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Narrator
A rich life isn't a straight line to a destination on the horizon. Sometimes it takes an unexpected turn, with detours, new possibilities, and even another passenger or three. And with 100 years of navigating ups and downs, you can count on Edward Jones to help guide you through it all. Because life is a winding path made rich by the people you walk it with. Let's find your rich together. Edward Jones Member, SIPC this episode is
Derek Thompson
brought to you by ServiceNow. Look, I have my dream job. I get to explain complicated ideas to folks who have better things to do than read white papers. But even dream jobs have not so dreamy parts. The stuff that gets in the way of the actual work. That's where ServiceNow's AI specialists come in.
Interviewer
They don't just tell you what what
Derek Thompson
you should do about your busy work. They actually do it. Start to finish, cases closed, requests handled, no extra work for you.
Interviewer
That way you and your team can spend more time on what matters.
Derek Thompson
Which for me is finding that one elusive stat that just makes everything click. To learn how to put AI to work for people, visit servicenow.com
Interviewer
Freedom is good. It's hard to think of a less controversial set of three words. In politics, freedom is the rare virtue that enjoys bipartisan support. Democrats and Republicans agree.
Derek Thompson
In the realm of career advice, we
Interviewer
urge young people to chase their dreams and do what you love. This gospel covers everything from commencement speeches to self help publishing. In a 2001 international survey of people's assumptions about creativity, 70% agreed with the idea that one is most creative when with total freedom in one's actions. End quote. We have a historically unprecedented number of options regarding what to do, who to be, how to spend our time. The Oxford professor Eric Beinhocker once tried to calculate how many things a person could buy in today's economy compared to the pre industrial world. We're talking SKUs here, stock keeping units distinct purchasable items. How many different boxes of cereal, button down shirts, cars, movies, books. He calculated that compared to pre industrial worlds we have 10 million times more choices. We are more free than our ancestors in practically every way, our lives less constrained by religion and ancient bigotries. The modern world, democratic capitalism itself thrives at giving people more freedom, more choices, more autonomy than or agency. Surely one of the dumbest things you could possibly do is to argue that this search for freedom is overrated. So that's what we're going to do today.
Derek Thompson
Sort of.
Interviewer
Our guest is a most unusual person
Derek Thompson
to make this argument.
Interviewer
Several years ago my friend David Epstein wrote a book called Range, and it became one of those bestselling nonfiction books of the last few years that you see in all sorts of people's libraries and bookshelves. Range is about the case for being a generalist in a world that's designed for specialists. But his new book, Inside the Box, takes on the opposite side of the equation. In a world that celebrates absolute freedom, David encourages us to see the virtues of constraint. If you ask people what they want from life, they'll describe examples of agency and autonomy. Give me a job with more money, a life with more flexibility, a contract with more optionality. But what people tend to enjoy most about their lives are the relationships and achievements that require responsibilities, limitations, rules, constraints. The philosopher Soren Kierkegaard once wrote that anxiety is the dizziness of freedom. It is the sickness that comes from the person who spends so much time keeping their options open that they forget that becoming a real person requires making decisions. We live in an age of anxiety. So perhaps this is the best time to remind ourselves of the ancient wisdom that, ironically, it is our limitations that set us free. I'm Derek Thompson.
Derek Thompson
This is plain English.
David Epstein. Hello.
David Epstein
Hi.
Thanks for having me.
Interviewer
So I want to go back to 2019.
Derek Thompson
Your book range comes out. It's a super massive bestseller.
Interviewer
Take me back to May 2019. Remind us, what was Range about? And in the aftermath of a book
Derek Thompson
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 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.
Interviewer
And.
David Epstein
And so it was also so much work, and I felt like I needed to live up to it again after that that I decided I was only gonna write another book if I could find the perfect topic.
Right.
And so over the course about the next two years or so, I started dabbling in a whole bunch of different topics. Cause I never have a problem finding
enough things to be interested in. Right.
That's not 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, you know. And then I was reading some work by Mihaly Csikszentmihaly, 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.
Interviewer
I actually have the Sheikhs Enmihalyi quote right here in front of me. Yeah, yeah. Before turning things back over to you. 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.
David Epstein
Yeah. And this hit me in the face
like a kick with a golf shoe, you know?
And I said, oh, my gosh. This is what I'm doing with topics like, I'm finding really fascinating stuff, but I'm swiping right is that I've never
been on the dating app.
Interviewer
The left is.
Derek Thompson
No, you were swiping the left.
Interviewer
Cause you were rejecting. Swiping left is not accepting.
David Epstein
Well, no, I wasn't totally rejecting. I was, like, keeping them in the hopper. But then, like, but what else is there? So I was, like, keeping a lot of things open. I want to.
Derek Thompson
I'll accept the right.
David Epstein
So. And as soon as I read that quote, I said 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 ten times as fascinated.
And that was the beginning of this book.
Interviewer
So I want to put these two
Derek Thompson
projects next to each other. Range and your new book, Inside the Box.
Interviewer
So Range essentially argues that we need to reject the pressure to specialize and be generous. 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 like a. 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?
David Epstein
Yeah, I think it's. 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 okay, 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 okay, 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.
You know, 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, I wrote 150% 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 have seen wasn't going to work. Then when I became a parent and was like, I can't be writing a book and a half to get a book. I realized, you know, 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 I really changed my writing process a lot.
But that's a whole other thing.
Interviewer
There's several themes from this book that
Derek Thompson
I think are worth a deep dive.
Interviewer
And the first that I want to discuss is this idea that individuals and
Derek Thompson
organizations with ultimate freedom and few constraints often struggle and fail.
