Jan. 23, 2023

Why Quitting Can Actually Help With Growth

You gotta know when to hold ‘em, know when to fold ‘em…

Nora speaks with bestselling author and former professional poker player Annie Duke about her new book Quit: The Power of Knowing When to Walk Away. She details why quitting is actually an important decision-making skill that’s worth developing, and offers tips on how to get good at quitting and what red flags to look for when it comes to decisive moments in your career and personal life. Source for the game: Time’s Top 10 Quitters.


Host: Nora Ali

Producers: Olivia Meade and Raymond Luu  

Video Editor: Sebastian Vega

Production, Mixing & Sound Design: Daniel Markus

Music: Daniel Markus & Breakmaster Cylinder

Fact Checker: Kate Brandt 

Senior Producer: Katherine Milsop


Full transcripts for all Business Casual episodes available at https://businesscasual.fm


Nora Ali: For Morning Brew, this is Business Casual, bringing you convos with people you know, and some you may not know yet, to make business less intimidating. Because money talks, but it does not have to be dull. I'm your host, Nora Ali. Now let's get down to business.

When it comes to pursuing our goals, we are often told to never quit or never give up. It's so that we can develop the grit to withstand the hardships that might come our way. The problem is we don't often learn when it's actually a good time to quit because the truth is quitting is part of growth. If you want to get to something new, you sometimes have to quit that something old. Now at the start of the new year, we take this time to reflect and set new goals for the year. So why not also consider which things we need to cut loose?

Annie Duke is a former professional poker player and the author of Quit: The Power of Knowing When to Walk Away. And she details why quitting can actually help you make sound decisions in your life both personally and professionally. Take a listen to this episode from October after the break.

Annie, I have so many questions for you. I'm a big quitter. I've quit every one of my jobs I've had, and we'll get into that.

Annie Duke: Good.

Nora Ali: First, let's start with a quick icebreaker. This is for a segment called OG Occupations. So Annie, what was your first ever job that you've ever had?

Annie Duke: Not counting babysitting?

Nora Ali: Counting everything. Counting anything.

Annie Duke: My real first job was at Kentucky Fried Chicken when I was 14 years old.

Nora Ali: Really? Oh.

Annie Duke: Brown polyester slacks and smock situation.

Nora Ali: Wow.

Annie Duke: Yeah, it was something. I don't have pictures of it. I wish I did.

Nora Ali: I'm a big KFC fan. Did you enjoy it?

Annie Duke: I mean, did I enjoy memorizing what goes in a three-piece box? I don't know. It's some sort of life skill, I'm sure. I like the mashed potatoes, which looking back is a little embarrassing.

Nora Ali: A little sauce, maybe?

Annie Duke: They're powdered. But at 14 years old I thought they were delicious.

Nora Ali: I know. I used to love the coleslaw so much. Okay, let's get to quitting. The word quitting obviously comes with a negative connotation a lot of times. It implies you've given up, you've been defeated, but that is not your stance at all. And I agree with your stance. First of all, what exactly do you mean by quitting in the context of your book?

Annie Duke: So I think first of all, you're absolutely right. If I called you a quitter, I would be completely insulting you. I mean, I wouldn’t, but you would take it as an insult because I'd be calling you a loser. But it shouldn't be that way. We want to change that. So I think that one thing that people need to realize is we think about quitting as one particular thing, which is stopping some large thing. So you're in a job, you quit your job, but there's all sorts of small acts of quitting that we do all the time. You're watching a TV show...if you decide that it's not for you and you don't watch the next episode or you stop in the middle of an episode, that would be quitting. If you are managing a project at work and you decide that's not the right project for you to be doing in order to reach your goals, that would be quitting.

What I think about is you can change directions...that would be quitting, or you could exit the court and that would be also quitting. But there's also other things that go under quitting. If you change your mind, if you abandon a belief. So I used to believe that Pluto was a planet, but now I don't. So that's a form of quitting. If I fold a hand in poker, I'm not getting up from the game, but I'm giving that hand up. It's called cutting your losses. That would be a form of quitting. If I sell a stock, selling things is a form of quitting, because you're quitting your ownership. And if you fire someone, it's quitting. We just have a different word for it, because as an employer, if I let somebody go, I'm quitting that employee/employer relationship. So it's really covering basically any kind of situation where you started something and then you decide that you don't want to be on that path anymore.

