After finishing this book in January of 2023, I wrote an email to the author. It's actually the first email I ever wrote to an author. Whether or not Annie replies, I am happy I wrote the email. Here it is:

 

Dear Annie,

 

I suspect that, in writing to you, I am taking a significant risk that you personally will not reply to this email. Regardless, I’ve already decided that I’ll get enough value just for myself in writing to you. 

 

And, if you reply, that would be tiramisu icing on the cake.

 

Below, I have an observation and question for you. I am very curious about what responses you may have.

 

As a life and lifestyle coach for almost 36 years, I devour books like yours. 

 

I read your “Thinking in Bets” first. Then “How to Decide.” I have just finished “Quit.” I am recommending them, especially the last, to all my clients.

 

In my book, “Courage: The Choice that Makes the Difference” and also on my website AskDwightHow.org, I use the term “quitaverance,” which to indicate the joys and wisdom of quitting in contrast to the joys and wisdom of perseverance.

 

I’ll ask my questions first and then hazard a guess as to how you might answer.

 

In “Quit,” you provide compelling stories and examples of the importance and power of knowing when to quit for many important areas of our lives. However, you neglected to give any compelling examples for two life areas that would stand out for many people as more important than any of the domains where you did give great life examples (as in when to quit your job or change your career…or not).

 

The first of these life areas is marriage. I know you did mention “dating” several times, but the issue of knowing when to quit a marriage, for most people, has a different order of magnitude. As a life coach, I have often coached clients on this issue, pointing out all the cognitive biases that gaff the scales in favor of perseverance in other areas of life apply in spades with the grit-quit issue of staying married or getting divorced. I would have appreciated a compelling story in your book of how someone applied your “quitting principles” in deciding whether to quit a marriage or not.

 

The second of these life areas is death. The issue of quitting in the area of life or death is even more controversial that deciding whether to stay married or get divorced. Perhaps understandably, you did not touch on this area at all, even in passing. It’s also severely complicated by the fact that it’s illegal, at least the US, to assist someone in dying. I personally, am acutely aware of how much unnecessary suffering is incurred because very few of us apply your grit-quit principles to the issue of whether to continue in life or to quit (when the quitting is good).

 

I would feel honored to getting your thoughts regarding why you did not include compelling examples of these two most important life areas where applying your principles would make the biggest difference for people.

 

Sitting over here (now living in Bogota, Colombia) with my non-mind-reading ability, I am projecting that you made a perhaps prudent decision to fight the battles you had a chance of winning and avoid the others. If so, that makes sense. 

 

With appreciation, Dwight

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My clippings below collapse a 334-page book into 42 pages, measured by using 12-point type in Microsoft Word.

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See all my book recommendations.  

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Here are the selections I made:

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Success does not lie in sticking to things. It lies in picking the right thing to stick to and quitting the rest.

 

Quitting means failing, capitulating, losing. Quitting shows a lack of character. Quitters are losers (except, of course, when it involves giving up something obviously bad like smoking, alcohol, drugs, or an abusive relationship).

 

The English language itself favors grit, describing those who persevere with positive terms like can-do, unwavering, steadfast, resolute, daring, audacious, undaunting, gutsy, and hardy. Or as having backbone, pluck, mettle, tenacity, or stick-to-itiveness.

 

As readily as positive words to describe perseverance come to mind, so do the negative terms for those who quit, all of which encompass the idea that quitters are failures who don’t deserve our admiration. They are backtrackers, chickens, defeatists, deserters, dropouts, shirkers, wimps, and wusses. They give up and abandon things, waver and vacillate. We consider them aimless, capricious, craven, erratic, fickle, weak-...

 

I’m certainly not knocking these books. But whether you say “pivot” or “moving on to the next chapter” or “strategic redeployment,” all of these things are, by definition, quitting. After all, stripped of its negative connotation, quitting is merely the choice to stop something that you have started.

 

There is a rich universe of science studying the human tendency to persevere too long, particularly in the face of bad news.

 

Chapter 5 describes why sunk costs make it so hard to walk away. I’ll dive deep into the fear of waste and how the money, time, effort, or other resources we have invested in a course of action negatively impact decisions about whether to move forward.

 

Chapter 6 offers up strategies to improve decisions about when to quit, including the importance of tackling the hardest part of a project first, as well as ways to develop benchmarks, criteria, and signals, called kill criteria, that will help ensure you quit sooner when persisting is no longer in your best interest.

