From Annie’s Duke’s “Quit”
My Favorite Quotes from Quit
“The second is that making a plan for when to quit should be done long before you are facing the quitting decision. It recognizes, as Daniel Kahneman has pointed out, that the worst time to make a decision is when you’re “in it.” On Everest, when the summit is within reach and you have sacrificed so much to be there, you are truly in it. That is when you will be the least fit to make a decision about whether to continue on or to quit. That is why turnaround times are set long before you are ever faced with that choice. Third, and perhaps most important, the turnaround time is a reminder that the real goal in climbing Everest is not to reach the summit. It is, understandably, the focus of enormous attention, but the ultimate goal, in the broadest, most realistic sense, is to return safely to the base of the mountain.” (p. 5)
“Quitting on time will usually feel like quitting too early.” (p. 29)
“There is a well-known heuristic in management consulting that the right time to fire someone is the first time it crosses your mind. This heuristic is meant to get businesses to the decision sooner, because most managers are reluctant to terminate personnel, hanging on to them too long.” (p. 30)
“The mistake of keeping people too long after you recognize it’s not working out carries with it a heavy price tag. Geoff Smart, a management consultant and expert on the topic of hiring talented teams, has found from studies done with his company’s clients that, in hard costs and lost productivity, an average hiring mistake costs fifteen times that person’s salary. Of course, once the hiring mistake has been made, hanging on to that employee too long contributes to that cost.” (p. 31)
“To get the stick-or-quit decision right, you need to make an educated guess at the probability that things will go your way and the probability that things will go against you, in order to figure out if the good stuff will occur enough of the time to warrant continuing on your path. Essentially, you need to think in expected value, which is what Stewart Butterfield was doing. Expected value (or EV) helps you answer two questions. First, it tells you whether any option you are considering is going to be, on balance, positive or negative for you in the long run. Second, it allows you to compare different options to figure out which is the better choice, the better choice being simply the one that carries the highest expected value.” (p. 32)
“To determine the expected value for any course of action, you start with identifying the range of reasonable possible outcomes. Some of those outcomes will be good and some will be bad, to varying degrees, and each of those outcomes will have some probability of occurring. If you multiply the probability of each outcome occurring by how good or bad it might be and add all that together, that gets you the expected value.” (p. 32)
“When thinking in expected value, the first step is to ask, “Does the course of action I’m considering (either a new course of action or continuing what you’re currently doing) have a positive expected value?” The second step is to compare that expected value with the expected value of other options you might be considering. Because time, attention, and money are limited resources, and we only have a limited number of things that we can do in our life, when we’re thinking about whether we should stick to something, we need to ask, “If I were to switch and do something else, would that have a higher expected value than the thing I’m currently doing?” If you figure out that another path carries a higher expected value, then walking away from the path you’re currently on and switching to the new one will get you to where you’re going faster. No matter whether you are thinking about flipping coins or buying stocks where wins and losses are measured in money, or you are thinking about who to marry or where to live, where wins and losses are measured in happiness and quality of life, expected value is a helpful concept for determining whether the path you are on is worth sticking to.” (p. 34)
“All that I had done was to reframe her quitting decision as an expected-value problem. She was considering two options: staying in her job or quitting to take the new position at the insurance company. Which one carried the greater chance of increasing her happiness and making her feel better about her relationship with her children? She realized taking the new job had the higher expected value. Dr. Olstyn Martinez’s story reminds us that expected value is not just about money. It can be measured in health, well-being, happiness, time, self-fulfillment, satisfaction in relationships, or anything else that affects you.” (p. 39)
“When you are making a decision about whether to quit, you need to listen to those people from the past who are giving you important advice. Sometimes, the person sending you a message is someone who has traveled a similar path before you. And sometimes, the person traveling from the past is an earlier version of yourself.” (p. 40)
“For now, you can consider this simple heuristic as a rule of thumb: If you feel like you’ve got a close call between quitting and persevering, it’s likely that quitting is the better choice.” (p. 42)
