Plain English with Derek Thompson - Why Too Much Freedom Is the Enemy of Success

Episode Date: May 1, 2026

Freedom is one of the few ideas everyone agrees on. Surely more choice and autonomy is a good thing, right? But what if our endless pursuit of freedom is actually making us more anxious, less creative, and holding us back from reaching our full potential?Today, Derek Thompson talks with bestselling author David Epstein about the surprising upside of constraints. After arguing for breadth in 'Range,' Epstein’s new book, 'Inside the Box,' makes the opposite case: that limits and rules can actually unlock creativity and satisfaction. They explore why more options don’t always make us happier, and how too many possibilities can lead to paralysis.As Søren Kierkegaard warned, anxiety may be the price of too much freedom. It’s the dizziness that comes from keeping every option open. So in a world obsessed with maximizing choice and opening doors, this episode makes the case for something radical: closing some. Subscribe to our YouTube channel here: Plain English with Derek Thompson If you have questions, observations, or ideas for future episodes, email us at [e-mail]. Host: Derek Thompson Guest: David Epstein Producer: Devon Baroldi Additional Production Support: Ben Glicksman Learn more about your ad choices. Visit podcastchoices.com/adchoices

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. In the realm of career advice, we 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, quote, 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, stockkeeping units, distinct purchasable items. how many different boxes of cereal, buttoned 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, more 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, sort of.

Our guest is a most unusual person to make this argument. Several years ago, my friend David Epstein wrote a book called Range, and it became one of those best-selling non-fiction 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. This is Plain English. David Epstein, hello. Hi, thanks for having me. 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? 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. 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 going to 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. 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 Miha, Chicks, and Mihai,

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 he'd be applied to anything, where he basically says the great thing about being committed, if you commit by your choice, is that all 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. I actually have the she sent me high quote right here in front of it. Yeah, please. Yeah, please. Yeah, please. 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 is 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, quote, limitations are liberating. 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 dating. Left is, no, you were swapping the left because you were rejecting. I was swiping right. Well, no, no. I wasn't totally rejecting. I was, like, keeping them in the hopper, but then like, but what else is there? Oh, I say, okay, got it.

Okay, I'll accept the right. Okay, 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 10 times as fascinated, and that was the beginning of this book. 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? 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 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 draw. on 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. 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. What was General Magic? Most important company nobody's ever heard of.

It's exactly right. Most important because of the people who came out of it. So this was a company, it was a 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, the Apple Macintosh, and then a third Apple employee whose job was seeing the future of technology. And by the way, if you read, I got to give you his PhD dissertation, this guy Mark Parrat,

1976 at Stanford, he coins the term information economy on the first page. Reading this thing is eerie as hell. Like, 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 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, while I 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 out as a total disaster. Like the stock price doubles on the first day. Two years later, the company is basically worthless.

And because when the communicator comes out, it's like 200-page manual. 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. When you say calendar function, like, why is the calendar function going back to 1904 here? 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 got to 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 1904 to 2096 instead it drags on for months. And this was how everything worked at General Magic because they could do anything. So they did. There's a line by Bill Gurley, the venture capitalist, that says, more startups die of indigestion than starvation.

That seems appropriate. Yeah, actually, multiple people claim to me that they coined that line in my interviews. Multiple discovery of the same quotation. 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, my book projects are usually about two years. I'm interesting 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 100,000 word note sheet, much longer than the book, and made it into a one-page, outline the structure 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. One thing that's really cool about the General Magic story is that the expats who come out of General Magic. Amazing. That's why it's an important company. They go on to build. I mean, it's almost like... Everything. It's like Stanford. It's like the people who graduated from General Magic went on to found all these companies. Every person listening to this uses something made by a General Magic alum. The iPod, the iPad, the iPhone, Nest, Android, LinkedIn, eBay. Can you tell me how they applied the lessons they learned from the implosion of General