Nora Ali: A change in course. And you say it's a decision skill that is worth developing.

Annie Duke: Yes.

Nora Ali: Why do you think quitting is a skill in itself?

Annie Duke: So I actually think it's the decision skill that you need to develop in order to be a good decision-maker. So the reason is that when you start things, you're deciding to start it with very little information. And then also the way that thing turns out is going to be partially...luck is going to have a huge influence over it..

So if you think about most things that you start, imagine that you're taking a job or even that you're hiring somebody. So let's say I'm hiring you for a job. What do I really know about you, right? I've got a CV, I've had a few interviews, I've got a couple references, but I actually know very little when I enter into that relationship with you. And that's true pretty much of all decisions that we have to make in terms of starting things. So there's this huge influence of uncertainty, and I assume, Nora, that you've had that feeling after the fact of saying, "Ugh, I wish I knew then what I know now." So this is why quitting becomes really important. Because when you have that feeling of "I wish I knew then what I knew now," you actually have a way to address it, which is to take on the option to quit. So I found something new, I wish that I had done something different, and so I can, and I can quit.

Nora Ali: And there are a lot of forces that are working against us when it comes to making that decision to quit, cognitive forces and otherwise. You talk about something called the "escalation of commitment" in your book. Explain what that is and why that works against us.

Annie Duke: So we have the intuition, and I think you do too. So I assume when you start something, whether it's a job or relationship or maybe you make an investment, I bet you have the intuition that when the world gives you signals that thing isn't going as you had hoped, that you'll pay attention and you'll stop doing the thing that you were doing before. So I think that's an intuition that we all share. But there's decades and decades of science that shows that not only do we not do that, but we escalate our commitment to the cause when we get bad news.

One of the best ways to see that is actually in war. Think about the Vietnam War for example, or the war in Afghanistan. You start it and then things aren't going well, right? It's very clear you're not gaining ground; the war isn't going as you hoped. You know, Vietnam War, I don't think there was any point where anybody thought we were winning that war, yet we stayed in it for a really long time. Because even though you're getting this information that if you knew it at the time that you were thinking about starting, you wouldn't actually start. But when you're in it, once you started accruing losses and having all that stuff happen, you actually tend to escalate and increase your commitment to the cause, and it gets you stuck in stuff. And it's not just wars, but it's also jobs and relationships.

Nora Ali: This also reminds me of the sunk cost effect, which you write about which I think everyone's pretty familiar with that. Can you apply the sunk cost effect and the quitting mentality to, say, accepting mistakes or bad situations that seem to have absolutely no upside? And I say this from personal experience, because if there's something bad that's happened to me, I tend to walk away from it and try to think about, what lesson did I learn? Is there a reason for this to have happened? Is there some benefit that I've gained versus just letting this bad thing happen and walk away? So how can you use this sunk cost mindset to get over something bad that has just happened, and not just in the quitting scenario?

Annie Duke: So just for people who aren't familiar with sunk cost, it's just basically, once you put time or effort or money or attention into something, it becomes really hard to quit it. Because if you quit without actually having achieved whatever the goal is, you'll feel like you wasted all the time and effort and money. So you can see that with, say, the Vietnam War. Once you start to have casualties and you've spent a lot of money on it, people say, if I exit before we've won, then the lives that we lost will have been wasted; the taxpayer money will have been wasted. But the problem is that waste isn't a backward-looking problem, it's a forward-looking problem. And this addresses what you're talking about. How do you actually get yourself out of this? Is the next life that I might put at risk worthwhile, or is the next month that I spend in this job actually going to get me what I want? Is the next month that I'm going to spend in this relationship worthwhile? 

Because what you don't want to do is say, the relationship is not at all what your hopes and dreams were, it's not aligning with your values, you're really unhappy, you don't want to stay in it because you don't want to have wasted all the time that you've already put into it. What you don't want to do is waste the time you're going to continue to spend in it. So that's like the first problem, which kind of is a way that you have to change your mindset. But a second thing that you can do, which you alluded to, is that the other problem that we have is we tend to think when we go to quit about how short we are of our goals, and what we want to do is shift to, what's the progress that we've made along the way? 