 

That’s why, if I had to skill somebody up to get them to be a better decision-maker, quitting is the primary skill I would choose, because the option to quit is what allows you to react to that changing landscape.

 

When you are weighing whether to quit something or stick with it, you can’t know for sure whether you can succeed at what you’re doing because that’s probabilistic. But there is a crucial difference between the two choices. Only one choice—the choice to persevere—lets you eventually find out the answer.

 

And pros are just better at that choice, playing a mere 15% to 25% of the two-card starting combinations they are dealt in Texas Hold’em. Compare that to an amateur, who will stick with their starting cards over half the time.

 

We tend to celebrate people who respond to adversity by soldiering on. The quitters, in comparison, are invisible. If we don’t notice the decision-making of the quitters, it’s hard to learn from them. Quitting a course of action is sometimes the best way to win in the long run, whether you’re cutting your losses at the poker table or getting to climb another day. Quit and grit are two sides of the exact same decision. Decision-making in the real world requires action without complete information. Quitting is the tool that allows us to react to new information that is revealed after we make a decision. Sticking with a course of action is the only way to find out for sure how it will turn out. Quitting requires being okay with not knowing what might have been. Having the option to quit helps you to explore more, learn more, and ultimately find the right things to stick with.

 

Quitting on time will usually feel like quitting too early. If you quit on time, it’s not going to seem like anything particularly dire is happening at that particular moment.

 

Contrary to popular belief, quitting will get you to where you want to go faster.

 

The corollary of this is also true. When people quit on time, it will usually feel like they are quitting too early, because it will be long before they experience the choice as a close call.

 

This is consistent with the idea that the scale is gaffed against quitting. It turns out that our psychology puts a thumb on the scale such that by the time we think the options of quitting and sticking are 50-50, it’s not even in the vicinity.

 

If you feel like you’ve got a close call between quitting and persevering, it’s likely that quitting is the better choice.

 

Quitting on time usually feels like quitting too early. The hardest time to make a quitting decision is when you’re in it. 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. When the time is objectively right to quit, nothing particularly dire will be happening right at that moment. Getting the timing right means looking into the future and seeing that the chances things will go your way are too slim. Thinking in expected value helps you figure out if the path you are on is worth sticking to. EV 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. If you feel like the choice between persevering and walking away is a close call, it’s likely that quitting is the better choice. In hindsight, we can see when someone has waited too long to quit, and we tend to be harsh in our judgment of those people. But when someone quits before it seems obvious to others, we mock them for quitting too early. That’s the quitting bind.

 

That we make both types of errors, sometimes sticking too long and sometimes giving up too early, shouldn’t be that surprising because whether to stick or quit aren’t separate decisions. They are one and the same. Whenever you choose to stick, you are, by definition, not quitting. The reverse is true when you choose to quit.

 

When we’re choosing among new options, loss aversion causes us to favor the ones that have the lowest absolute loss associated with them, even if those options come at a lower expected value. In other words, our aversion to taking a loss causes us to make decisions a rational actor would not.

 

Quitting on time usually feels like quitting too early, and the usually part is specifically when you’re in the losses.

 

But there is one aphorism that actually encourages people to quit: Quit while you’re ahead. Just as so many of those inspirational quotes lauding unlimited persistence are bad advice, this single piece of pro-quitting wisdom, despite surviving for more than four hundred years, is no better.

 

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.

 

The result is that we’ll quit when we’re ahead, even if we’re giving up good opportunities to win more. If we’re behind, we don’t want to quit, even if persisting—to try to get to the other side of zero—is more likely to make things worse.

 

A key finding of prospect theory is loss aversion, the phenomenon whereby the emotional impact of a loss is greater than the corresponding impact of an equivalent gain. Loss aversion creates a preference for options associated with a lower chance of incurring a loss. It makes us risk averse. When we are in the gains, we have a tendency to quit too early in order to avoid the risk of giving those gains back. In other words, we like to quit while we’re ahead. When we are in the losses, we become risk seekers. We want to keep going, hoping we can avoid ever having to realize the loss. Daniel Kahneman has characterized this as sure-loss aversion. In other words, we like to stick when we’re behind. Quitting on time usually feels like quitting too early, and the usually part is specifically when you’re in the losses. Retail investors show this pattern of quitting when they’re ahead and sticking when they’re behind. Even expert investors don’t get their quitting decisions just right. They outperform on their buying decisions but underperform on their selling decisions. We naturally track and get feedback on the things we are doing. But once we quit something, we also quit keeping track of that course of action. This creates a problem with getting high-quality feedback, which in turn makes it hard to hone our quitting skills.