“In hindsight, we can see the moment when somebody should have quit. When your favorite quarterback hangs on a few years too long, it’s easy to spot the exact point when they started the decline from their peak. It’s easy to look back at a relationship and realize when things began to go irreparably downhill. It’s easy to look back and see the moment when it was clear that Blockbuster was going to lose to Netflix.” (p. 43)
“But the sad thing is that as much as we make fun of people who quit too late, when someone does manage to quit on time, we mock them for quitting too early. That’s the quitting bind.” (p. 44)
“Our intuition is that quitting will slow down our progress. The reverse is actually true. If you walk away from something that is no longer worthwhile, that frees you up to switch to something that is more likely to help you achieve your goals—and you’ll get there faster.” (p. 47)
“The real advice we should give people is more complicated than you can fit in a four-word slogan: Quit while you’re ahead . . . when the game you are playing or the path you are on is a losing proposition. If you are in a situation that carries with it a negative expected value, by all means quit. But keep going when you have a positive expected value.” (p. 56)
“The work on escalation of commitment over the last forty-five years—in different laboratory experiments, field experiments, and explanations of commonly observed behavior—has shown that this type of entrapment in losing causes occurs across a variety of settings and circumstances. There are all sorts of ways we get stuck in our decisions. Presented with the opportunity and the relevant information, we will over-persist, rejecting the chance to quit and backing up our original decision by spending even more resources to try to save the endeavor. This is true whether it involves spending more time waiting in line or waging an unwinnable war, or staying in bad relationships and bad jobs too long, or pouring money into a car that’s worth less than the repairs are costing us. It’s why a house can become a money pit. It’s why we won’t leave a terrible movie because we have already started watching it. It’s why businesses continue to develop and support products that are clearly failing, or pursue strategies long after conditions have changed.” (p. 83)
“When we are in the losses, we are not only more likely to stick to a losing course of action, but also to double down. This tendency is called escalation of commitment.” (p. 84)
“A perfectly rational decision-maker would consider only the future costs and benefits in deciding whether to continue with a course of action. In other words, if continuing on has a positive expected value, a rational actor would persevere. If it has a negative expected value, they would quit.” (p. 89)
“To illustrate, imagine this simple thought experiment: A band you love is coming to town for an outdoor concert. On the day of the show, it is freezing cold, rain is pouring down, and that is expected to continue all night. A friend tells you they have an extra ticket and they are happy to treat you to the concert. You thank them but decline, because, as much as you love the band, you have no interest in standing in the crowd, soaking wet for hours, risking hypothermia. Now imagine that you had bought a ticket when they originally went on sale for $95. It’s the day of the show and it is freezing cold, rain is pouring down, and that is expected to continue all night. Do you go to the concert?” (p. 89)
“The fact that you spent money on the ticket should matter very little, in fact not at all, because those costs are already sunk, the money is already spent. But so often we think, “If I don’t go, I’ll have wasted the money that I blew on the ticket.” (p. 90)
“Another simple way to understand the sunk cost effect is to think about investing in the stock market. In deciding whether to purchase an individual stock, all that matters is whether it has positive expected value going forward. Do you believe you’re going to make money on the purchase? That’s how you do it when it’s a fresh decision, but when you already own the stock and the price has declined since you bought it, you are more likely to hold on to it, trying to win back what you’ve already lost in the position. That’s why retail traders blow through their stop-losses. But this is irrational. If you wouldn’t buy a stock today, you ought not hold it today, because a decision to hold is the same as a decision to buy.” (p. 90)
“A relationship that’s not working out turns into a game of Katamari. Your friend complains about being in a bad relationship. If you ask, “Why don’t you just break up?” they’ll frequently say, “Because I’ve put so much time into trying to make this relationship work.” Sometimes, they’ll even say, “I put my heart and soul into it.” The more time they put in, the less likely they are to break it off, which leads to them investing more time to get it to work. That makes them even less likely to break up. And so on. No wonder that once you have this talk with a friend, you end up having it over and over again. Their dysfunctional relationship keeps rolling up mass—living arrangements, friends, pets, consumer purchases, property—until they’re ripping rainbows out of the ground.” (p. 97)