If you're climbing Mount Everest and you turn around 300 feet from the summit, you've failed. Because goals are really pass/fail. But you didn't fail. You climbed 29,000 feet in the air, which is a lot more than most people did. And so one of the things that I try to recommend is first of all, think about, when you're walking away from something, what have I achieved and what are the things that I've learned along the way? But then also it's really good to prioritize projects and goals where even if you don't make it to the ultimate goal, there's a whole bunch of learning and achievement that you could take out of it. Things that aren't so all or nothing.

Nora Ali: And there is preparation that you can do ahead of going into a new task or a new job. You highlight something called "kill criteria." So some practical guidelines for overcoming those negative assumptions about quitting. What do you mean by kill criteria and how can we start to come up with our own?

Annie Duke: Let's imagine in the future, so I'm going to start something, it could be a relationship, it could be a job, it could be investing in something, it could be running a race, whatever it is. A really simple example of a kill criteria is when people are mountain climbing, they have something called a turnaround time. So when you're going up Everest, let's say on summit day, and you leave camp four to go head toward the summit; the turnaround time is 1:00pm. Which means, no matter where I am on the mountain, it doesn't matter whether I make it to the summit or not, I have to turn around at 1:00pm because otherwise it's too dangerous, because that means I'm going to be coming down the mountain in darkness and that's not good for anybody. So that's a really good example of just a very simple kill criteria, and you do that in advance, because if you're actually in it and it's 1:00pm and you haven't thought about it in advance, you'll convince yourself you're close enough to keep going. Because we don't like to abandon things, right? We have a real bias against it.

Nora Ali: It feels like it might be difficult to know what your kill criteria might be going into a job. So let's say, for our listeners sitting at home or sitting at work who have not come up with their kill criteria to leave a job or situation, what are some red flags that you should look for in the moment to know that it's time to quit and not too late to quit? What question should you be asking yourself?

Annie Duke: What you want to do is, you want to be on a regular basis assessing your situation. So think about what you were hoping for in terms of your own happiness, your own eagerness to do the work. Collegiality, fulfillment, maybe it could be monetary. Where do you expect it to be in terms of compensation? What were those things that made you think that this was a good job for you to take in the first place? And then reassess that and do that on a regular basis. So I suggest, just like people do quarterly business reviews, you should do a quarterly personal review. And you should say, is this still aligning with my values? Am I actually getting where I want to go? Am I enjoying my work? If I were thinking about taking this job today, would I? Now that's actually kind of a hard thing to do. So what is really actually even better to do is not to try to say, "Is this something I would want to start today?" But instead, when you're doing that quarterly personal review, say, "What am I hoping to see at the end of the next quarter?" 

And it just turns out thinking in advance like that is easier for us than thinking in the moment. Think about, what are the red flags I might see over the next three months? And at that point you have more information about the situation you're in anyway, so you can predict what those things are. So you have a really annoying coworker who doesn't do their job and expects you to clean up after them. Say if that's still going on in the next three months, even if I've talked to my supervisor, I've talked to my coworker and it's still happening and I'm having to do two jobs, basically, because I'm picking up their slack, that's going to be enough for me to say, walk away.

Nora Ali: So it's never too late to start thinking ahead. Even if you didn't do it the last quarter...

Annie Duke: It's never too late.

Nora Ali: ...you can do it today.

Annie Duke: You can do it this quarter. That is exactly right.

Nora Ali: Yes. I love the practical advice. We're going to take a very quick break. More with Annie when we come back.

So before we get into the buzz phrase "quiet quitting," which has existed for a long time, we're just talking about it more now.

Annie Duke: Just gave it a different word.

Nora Ali: Exactly, right. And it's on TikTok more, that's why we're talking about it. So let's talk about actually quitting your job. And I've come across at least two different schools of thought. One, quit your job if you don't like it and then put in your fully committed time to finding the next thing or starting a company, whatever you want to do. Or two, on the other side, have something else lined up before you quit your job, have something else that you can walk away to. What is your take on that, if hypothetically your financial situation is not a consideration?

Annie Duke: If you're in a world where the financial situation doesn't affect you at all, and you're taking into account the risk of a resume gap, which is something that you would want to consider. So let's take those two things out of the equation. A resume gap isn't going to hurt you and financially you're fine, then you should quit. And really honestly, the reason that you should quit is that when you are engaged in something, it just blocks you from being able to really truly explore other options. But also you may find other things that are more fulfilling, and you're going to be more likely to explore options that are farther away from what you might think. You may actually explore switching functions, you may be more likely to do that kind of thing. Or you may decide in the meantime you want to go get skilled up on something so that you could actually switch, truly switch your career.

