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Annie Duke studies decision making. For nearly twenty years, she did so as a professional poker player. According to PokerNews, she’s the fifth-highest earning woman ever in live poker tournaments. But for the last decade, Annie has been researching and writing about the psychology of risk and decision making far beyond the poker table — from the office to personal relationships.

I jumped at the chance to talk with her about her new book, Quit: The Power of Knowing When to Walk Away, on how to know when “quit” is better than grit. Below is a condensed version of our chat, which was hosted by Powell’s Books. (You can watch the entire thing here.)

David Epstein: So Annie, your book has the bold word “QUIT” across the cover, with boxing gloves hanging from the “Q” — evocative of a boxer who throws in the towel rather than continuing to fight. I was just in an airport yesterday, and I must say, this imagery is pretty much the opposite of what I saw in the window displays of self-improvement books. How did you pitch this to your editor?

Annie Duke: I told my editor, you know, “quit, like the opposite of grit,” and she kind of got it right away. In a lot of my writing, I talk about the problem we have as decision makers, which is that we have to decide under conditions of uncertainty. So when we start things, we usually know very little, and I’m sure you’ve had that feeling of, “I wish I knew then what I know now.” Well, we have this really valuable option, that when we discover new information that things aren’t going the way that we had hoped, we can quit. But all we’re taught is that we’re supposed to stick to things. What ends up happening is that we don’t actually use the option to stop things when we get signals that they aren’t going very well, and that’s such a shame because it slows our progress down.

DE: So you’re trying a really big rebrand here, of quitting. And I’m wondering to what extent your poker career influenced that.

AD: Honestly if I had to pick the thing that distinguishes poker experts from amateurs, it would be quitting. In a game like Texas hold ‘em where you get two down cards, professionals will choose to play about 15-25% of the time. Amateurs will play over 50% of the two-card combinations they’re dealt. Professionals are quitting twice as often before you’ve even gotten into the hand. Then once you get involved in the hand, now you’ve bet money. And the money that I’ve put in the pot creates resistance to letting the hand go even when I find out new information that the hand isn’t going my way. Professional players are just way better at saying I’m going to cut my losses and move on because it’s not a good use of chips. And professionals are also better at quitting not just a hand, but quitting the game. Game conditions change; you get tired, you’re not playing your best, better players come in — when you’re losing it’s very hard to get up and walk away from those situations, and professionals are better at doing that. They’re better at using their chips for the really good opportunities, and ditching the rest.

DE: You glanced off several things there I want to talk about. First: the sunk cost fallacy. That once someone has invested time, emotion, money, anything, they’re more likely to continue with it because of that investment, not because it’s a good idea to continue. You wrote about how that plays out in public works projects. You wrote about a waterway project that had insane cost overruns and that no longer looked like a worthwhile project, and you quoted politicians saying basically, “Well we can’t shut it down now because that would mean we wasted all this taxpayer money.” Even scarier you wrote about generals in war being told by Gold Star Families, “Make sure my child didn’t die in vain. Finish this thing.” And I think we can all understand and sympathize with or even admire that sentiment, but maybe it’s also an aspect of getting mired in wars that I hadn’t thought about. I wonder if, say, someone told Vladimir Putin back in January where he’d be in November, would he have gone forward.

AD: I think we can all intuit that the answer is “no.” And it’s not particular to Vladimir Putin. We got stuck in Vietnam for a very long time, even though very quickly there was a point where — knowing what you know now — would you have started this war? And I think the answer was “no,” and I think that’s true for Afghanistan as well.

I listened to Biden talking about, is there an off-ramp for Putin. And, as a betting person, I would bet on no off-ramp. And the reason I don’t think he’d take an off-ramp is partly for the reasons we’re talking about — the sunk cost problem. Once you put something into something — lives, money, effort, time — it becomes very hard to let those things go. This happens with jobs and relationships, but a simple example is a stock: I bought it at $50 and I don’t want to sell it at $40, because I want to get my $10 back. Now, of course that’s a fallacy. What matters is: would you use that $40 to buy that stock today? If the answer is “yes,” you should hold it, if the answer is “no,” you should sell it. It matters very little that you used to own it at $50. That $10 is already gone, and what you care about is whether it’s a good use of your money going forward. What the sunk cost fallacy shows us is that we naturally think of waste as a backward looking problem; I don’t want to have wasted my time, my energy, my money. But what waste really is is a forward looking problem. Is it right for me to waste time and money going forward? And the irony is that the fear of having wasted then causes us to waste more.