 

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. Escalation of commitment is robust and universal, occurring in individuals, organizations, and governmental entities. All of us tend to get stuck in courses of action once started, especially in the face of bad news. Escalation of commitment doesn’t just occur in high-stakes situations. It also happens when the stakes are low, demonstrating the pervasiveness of the error.

 

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.

 

Our track to nowhere could be refusing to quit our college major even though it’s making us unhappy, because we already took so many classes and put so much time into it.

 

Or we don’t leave a career we spent years training for, because that would mean our training was for nothing. Or we keep watching a bad movie because of the time we’ve already spent watching it.

 

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.”

 

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.

 

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?”

 

The sunk cost effect is a cognitive illusion where people take into account resources they have previously sunk into an endeavor when making decisions about whether to continue and spend more. The sunk cost effect causes people to stick in situations that they ought to be quitting. When deciding whether to stick or quit, we are worried that if we walk away, we will have wasted the resources we have spent in the trying. You might be experiencing the sunk cost fallacy if you hear yourself thinking “If I don’t make this work I will have wasted years of my life!” or “We can’t fire her now, she’s been here for decades!” Sunk costs snowball, like a katamari. The resources you have already spent make it less likely you will quit, which makes it more likely you will accumulate additional sunk costs, which makes it again less likely you will quit, and so on. The growing debris of your prior commitment makes it increasingly harder to walk away. We don’t like to close mental accounts in the losses. Knowing about the sunk cost effect doesn’t keep you from falling prey to it. You can’t trick yourself into not taking sunk costs into account by trying to view the situation as a new choice. Asking whether or not you would continue if the decision were a fresh one doesn’t mitigate the sunk cost effect the way you might intuitively think it would.

 

To pursue radical ideas, he has to be a radical loss-cutter. Every dollar they save by getting to no quickly is a dollar they can spend on something that could change the world.

 

“If we find the Achilles’ heel,” Teller told me, “thank God we found the Achilles’ heel after $2 million instead of after $20 million.”

 

One of Teller’s valuable insights is that pedestal-building creates the illusion of progress rather than actual progress itself.

 

Monkeys and pedestals boils down to some very good advice: Figure out the hard thing first. Try to solve that as quickly as possible. Beware of false progress.

 

Kill criteria could consist of information you learn that tells you the monkey isn’t trainable or that you’re not sufficiently likely to reach your goal, or signs that luck has gone against you.

 

Essentially, kill criteria create a precommitment contract to quit.

 

Monkeys and pedestals is a mental model that helps you quit sooner. Pedestals are the part of the problem you know you can already solve, like designing the perfect business card or logo. The hardest thing is training the monkey. When faced with a complex, ambitious goal, (a) identify the hard thing first; (b) try to solve for that as quickly as possible; and (c) beware of false progress. Building pedestals creates the illusion that you are making progress toward your goal, but doing the easy stuff is a waste of time if the hard stuff is actually impossible. Tackling the monkey first gets you to no faster, limiting the time, effort, and money you sink into a project, making it easier to walk away. When we butt up against a hard problem we can’t solve, we have a tendency to turn to pedestal-building rather than choosing to quit. 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. In organizations, kill criteria allow people a different way to get rewarded beyond dogged and blind pursuit of a project until the bitter end. 

 

A common, simple way to develop kill criteria is with “states and dates:” “If by (date), I have/haven’t (reached a particular state), I’ll quit.”

 

The endowment and sunk cost effects live together in a way that amplifies escalation of commitment. Status quo bias adds to the mix of cognitive forces gaffing the scale.

 

We are much more bothered by the downside potential of changing course than we are by the downside potential of staying on the path we’re already on.

 

We can see this at work in Dr. Olstyn Martinez’s dilemma. She clearly recruited loss aversion into her thinking about changing careers. “What if I go and do the new thing and get a bad outcome?” That’s part of what was creating the friction that was stopping her from taking the new role. Meanwhile, she wasn’t nearly as averse to the prospect of the same bad outcome—unhappiness—from staying in her current job, even though she had already acknowledged that unhappiness was a 100% certainty if she didn’t quit.

 

A higher chance of failing is more tolerated on paths that don’t rock the boat. After all, what’s the go-to defense in a postmortem after we make a decision that doesn’t work out? “I followed procedure,” or “I stuck with the status quo,” or “I made the consensus choice.”