I think one of the best examples of this actually comes from the Great Resignation. So we think of the Great Resignation as "everybody just quit," but that's actually not what happened. What happened was that the people who were specifically furloughed, let go, or laid off—so the service workers—so they were the ones who really got affected at the beginning of the pandemic. People like us who work on Zoom kind of continued on. So they got let go, and then when the great reopening happened, when all of a sudden there was lots of employment available, they quit their jobs.

Now they didn't quit them to do nothing, they quit them to go to another position. And the thing that you can surmise there is that they were probably unhappy beforehand, but had that event not occurred where the cord was cut, they probably wouldn't have explored and found out, you know what, I don't really actually like this job that much. I think there's other opportunities for me that I want to go do. So there's something really freeing about not being in something, that lets you go and really do true exploration of the space. But again, that's assuming there isn't a monetary issue or resume gap issue. I just want to give that big caveat.

Nora Ali: Definitely. So you can cut the cord for yourself then...if not because of the pandemic, if you quit, you've cut the cord.

Annie Duke: If you quit, that's right. Because sometimes quitting is voluntary, sometimes it's foisted upon us. And obviously when it's foisted upon us, we don't get to make a decision about our monetary situation or resume gap situation, but we can also do it voluntarily. Do you think you'll make a better choice about your next partner if you look for them while you're in a relationship or you look for them after you've already left a relationship? So it's true with everything, that's true of all forms of quitting, whether it's a relationship or a job. You're probably going to do a better job picking if you're not in the other thing.

Nora Ali: Yeah, it's not going to be good if you're casually swiping through Hinge when you're still in a relationship, looking for the next best thing.

Annie Duke: But you know what, that's actually kind of like relationship quiet quitting.

Nora Ali: Yeah, you're right.

Annie Duke: It's sort of the same thing.

Nora Ali: Actually, that brings me to another point, where even if you're objectively happy in a role doing what you're doing, there's this desire for what's next, what's the next best thing, how can I do even better? How do you quit trying to strive for something else even though you are happy in your current situation?

Annie Duke: First of all, I think that you should always continue to strive for other things. Not because you would necessarily switch, but because your circumstances can change. So you could be super happy in a relationship and then things could change. You could be really, really happy in a job, but then something could happen, your leader could leave and somebody new could come in. So I think that we want to make sure that we're striving, in the sense of always sort of keeping our eye on the landscape. If recruiters are calling, it's okay to have conversations with them. Not in the sense that you're going to leave, but in the sense that your situation may change.

I really recommend two things. One is, often those feelings are very transitory. It's an impulse. Stop and say, "Ooh, I just had a thought that maybe I'd like to strive for something else. How long do I need to find out that this isn't the place for me anymore, that I really do want to go?" And maybe that's three months. The other thing that you can do, though, that I think is really important, and this is a little bit what a parent's role is, is to get someone to help you with the decision who's been there, done that, who you really trust, who totally has your back. You hate the piano and you're saying "I want to quit," and they're sort of helping you to figure out, do you just hate it because it's hard right now, but it's worthwhile in the long run. Parents aren't perfect at it, but this is what they're attempting. And I think that's just super helpful, is go find someone to help you with the decision.

Nora Ali: On that topic, you talk about enlisting the help of a quitting coach. So what quality should this person have, and should it be your friend or not your friend?

Annie Duke: It has to be someone who has your long-term best interests at heart. So if you're asking a friend for stock advice, that's probably bad unless they're an expert. So you want to make sure that their opinion's going to be valuable for the thing that you're asking them about. But other than that, it's actually mostly on you. And in particular where it's mostly on you is that you have to give them permission to tell you the truth. Because the problem is that friends tend to want to cheerlead, which is reasonable. When you're complaining about a relationship, they're not going to speak up. They're going to be like, "Yeah, I'm sure you can work it out." You have to give them permission and you have to say, "Look, I'm asking you to say some things that you think I'm not going to want to hear, but I do want to hear them even though they're hard, because it's going to help me in the long run." So yeah, it shouldn't just be like a random friend, it should be a friend who has a good opinion about the thing you're asking. And then you have to give the person permission and trust that they're going to tell you the truth.