DE: So how do we get better at it?

AD: Bad news first: just knowing about it doesn’t help you.

DE: In fact, several researchers in your book, who actually study this stuff, fell prey to it in dramatic fashion.

AD: Jeffrey Rubin studied this entrapment problem, getting stuck in things. And he had a goal to climb 100 peaks in New England, and he was on his last one, so this sort of “summit fever” situation. Now remember, he spent his whole life studying getting stuck in losing endeavors. That’s his life’s work. So he’s climbing with a graduate student, and a very heavy fog rolls in. The student says, “I don’t think we should continue”, and turns around. Jeffrey Rubin continues on, and his body was found two days later.

Just knowing about it will not help you. It’s a very strong illusion, and it’s disheartening. It’s like a visual illusion; I can show it to you, explain it, and you still see it. That’s kind of how sunk cost is.

DE: Is there anything we can do to improve?

AD: Luckily, there are a few things. The first one is to think in advance. When we think in advance about the signals we might see in the future that would tell us we ought to walk away — and then commit in advance to actually walking away when we see those — we are better off. If you say in advance that when I’m climbing this mountain, if a fog rolls in, I’m going to walk away, it does make a difference when that fog rolls in, and by a lot. Barry Staw’s research has shown that if you employ that tactic, you can actually get yourself to behave like someone who is fresh to that decision. That’s what I call “kill criteria,” and I think that’s one of the most powerful things you can do to get to better quitting decisions.

And turnaround times in mountain climbing are a simple example. On Everest, when you leave for the summit from Camp 4, you leave at about midnight and they tell you in advance that no matter where you are on the mountain, if it gets to be 1pm, you turn yourself around. You don’t want to descend in darkness. They’re setting that in advance, way down at basecamp. But you can imagine something more complex, like if you have an employee who’s underperforming, you could sit the employee down and say this isn’t really working out. They’ll say, “I know I can turn it around.” That’s fine, agree with them, but then say, alright, this is what I expect to see in the next six weeks that would indicate to me that your performance has turned around enough, and here are the signals that would tell me that that hasn’t happened. And then you’re going to be able to get to those decisions to part ways a little more rationally and quickly in a way that’s a little more palatable to everybody.

DE: So obviously you want things to go well with a new job, but when is the right time to make “kill criteria”?

AD: All times! When you start the job you have expectations, but the key is to set the right time horizon. When you first go in and things are uncertain, the threshold for saying this is something I’m going to kill would be higher. So maybe you’d say, there’s toxic behavior in the culture, and you sort of write down those things that would tell you that this is not a culture that’s right for you. That’s something you shouldn’t stick out assuming you have the option to go somewhere else. When you’re new, it should be strong signals. But you can also do it along the way. A good moment to make kill criteria would be when you start thinking, “Maybe I should quit.” In that case, you really have good knowledge of the things that are making you unhappy in the job or relationship. That’s a good moment to say, let me think about what the signals are at the end of six weeks that would tell me this is no longer worth pursuing.

DE: So you’re labeling concrete signals that would tell you it isn’t working out. Do you need that concrete deadline as well so you don’t move the goalposts infinitely?

AD: That is something very important about kill criteria, it’s not just a state of the world that you need to be identifying, it’s actually a date. You need to put a deadline on it.

DE: That’s related to the thing from your book I most applied in my own work. I’ve had an interest that I thought might become my next book, but have been going back and forth, unable to decide. So finally I told myself: “Well, you’ll write a book proposal, and it has to be done by the end of the year. If you finish the proposal and want to learn a lot more about the topic, go forward with a book. If you finish the proposal and feel bored of the topic already, bag it.” And I’m almost done, so decision-time is coming soon!

