Feb 23·edited Feb 23Liked by Annie Duke

It’s a complicated problem, isn’t it? Kanaman and Twersky showed that people rarely think in mathematically logical ways. A host of decision and perception biases are even named, but that still doesn’t stop people from having and exhibiting them. And then, there’s selective memory: bad relationship, but—since we’re stating rationalizations for not quitting—“better the devil you know.”

For me, relationships probably represent the clearest way I can understand my counterproductive self. It became clear to me about 20 years ago that I knew a relationship was doomed quite a while before I let go. I also knew that something had to happen for me heart to catch up to my mind. Once that event happened, and it would always be different, but recognizable, things would be officially over and done with. And so it has happened. Romantic situations, work situations, inventions that I made and fell in love with. Sooner or later, I hit walls.

But there’s a flip side to that coin, too. The idea of “fail early” in business has been clearly debunked. What seemed like a great idea when I first heard it isn’t so great after all. People who fail early typically have little more than a longer string of failures behind them. And those who have started successful businesses are in high demand. This is certainly true in the medical device space, which boasts a 90-95% mortality rate. I started a company in ‘96 which, by any criterion, succeeded. Now, trying to start another one, the mere fact that the company exited successfully gets me in all kinds of doors. My background is in sciences and medicine, not business; this had been a pleasant surprise to me.

But why should having been successful once be such a big deal? Lots of possible reasons present themselves: the basic idea was a winner, I could tell when a bad idea was creeping in and could steer away from it, we were able to solve the inevitable problems that arise from time to time in every company that does succeed, and more. While this was happening, we were also dealing with a coworker who was eventually fired for cause. That, not the R&D, was the biggest go/no-go factor determining whether we were viable.

Surgery, like battles, suffers from the maxim that no battle plan survives its first encounter with the enemy. Quitting early when plans aren’t realized is a recipe for being consistently ineffective. It takes a hopelessly naive one begin with nothing more than Plan A. But even Plans B-Z can fail, so if someone can’t improvise in real time, they won’t be suited for the job. Wargaming WWII battles tells you how close-run things were much of the time.

Each battle is unique, so falling in love with a formula for winning is guarantee for failure. Surgery is a little more formulaic since anatomy and pathology are at least relatively constant from patient to patient, but even so, a surgical plan, like a battle plan, rarely survives its first encounter with the enemy, i.e. the disease process.

I hadn’t thought about this until some observers were spending a week or so shadowing me. Before each case began, I’d tell them what I was planning to do so they would be oriented. Toward the end of the week, one asked whether things ever went exactly to plan. Turned out the answer was no, beyond very basic procedures. It hadn’t crossed my mind to think in those terms. If a general can’t see around a hill to determine enemy positions and strengths (cannons, mortars, etc.), a surgeon can only see so much through opaque skin. X-rays are essential, but rarely tell the whole story. Adaptability is what identifies effective warriors and surgeons. They know when to modify plans, and, as the article implies, when to quit.

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Hi Annie,

Thank you for this. This is such an overlooked skill, perhaps because, as you say, the word "quit" has a pejorative connotation. Maybe a change in vocabulary would help--the 'art of quitting' is so different from the act itself.

The word volte-face comes to mind. It certainly sounds better, but is generally used for a change in opinion rather than an act like quitting one's job. Quitting a job is made to seem more consequential than say...'quitting' one's stance on war, but the latter could save the world. So in addition to having the superhuman power of being objective in subjective situations, "artful quitters" are expert at contextualizing and prioritization, regardless of social trends, which takes a high level of self knowledge. I suspect much of the 'quiet quitting' trend hitting the labor force is about people in the midst of and/or stuck in this personal transition.

Unlike the 'act of quitting', the 'art of quitting' is difficult because it requires an objective and nuanced understanding of a situation that you are most certainly invested in and therefore prone to be highly emotional about. In my studies "artful quitters" are also fearless and expert at assimilating information through iteration. Like a poker game, each successive hand, whether you bet or fold (quit) is turned into a lesson learned about the next hand.

In other words, 'artful quitting' requires an unnatural duality that takes time to master, but those that do attain some sort of magical ability. It is the ability to leapfrog over the rest of us mortals in the decision making process. It is also THE mark of leadership.

May these random thoughts serve as inspiration for future posts on the subject.

Thank you,


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