Nora Ali: Let's say you have a friend who has not given you permission but they're a good friend, and you see that they're in a situation they need to get out of, whether it's a job or a toxic relationship. And I only ask because I've had these kinds of conversations in recent history with my friends. In that case, if you haven't been given permission, do you just not say anything?

Annie Duke: I try to obliquely probe. "So how's that job going? How's that relationship going?" There's a couple of things you can do. One is when they start saying, "Oh, it's actually not going well...what do you think?" You can actually say, "Well, I need to understand. Do you want me to tell you really what I'm seeing, because I need to know? Or is this something where you're really looking to vent and you're looking for just an ear, someone to hear what you have to say?" 

So you can create that permission by being really clear. What I found is that mostly people actually just kind of want to vent, and that's normally what they'll say to you, is "I want to vent" and then you accept it. But what I think as a good friend you should do is say, "Okay, they're venting now and I recognize they're not going to be in a position to hear what I see," but you can use the kill criteria trick and you can say to them, "Oh yeah, this seems like a really bad situation. Have you sat down and had a really hard conversation with leadership at your work, and how do you think things will have changed?" And what you can throw in there is, "How long do you think this situation is sustainable for you?" So now you can kind of get a deadline. So let's say they say, "I think I can only take it for three more months." You're like, "Oh yeah, no, I think that's good. Three more months, that's really good." So at the end of three months, what does that look like? If things are better, what does that look like? And if things are worse, what does that look like? And have that conversation with them. And generally that then implies permission to have the discussion in three months. 

And it's a little bit of a trick to do it. And the thing to realize is that, are they going to be in that situation three months longer than if you were the ultimate ruler of the world? Sure. But we all know what happens otherwise, is they complain to you and then three months later they complain to you again, and then three months later they complain to you again. So you're getting them out of it maybe in three months instead of a year, and that's huge when we all have short lives. Let's save some time.

Nora Ali: So you're not imposing your opinion on your friend, necessarily. You're asking questions such that you're helping them arrive at the conclusion themselves.

Annie Duke: Right. If they happen to give you permission, you can give it to them right there. You have to sort of tread lightly on that stuff and understand that in the moment, it's very hard for people to hear that you're telling them that they should walk away. Because again, that's the moment where you go from "This thing that I'm doing is failing" to "Now it's failed."

Nora Ali: Yeah, that makes sense. Another very quick break. More with Annie when we come back.

Let's talk about some quitters specifically, starting with you yourself, Annie. You were at a crossroads early in your career. You were a graduate student in cognitive psychology, an aspiring academic, but you quit academia and turned to professional poker. Why was that? It does sound very useful as a skill though, in playing poker.

Annie Duke: It's really useful as a skill, as it turns out. You know what, that was forced quitting. It was kind of a Great Resignation moment for me. So what happened was, I did five years of graduate school at the University of Pennsylvania...just in terms of five years, it means that I did all of my exams, I was already teaching, I was actually on the job market already, and I was about to defend my dissertation. So this is a real [inaudible].

Nora Ali: Wow. Oh my gosh.

Annie Duke: I had been struggling with a pretty chronic stomach illness and it got to be really acute. And at the time I was thinking, well, I'm just going to go out on the job market and then hopefully I'll be able to figure out this health issue. And my body was like, nope, that's not going to happen, as I ended up in the hospital for a couple weeks. So that happened to be right when I was supposed to be going and interviewing for jobs, and then it became clear that it was a really bad stomach issue, so I had lost 25 pounds or something like that. It wasn't like I could postpone the job talks, I just kind of had to cancel it for that year and take a year off of school so that I could try to assess what was going on. 

And when I left school I needed money, so I was forced to quit because I got sick. And then I started exploring and the thing that I explored was poker, and I started playing it and I really loved it, and it turned out I had some talent for it. And what I was going to do for that year in the meantime before I went back out on the job market ended up being a career for almost two decades. I think that that's the big lesson from that, right? Look, when you're forced to quit for whatever reason, it doesn't always work out well, but there's a lesson in there, which is, that causes you to explore other things. And when I was an academic, I knew how to play poker, I had played a little bit of poker and my brother played poker. It never crossed my mind ever that this would be a job until I was forced to consider it as a job. And then I found something that was amazing for me, right? I mean, I get that there's luck involved in that, but there's a lesson involved in that as well.

