Kelly has a fascinating conversation with New York Times bestselling author David Epstein about his new book “Inside the Box: How Constraints Make Us Better.” 

Broadly speaking, your book is about how creativity desires constraints and this is so true to improvisational theatre where many people think it’s created through total freedom. 

“I talked to the music producer Rick Rubin about this a little bit too. And he said just what you said, that from the outside, people think that when they see these creative outputs, that this must be just the product of this total freedom, right? Like, if only I were unbound from the stuff that I do every day, creativity could flourish. And it turns out to be totally the opposite, whether it’s it’s ritual and structure that actually builds the sandbox that you’re then free to play in, or even putting down rules that actually purposely restrict your choices. Because as the cognitive scientist Daniel Willingham likes to say, I love how he put it, that you may think your brain is made for thinking, but it’s actually made for preventing you from having to think whenever possible. Because thinking is energetically costly, and your brain is wired for convenience, not for working hard.” 

There’s a term we use at Second City called the ‘good enough’ show and you write about Herbert Simon and a term he came up with that means the same thing. 

“So, he coined that term ‘satisficing,’ which is a portmanteau of satisfy and suffice. And what it means is because our brains are not really capable of evaluating all the options, we’re definitely not capable of understanding the repercussions of all of our decisions. Really the way we operate is by sort of having good enough rules and using mental shortcuts and all these kinds of things. And what he argued was that we should actually do this more proactively. And because on the other end of the spectrum is what’s called maximizing.  And researchers like Barry Schwartz and others who created a maximization scale that determined how much of a maximizer versus satisficer someone is, what they basically found, if I can simplify a big body of work in a nutshell, is that it’s almost always bad to be a maximizer.” 

I’m so happy we have remote work options, but creativity is so social that I have concerns that we’re losing the live spaces where we really learn how to connect and create. 

“100% agree. When I think about my time at Sports Illustrated, starting as a temp fact checker, I don’t know how I could have gotten that education. I was surrounded all day by people better than me at the thing that I wanted to get better at. And I just don’t know how I would ever recreate that education from just talking to them, listening to them, bouncing ideas off of them. There is actually Northwestern research that showed that most of the benefits to mentorship are implicit knowledge, not the things that the mentor tells you, but just like seeing what they’re doing and how they behave. So, I really worry about this, especially for younger people , when they’re so remote, but kind of for everybody.”