But before we leave this topic, I loved the section in the book where you became part of a story. A doctor, Sarah Olstyn Martinez, contacted you through your website because she was at a crossroads. She was very good at her job at a hospital, but was not enjoying it. And you reframed her job with two questions. Can you share those?

AD: She was an ER doc who had been promoted to hospital administrator. So she was doing fewer ER shifts, which was her original love, and had all this administrative work, and that work came home with her. Her children were 4 and 2 at the time, and they’re complaining because she’s not paying attention to them. Not only is she miserable, but it’s clear she’s been miserable for a while, and she has another job offer from an insurance company. So I was a little confused. She’s telling me how miserable she is, so where is the question here about whether she should take the other job? So I asked her outright: “What’s making you question this?”

And she said something that we should all think about when we have this dialogue with ourselves. She said: “What if I take the new job and I don’t like it?” And I said to her: “Imagine it’s a year from now and you stayed in your current position. What are the chances that you’re happy?” And she said “zero.” So I said, “Ok, well this other job, I understand it may not work out, but maybe it will. What do you think the chances are if you switch to this new job that you’ll be happy in a year?” And she said, “Well, I don’t know. I guess maybe 50/50.” And I said, “Well, is 50% greater than 0%?” It was like this lightbulb went off for her, and she quit. Last time I checked, she was really happy.

DE: I’m definitely going to steal that framing from you to use on myself or with friends.

AD: I use that framing when people are really unhappy in their relationships, and they’ll say “But what if I end up alone?” I say, “Well, what are the chances you’re going to be happy in this relationship and what are the chances you’re going to be happy alone?” And it’s always greater than whatever the situation is that they’re in now. So I don’t even frame it as: “Do you think you’ll find someone better and it’ll be great?”

And I do that with employers also who are really worried about letting somebody go who’s really underperforming, particularly in a way where they’re toxic to the team that they’re on. But the employer’s really worried about just having that function not filled. And I’ll say to them, “Well, imagine that person wasn’t there, do you think the team will be better off?” And in those cases, where the person isn’t just underperforming but is toxic to the team, the answer is of course you’re better off with nobody in the role. So we have to start to think about the alternative, and what is the happiness or unhappiness associated with the alternative compared to what’s going on now. But we don’t really focus there naturally.

DE: One more question. Since we’re so bad at quitting, it seems to me that getting even a little better might be a big advantage. We already talked about setting kill criteria. Is there anything else you typically recommend to enable smarter quitting?

AD: Get a good coach! Find yourself a mentor, a colleague, or somebody who has experience in whatever you’re thinking about to help understand the difference for you. Is this an issue that you’re not trying hard enough, or it’s not a good fit? Other people looking from the outside can see our situation more clearly than we can. I think we’ve all seen that from the other side, when we see someone who’s stuck in a job, who we can see very clearly ought to be quitting, or we can see they should walk away from a relationship or project and pivot to something else. But when we’re in it, it’s very hard to see it. How do we distinguish between worthwhile and not worthwhile? That’s the big problem we have. Think in terms of kill criteria, and get yourself outside help.

DE: Doesn’t Daniel Kahneman, the Nobel laureate who studies cognitive bias, have a quitting committee…

AD: He has a quitting coach. His quitting coach is Richard Thaler, also a Nobel laureate. We should all be that lucky! But I think the importance of that story is: Daniel Kahneman literally founded the field; he’s the one who started saying, hey, we’re not as rational as we think we are. And he wrote the book, Thinking Fast and Slow, which was looking at decades of research saying we make all these cognitive errors. And he feels like he’s bad at quitting. So if he feels like he’s bad at quitting, and feels like he needs help with it, I think we should all go find someone to help us with these decisions.

Thanks to Annie Duke for her time, and thank you for reading. Her new book is Quit: The Power of Knowing When to Walk Away. And as your quitting coach, I applaud your decision not to quit until you reached the end of this newsletter.

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Until next time…

David

P.S. Please feel free to join the conversation! In case you’re new here: I respond to many of the comments, and they also help me learn what posts or parts of posts readers find thought-provoking.

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