Nora Ali: And the quitting piece of poker obviously is a big part of why you wrote this book, and you cite, one of the biggest differences between most players and the world's best players in poker is how often they quit. So I'm going to cite a stat that you have in the book. In Texas Hold 'Em poker, after professionals and amateurs peek at the starting cards they're dealt, the pros play fewer than 25% of their hands before other cards hit the table, whereas the amateurs play more than 50%. Why is that? Take us real quick into the psychology of a professional poker player.

Annie Duke: Okay, so professional poker players are thinking about two things. Is this hand worthwhile? And then the other thing they're thinking about is something called opportunity costs, which we've alluded to, which is, if I put this money toward this hand, that's money that I can't put toward another hand. And so you're trying to get your money into the best situations possible. And when you're playing a game of Texas Hold 'Em and there's nine people at the table, you want to make sure that you have a better than average hand. And those are few and far between when there's nine people at the table. So actually if you think about it, with nine people at the table, 25% of the hands is a lot. So they're saying, I'm more skillful than you are so I'm willing to play more than my fair share of hands, but we don't think we are because we're good players and so we play 25%, partly because we know we're going to ditch the hand pretty quickly as soon as we find out it's no good

So compare that to amateurs who are playing over 50% of the hands they're dealt. What is going on? So why are they so much worse at ditching their hands? It's really hard to walk away when you don't know for sure that you had to. So remember, when you're playing a poker hand, you've invested money in the pot, and if you fold, that's when you're saying "I'm not getting that money back." It's very hard for people to say, "I'm okay folding and not getting my money back," unless they're absolutely sure. So this is something that's just true of quitting, is we often won't do it until we just don't have another choice. Until the choice is so clear that there's nothing else we can do.

Nora Ali: The possibility's...yeah.

Annie Duke: And what's weird is this turns into an excuse. So somebody will start a company, let's say, and it's not going well, and then they'll always point out, "Oh, but that guy's company was totally on the brink of death, but they kept at it and ended up succeeding."

Nora Ali: So you brought up the company example first, startup founders who are going through troubling times, it doesn't feel like they're getting any traction with their customer base, they're using up their investor dollars. How do you know if you should persevere and keep pushing and keep trying versus quitting? And you have a great example with Stewart Butterfield as an example of the quit version of that. But when do you know it's the right time to keep going?

Annie Duke: I think Stewart Butterfield demonstrates both sides of the equation. There's lots of lessons in here. His second company, which was called Glitch, and it was developing a game called Game Neverending, which was this massive online role-playing cooperative world-building game, which was a huge critics' darling. And they actually had 5,000 diehard users and $6 million in the bank with Andreessen Horowitz and Accel having backed them. So they had lots and lots of money in the bank and they had users, but they all kind of had figured out that there was a problem, which is for every user that they got, 95 people visited the game—I think it was more than that, it might have been 99 people—and they played it for seven minutes and left. So in order to get these diehards who played 20 hours a week or more, you had to get the game in front of a lot of people.

So on the weekend of November 11th and 12th, they have a really huge weekend that's sort of the end of this marketing push, and Stewart Butterfield goes to bed and he can't sleep. He's restless. And he wakes up the next morning and he sends a note to his co-founders and investors saying, "I woke up this morning with the dead certainty that Glitch was dead." So it's like, well, what's going on there? Because they're growing users. But he's thinking more like a poker player. And he's like, well, if we were to maintain this growth, it would take us 31 weeks to break even, and I don't think we can maintain this growth because at some point you've saturated the gaming audience; we're not going to be able to maintain it. So it's going to be way more than 31 weeks to break even. At which point he just realized it wasn't a venture scale business.

And what was I think important about this is, one of the things that really concerned him was that his employees were taking basically no cash in exchange for equity. He felt like a moral obligation that once he realized the equity wasn't worth their time, he needed to let them go. Now notice, this is sort of to your point about progress versus being short of the goal; it's turned on its head because most people think "I owe it to my employees to keep going." Now going back to that idea of forced quitting or what quitting does for you in terms of exploration, once he shuts the company down, literally two days later, he's like, "Oh, we have an internal communication tool here that we really like around here. We don't have a name for it, but I don't know, maybe that's the next product. Let me give it a name." Which was "searchable log of all company knowledge," which is Slack.

