An insightful book on the underappreciated art of quitting. Behavioral psychologist Annie Duke on the purpose of the book:
The aim of this book is to create a better understanding of those forces that work against good choices about what and when to quit and the circumstances in which we are reluctant to walk away, and to help all of us view quitting more positively so we can improve our decision-making.
I hope that as a result of reading this book, you will learn to recognize why quitting should be celebrated and how it can become a skill you can develop and use to enrich your life, encouraging you to value optionality, execute better on the things you stick with, and continue exploring so you can flexibly change with (or in advance of) a changing world.
Having the option to quit helps you to explore more, learn more, and ultimately find the right things to stick with.
I was familiar with many of the cognitive biases covered in this book but it’s always refreshing to read Duke given her prowess as a storyteller, writer, and philosopher. Most of the evidence presented is anecdotal, yet there are still many valuable lessons to glean from the examples.
Main takeaway:
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.
4.5 / 5. October 2023 (Thinking in Bets is a more comprehensive but different book on decision making. I strongly recommend it.)
Notes
The Truth about Grit & Persistence
Persistence is not always the best decision, certainly not absent context. And context changes.
While grit can get you to stick to hard things that are worthwhile, grit can also get you to stick to hard things that are no longer worthwhile.
We ought not confuse hindsight with foresight, which is what most aphorisms do.
Success does not lie in sticking to things. It lies in picking the right thing to stick to and quitting the rest.
It’s not as if there aren’t any negative words for grit (like rigid or obstinate), or positive words for quitting (like agile or flexible). But if you tried filling a two-by-two table with positive and negative terms for both concepts, you would soon see the imbalances.
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.
But anybody who reads Grit as suggesting that perseverance, absent context, is always a virtue, is misinterpreting Angela Duckworth’s work. She would never say, “Just stick with things and you’ll succeed.” She has herself written about the importance of trying lots of things (which requires that you quit lots of other things) to find the thing that you want to stick with.
The Psychology of Quitting
Quitting is ultimately a forecasting problem, meaning that when to quit is a problem of whether the future looks dire, not whether the present is dire. And a rosy present is a hard thing to walk away from.
Success is not achieved by quitting things just because they are hard. But success is also not achieved by sticking to hard things that are not worthwhile.
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. The desire for certainty is the siren song calling us to persevere, because perseverance is the only path to knowing for sure how things will turn out if you stay the course. If you choose to quit, you will always be left to wonder, “What if?”
For each of us on an individual level, the road to happiness is not in sticking blindly to the thing that we’re doing, as so many aphorisms cajole us to do. We need to see what’s going on around us so we can do whatever will maximize our happiness and our time and our well-being.
As Kenny Rogers sang in The Gambler, “You gotta know when to hold ’em, know when to fold ’em, know when to walk away, and know when to run.” Notice that three of those four things are about quitting.
This is the fundamental truth about grit and quit: The opposite of a great virtue is also a great virtue.
Anytime you stick to something when there are better opportunities out there, that is when you are slowing your progress.
Quitting 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.
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.
Actionable Advice & Mental Models on Quitting
Making a plan for when to quit should be done long before you are facing the quitting decision. It recognizes that the worst time to make a decision is when you’re “in it.” (turnaround times climbing)
Silicon Valley is famous for mantras like “move fast and break things” and implementing them through strategies like “minimum viable product” (MVP). These types of agile strategies can only work if you have the option to quit. You can’t put out an MVP unless you have the ability to pull it back. The whole point is to get information quickly, so you can quit the stuff that isn’t working and stick with the things that are worthwhile or develop new things that might work even better.
Quitting on time will usually feel like quitting too early. 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.
It shouldn’t be surprising that making good decisions about quitting requires mental time travel since the worst time to make a decision is when you’re in it.
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.
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.
“Imagine it’s a year from now and you stayed in the job that you’re currently at—what’s the probability you’re going to be unhappy at the end of that year?” She said, “I know I’m going to be unhappy, one hundred percent.”
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.
One of the key findings of prospect theory is loss aversion, recognizing that the emotional impact of a loss is greater than the corresponding impact of an equivalent gain. In fact, losing feels about two times as bad to us as winning feels good to us.
When we are in the gains, we don’t want to recruit luck into the equation, luck that might wipe out what we have already won. We want to quit while we’re ahead. But when we are in the losses, we’ll take the gamble, recruiting luck into the equation in the hopes that we can wipe out what we have already lost.
loss aversion creates a preference for options associated with a lower chance of incurring a loss. It makes us risk averse and stops us from getting started, from choosing options where we might lose.
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.
Even expert investors don’t get their quitting decisions just right. They outperform on their buying decisions but underperform on their selling decisions.
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.
Forty years of experiments and fieldwork across a variety of domains show that people behave as Thaler hypothesized regarding sunk costs. In decisions about whether to move forward, they do take into account what they’ve already spent.
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.
To help X-ers become better quitters, Astro Teller has come up with a unique mental model that has been woven into the fabric of X: monkeys and pedestals.
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.
The lesson here is, when you’re starting your business, the first thing you tackle shouldn’t be designing the perfect business card or investing in the most beautiful logo or coming up with the coolest name.