Magic? Because it did implode. Yeah, it imploded. It was a disaster. It 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 it's 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 Fidel, who, when I first called him and said, as 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. 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 it's 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 fur 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 them to say, what are the priorities that are so important, we communicate them on the box to the end user. And so, you know, 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 it. education. And she was like, I've seen what happens when you say, we're going to 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. One of my frustration is talking to you, and for people watching us or listening to us, this is not the first or tenth time that David and I have hung out, is that every question I have for you always, like, opens up like 10 to 15 different tabs in, like, the browser of my own head because I'm like, there's like all these different things I want to like follow up on. One of them is, as you were offering the last story on how Tony Fidel went from the disaster of general magic, too much freedom to Nest, which is hyper constrained by the design process of, first design the box in order to design the exterior of the product, in order to design the interior of the product. One way that I think about that with my own work is it's often instructive, I think. If you're stuck 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. You need to talk to more people. You need to read more books. You need to read more papers. If you can't write the tweet,

you haven't written the essay or you're not ready to. I feel like it's similar because the tweet is the packaging. The tweet's not the essay. 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 explains why this, weird habit that I've developed works 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 make here

in the world? That's pretty really, 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, who he 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, you know, 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. Like, 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-constra 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.

Yeah. This idea that when we fail to constrain ourselves, our focus often suffers, also clicks into a wonderful idea from the book by the Focus and Attention Researcher, Gloria Marx, who introduced a concept I had not heard of before I read your work. called self-interruption. Yeah. What is self-interruption? Ooh, yeah, this was the scariest research in the book.

So what Gloria Mark, 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 email 70, 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. One reason why this approach is so counterintuitive, is that I think our creativity myths and our mythologies of genius and invention tend to associate

the moment of discovery and the moment of invention with a kind of mindless freedom. Go take a shower. Go have a bath like our comedies. And not that those things can't act. I'm not telling people not to shower, that's for sure. They should do so.

But it's interesting, because your book is organized in many ways around one, big story that you're trying to myth bust. And that is the story of Dmitriy Mendelayev. Tell me what most people understand to be

the story of Dmitriy Mendeleev and the periodic table. Tell me the story that most people know and then we'll tell the story that you discovered Israel. 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. 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. And 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 snapped 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, 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 epitome, the paradox example of the power of our sleeping brains to our dreaming brains to freed from the bounds of reality. 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 Mendelais have actually had a publishing contract to do a two-volume intro to chemistry textbook. He had a book deadline. He had a book deadline. And even more importantly, so in the first volume, he'd gotten eight of the 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. Yeah, exactly. Casper's not going to advertise that, I think. So the gap between the myth and the reality of Mendelaya, I think, for me, draws a bridge between the two big principles I want to discuss with you. Principle number one, that we overrate the degree to which

freedom makes us creative and freedom allows us to flourish. And number two, the fact that it is wise limitations and wise constraints that often unleash our creativity and allow for flourishing. 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. Keith Jarrett, we're talking mid-1970s in the story I tell. He's a jazz piano phenom.

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, test the piano at the opera house and says, concerts off. And Vera Brandis was the name of the teenager who was promoting. It 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, so worn felt hammer. 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 going to be useful. And they're like, whatever, they're already here. Let him 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, 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. I listened to it today while writing these questions. I listened to it, I'm reading your book and it is on my deep work playlist. I mean, there are tracks. It's incredible music to work by. There are tracks on the Cologne album by Keith Jarrett that are among just my favorite pieces of 20th century music, bar none.

I mean, it's just, and you can hear one thing that I think is, it was interesting, you know, reading your reporting on this, it's just repetitive enough. And in my first book, Hit Makers, I talked a lot about how what we want for music is this idea that it is, 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 some. stuck in our ear. And it's, it's just an amazing piece of work. You call this idea, this concept that Keith Jared stumbled on with Vera, the teenager. You call it the Green Eggs and Ham theory of creativity. Yeah. Why? Yeah. That's actually a phrase I took from the psychologist Katrinel 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 going to 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 convenience 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 you're not. 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. What kind of limits and constraints do you think are most helpful? Because obviously there are some kinds of limits and constraints that aren't helpful.

