While grit is celebrated as a virtue, quitting is cast negatively as a vice. Quitting means failing, losing and not being determined; quitters are losers. Society emphasizes not giving up and perseverance. Quitters never win, and winners never quit. Keep trying. Quitting is not an option. Finish the marathon! See you at the top! Stories are about victories and successes, not about quitting. Quitters are not remembered.
Keep fighting
The grit that helped Muhammad Ali become a great boxing champion became his undoing as he continued to fight until he was nearly forty when he had already shown signs of neurological damage. The latter may have contributed to the 1984 diagnosis of Parkinson’s disease and his physical and mental decline thereafter.
Contrary to popular belief, winners quit a lot. That is how they win.
To persist and not quit should not be a default and non-negotiable single-directional path. Sometimes, reaching the goal stubbornly can become dangerous, harmful and rationally not possible where the risks have increased and the rewards are no longer attractive. Instead, we should weigh the pros and cons of quitting.
Success does not mean sticking to things; it is about picking the right thing to stick to and quitting the rest.
The opposite of a great virtue is also a great virtue.
To the summit
During the 1996 Mount Everest disaster, there were delays in reaching the summit caused by bottlenecks (ropes not setup and installed for the climb) and about 34 climbers attempting the summit. The team leaders decided to exceed the normal turnaround time of 14:00 (instead of quitting) and many summiting after 14:30. As the climb took longer and there were insufficient stores of oxygen, severe oxygen deprivation sickness compromised both the climbers’ and guides’ ability to make decisions or help others. By 15:00, snow started to fall and the light was diminishing. Eight climbers caught in a blizzard died on Mount Everest while attempting to descend from the summit. The movie, Everest (2015), documented the disaster.
Grit (continue) and quit (stop) are two sides of the same decision. Often, we make decisions without complete information and assumptions. We operate with uncertainties and probabilities; unsure of the path ahead and outcomes. As we progress, new information will reveal which serves as critical feedback to decide whether to continue as planned, change course or quit.
Silicon Valley is famous for mantras like “move fast and break things” and implementing them through strategies like “minimum viable product” (MVP). The purpose 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 is what allows companies to maximise speed, experimentation and effectiveness in highly uncertain environments. If we are moving fast, by definition, expect greater uncertainty. We are taking less time to gather and analyse information before acting. Having the option to quit allows us to walk away when we find out that the thing that we are doing is broken.
Unfortunately, the only time we can be sure that we should quit is when it is no longer a decision — when we are at the edge of the abyss or we have already stumbled into it. By then, we have no choice but to abandon the course.
Sticking to a course of action (grit) 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.
Top poker players are better at quitting than amateurs. The most obvious is that they know when to fold them. Deciding which hands are worth playing and which hands are not is the first and most consequential choice a player makes. 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.
A necessary part of succeeding in poker is to fold some hands that might have won. To be good at the game you just have to learn to live with that possibility. Playing every hand you are dealt is an easy and fast way to go broke since you would be playing too many hands that are not profitable in the long run though what you get in return for that cost is peace of mind of knowing the outcome. Even playing 50% of your hands comes at a great price. The best poker players avoid that trap.
If folding is difficult for amateurs at the beginning of the hand, it is even more difficult once a player has committed money to the pot (sunk cost fallacy). It is hard to overcome the urge to protect the money you have already bet, regardless of the likelihood that the next bet is a favourable choice.
Great players know when to walk away. When the experts are in a game, they are more likely than other players to recognise when the game conditions are not favourable or when they are not playing well that they are more likely to quit the game. Quitting a game is a decision fraught with uncertainty because it is never clear exactly why you are losing.
Are expert poker pros perfect at these decisions? No. Sometimes, they are far from perfect. But they are better at making quitting decisions than their opponents which is all you need to win.
Many decisions we make are similar to that of poker games; it involves uncertainty. Should we quit the job? Should we change the strategy? Should we abandon the project? Should we cut our losses? Should we take profits? All we have is our best assessment of an uncertain and changing landscape and the hope we have honed our quitting skills enough to walk away when conditions turn against us.