“This is one of the reasons that retail traders hold on to losing positions. Imagine you’re in that situation: Once you’re losing in a position, you cancel your stop-loss order because you want to recover your losses. That often causes you to accumulate even more losses, making you even less likely to give up on the position. I could see the escalating commitment happening in front of my own eyes at the poker table. Players would lose, and they would start to bet more to try to recover the losses that they had previously accumulated, which then would make them bet even more still. That decision would generate more losses, which made them bet more still, and sometimes even move up in stakes.” (p. 97)
“There’s a saying among top poker players that poker is one long game. It’s a reminder that the particular hand they’re playing is not the last hand they’ll ever play or that any particular day that they’re playing is not the last day they’ll ever play. A poker player will play thousands upon thousands of hands over their lifetime, so in the grand scheme of things whether or not they lose one single hand of poker matters very little. What matters is that they’re maximizing their expected value over all those days and all those hands. That’s what they mean by one long game.” (p. 100)
“If we’re losing in a hand of poker, we don’t want to fold because that means we have to realize the loss of the money we put in the pot. If we’re losing in a poker game, we don’t want to quit because it means that we have to leave with less money than we started with. If we’re in a relationship or a job, we don’t want to walk away because we’ll feel like we will have wasted or lost all the time and effort that we put in. Of course, that’s irrational. What really matters is maximizing your expected value across all the things you start, across all of your mental accounts. If you’re investing in a number of stocks, some are going to win and some are going to lose. What matters is whether you’re winning across your whole portfolio not whether any one investment is up or down.” (p. 101)
“This is why poker players remind themselves that poker is one long game. We would all do well to remember that life is one long game as well.” (p. 102)
“This should be a warning to all of us. Don’t think that, just because you’ve read up to this point in the book or understand the sunk cost fallacy, this knowledge alone is going to help you overcome it. If Rubin was unable to quit, that should open our eyes to how hard it is for the rest of us. Knowing is not the same as doing.” (p. 104)
“A lot of people who know about the sunk cost fallacy tell me they’ve come up with a solution. Essentially, regardless of the history they have with the decision, they ask themselves, “If I were approaching this decision fresh, would I want to enter into this course of action?” (p. 105)
“We already know that we’re not particularly good at responding rationally in the moment to signals that tell us that we ought to quit. In fact, we tend to react to bad news by increasing our commitment rather than cutting our losses. Just knowing about the problem doesn’t help, nor does the Jedi mind trick of saying, “What if I imagine coming to this decision fresh?” But there is something that can help. If we can identify in advance what the signals are that we should pay attention to and make a plan for how we will react to them, we can increase the chances that we’ll cut our losses when we ought to. Essentially, when you enter into an endeavor, you want to imagine what you could find out that would tell you it’s no longer worth pursuing. Ask yourself, “What are the signs that, if I see them in the future, will cause me to exit the road I’m on? What could I learn about the state of the world or the state of myself that would change my commitment to this decision?” That list offers you a set of kill criteria, literally criteria for killing a project or changing your mind or cutting your losses. It’s one of the best tools for helping you figure out when to quit closer to on time.” (p. 115)
“We can imagine potential kill criteria for many of the examples we’ve explored. For Harold Staw, it could be that if the profitability of your stores drops below a certain threshold, you might look to sell. Or your kill criteria could be in the form of a loss limit where, if you had to personally contribute additional money to keep the stores going (or contribute beyond a certain amount), you would sell or close the business. Or, in the extreme case, it could be that trusted advisers are telling you to abandon course, like if your best friend and lawyer switches sides in a lawsuit. In the case of Glitch, a kill criterion might be if you haven’t reached a certain number of sticky customers by a particular date, you’ll quit. Given the California bullet train, you can imagine a lot of applicable kill criteria, like quitting if your original projected budget has more than tripled. One of the clearest examples of a kill criterion is the turnaround time on Everest. If you haven’t made it to the summit by 1 p.m., you cannot safely descend to Camp 4 before dark, so you must abandon the climb.” (p. 116)