Nora Ali: Yep. The theme I'm seeing here is, always look ahead and don't dwell on what could have been. Don't look backwards. It is about what's happening now and how that's going to impact you in the future. I want to get your take, Annie, on how you quit when the stakes are really high and, specifically, very public. So let's say your reputation and public embarrassment are on the line. And I'm thinking about two pretty recent high-profile examples, like Quibi launching and shutting down within the same year and they had raised over $1.75 billion; CNN+ shutting down after a month. They had spent a reported $300 million that they sunk into it. So if you're a high-profile company or you're a leader of a high-profile company, what is going through your mind in these situations that leads you to quitting as a strategy?

Annie Duke: So first of all, let me say, good for them. Because again, okay, yeah, they had spent a bunch of money, but were they going to spend a lot more? And I think most people in that situation, particularly when it's high-profile, would be unwilling to shut it down in such a public way. And a lot of the reason is that, again, it's super public. And when it's really public, the people who are the decision-makers have their identities kind of on the line. And it's really hard to quit your own identity. And this is particularly true when you've done something public that is out of the mainstream in some way.  

So there's two issues that play together. So the first is called internal validity, which is this desire for us to see ourselves as consistent. And then there's external validity, which is, how are other people going to view us? What I think is interesting is that we think of them as the same. So the things that we're worried we're going to think about ourselves, we think that other people will think about us. But in general, it's actually not. 

There was a great story that Ken Kamler told me, who was a doctor, he's a doctor who has been a doctor on Everest, part of the medical team for expeditions climbing. And he was actually trying to summit in 1994 and they were on the Southeast Ridge, which is pretty darn close to the summit, but the climbing conditions were terrible. And so they all made the decision to turn around. And what he said was, "I just thought the whole time about when I got home, everybody was going to think I was a failure." He just had this whole talk track in his head about what they were all going to think. And when he got home, everybody was like, "Oh my god, that was so amazing. I don't think I could have done that. How'd you actually turn around?" They had the intuition. They were like, "That would be really hard." And it turned out people were actually really proud of him. And that was the moment that he said, "I realized that the goal wasn't to get to the top of the mountain. It was to get back down."

Nora Ali: It sounds like it's a good signal if when you shut something down, you quit something, other people are surprised by it. "Wow, that was quick," versus waiting until people are like, "Oh, I saw that coming."

Annie Duke: Well, and in fact it's usually worse than that, which is if you wait for that, they'll usually say, "Oh yeah, you should have done that a lot earlier."

Nora Ali: Right. A couple more things before I let you go, Annie. We have a fun segment called Shoot Your Shot. So this is where you tell me your wildest ambition, your biggest dream, your moonshot idea. It could be personal or professional. It is your chance to shoot your shot.

Annie Duke: Okay, so my moonshot idea is something that I'm actually kind of already doing. So I'm co-founder of something called the Alliance for Decision Education. And what we're trying to do is get decision education into every K through 12 classroom. So I write about it. I wrote Thinking in Bets, How to Decide, Quit. This is the space that I write in. And when you look at books like Daniel Kahneman, right? Thinking, Fast and Slow. Or Richard Thaler and Cass Sunstein with Nudge, or Katy Milkman with How to Change. There's so much work that's done on adult decision-making and what goes wrong and what goes right, but we spend all our time teaching kids trigonometry. Like, why? We should be teaching them to make better decisions, right?

Nora Ali: Yeah, totally.

Annie Duke: We want to define this field of decision education, get it into every single K through 12 classroom. And it's a total moonshot. Because first of all, the education system's really...it's really hard to turn that boat around or even change directions slightly. It's just really hard. And when you look at other educational movements like social emotional learning, for example, it took 30 years to get into classrooms, but aren't we really happy that it's there? So this is the definition of a moonshot.

Nora Ali: How I wish that could have been a part of my curriculum. I love trig, but I'd rather learn about decision-making than about triangles.

Annie Duke: Well, the thing is that you can learn trig later in life.

Nora Ali: If you need it.

Annie Duke: I'm not sure why we're torturing ninth graders with trig.

Nora Ali: Okay, final thing for you, Annie. We have a very quick game. It's called Who Quit What? So I'm going to give you a few clues and you have to try to guess who the famous quitter is based on those clues. And this is from...

Annie Duke: Oh no, I'm going to be so bad at this game.