Interviewer
And the canonical example from your book is this company called General Magic.
Derek Thompson
What was General Magic?
David Epstein
Yeah, most important company nobody's ever heard of.
Derek Thompson
That's exactly right.
David 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. 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, the Apple Macintosh and then a third Apple employee whose job was seeing the future of technology. And by the way, if you I gotta give you his PhD dissertation. This guy, Mark Peratt, 1976 at Stanford, he coins the term information economy on the first page. Reading this thing is easy. Eerie as hell. Like he saw the next half century of technological change. Not just a 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 touchscreen 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 Sixpack.
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, Mark Peratt, says, why raise 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 Perlman. So the thing comes on as a total disaster. Like, the stock price doubles on the first day. Two years later, the company's basically worthless. And because when the communicator comes out, it's like it has a 200 page manual.
Nobody really. It's so many features, like, nobody really understands how to use it.
So Perlman's supposed to create the calendar
function for this thing, and he writes it from 1904 to 2096 and checks it in. Done.
Derek Thompson
When you say calendar function, like, why is the calendar function going back to 1904 here?
David Epstein
It's just because there may be old apps that people use or because they were readying themselves for the world of apps that people might build, things that have historical stock prices or historical news or whatever. And so he checks it in and he's done, right? And then one of the leaders comes
to him and says, steve, people might write historical apps that go way back. You gotta make it bigger. So he opens it back up, makes it go from year one, thinks he's done. Then another team comes to him and says, why are you tying it into
this arbitrary religious context of year one? Make it go back to the beginning of astronomical time. So he opens it up and writes the calendar function to go from the big bang.
To the future.
It would have been four lines of code if he left it in 1904-2096.
Instead, it drags on for months.
And this was how everything worked at General Magic. Because they could do anything. So they did.
Derek Thompson
There's a line by Bill Gurley, the venture capitalist, that says more startups die of indigestion than starvation. That seems appropriate.
David Epstein
Yeah. Actually, multiple people claim to me that they coined that line in my interviews.
Interviewer
Multiple discovery of the same.
David Epstein
Yeah, that's right. Of the same quotation. Yeah.
And this idea that, you know, it's
really counterintuitive, the idea that they die
of too much, not too little, but
it's often the case because it doesn't force you to. I mean, I think the things that useful constraints can often do is force you to clarify your priorities and launch productive experimentation. And with so many resources, places like General Magic don't have to do that. They're not forced to prioritize ruthlessly. When I was talking about changing my own writing process, so my book projects are usually about two years.
I'm interested in the idea before that, but the formal process, two years this time around, I didn't start writing for a year. Not a word. At the end of a year, just researching.
I took a hundred thousand word note
sheet, much longer than the book, and made it into a one page outline
with the structural architecture of the book, which forced me to prioritize ruthlessly. And if it's not on that page, it's not in the book. So there's all these other things I think are interesting.
Right.
But that forced me to really prioritize and places like General Magic never have to ruthlessly prioritize.
Derek Thompson
One thing that's really cool about the General Magic story is that the expats who come out of General Magic.
David Epstein
Amazing. That's why it's an important company.
Derek Thompson
Yeah.
Interviewer
They go on to build. I mean, it's almost like everything.
Derek Thompson
It's like Stanford.
Interviewer
It's like the people who graduated from
Derek Thompson
General Magic went on to found every
David Epstein
person listening to this uses something made by a General Magic alum.
Derek Thompson
The iPad.
David Epstein
Every day.
Derek Thompson
The iPad, the iPhone, Nest, Android, LinkedIn, eBay.
Interviewer
Can you tell me how they applied
Derek Thompson
the lessons they learned from the implosion of General Magic?
Interviewer
Because it did implode.
David Epstein
Yeah, it imploded.
It was a disaster. Ruined various people's lives and stuff like that.
But some of these especially younger employees
were kind of, you know, I don't want to say traumatized because not like trauma in the real Psychological term.
But it left a scar for them and they took that to the next places they went and all became kind
of constraints obsessed to various degrees.
The guy who was the most constraints
obsessed was this guy Tony Fadell, who, when I first called him and said it was Bill Gurley, had introduced us. And I said, you know, I want to talk about constraints.
If you don't have constraints, make up constraints.
He's like almost yelling at me. He's a very enthusiastic guy in general.
But he went on to design the ipod. He was the lead designer of the ipod and he pitched Steve Jobs a Styrofoam model in March of 2001 and got the green light and said, we're shipping by Christmas and just a few weeks to make a first prototype. Clear customer problem, right?
Growing music collections in the MP3 age. No way to carry them on the go.
And it forced them to because he set these really tight deadlines for when they would stop, learn lessons, and then
do a next version, sometimes called Design
Freeze, where you force a stop. It forced them to start borrowing technology instead of building from scratch like they
did at General Magic.
So the scroll wheel that was the iconic feature of the ipod came from a team member who brought in a Danish cordless phone that had a wheel on it and they had to repurpose stuff. But his.
The apotheosis, I think, of his fervor
for constraints was Nest, where he forced the team to work inside a literal box.
Like he made them prototype the packaging
box before the product because it forced him to say, what are the priorities that are so important we communicate them on the box to the end user. And so his whole career became like
centered around constraint driven innovation.
He wasn't the only one.
I mean, interesting one in government, which you might appreciate because of all of your writing about government, was Megan Smith, who was another young engineer there, went on to become.
She like led some stuff dealing with
Google Maps and all these other things.
And then she went on to become
the first female Chief Technology Officer of the United States under President Obama.