 

Wrapped within all these forces interfering with quitting decisions is that we do not think of sticking with the status quo as an active decision in the same way that we view switching as one. We are much more concerned with errors of commission than errors of omission (failures to act). We’re more wary of “causing” a bad outcome by acting than “letting it happen” through inaction.

 

This phenomenon is known as omission-commission bias.

 

Switching to something, like a new job or a new major or a new relationship or a new business strategy, is perceived as a new decision, and an active one. In contrast, we don’t really view the choi...

 

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 o...

 

One of the steps to becoming a better quitter is to not accept “I’m not ready to make a decision right now” as a sentence that makes sense. At every moment of your life, you have a choice about whether to stay or whether to go. When you choose to stay, you are also choosing t...

 

But omission-commission bias causes us not to view these decisions as equivalent. That’s why we accept that explanation of “I’m not ready to make a decision yet” from others and why we accept it from ourselves. Of course, what that really means is “I’m not ready to veer from the status quo.”

 

The next time that you find yourself saying, “I’m just not ready to decide yet,” what you should actually say is “For now I think that the status quo is still the best choice.” Maybe you need more information to know whether to switch. But what shouldn’t stop you from quitting (or getting that information) is that it’s too scary to switch because loss aversion is too intense.

 

By asking her if she would be happier in the new job more than 0% of the time, that helped her see that there was some certainty in changing jobs. Specifically, she had a better chance of getting to where she wanted to go faster if she switched. In that moment, she realized the devil that she didn’t know was the better choice.

 

The endowment effect is a cognitive bias where we value something we own more than we would if we didn’t own it. We can be endowed to objects but also to our own ideas and beliefs. Endowment is an obstacle to quitting because when we irrationally value things we own, we miscalculate their expected value. We might think the company we started or the project we devised or the belief we have is worth more than it actually is. We prefer to stick with the status quo. We are more tolerant of bad outcomes that come from sticking with what we are already doing than bad outcomes that come from switching to something new. This phenomenon is part of omission-commission bias. When you say, “I’m just not ready to decide yet,” what you are really saying is, “For now, I am choosing the status quo.” Even in highly data-rich environments like professional sports, sunk cost, endowment, and status quo bias distort decision-making.

 

Adults ask children, “What do you want to be when you grow up?” We don’t ask, “What job do you want?” We are asking who they will be, not what they will do. This is a difference with quite a large distinction.

 

When your identity is what you do, then what you do becomes hard to abandon, because it means quitting who you are.

 

We are all trying to defend ourselves against how we imagine other people are going to judge us.

 

Be picky about what you stick to. Persevere in the things that matter, that bring you happiness, and that move you toward your goals. Quit everything else, to free up those resources so you can pursue your goals and stop sticking to things that slow you down.

 

When it comes to quitting, the most painful thing to quit is who you are. Our ideas, beliefs, and actions are part of our identity. When new information conflicts with a belief, we experience cognitive dissonance. To resolve the conflict, we can either change the belief or rationalize away the new information. Too often, we choose the latter. Dissonance can also result from new information coming into conflict with our past actions. We have a desire to maintain internal consistency, where our past beliefs and actions line up with our present beliefs and actions. We also want others to view us as consistent. We worry that if others see inconsistency between our present and past decisions, beliefs, or actions, they will judge us as being wrong, irrational, capricious, and prone to mistakes. When we know or believe our decisions are being evaluated by others, our intuition is that we will be more rational, but the opposite is true. External validity increases escalation of commitment. The more extreme a position is, the more cognitive gymnastics we’ll do to defend it. The facts are more likely to persuade you away from the consensus opinion than a fringe view. Fears about how others will view us if we quit are usually overblown.

 

What is true for grit is true for optimism. Optimism gets you to stick to things that are worthwhile. But optimism also gets you to stick to things that are no longer worthwhile. And life’s too short to do that.

 

Quitting is hard, too hard to do entirely on our own. We as individuals are riddled by the host of biases, like the sunk cost fallacy, endowment effect, status quo bias, and loss aversion, which lead to escalation of commitment. Our identities are entwined in the things that we’re doing. Our instinct is to want to protect that identity, making us stick to things even more.

 

That’s why Daniel Kahneman thinks he needs a quitting coach, and why we all ought to see that need.

 

Optimism makes you less likely to walk away while not actually increasing your chances of success. That means that being overly optimistic will make you stick to things longer that aren’t worthwhile. Better to be well calibrated. Life’s too short to spend your time on opportunities that are no longer worthwhile.