I mean, one can, and you say this in the book, I'm not exposing any anything that you didn't observe already, but like, poverty is obviously a constraint. Bad constraint, yeah. 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 to Keith Garrett. No one's saying that. You're not saying that. But what is a useful way to think about the kind of constraints that hurt and the kind of constraints that help? 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 two key principles of a useful constraint is that it forced 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 suppose? prize 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 or 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. No, not a track at all. In a way, I want to go deeper. I mean, it sounds to me like you're saying that limitations are good when they fight one of two different enemies, distraction and delay. Yeah. Right? By fighting distraction, we force prioritization.

Yes. 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 think of

as breakthroughs in the shower. Yeah. But in fact, they're all about deadlines. Yeah, yeah. Tell me about Frank Floyd, right? 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. So Frank Lloyd Wright. 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, have all these deadlines

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 drawing. And Frank Lloyd Wright, you know, according to one of his apprentices,

marches across the room, sits down and goes to work, and 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 like 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 there was, he worked with an intensity that, like, surprised everyone around him. But again, these were creators who saw the deadline as caused to monotask. And if people use it that way, it's incredibly powerful. How does this change your work?

Like, how has it changed your creative life? 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 work day 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 Isabella Allende, one of the greatest living writers who I profile on 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 in 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 Zagarnik 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. Because there are also some personal things that I took from this book that were not about my work. I want the personal stuff too. So let's finish work and then go personal. Okay. So mechanically, one of the, probably the greatest creative prompt you can have is saying somebody like, how would 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 was 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 because 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 cross that out and force myself to write two other leads. Painful, right? Because you get attached to the thing you put down. But I'd say two thirds 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 changed my work. In my life? Should I move to the life? Yeah, I actually want to go to life. Because let me set up life. I'm very interested in happiness. 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 2020s. And 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 with kids tend to be economically advantaged. And I think there's something to that, so I don't want to roll that out.

But it's interesting in the concept or in the context, I should say, of our conversation because married people with kids have the most constraints, the most responsibilities. I mean, I have two children now, two and a half and about four or five months old. I cannot work after 5.30.

I can't because I'm taking care of my children until they're in their beds, until, you know, 8.30. At the time they're in their beds by 8.30, I'm exhausted. Like, my brain is complete mush by 8.45. Yeah. So I can't physically work past 5 p.m. 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 found is, like, sort of counterintuitively helpful. If I structure my day around my workouts, if I say I, no matter what, I have to go to the gym for 35 minutes and I go, forcing myself to organize the day around this thing that has nothing to do

with 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 945 and 1115 let's go right the other time laser focused monotask

on that writing it's so unbelievably clear to me that I can't fuck around the same way I could when I was 25 years old, when, to your point, it was like, if I don't finish this writing now, I'll go home and I'll write it at 9 p.m. I'll wake up at 2 a.m. and write it.

Who cares? I'll wake up at 5 a.m. 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 want to hear, now that I've given you my little sermon, I want to know about how writing this book has changed your life,

change your organization of time or your conception of a family life or what's important to you. 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, is 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, and 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's, 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 going to be great.

We're all going to 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 satisfacer 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.

He was a, it's a combination of suffice and satisfy. He was a trained as a political scientist, but he won the highest awards in computer science, um, 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 us. 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 satisfying 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. I want to end with a character that you and I have talked a lot about as you were read in this book,

my favorite philosopher, Shoring Kierkegaard, a Danish gentleman from the early to mid-19th century. I remember you telling you when I first mentioned I was writing about constraints, you mentioned in Kirkgaard. Well, one of the ideas I love 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 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 the problem of modernity. We're not lost in finitude. We're lost in infinitude. We are told we can be anything. We are told that we should seek absolute freedom,

maximize our happiness, and all these different things at once. and in the most famous line that he wrote is that anxiety is the dizziness of freedom. Standing at the edge of a cliff and looking down and fearing that you're 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 of that cliff, that is the dizziness of freedom. That is anxiety. And the reason I think that this project is such a good matter for 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. I really appreciate it. Very elegant. Thank you.