And she told me people had these huge ideas of things they want to do. They'd be like, let's remake education. And she was like, I've seen what happens when you say we're gonna remake everything. It doesn't work.
So she developed this philosophy she called Scout and Scale, where she's like, all
these people are doing these little prototypes in their communities and some of them might be working.
So what we need to do is
go find those people that have already learned these lessons in a small way
and then just help their good solutions scale. So it's in all these different ways. They all came out with these lessons about putting a bounding box around projects.
Interviewer
One of my frustrations, talking to you
Derek Thompson
and for people watching us or listening to us, this is not the first or tenth time that David and I
Interviewer
have hung out is that every question I have for you always opens up
Derek Thompson
like 10 to 15 different tabs in the browser of my own head.
Interviewer
Cause I'm like, there's all these different
Derek Thompson
things I want to follow up on.
Interviewer
One of them is as you were
Derek Thompson
offering, the last story on how Tony Fadal went from the disaster of General Magic. Too much freedom to nest, which is hyper constrained by the design process of
Interviewer
first design the box in order to
Derek Thompson
design the exterior of the product. In order to design the interior of the product.
Interviewer
One way that I think about that
Derek Thompson
with my own work is it's often instructive, I think, if you are stuck
Interviewer
in an essay wondering what it is you want to say, write the tweet. If you can't write the tweet, if you can't express not just the headline, if you can't express in 200 or 300 words why you are excited to share this idea with the world, you don't have an idea, you haven't done the work.
Derek Thompson
You need to talk to more people, you need to read more books, you
Interviewer
need to read more papers. If you can't write the tweet, you
Derek Thompson
haven't written the essay or you're not ready to.
Interviewer
And like, I feel like it's similar because the tweet is the packaging, the
Derek Thompson
tweet's not the essay.
Interviewer
The tweet is the box in which the essay travels through the world, right? Meets its ultimate customer. But in a way I was like, oh, that that explains why this weird
Derek Thompson
habit that I've developed works.
Interviewer
Because in a weird way, if you reverse engineer from the box, that can provide enough focus to ask the question, what is it that I'm trying to
Derek Thompson
make here in the world?
David Epstein
That's pretty brilliant. That's very Fidel esque of you.
And in fact, he told me that one of the reasons I did the
one page outline was he said his
the most important advice he gives entrepreneurs or mentors now is to write the
press release before they start the project.
That's funny. One page press release only, right? Which I think is a very similar thing. And as he said, whether it's the nest box or the press release, because that Forces you to try. Why are you doing this thing? Like you said, what problem am I solving? And he said, it does slow you down. It kind of sucks, right?
I didn't enjoy taking 100,000 words and condensing it into a one page outline.
I don't know how you feel about
doing those tweets, but it's probably hard.
But that's the point, right? I think his words were something like
with these ultra constraint based things, it
slows you down, but it forces that thinking. So when I hear you say that, I'm immediately like, oh, I don't want to do that, but it would absolutely
be great for me to do.
But it's a little painful, but that's why it's helpful. And then you're liberated within that to do your thing.
Derek Thompson
Yeah.
Interviewer
This idea that when we fail to
Derek Thompson
constrain ourselves, our focus often suffers also clicks into a wonderful idea from the book by the focus and attention researcher Gloria Marks, who introduced a concept I had not heard of before. I read your work called self interruption.
David Epstein
Yeah.
Derek Thompson
What is self interruption?
David Epstein
Ooh. Yeah. This was the scariest research in the book. So what Gloria Marks, she's been following
people at work for about a quarter
century and finding that we're switching tasks.
You know, it was about three minutes. Every three minutes you'd switch a task when she started.
Now it's about every 45 seconds.
And what she found is with all these constant interruptions like that, whether it's phone notification, other people, whatever, and then often people will say, okay, now today or this week, I have to focus on putting that stuff away. But even if you do that, you will start self interrupting with intrusive thoughts about stuff you should check, things you should respond to at the cadence to which you've become accustomed. As if we have some internal distraction barometer that's like, no, I've become used to this. I'm going to interrupt you with your own thoughts, even if you put the phone away. And so you actually have to train
your attention if you want to be able to focus by having, you know. One of the things she recommends is having blocks of focus.
So she found that people in offices check emails 77 different times a day on average.
Right.
That's not 77 emails, that's 77 times checking.
Maybe you have to answer all that email, but if you can put it
into one or two or three blocks
where you're just doing email and then
your other blocks, you're not doing that.
And try to structure all your work like that.
I mean, part of her point is
that if you're not structuring your attention
now, it is being structured for you.
So you either have a choice to structure it and train yourself to be able to have blocks of focus, or it's going to be done to you.
Interviewer
One reason why this approach is so
Derek Thompson
counterintuitive is that I think our creativity myths and our mythologies of genius and
Interviewer
invention tend to associate the moment of
Derek Thompson
discovery and the moment of invention with
Interviewer
a kind of mindless freedom like go take a shower, go have a bath like our gate.
David Epstein
And not that those things can't act.
Interviewer
I'm not telling people not to shower, that's for sure.
Derek Thompson
They should do so.
Interviewer
But it's interesting because your book is
Derek Thompson
organized in many ways around one big story that you're trying to myth bust, and that is the story of Dmitri Mendeleev.
Interviewer
Tell me what most people understand to
Derek Thompson
be the story of Dmitri Mendeleev and the periodic table.
Interviewer
Tell me the story that most people
Derek Thompson
know and then we'll tell the story that you discovered Israel.
David Epstein
Yeah, if they know it, I mean.
So I'll tell you.