“This is in line with lots of subsequent work that’s been done on all sorts of precommitment contracts. Whether it comes to following through with diet plans or work plans or study plans, these types of precommitment contracts get people to act more rationally. Essentially, kill criteria create a precommitment contract to quit. Funnel Vision You can likely imagine lots of applications of kill criteria in your personal life. When you start dating someone, think ahead. What could be happening that would make you think that it was time to end the relationship? Or, in the case of a single date, what would make you want to end the date? You could do that with going to a particular college, picking a major, starting a career, or taking a job. An obvious and high-value application of kill criteria has to do with funnel management for a business’s sales function. A big problem for sellers is managing all the opportunities at the top of the funnel: Which do you pursue? And, once you’ve started pursuing a lead, when do you give up on it?” (p. 117)
“A sales professional’s time is a valuable and limited resource. Any time spent on a low-value lead is time they can’t spend on higher-value leads, or developing new opportunities. That means that if they don’t quickly identify and quit the likely dead ends, that is what will, in reality, slow progress. Creating a set of kill criteria would help the team to cut their losses faster when the signs were clear. To develop such criteria, we started by working with the sales team to generate a list of signals that would tell them that an opportunity wasn’t worth pursuing. To do that, we sent out the following prompt to the sellers and the sales leadership: Imagine you were pursuing a lead that came through an RFP (request for proposal) or RFI (request for information). It’s six months from now, and you have lost the deal. Looking back, you realize there were early signals that the deal was not going to close. What were they? In general, this idea of casting yourself into the future, imagining a failure, and then looking back to try to figure out why is called a premortem. Using a premortem is a great tool to help develop high-quality kill criteria.” (p. 119)
“This particular prompt targeted the early signals of failure that the sellers (and all of us) tend to overlook, rationalize, or ignore. In other words, we were looking for the kinds of indicators of things not going well that intuitively we should pay attention to, but don’t.” (p. 119)
“You can set kill criteria before you accept a position at a company, or before you decide on your major or what college you’re going to, or the house that you want to buy, or the place that you want to live. When you’re shelling out money for a concert ticket, you can think about what the weather conditions would have to be for you to eat the cost and stay home. Kill criteria work well for investing in the market. Setting a stop-loss or a take-gain are examples of kill criteria, but you could also set criteria more broadly, asking yourself in advance what the signals in the market might be that would cause you to change your investment strategy. The good news about kill criteria is that you haven’t missed your chance to set them once you have already started an endeavor. At any point, no matter whether it comes to someone you are dating or a house you already own or an investment you are in or a college you are attending, you can think about some time frame in the future, imagine you are unhappy with your situation, and identify the benchmarks you will have missed or the signals you will be seeing that will tell you that you ought to walk away. You may not have set a stop-loss or take-gain when you bought a stock but you can set one now.” (p. 121)
“The best quitting criteria combine two things: a state and a date. A state is just what it sounds like, an objective, measurable condition you or your project is in, a benchmark that you have hit or missed. A date is the when. Kill criteria, generally, include both states and dates, in the form of “If I am (or am not) in a particular state at a particular date or at a particular time, then I have to quit.” Or “If I haven’t done X by Y (time), I’ll quit.” Or “If I haven’t achieved X by the time I’ve spent Y (amount in money, effort, time, or other resources), I should quit.” For mParticle, one of the kill criteria was a lack of a decision-maker in the room, triggering an offer of executive alignment for the next meeting. Translated into states and dates, “If I can’t get an executive in the room (the state) by the next meeting (the date), then I’ll kill the deal.” (p. 122)
“He gave two examples of the criteria that would cause them to kill the mission. If at any point they fell an hour behind schedule, they would abort. Or, if they discovered that, at any time up to 50% of the way to bin Laden’s compound, they had been detected and compromised by the Pakistani government, they would turn around. If they were compromised beyond the 50% mark, that would be a command decision McRaven would have to make on the fly.” (p. 123)