One of Teller’s valuable insights is that pedestal-building creates the illusion of progress rather than actual progress itself. When you are doing something that you already know you can accomplish, you’re not learning anything important about whether the endeavor is worth pursuing. You already know you can build the pedestal. The problem is whether you can train the monkey.
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.
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.
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.”
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.
Taken together, the monkeys-and-pedestals mental model and kill criteria help us overcome our aversion to closing accounts in the losses.
Wilkinson’s story demonstrates how ownership can interfere with our ability to walk away, especially when the thing we own, we created.
Richard Thaler was the first to name this cognitive illusion, calling it the endowment effect. In fact, he introduced the endowment effect in that same 1980 paper where he coined the term “sunk cost.” He described the endowment effect as “the fact that people often demand more to give up an object than they would be willing to pay to acquire it.”
As the research on the endowment effect has expanded, it has become increasingly clear that we can also become endowed to our beliefs, our ideas, and our decisions. As we carry around beliefs and ideas, they become our possessions. We own what we’ve bought and what we’ve thought. (IKEA effect)
Simply put, the status quo is the path you’re already on or the way you’ve always done things. The bias is that we have a preference to stick with those decisions, methods, and paths that we’ve already set upon, and a resistance to veering from them into something new or different.
Individuals overwhelmingly stick with the status quo option, even when that option is associated with a lower expected value. The bias is widely acknowledged, robust, and has been established as applying to decisions by individuals and organizations.
“Worldly wisdom teaches that it is better for reputation to fail conventionally than to succeed unconventionally.” Succeeding unconventionally carries with it the risk of experiencing failure as a result of veering from the status quo.
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 choice to stick with the status quo as a decision at all.
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.”
In business as well as in personal decisions, we’ve seen how all these cognitive effects—loss aversion, sure-loss aversion, the sunk cost effect, endowment, status quo bias, and omission-commission bias—create a heady brew that makes it hard for us to quit on time.
The Problem with Identity
Sears: Retail was their identity. If they had held on to the financial services assets and shuttered or sold the retail company, they would have, in some sense, ceased to be Sears, at least the Sears that everyone knew them as. That’s the choice that they faced. When it comes to quitting, the most painful thing to quit is who you are.
But what you need to understand is that we’re all in a cult of our own identity. When you say, “I’m a teacher,” or “I’m a doctor,” or “I’m a gamer,” you’re making a statement about who you are. Adults ask children, “What do you want to be when you grow up?” We don’t ask, “What job do you want?”
Every time you rationalize away new information in order to cling to a belief, that belief becomes more tightly woven into the fabric of your identity.
This desire to maintain internal consistency stops us from quitting. As does the worry that other people are going to judge us as harshly as we judge ourselves.
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.
Conclusion
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.
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. Daniel Kahneman advice: “What everybody needs is the friend who really loves them but does not care much about hurt feelings in the moment.”
If you spend months or years in a job or a relationship that’s not contributing to your long-term happiness, that’s time you can never get back.
When people ask for advice, don’t confuse that with being given permission. Instead, when someone comes to you, it’s better to use Ron Conway’s approach, which can be summarized in these four steps.
1. Let them know that you think they should consider quitting.
2. When they push back, retreat and agree with them that they can turn the situation around.
3. Set very clear definitions around what success is going to look like in the near future and memorialize them down as kill criteria.
4. Agree to revisit the conversation and, if the benchmarks for success haven’t been met, you’ll have a serious discussion about quitting.
The choice of how you allocate your time to finding new things or taking advantage of things you’ve already discovered is part of the classic explore-exploit problem.
The ants strike the right balance between exploiting and exploring. The strength of the pheromone trail determines the percentage of foragers that continue to explore, but no matter how strong that scent is, the number of ants exploring never drops to zero.
When we find something that’s working for us, whether it’s a job, a career, a product that we’re developing, a business strategy, or even a favorite restaurant that we love going to, continuing to explore what other options might be available is a good strategy in a world as uncertain as the one that we live in. Never stop exploring.
Whenever you’re pursuing a goal, there are always other opportunities you’re neglecting. You simply don’t see them because you’re not looking for them.
It’s not always the world that changes. Sometimes, it’s you that changes. Your tastes, preferences, and values evolve over time. A job you love in your twenties might not be a job you love in your thirties. Maybe when you’re younger, high-pressure and eighty-hour workweeks are just what you’re looking for. But in your thirties, you may value your time differently, and be less willing to sacrifice time with your family to advance your career.
The power of diversification is, of course, well known in the investment world. Investors want a diversified portfolio for the same reason the ants do, to reduce the impact on their bottom line in case any one of their investments craters. That’s not just true for investors or ants. For any of us, having a diversified portfolio of interests, skills, and opportunities helps to protect us from uncertainty.
The unlesses we attach to the goals we set allow us to follow through on the trope “process over outcome.” The goal itself is outcome oriented, but the unlesses focus on process.
Success means following a good decision process, not just crossing a finish line, especially if it is the wrong one to cross.
Waste is a forward-looking problem, not a backward-looking one.