The one that I learned in college
chemistry, which is the status quo story,
is that he's this Siberian genius in the winter of 1869. He's trying to put all the elements,
you know, the chemical building blocks of
the universe in order. He senses there's some order, but he can't find it and he's maniacally focused on it. He, he stays up for three days,
no sleep, and finally he can't stay awake any longer. And he drifts off into the most
impactful nap in human history. And he dreams of the elements sort of swirling around and they snap together in columns and the columns snap together in a grid. And as you move across that grid, the chemical and physical properties repeat periodically,
which is why it's called the periodic table.
And by the way, and he wakes
up and writes it down, finished product.
And it's not just a poster that hangs in high school classrooms. It showed us where to find new elements, the gaps in the table, and that motivated the search for the underlying cause of this pattern, which was Adam. So it was a huge breakthrough. Not just a poster. And that's the story that I learned in college chemistry. The Royal Society, you know, one of
the most biggest scientific societies in the
world, celebrated the anniversary. Matthew Walker and why we Sleep called it the, the epitome, the paradox example of the power of our sleeping brains
to our dreaming brains to freed from the bounds of reality.
And there's all these funny uses, like
Casper used it in mattress marketing and all this stuff like that. That's the story. If people know the story, that's the one they've heard and what's the truth?
None of that.
So Mendeleev actually had a publishing contract to do a two volume Intro to Chemistry textbook.
Derek Thompson
He had a book deadline.
David Epstein
He had a book deadline.
And even more importantly so in the first volume he'd gotten eight, then 63 known elements in. So he had to get the other
55 into volume two.
And he realized, and it had to make.
He had a customer problem too. It had to make sense to intro students.
And he realized he couldn't keep going
one element at a time. So he started experimenting with groups and saying, maybe I can find sort of representative families that I can describe at once instead of individual elements. He was absolutely not looking for a law of nature. He was looking for an organizational scheme for his textbook.
And it was in doing that that
he started to think in families and found the periodic pattern. So it was very much the constraints of a textbook contract, which is like the polar opposite end of coolness from discovering something in a dream, right?
Derek Thompson
Yeah, exactly.
Interviewer
Caspar's not gonna advertise that, I think.
Derek Thompson
So.
Interviewer
The gap between the myth and the
Derek Thompson
reality of Mendeleev, I think for me draws a bridge between the two big principles I wanna discuss with you.
Interviewer
Principle number one, that we overrate the
Derek Thompson
degree to which freedom makes us creative and freedom allows us to flourish.
Interviewer
And number two, the fact that it is wise limitations and wise constraints that
Derek Thompson
often unleash our creativity and allow for flourishing.
Interviewer
To get us started on part two, this idea that throughout history, the greatest musicians and writers and thinkers have been empowered by constraints. Tell me about Keith Jarrett.
David Epstein
Keith Jarrett, we're talking mid-1970s. In the story I tell, he's a jazz piano phenom, right? He's becoming world famous, he's touring the world.
And one of his concert stops is
in Cologne, Germany, for a concert promoted
by a teenager who has rented out an opera house and all these things. And he shows up ready to play, tests the piano at the opera house and says, concert's off. And Vera Brandes was the name of
the teenager who was promoting.
She freaks out like, what are you talking about? And it turns out the wrong piano had been brought. In fact, it was untuned. It had like worn felt hammers. So the upper register was tinny. It was too small, it had fewer keys than the piano that he had Requested.
And so he says, nope, he's leaving.
And she basically begs him to do it, and, you know, she's a teenager. And he gives in and says, just this, just for you, this once. And so he ends up playing, and
the piano forces him to work in all these different ways.
He doesn't want to use the tinny areas, so he kind of stays to the middle registers. He finds one area that sounds okay
enough with his left hand. So he just keeps repeating things there,
sometimes for 10 minutes at a time
while he's improvising with his right hand.
The piano's not big enough to get sound to the back of the opera
house, so he adds a percussion by
stepping on the pedal without pushing it down. All these innovative elements. And then he, you know, he kind
of walks away and he's like, whatever,
and goes off to his next gig. And he had almost told once the piano.
He had a recording crew there.
He was with his manager, and they
were starting to tell the recording crew, like, just this one's not gonna be useful. And they're like, whatever, they're already here. Let them stay here. It gets turned into an album, about an hour long improvisation, way too long to play on the radio.
But people start playing it in record stores, and everyone who walks in starts asking, what is that? Give me that. And it builds and builds and builds and becomes the best selling solo piano
album of all time.
And as Jared would say in he. He. He sort of came to have a dimmer view of it later on because
it got associated with this sort of atmospheric jazz that he didn't like.
But his album that he did say was his best was another piano that had these imperfections. And he said it forces you to work in these ways that you just can't envision ahead of time.
So it forced him to create something amazing that I think you and I actually both legitimately also love this album.
Interviewer
I listened to it today while writing these questions. I listened to it while reading your
Derek Thompson
book, and it is on my Deep Work playlist. I mean, the.
Interviewer
There are.
David Epstein
It's incredible music to work on.
Interviewer
There are tracks on the Cologne album
Derek Thompson
by Keith Jarrett that are among just my three favorite pieces of 20th century music. Bar none.
David Epstein
I mean, bar none.
Interviewer
It's just. And you can hear one thing that
Derek Thompson
I think was interesting, you know, reading your reporting on this.
Interviewer
It's just repetitive enough. And in my first book, Hitmakers, I
Derek Thompson
talked a lot about how what we want from music is this idea that it is.