“The importance of thinking about states and dates in setting kill criteria in advance has been developed and tested in situations with the highest possible stakes, affecting large numbers of people and gigantic, world-changing decisions. But the concepts are broadly applicable to your personal decisions, where you are trying to spend your resources on things that matter and avoid pedestal-building when you ought to be quitting.” (p. 123)
“To avoid becoming entrapped, set benchmarks, in the form of states and dates, in advance. Find out the average time it takes a newly minted PhD to secure a tenure-track position and circle that date on the calendar as a quitting deadline. If, for example, that’s four years from the time you get your PhD, then if you haven’t secured a tenure-track position (the state) within four years (the date), you ought to quit.” (p. 124)
“You can apply states and dates to relationships. If your goal is marriage (or an equivalent long-term commitment), then if your relationship partner hasn’t proposed (or accepted your proposal or otherwise demonstrated a long-term commitment) by a certain date, you should move on and find someone who is as excited about committing to you as you are to them. You can do the same for career advancement. If you’re working at an entry-level position that has some prospect for advancement, figure out as early as you can the interim milestones for those who succeed, whether it’s raises, or initial promotions, or additional responsibilities, or whatever is specific in that company or practice. Get information about when others who’ve succeeded got those signals on the way up and include those states and dates in your kill criteria.” (p. 125)
“Second, when you set out clear kill criteria in advance and make a precommitment to walk away when you see those signals, you are just more likely to follow through, even when you are losing. Anytime you can make a decision about cutting your losses in advance, you’ll do better at closing those mental accounts.” (p. 127)
“In large part, we are what we do, and our identity is closely connected with whatever we’re focused on, including our careers, relationships, projects, and hobbies. When we quit any of those things, we have to deal with the prospect of quitting part of our identity. And that is painful.” (p. 132)
“To anybody who thinks they can be objective about quitting decisions, the results of the field studies in major professional sports should be super alarming. You’ve got smart people, a data-rich environment, a tight feedback loop, and a lot of motivation. For most of the quitting decisions we make, we have much less information and we have longer, noisier feedback loops.” (p. 149)
“You’ve probably heard people (including yourself), when thinking about taking a new path, say, “I don’t want to make a decision right now.” You likely accepted that as a reasonable thing to say. But once you step back and think about it, you realize that deciding not to change is itself a decision. At any moment, when you’re pursuing a goal, you are choosing to either stay on the path you’re on or change course. Sticking with the path is as much of a decision as choosing to quit. In fact, the decision about whether to stay or go is by definition the same choice.” (p. 152)
“Advance planning and precommitment contracts increase the chances you will quit sooner. When you enter into a course of action, create a set of kill criteria. This is a list of signals you might see in the future that would tell you it’s time to quit. Kill criteria will help inoculate you against bad decision-making when you’re “in it” by limiting the number of decisions you’ll have to make once you’re already in the gains or in the losses.” (p. 128)
“What does Conway do to counter these vehement arguments? Nothing. He agrees with them that they can make it work. He doesn’t try to convince the founders that they’re wrong. Instead, he asks them what success would look like over the next few months. And he asks them for specifics. That conversation allows him to sit down with the founder and set performance benchmarks that would signal that the company was heading in the right direction. Then, they agree when to revisit those benchmarks and, if the venture is falling short, to have a serious discussion about shutting it down. This probably sounds a lot like Conway is using kill criteria, and that’s because he is. The founder comes away from the conversation believing they’ve convinced Conway they can turn it around. Conway’s opinion, you’ve probably guessed, hasn’t changed. He comes away still believing that if the founder could see what he sees, they would shut the endeavor down that day. But he knows it’s generally futile to try to persuade them right then. Having set these kill criteria, which the founder has helped generate, Conway has markedly increased the probability that, when they revisit the issue, the founder will be able to see past their own biases and come to the right decision.” (p. 182)