Nora Ali: It's totally fine. It is challenging. I will say that up front. So if you get them all wrong, I understand, because I would've gotten them all wrong. So this is from Time's list of famous quitters. Okay? Number one, here's your clue. In 1969, after finishing his band's final album, this singer/musician decided to call it quits. While lots of factors contributed to the group's breakup, he was especially miffed when he offered his new song, "Cold Turkey," as a potential single to the band and they didn't want it. He released the song under the name of his new side project. Who is this quitter? 1969, it's a band...

Annie Duke: Was it Eric Clapton?

Nora Ali: Uh-uh.

Annie Duke: Okay, I give up.

Nora Ali: Think of the most famous band.

Annie Duke: In the sixties? Well, it's not The Beatles, because they didn't break up before then.

Nora Ali: It is The Beatles.

Annie Duke: It is The Beatles?

Nora Ali: It is The Beatles. John Lennon is the person.

Annie Duke: It's John Lennon?

Nora Ali: So Lennon broke this decision to his bandmates in September of 1969, though the band's demise wouldn't be confirmed until a couple months later when Paul McCartney delivered the bad news in a Life Magazine interview.

Annie Duke: Oh, okay. But I just watched that wonderful documentary, so I'm so sad that I...I thought The Beatles broke up in like 1972. So that was my bad.

Nora Ali: Okay, next question. This 42-year-old gave up his inherited job for love in 1936, and to this day, he remains the only English sovereign in history to voluntarily abdicate.

Annie Duke: It's the king of England. Is it Edward?

Nora Ali: Yes. Wow. I would've had no idea about this one. I had no idea. Edward VIII. You're a genius. Okay, so more info for our listeners. He said this in a televised speech: "I have found it impossible to carry the heavy burden of responsibility and to discharge my duties as king as I would wish to do without the help and support of the woman I love.” 

Okay, final one. This athlete retired at arguably the height of his career in 1993, topping the NBA in scoring for seven consecutive seasons, and had been named most valuable player three times.

Annie Duke: Oh, is it Michael Jordan? Because then he came back.

Nora Ali: Yes, he quit to play baseball and then he came back.

Annie Duke: And then he came back.

Nora Ali: And then he quit again in 1998.

Annie Duke: I got two of them.

Nora Ali: You are so good, Annie.

Annie Duke: I'm so excited. Wait, let's play this game more.

Nora Ali: I don't have any more for you, but you can come back and play and we can just do a whole episode on this. 

Annie Duke: So wait, the reason why I know the Michael Jordan one is because I watched, what was it, The Last Dance? Is that what it was called?

Nora Ali: Yeah. So good.

Annie Duke: There was a documentary that came out during Covid that was so good. And so, thank god for Netflix because that's how I know the answers to the last two. But I watched the Beatles thing, so I should have known that answer.

Nora Ali: I’ll give it to you, Annie. I'm going to call this a three for three because you just know all the facts. You knew everything, so you win this game. Annie, let's leave things there. This was so fun. Thank you for joining us on the podcast. We appreciate it.

Annie Duke: Well, thank you for having me.

Nora Ali: This is Business Casual and I'm Nora Ali. You can follow me on Twitter @norakali. That's Nora, the letter K, Ali. And I would love to hear from you. If you have ideas for episodes, comments and thoughts on episodes you loved, fun segment ideas, just shoot me a DM and I will do my very best to respond. You can also reach the BC team by emailing businesscasual@morningbrew.com, or call us. That number is (862) 295-1135. And if you haven't already, be sure to subscribe to Business Casual on Spotify, Apple Podcasts, or wherever you listen. And if you like the show, please leave a rating and a review. It really, really helps us. And guess what? We are on YouTube. So if you've ever wondered what I look like, what our guests looks like, or what anything else looks like, full episodes are available on our very own YouTube channel. That's Business Casual with Nora Ali. Again, Business Casual with Nora Ali on YouTube. Business Casual is produced by Katherine Milsop, Olivia Meade, and Raymond Luu. Additional production, sound design and mixing by Daniel Markus. Kate Brandt is our fact checker and AB Silver is our senior booking producer. Sebastian Vega edits our videos. Our VP of multimedia is Sarah Singer. Music in this episode from Daniel Markus and the Mysterious Breakmaster Cylinder. Thanks for listening to Business Casual. I'm Nora Ali. Keep it business, and keep it casual.