Interviewer
We want hooks that don't announce themselves as hooks. So they can't be too repetitive. But if they're just repetitive enough, they get stuck in our ear, and it's just an amazing piece of work. You call this idea, this concept that
Derek Thompson
Keith Jarrett stumbled on with Vera the
Interviewer
Teenager, you call it the Green Eggs
Derek Thompson
and Ham theory of creativity.
David Epstein
Yeah.
Derek Thompson
Why?
David Epstein
Yeah, that's actually a phrase I took from the psychologist Katronell Trump.
And it's after the book Green Eggs
and Ham, which Theodore Geisel, aka Dr.
Seuss, wrote on a bet that he couldn't write a book using only 50 words.
And that forced him to experiment with rhythm in all these new ways. He obviously did it.
But actually, even before that, the first bet was he was given a vocab list for kids and asked to use about 200 words to write a book. And first he starts complaining to his
wife because there's almost no adjectives. He says, it's like trying to make
a strudel with no strudels, which I love. And then he just throws up his
hands and says, you know what? I'm just gonna take the first two rhyming words on the list and make a book. And the first two rhyming words, cat and hat. Right.
And the rest is history. And it's the idea that having these constraints forces you off what cognitive psychologists call the path of least resistance when you're hemmed in when the typical convenient solution is blocked. So, like the cognitive scientist Daniel Willingham,
I love how he puts this. He says, you may think your brain's
made for thinking, but it's made for
preventing you from having to think whenever possible, because thinking is energetically costly.
And so you'll go for the low friction easy solution, the path of least resistance, unless that is forcibly blocked, and
then you're forced to do totally new things.
So it's actually almost kind of impossible
to be creative when you have too
much freedom, because your brain is wired
for convenience, not for innovation.
Interviewer
What kind of limits and constraints do
Derek Thompson
you think are most helpful?
Interviewer
Because obviously there are some kinds of
Derek Thompson
limits and constraints that aren't helpful. I mean, one can.
Interviewer
And you say this in the book,
Derek Thompson
I'm not exposing anything that you didn't observe already.
Interviewer
But, like, poverty is obviously a constraint.
David Epstein
Bad constraint.
Yeah.
Derek Thompson
And no one would argue that, like, the best thing we should do for America's children is to make their parents poorer, because that's going to introduce an economic constraint that will turn their children into Keith Garrett. No one's saying that. You're not saying that.
Interviewer
But what is a useful way to think about the kind of constraints that
Derek Thompson
hurt and the kind of constraints that help.
David Epstein
Yeah.
And to that point, in fact, late
in the book, I talk about constraints that have led to shared prosperity. Right. Because that's what we want. And obviously you've written about that eloquently.
And I think the whole idea that
there could be such a thing as too much freedom would have been laughable for most of human history. Right.
This is sort of a more recent problem. And I think if we're thinking about, say, our own life and work. So again, I think the, the two key principles of a useful constraint is that it forces you to clarify priorities or to launch into productive exploration, typically. Now, if someone's telling you how to do something so specifically that you say, could I surprise myself? And the answer is no, then you're way too constrained. But in terms of clarifying priorities, let's say there's a genomics lab that I write about in the book that was a leader in the world and was losing its lead because the work was getting so messy. And they decide to make all of their current commitments visible on a wall, post it notes on a wall, and immediately realize we've got way too much going on. Because they only ever add, they never take things away. And I think modern life is insidious at adding things to our plate in
work and in life.
And we are hardwired to overlook taking stuff away. It's called subtraction, neglect, bias. We easily add things and don't take them away. So I think a form of doing that for everyone, of making all your current commitments visible and then making a funnel that's like nothing else is coming in the top of this funnel until something else comes out the bottom can be incredibly useful. So that's something where you're not, you know, you're not impoverishing somebody, you're not even telling them not to do things they want to do, but clarify your priorities. Because I think so much, you know, I think it's never been easier to do too much and compared to now. And I think a lot of the optimization and productivity hacks and all these
kinds of things that people want are
illusions where they are not being forced
to grapple with the fact they have limited time and attention and should be prioritizing ruthlessly. And so we're giving into all these illusions where we're taking on way more than we can do. So that's what some. I don't know if I went too far off track.
Interviewer
No, not off Track at all. In a way, I want to go deeper. I mean, it sounds to me like
Derek Thompson
you're saying that limitations are good when they fight one of two different enemies, distraction and delay. Right.
Interviewer
By fighting distraction, we force prioritization.
David Epstein
Yes.
Interviewer
And by fighting delay, you're saying, no, do the thing now. And this is one reason why I think deadlines are so important. There's so many characters throughout this book just strewn throughout the book of these incredible achievements that we would want to
Derek Thompson
think of as breakthroughs in the shower. But in fact, they're all about deadlines.
Interviewer
Tell me about Frank Lloyd Wright and then just keep going on this principle, please, about the idea that what constraints do. The kind of constraints that are useful aren't constraints like poverty, but rather constraints that promote and require us to focus.
Derek Thompson
So Frank Lloyd Wright.
David Epstein
Yeah.
And to set a little bit of
the research background for Flankroid. Right.
Deadlines. Because I think this is a great
example of where you're asking me to differentiate between the good and bad constraints.
Deadlines can be either good or bad.
Deadlines boost people's creative problem solving and
creativity and productivity when it leads them to monotask. And they say, I have to do this thing now. When it leads them to multitask, which
it sometimes also does, people say, I have all these deadlines, I have to
do a million different things. Then all those good things go down. So it really depends how you use it. But in the case of Frank Lloyd Wright, so Falling Water, probably the most
famous work of architecture in the United States,
he had months to work on this, thinking about it, but hadn't done anything.
