Seven Types of Serendipity

From untidy desks to post-it notes to the brewery next door—so much of the creative process is about being open to happy accidents. But how do you make them more likely to happen?

[This is the latest post in my series on designing a workflow for thinking.]

“One thing a person cannot do, no matter how rigorous his analysis or heroic his imagination,” the Nobel laureate Thomas Schelling once observed, “is to draw up a list of things that would never occur to him.” Schelling’s original point was part of a larger argument defending the intellectual exercise of wargaming. Well-designed war games—like the ones created by the RAND Corporation, where Schelling worked in the late 50s—were a way of helping military strategists stumble across new opportunities or vulnerabilities that would have never otherwise occurred to them. But there’s a general applicability to Schelling’s quip as well: so much of trying to think imaginatively is figuring out ways to trick your brain into coming up with an idea that would have not occurred to it otherwise. Now, it’s true that one way to do this is obvious: go read—or have conversations with—other people, and borrow whatever interesting new ideas you uncover from those interactions. But I think there’s a more general problem here, one that requires more devious methods to get around. And it boils down to the question: how do you surprise yourself? What part of your workflow supports unplanned discoveries?

In the last installment of this series, I made a passing reference to the ReadWise daily email algorithm as a “serendipity engine.” I didn’t fully spell out what I meant by the phrase, though the folks at ReadWise seemed to take to it immediately:

Readwise @readwiseio

💖 serendipity engine 💖

Steven Johnson @stevenbjohnson

I’ve become a big fan of a feature offered by @readwiseio, which sends me a daily email with five quotes algorithmically curated from my entire history of e-book reading. (Plus a bonus quote from a book I haven't read yet.) https://t.co/ZpLKh36GDt https://t.co/RBO98ia1lQ

When I was first sketching out the chapter structure for Where Good Ideas Come From, serendipity was one of three topics I knew I had to devote a whole chapter to. (One of the others, the Darwinian concept of exaptation, is a close cousin of serendipity, for reasons we’ll see.) I hadn’t stumbled across the Schelling quote at the time, or if I had I subsequently forgot it, but I can see now that the whole idea of serendipity was a way of getting around the Schelling paradox. You trick your brain into coming up with an idea that would never occur to it through some kind of randomizing event, a happy accident. That’s what serendipity is all about.