples in the book where people are just sloppy, like when they, when they have too much, right. It leads to sloppiness. It leads to not feeling like you need to define these boundaries. And I think one of the things, um,
This gets at one of the things that I hope, maybe the mindset shift that I hope the book engenders, which is from seeing limits as only bad to seeing them as opportunities to clarify priorities and launch productive exploration. And I think when people have too much, like to Bill Gurley's more startups die of indigestion than starvation quote,
you're not forced to be resourceful and you're not forced to clarify priorities. And so you don't, and I actually don't think that's a good thing for people, right? It's like you, I don't think it's good for work and I don't think it's good for having meaning in your life to kind of always have your options infinitely open. I feel like
Because I'm conscious that it may sound like sometimes I'm contradicting, at least the title of the book sounds like I'm contradicting range, my previous book, which is about broad experiences. But it actually felt like a natural next question to me where it's, okay, you get this broad tool set.
At some point, you have to focus this into something, into achievement, hopefully into meaning and satisfaction. And I've kind of found that in a lot of really talented or hardworking people, they may over-index on optionality, like keeping their options open all the time because they can. Maybe they're very talented or they're very hardworking or lucky or whatever it is.
But sometimes I think that can actually really backfire if people start making decisions, if keeping your options open becomes an end unto itself. And so I think I've seen some very talented peers and friends endlessly keep their options open in a way that actually doesn't help them reach better satisfaction. I'm not sure I'm articulating that well.
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Chapter 8: How does David Epstein view the role of constraints in personal wellness?
I think I hear what you're saying. It's like there comes a sort of phobia towards commitment. And you sort of tell yourself that if I commit to this one thing, I'm saying no to all these other possible things that could land on my plate. And so it leads to someone being unfocused. I think a good example would be something like marriage. Right? Totally.
It's like that is sort of the ultimate commitment. I feel like you see a lot of men are like, they're afraid to get married because like, well, what could happen? I'm going to be tied down. But I think when you survey people in general at a population level, married people tend to be happier because it's like, I was talking to my friend, John Deloney, who has a podcast on relationships.
And he's doing a book about marriage. And he asked me, he's like, well, why did you get married? Like, you don't have to. You know, he's asking all these people this. And I was like, you know, that's a good question. And the way I thought of it was, now you're doing the crossword puzzle in ink. So you got to like, you know what I mean? Like you're committed.
You're into this thing and you're into it for the long run.
Makes you think a lot harder about what your decisions if you're doing it in ink.
Totally. One thing you brought up in the book too is that So many people think about, well, what should I do? When oftentimes a better question to ask yourself is, what should I not do in different situations? Where did you see that manifest?
I mean, again, that was like part of General Magic's big problem was deciding what not to do. But I think about that all the time in things like our information diet, right? Like people are overwhelmed, right? there's so many things that seem interesting. There's so much information coming at you.
And I think it's a constant question of, I'm curious, I want to learn things, but how can I stay sane? And I mentioned, I described this in one genetics lab in the book where they take Post-it notes and put them on the wall and each one representing one of their current commitments or projects.
And the first thing that happens is once they put them on the wall, so making all their current commitments visual, is they realize that, There's way more than they could ever get done already in process. And so immediately they see it and say, we have to start moving some of this stuff out or we'll never get anything done.
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