And the client then calls and says,
hey, I'm a few hours away. I want to stop by and see the drawings.
And Frank Lloyd Wright, according to one
of his apprentices, marches across the room,
sits down and goes to work.
And they.
He's wearing out pencils so fast, they
have multiple people, like getting them ready to sharpen. And in a few hours, he does the plan for falling water, period. Done.
And that's the plan that stuck.
So it led him to monotask maniacally. And there are all these examples of people like that. Like another that's near him in the
book is Duke Ellington, who was the
most chronic of procrastinators. Right, left, compositions unwritten, watches unworn, partners unwed.
Like everything he put off.
So as he liked to say, I don't need time. What I need is a deadline. He got. He wrote almost 2,000 original compositions. I mean, I think he was one of America's eminent creative geniuses. Like the stuff in the 30s he's
most famous for to me doesn't hold a candle. The stuff in the 60s, that's total creative reinvention.
But he could not work unless there was a deadline pressing him. And then when it when there was, he worked with an intensity that like surprised everyone around him. But again, these were creators who saw the deadline as cause to monotask. And if people use it that way,
it's incredibly powerful on any journey.
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Derek Thompson
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Derek Thompson
episode is brought to you by Spotify Advertising. Right now you're listening to my voice. It's the way I communicate, how I connect, share stories and for most of human history, this is how culture moved at the speed of voice. We told stories out loud, we built trust through tone. Then the screens took over. Attention was reduced to clicks and scrolls. Tech made us faster, but also more fragmented. Now, thanks to AI and connected devices, voice is re emerging as a primary interface and it's helped audio and sound become more integrated and interactive than ever. Spotify calls this shift the Sound on Era. It's the focus of a new report exploring how sound has become the bridge connecting modern media and why brands need a sound on strategy to be heard. If you're curious about the trends reshaping consumer behavior, go to ads.Spotify.com, download the sound on Era report and learn how to turn up the volume on your business. This message is brought to you by Apple Card. Hey, you could be earning 2% daily cash back on that purchase and that one.
Interviewer
And even that one.
Derek Thompson
That's because Apple card users earn 2% daily cash back on every purchase, including everyday items they buy online or in store when using their Apple Card. With Apple Pay, not an Apple Card customer, you can apply in the Wallet app on iPhone subject to credit approval. Apple Card issued by Goldman Sachs Bank USA Salt Lake City Branch Terms and more at Apple Co Benefits how has
Interviewer
this changed your work. Like, how has it changed your creative life?
David Epstein
Yeah.
So first of all, there's the process aspect of my work where with my first two books, I wrote 150% the length of a book. This is the first time I wrote
one book to get one book. And I turned it in early because I had this. I took longer time to start, but I gave myself a much more defined box once I started working. And that really liberated me to then enjoy the writing and play with the
sentences and things like that. Because I wasn't thinking about the architecture
while I was doing that. So I would never not work this
way again if I ever write another book.
But it also changed the things I do within my workday in a few ways.
One, I end my workday now.
I used to say, oh, one of
my competitive advantages is that I'm going to let my workday go on forever. And I can just do more work than other people, you know.
And one, I realized just like when I was an athlete, that's stupid, because
recovery is really important if you want
to be good again later.
But also having a kid and, you know, not wanting the workday to drag on forever. So I stole something from Isabel Allende, you know, one of the greatest living writers who I profile in the book where she lights a candle to start her workday and blows it out at the end every day to be like. And closes the door. Done. I use electric candles because, like, too much paper. I don't want to burn down my office.
But having a real end of my
workday and a period of recovery, so I'm cycling.
And then during the day, I really
do batch my work now.
So, you know, not everybody can not
check email as much as I do during some periods. But I definitely don't start with it because in looking at Gloria Mark's work, I learned about the Zeigarnik effect, which
is an unfinished task. Leaves this residue on your brain that
interferes with the other stuff you're going to do. And the inbox is always an unfinished task.
So I make sure to do some
of my important work before I open that. And then I try to make monotasking blocks for whatever I'm doing throughout the day so that I'm minimizing my number of toggles. Another. I'll give you one more that's, like, really mechanical for me. Cause there are also some personal things
that I took from this book that
were not about my work.
Derek Thompson
I want the personal stuff, too. So let's finish work and then go personal.
David Epstein
So mechanically,
one of the, probably the
greatest creative prompt you can have is saying to somebody like how did you solve this problem? And then say, oh, and you can't do it that way. Whether it's like a client meeting or a painter and say whatever the thing they start doing, then say, no, no, sorry, that one's gone. Preclude constraint, right? And I married that with something I learned while I was reporting on Pixar that they used called the three pitches rule, where they would have directors force them to pitch three story ideas. Cause they found that they would fall
in love with their first idea and
it usually wasn't their best, so they had to pitch three. So for me, my leads for every chapter in the book, I wrote the lead that came to mind. Then I crossed that out and forced myself to write two other leads. Painful, right?
Because you get attached to the thing you put down.
But I'd say 2/3 of the chapters I probably used not the first one, the second or third one. Because the first one is just the
convenient things that comes to mind.
It's not the best. So that's a way I change my work in my life. Should I move to the life?
Derek Thompson
Oh yeah, I actually wanna go to
Interviewer
life because let me set up life. I'm very interested in happiness.
Derek Thompson
I write a lot about happiness, I podcast a lot about happiness. Happiness is on my mind right now because I just wrote this long piece about how according to basically every single social survey we have available to us, American happiness just fell off a cliff in the 2000s. And
Interviewer
if you look at which groups have the highest level of self reported happiness, it's often married people with kids. And on the one hand you could say that's not surprising because married people
Derek Thompson
with kids tend to be economically advantaged.