 

When someone is on the outside looking in, they can usually see your situation more rationally than you can. The best quitting coach is a person who loves you enough to look out for your long-term well-being. They are willing to tell you the hard truth even if it means risking hurt feelings in the short term. Decisions about when to quit improve when the people who make the decisions to start things are different from the people who make the decisions to stop those things. Getting the most out of a quitting coach requires permission to speak the truth. INTERLUDE III The Ants Go Marching . . .

 

The lesson here is that we shouldn’t wait to be forced to find a Plan B. We should always be doing some exploration, especially because sometimes Plan B can turn out to be better than the thing you’re already pursuing.

 

They learned the lesson the ants have down pat: Don’t wait to be forced to quit to start exploring alternatives.

 

Being forced to quit forces you to start exploring new options and opportunities. But you should start exploring before you’re forced to. Even after you have found a path that you want to stick to, keep doing some exploration. Things change, and whatever you are doing now may not be the best path for you to pursue in the future. Having more options gives you something to switch to when the time is right. Exploration helps you to diversify your portfolio of skills, interests, and opportunities. A diversified portfolio helps to protect you against uncertainty. Backup plans are good to have especially because some backup plans can turn out to be better than what we’re already pursuing.

 

Finish lines are funny things. You either reach them or you don’t. You either succeed or you fail. There is no in between. Progress along the way matters very little.

 

But just because there are a lot of benefits to setting goals doesn’t mean that there isn’t a downside to them as well. As you might already suspect, clearly defined finish lines should come with a warning: Danger, you may experience escalation of commitment.

 

They point to numerous negative consequences of goal setting, several of which interfere with rational quitting behavior. In particular, they note the pass-fail nature of goals, their inflexibility, and how pursuing them leads to ignoring other opportunities that might be available.

 

As you already know, grit is good for getting you to stick to hard things that are worthwhile, but grit also gets you to stick to hard things that are no longer worthwhile.

 

But for so many of us, that fear of falling short makes us not want to start. As Richard Thaler quipped, “If a gold medal in the Olympics is the only grade that passes, you do not want to ever take your first gymnastics class.”

 

Being in the losses is as much a state of mind as anything else. We don’t see ourselves as being in the gains, even though we’ve gone farther than where we started, because we’re not measuring ourselves by how far we are past the starting line. We’re measuring ourselves by whether we’re short of the finish line.

 

Progress along the way should count for something, but we discard it because goals are pass-fail, all-or-nothing, yes-or-no. There’s no partial credit given.

 

But the goals we set are remarkably unresponsive to new information.

 

The goal becomes fixed even as all the inputs that led to choosing that particular goal evolve. The conditions in the world change. Our knowledge changes. The weights we attach to the benefits and costs change. Our preferences and values change.

 

As these things change, if we were to rerun the cost-benefit analysis, the output would surely be different. But we don’t rerun it.

 

It’s not just that we need to set more flexible goals. We ourselves also need to be more flexible in the way we evaluate success and failure.

 

Goals can make it possible to achieve worthwhile things, but goals can also increase the chances that we will escalate commitment when we should quit. Goals are pass-fail in nature. You either reach the finish line or you don’t, and progress along the way matters very little. Don’t just measure whether you hit the goal, ask what you have achieved and learned along the way. Set intermediate goals and prioritize goals that allow you to recognize progress along the way or acquire something valuable even if you don’t reach the goal. Goals, when set, are a proxy for an expected-value equation, balancing the benefits that you’re trying to gain against the costs you’re willing to bear. Inflexible goals aren’t a good fit for a flexible world. With better advance planning (like identifying monkeys and pedestals and kill criteria) and the help of a good quitting coach, you can make goals more flexible, setting at least one “unless” and planning regular check-ins on the analysis that initially led to setting the goal. In general, when we quit, we fear two things: that we’ve failed and that we’ve wasted our time, effort, or money. Waste is a forward-looking problem, not a backward-looking one. ACKNOWLEDGMENTS

 

(quoting an August 2005 speech by then president George W. Bush justifying staying the course in Iraq by saying, “We owe [the two thousand soldiers who had already died] something. We will finish the task that they gave their lives for.”); Van Putten, Zeelenberg, and Van Dijk, “Who Throws Good Money after Bad?,” 2010, 33 (“one of the most important reasons to continue the way in Iraq was to prevent acknowledging that soldiers who fell in battle died in vain”).