“When you find that friend, ask them to be your quitting coach, to be that person who helps you figure out when to abandon course. If Daniel Kahneman, whose life’s work has been studying cognitive biases and decision errors, needs a quitting coach, then everybody needs one. Kahneman’s happens to be fellow Nobel laureate Richard Thaler. Most of us aren’t lucky enough to have somebody of that stature play that role for us, but we should all try to find someone to be that person in our life who tells us the truth, whether it’s a close friend, a mentor, a coworker, a sibling, or a parent. They just have to be someone who has our long-term best interests at heart and is willing to tell us what we need to hear, not what we want to hear.” (p. 189)
“While a quitting coach can help by offering you a fresh perspective, uncontaminated by your growing katamari, you’re ultimately still the one who has to choose to walk away, and that means you can ignore the advice of your quitting coach. Having a coach improves the chances that you’re going to get to quitting sooner than you otherwise would without one. But, just like Conway’s founders, a lot of times you’re going to rebuff the attempt.” (p. 190)
“Instead, when someone comes to you, it’s better to use Ron Conway’s approach, which can be summarized in these four steps. STEP 1 | Let them know that you think they should consider quitting. STEP 2 | When they push back, retreat and agree with them that they can turn the situation around. STEP 3 | Set very clear definitions around what success is going to look like in the near future and memorialize them down as kill criteria. STEP 4 | Agree to revisit the conversation and, if the benchmarks for success haven’t been met, you’ll have a serious discussion about quitting. Implicit in steps 3 and 4 is that the person you’re counseling has now given you permission to speak freely and bluntly about abandoning course. Of course, all the while, you should remind them that life’s too short.” (p. 195)
“If there’s one thing that you’ve learned from this book, it’s that just knowing about the problem, doing a thought experiment of taking somebody else’s perspective and trying to see it from the outside, looking in on yourself, is something you cannot do. That’s why Daniel Kahneman thinks he needs a quitting coach, and why we all ought to see that need. Life is just too short to be spending our time on things that aren’t worthwhile. We all need people around us who will tell us when we’re on the wrong path.” (p. 196)
“One of the goals for all of us should be to, as much as possible, maximize the diversification of interests, skills, and opportunities in each of our portfolios. There are all sorts of ways you can execute on that in your own life. For example, in your job, it’s a good idea to explore other functions by asking to participate in any onboardings or trainings that might be available to you, as long as that doesn’t have a negative effect on the work you’re primarily responsible for. Exploring those other functions benefits you in several ways. It will maximize the number of jobs that you’re qualified for and it allows you to sample other careers you might not have otherwise considered. Then, if your job goes away for some reason, you will have more things that you can move on to.” (p. 222)
“An “unless” is a powerful thing. Adding a few well-thought-out unlesses to our goals will help us achieve the flexibility that we’re seeking, be more responsive to the changing landscape, and reduce escalation of commitment to losing causes. “I’m going to pursue this lead unless I can’t get an executive in the room.” “I’m going to stay in my job unless I have to consistently take my work home or I find myself dreading the start of the workday and that feeling persists.” “I’m going to keep developing this product unless I fail to hit clear benchmarks within the next two months that I’ve set with my quitting coach.” “I’m going to continue to run this marathon unless I break a bone.” This is why having kill criteria is so important. When you set a goal, creating a list of kill criteria gives you the unlesses that you need to be more rational about when it’s the right time to walk away. Those kill criteria could be about what the world is signaling to you, like observing behavior that tells you that your boss is toxic, or interest rates are rising, or a fog is rolling in, or there’s an onset of a pandemic. Or they could be about changes in yourself, whether it’s the pain you might feel that precedes your fibula snapping or, as in my case, an illness you’ve been struggling with becoming acute. Or it could just be that your preferences change or that the things you value evolve. That a job in the service industry is no longer for you. Or that the sport you used to love now makes you miserable. To make these unlesses most effective, we need to create strong precommitment contracts that set out how we’re going to follow through on those kill criteria. Then, to make sure that we’re picking the unlesses that are going to get us to the fastest answer about whether the thing we’re doing is worth pursuing, we need to do the work of identifying monkeys and pedestals. Doing this work with a quitting coach who can hold you accountable to those unlesses is even better.” (p. 238)