Interviewer
And I think there's something to that.
Derek Thompson
So I don't want to rule that out.
Interviewer
But it's interesting in the concept or
Derek Thompson
in the context, I should say, of
Interviewer
our conversation, because married people with kids have the most constraints, the most responsibilities.
Derek Thompson
I mean, I have two children now, two and a half and about four or five months old. I cannot work after 5:30.
Interviewer
I can't because I'm taking care of
Derek Thompson
my children until they're in their beds, until at 8:30.
Interviewer
By the time they're in their beds
Derek Thompson
by 8:30 I'm exhausted.
Interviewer
Like my brain is complete mush by 8:45. So I can't physically work past 5pm anymore and I can't work on the weekends either. But in a weird way, that constraint Promotes such extraordinary focus. And there's one more piece that I
Derek Thompson
found is like sort of counterintuitively helpful.
Interviewer
If I structure my day around my
Derek Thompson
workouts, if I say no matter what, I have to go to the gym for 35 minutes and I go, forcing
Interviewer
myself to organize the day around this
Derek Thompson
thing that has nothing to do with
Interviewer
productivity makes me more productive, I think, because I lose time. So now it's like, it's not just that I have to be home at 5:30, it's not just that I have to go to the gym. All these things are limiting my time. If I want to get any writing done, it has to be done between like 9:45 and 11:15. Let's go. Right?
David Epstein
Yeah.
The time laser focused monotask on that writing.
Interviewer
It's so unbelievably clear to me that
Derek Thompson
I can't fuck around the same way I could when I was 25 years old. When to your point, it was like,
Interviewer
if I don't finish this writing now, I'll go home and I'll write it
Derek Thompson
at 9pm, I'll wake up at 2am and write it.
Interviewer
Who cares? I'll wake up at 5am and write it. But that kind of freedom, that ability to do anything whenever always allows you to place your focus in the future rather than right here, right now. And so it ends up working against you. So I now wanna hear, now that I've given you my little sermon, I
Derek Thompson
wanna know about how writing this book has changed your life, changed your organization of time or your conception of family life or what's important to you.
David Epstein
Yeah, I mean, I think some of
the things will not surprise you. Right. And to go to your point, by the way, of people who are married with children, you know, being happier, I mean this goes back to like Durkheim in the late 19th century. He's one of the founders of sociology where when governments first started doing keeping statistics on suicide and he looked at, and at the time it was thought it was just a private psychological problem.
And he looked and said, oh no,
no, it's a social problem because it goes in waves. And if the economic fortunes of a country turn way down, suicide goes up.
But if they go up too fast and it unmoors people from all these
things they're used to, suicide goes up also.
And people without, basically people without. The less dense their network of reciprocal obligation was, the more likely they were
to be depressed and take their own life.
And then Robert Putnam in Bowling Alone
found basically the same thing where he
famously said, joining One club cuts your
risk of dying next year in half.
And that's a rule of thumb, but
it's kind of been backed up by
subsequent research that having a network of obligations that impinge on your freedom, you
have to be somewhere at certain times, right? But they make life more meaningful. And I had thought when I became a writer, as I started getting more traction in the industry, autonomy became my goal.
I actually went to a writer's retreat once, and we had to answer, what
were we all optimizing for that year? And I said, autonomy. Fast forward a few years, and I realized there is such a thing as too much autonomy. When we came in here, I was just like, I love coming into an office before we started this, and that's a very privileged thing to say, right? But I realized I was unhappy, and
I had to start reeling that back.
So I joined a nonprofit board in my community. I started going to dance meetups to have some embodied experience with strangers. I joined a regular dinner and discussion club.
And all these things that impinge on
my scheduling freedom, where I have to
be places where other people are counting on me to be there at certain
times that are annoying. But I'm so much happier doing that, having those connections and having those obligations and being a dad and all these things. So some of it was rebuilding my network of obligations that, even though annoying, are really important, because I think I ended up in kind of. Do you remember when Mark Zuckerberg first described the metaverse, and he was like,
it's gonna be great. We're all gonna live in a universe totally tailored just to us.
I'm like, wait, that's actually horrible. That's, like, what I was doing in real life. Like, you don't sync with anybody else's schedule. It's terrible. But also, I think I started becoming more of a satisficer in my life after doing some of this research where satisficing is a term coined by Herbert Simon. This guy who's a lot of his thinking is in the book.
It's a combination of suffice and satisfy.
He was trained as a political scientist, but he won the highest awards in computer science, psychology, and the Nobel Prize in economics.
And what he showed was that humans
don't conform to the rational actor model in economics, where we can evaluate endless options and make the best decision. We have to pick good enough solutions and satisfy.
And he said, we should do that proactively. You should have good enough rules.
So he wore one type of beret, one kind of socks, said, you need Three pairs of clothing, one on your back, one in the closet, one in the wash, same breakfast, same house for 46 years, et cetera.
You'd almost think he's like a low
ambition guy if he hadn't won the highest awards in three different scientific disciplines. And so I really took that to heart because I think I have the
opposite tendency, what's called maximizing tendencies, to
try to evaluate everything and take the best option.
And it's almost always a bad thing
to be maximizers are maybe we'd call optimizers now, less happy with their decisions, less happy with their lives, more prone to regret. So I'm now very proactive about making decision rules.
What would be good enough for this decision, this product?
I'm buying, this project. I'm doing, my newsletter. I started as a very proactive satisficing experiment where I say if a book has to be a nine or ten, if I hit six and a half on a newsletter post, it's going out. So I'm much more cognizant about setting good enough rules for all these things and then moving on and not reading all the other reviews or whatever it is for my decisions.
