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Scott Vejdani
Quit: The Power of Knowing When to Walk Away - by Annie Duke

Quit: The Power of Knowing When to Walk Away - by Annie Duke

Date read: 2023-03-05
How strongly I recommend it: 9/10
(See my list of 150+ books, for more.)

Go to the Amazon page for details and reviews.

A follow-up from Annie's previous books which focused on how to make better decisions, she does a great job of explaining the benefits of quitting and how to decide when you should quit. Full of great examples and a systematic way to make better decisions.


Contents:

  1. WHY YOU SHOULD QUIT
  2. MONKEYS AND PEDESTALS
  3. COGNITIVE BIASES
  4. QUITTING COACH STRATEGIES
  5. ALWAYS SEEK OUT ADDITIONAL OPTIONS

My Notes

That’s the funny thing about grit. 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. The trick is in figuring out the difference.

By definition, anybody who has succeeded at something has stuck with it. That’s a statement of fact, always true in hindsight. But that doesn’t mean that the inverse is true, that if you stick to something, you will succeed at it.

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


WHY YOU SHOULD QUIT
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.”

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.

Having the option to quit helps you to explore more, learn more, and ultimately find the right things to stick with.

The fact that he turned Tiny Speck’s internal communications tool into a unicorn just makes it even happier. Re: Butterfield quitting on his game Glitch which allowed him to pursue his new project which later became Slack.

Quitting on time will usually feel like quitting too early.

There is a well-known heuristic in management consulting that the right time to fire someone is the first time it crosses your mind.

Expected Value (EV) - 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.

As a simple example, imagine that you are flipping a fair coin, meaning the coin has a 50% chance of landing heads and a 50% chance of landing tails. Let’s say for this example that if the coin lands heads, you will win $100, and if it lands tails, you will lose $50. If you multiply the $100 you will win by 50% (how often the coin lands heads), you get $50, which will be your expected long-run gains. Multiplying the $50 loss when the coin lands tails by 50% gets you negative $25, your expected losses in the long run. Subtracting $25 from $50 gets you a net gain of $25. So this coin flip proposition carries a positive expected value of $25.

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

Prospect theory is a model of how people make decisions, accounting for systematic preferences and biases involving risk, uncertainty, gains, and losses. 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. All of a sudden, uncertainty doesn’t bother us. When we’re losing, we want luck to be involved.

Sure-loss aversion makes us not want to stop something we have already started. That is because the only way to make sure we turn those paper losses into realized losses is to quit and refuse the gamble. Taking the option to flip the coin opens up the possibility of avoiding having to do that.

I hope it’s becoming very clear how bad the advice “quit while you’re ahead” really is, because it’s encouraging our natural tendency to be irrational in these situations already.

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.


MONKEYS AND PEDESTALS
A mental model to quit faster and to avoid sunk cost fallacy.

Imagine that you’re trying to train a monkey to juggle flaming torches while standing on a pedestal in a public park. There are two pieces to becoming successful at this endeavor: training the monkey and building the pedestal. The bottleneck, the hard thing, is training a monkey to juggle flaming torches.

The point of this mental model is to remind you that there is no point building the pedestal if you can’t train the monkey. In other words, you ought to tackle the hardest part of the problem first.

The sooner you figure out that you should walk away, the sooner you can switch to something better. And the sooner that happens, the more resources you’re saving, which you can then devote to more fruitful endeavors.

Figure out the hard thing first. Try to solve that as quickly as possible. Beware of false progress.

Kill Criteria - 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.

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 example: “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.”


COGNITIVE BIASES
The Endowment Effect - when we own something, we value it more highly than an identical item that we don't own.

The endowment effect is particularly strong if the thing you own you also built. This is known as the IKEA effect, for obvious reasons. Most furniture you buy from IKEA, you have to put together yourself. We’ll value that nightstand that we built much more than an identical one that was preassembled.

The Status Quo Bias - 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.

Omission-Commission Bias - 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.

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 to not go. When you choose to quit, you are also choosing to not continue. It’s crucial to start realizing that those are the same, active decisions.

Re: how we define our identity: 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.

Cognitive Dissonance - We experience dissonance when new information conflicts with our prior beliefs. When that happens, it makes us uncomfortable, and we want to make that discomfort go away. So we rationalize away the new information so we can defend our prior beliefs.

Example of cognitive dissonance - ignoring certain information that goes against the political party we associate with.

We need to be careful about tying our identity to any single thing that we believe. And we need to be particularly cautious when a belief is outside the mainstream and public because it is so much harder to let go of those beliefs, facts be damned.

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.


QUITTING COACH STRATEGIES
When it comes to business endeavors, career choices, or decisions about your personal life, we should all be striving for two things: First, you should find at least one person to be your quitting coach. Second, you should try to serve in that role for the people you love.

A good strategy for businesses that want to get better at their quitting decisions: When possible, divide and conquer. Have the people who make the decisions to start things be different from the people who make the decisions to stop those things.

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.


ALWAYS SEEK OUT ADDITIONAL OPTIONS
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.

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.

Don’t wait to be forced to quit to start exploring alternatives.

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.

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. Similar to defining kill criteria.

Example of "unless" - “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.”

You have to keep checking back in on the cost-benefit analysis that the goal is a proxy for. You should reevaluate, on a regular cadence, whether the values that you’re trying to privilege are still being privileged and whether the values that you’re deprivileging, the costs that you’re bearing, are still worth it. Those check-ins also offer an opportunity to reevaluate old kill criteria and set new ones.

Don’t just measure whether you hit the goal, ask what you have achieved and learned along the way.