Derek Thompson
I want to end with a character that you and I have talked a lot about as you were writing this book. My favorite philosopher, Sren Kierkegaard, a Danish gentleman from the early to mid.
David Epstein
I remember you telling me when I first mentioned I was writing about constraints you mentioned in Kierkegaard.
Interviewer
Well, one of the ideas I love
Derek Thompson
most in his history of existentialism, maybe philosophy, is Kierkegaard's theory of infinitude. Infinitude, where he says, you know, you
can be lost in both.
People have been lost infinitude for centuries. That is to say, if you're a Catholic potato farmer whose dad is a Catholic potato farmer whose dad is a Catholic potato farmer, you have no ability to make choices that truly
Interviewer
author your individual authenticity. You can't become a true individual because you're locked in the grooves of life. And he said, the opposite though, is
Derek Thompson
the problem of modernity. We're not lost in finitude, we're lost in infinitude.
Interviewer
We are told we can be anything. We are told that we should seek
Derek Thompson
absolute freedom, maximize our happiness in all
Interviewer
these different things at once.
Derek Thompson
And in the most famous line that
Interviewer
he wrote is that anxiety is the dizziness of freedom, right? Standing at the edge of a cliff
Derek Thompson
and looking down and fearing that you're
Interviewer
going to fall, that's fear. But not knowing if you should jump or if you should step back or if you should climb down and being obsessed with thinking through all the different things you can do at the edge
Derek Thompson
of that cliff, that is the dizziness of freedom. That is anxiety.
Interviewer
And the reason I think that this project is such a good match for
Derek Thompson
our times is that I just think Kierkegaard was right. I think that we are told to maximize happiness in so many different aspects of our lives, and it's a process of insanity making, I think, for a lot of people. And so I thought from the second that I heard about this project that the idea of a book singing the gospel of constraint would be incredibly useful. And this book really is incredibly useful. So, David, thank you so much.
David Epstein
I really appreciate it very eloquently.
Plain English with Derek Thompson, The Ringer
Date: May 1, 2026
Guest: David Epstein, author of Range and Inside the Box
In this episode, host Derek Thompson speaks with bestselling author David Epstein about the paradoxical role of freedom and constraint in creativity, achievement, and happiness. Drawing from Epstein's new book Inside the Box, they explore why limitless freedom often leads to distraction, indecision, and mediocrity—while meaningful constraints and boundaries can foster innovation, focus, and fulfillment. The conversation weaves together historical examples, psychological research, and personal anecdotes, challenging the prevailing cultural wisdom that “more freedom” is always better.
"Compared to pre-industrial worlds we have 10 million times more choices … more freedom, more choices, more autonomy than our ancestors." (01:35)
“Anxiety is the dizziness of freedom.” (03:03)
"I found a lot of things that were interesting, but I could not find anything that was perfect … I was keeping a lot of things open." (07:22)
“By making up one’s mind to invest in a marriage … one is freed of the constant pressure of trying to maximize emotional returns.” (06:35)
“They could do anything. So they did … we just couldn’t figure out what not to do.” (11:24, 11:58)
“If you don’t have constraints, make up constraints.” (15:36)
“If it’s not on that page, it’s not in the book.” (14:18)
“If you can’t write the tweet … you haven’t written the essay or you’re not ready to.” (18:25)
Constraints like the “tweet” or the “box” clarify what matters, forcing productive focus.
“If you’re not structuring your attention now, it is being structured for you.” (21:53)
“It was very much the constraints of a textbook contract, which is like the polar opposite end of coolness from discovering something in a dream.” (25:05)
“Your brain’s made for preventing you from having to think whenever possible … you’ll go for the low friction easy solution unless that is forcibly blocked.” (30:14)
Work Process:
Life & Happiness:
“Having a network of obligations that impinge on your freedom, you have to be somewhere at certain times, but they make life more meaningful.” (45:20)
“I’m now very proactive about making decision rules. What would be good enough for this decision?” (48:02)
“Anxiety is the dizziness of freedom.” (49:34)
“We just couldn’t figure out what not to do.” – David Epstein (11:58)
“If you don’t have constraints, make up constraints!” – Tony Fadell (15:36)
“If you can’t write the tweet, you haven’t written the essay.” – Derek Thompson (18:25)
“Having a network of obligations that impinge on your freedom … make life more meaningful.” – David Epstein (45:20)
“Anxiety is the dizziness of freedom.” – Soren Kierkegaard, quoted by Derek Thompson (49:34)
| Example | Constraint Type | Outcome | |--------------------------|-----------------------|----------------------------------------------------| | General Magic | No constraints | Failed product/company; diffusion of focus | | Tony Fadell (iPod/Nest) | Artificial deadlines, packaging constraints | Iconic products, rapid prototyping | | Keith Jarrett (Köln) | Bad piano | Innovative album, all-time sales record | | Dr. Seuss | Word limit | Green Eggs and Ham, enduring children’s classic | | Frank Lloyd Wright | Impending meeting | Created Fallingwater in a single focused session | | Duke Ellington | Deadlines | Prolific, innovative music composition | | David Epstein’s writing | One-page outline | More focus, less waste, earlier completion |
Derek and David argue persuasively that our cultural overemphasis on freedom and optionality often saps our ability to act, create, and find meaning. The remedy—drawing from history, psychology, and their own lives—is to embrace wise constraints, set boundaries, and commit deeply. The “enemy” is not too little freedom, but too much; it is constraints that force us to create, decide, and flourish.