Quitting on time usually feels like quitting too early
Quit twice and 2 home runs
Story of Stewart Butterfield who cofounded Game Neverending but Flickr proved to be a more feasible project which was sold to Yahoo for $25 million a year later in 2005. He co-founded another gaming company with a game called Glitch. He quit Glitch as he felt that it would be difficult to succeed and would end up being a money pit. He turned the Glitch development team’s internal communications system into a standalone productivity tool which was later known as Slack. It went public in 2019 with a market capitalisation of $19.5 billion on its first day as a public company. In 2020, Salesforce agreed to buy Slack for cash, stock and assumption of debt in a deal valued at $27.7 billion.
A podcast worth listening: Masters of Scale with Reid Hoffman: The big pivot — Slack’s Stewart Butterfield
Quitting on time usually feel like quitting too early. The hardest time to make a quitting decision is when we are in it.
Our intuition is that quitting will slow down our progress. The reverse is true. If you walk away from something that is no longer worthwhile, that frees you up to switch to something more likely to help you achieve your goals — and you will get there faster.
When the time is objectively right to quit, nothing particularly dire will be happening right at that moment (we foresee a dire future).
Thinking in expected value helps us to figure out if the path is worth sticking to. It is not just about money. It can be measured in health, well-being, happiness, time, self-fulfilment, satisfaction in relationships, or anything else that affects us.
If you feel like the choice between persevering and walking away is a close call, quitting is likely the better choice.
In hindsight, we can see when someone has waited too long to quit, and we tend to be harsh in our judgement of those people. But when someone quits before it seems obvious to others, we mock them for quitting too early, This is the quitting bind. Our sense-making is unkind to the quitter.
By not quitting, we are missing out on the opportunity to switch to something that will create more progress toward our goals. Contrary to popular belief, quitting will get you to where you want to go faster.
Quitting decisions are expected value decisions.
Expected value helps to answer two questions:
- It tells us whether any option we are considering is going to be, on balance, positive or negative for us in the long run.
- It allows us 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.
Should I stay, or should I go?
A key finding of prospect theory is loss aversion where the emotional impact of a loss is greater than the corresponding impact of an equivalent gain. It creates a preference for options associated with a lower chance of incurring a loss. It makes us risk averse.
When we are in gains, we tend to quit too early to avoid the risk of giving those gains back; we like to quit while we are ahead.
When we are in losses, we become risk-seekers. We want to keep going, hoping we can avoid turning paper losses into realised losses (sure loss aversion). We refuse to quit and take the gamble. We like to stick when we are behind.
Quitting on time usually feels like quitting too early and the usual part is specifically when we are in the losses. Retail investors have this pattern of quitting when they are ahead and sticking when we are behind.
Even expert investors do not get their quitting decisions just right. They outperform on their buying decisions but underperform on their selling decisions. The best-quitting strategy would be to examine all the holdings, not just the ones at the tails of the portfolio and decide which were the least value going forward and sell those. That would maximise the value of the portfolio as a whole.
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.
Alex Honnold wanted to be the first person to climb El Captian (3,000 vertical feet) free solo (no ropes at all; not even safety ropes) and with a filming crew. In 2016, he climbed but he felt he could not trust his feet in Pitch 6. He climbed down. He had invested months in training and his friends have invested their time and money in the effort to film the attempt. Alex knows when to stick and when to quit. As it was the end of the season, he has to wait until next year. He successfully summitted free solo. The documentary, Free Solo (2018) won the Oscar for Best Documentary Feature — worth watching.
Escalating commitment
When we are losing, we are more likely to stick to a losing course of action and double down, committing more time, money and resources and strengthening our belief that we are on the right path. This tendency is called escalation of commitment. It is robust and universal, occurring in individuals, organisations (Sears) and governmental entities (the US for the Vietnam war and Afghanistan). We all tend to get stuck in courses of action once started, especially in the face of bad news. Escalation of commitment does not just occur in high-stake situations. It also happens when the stakes are low, demonstrating the pervasiveness of the error. As commitments keep escalating, it will make it more and more difficult to quit.
Sunk cost and fear of waste
The sunk cost effect is a cognitive illusion where people consider resources they have previously sunk into an endeavour when deciding whether to continue and spend more. The sunk cost effect causes people to stick to situations where 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 trying.
The resources you have already spent make it harder to 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 greater the sunk costs, the harder it becomes to quit.
Poker is one long game.
The mantra is a reminder that the particular hand they are playing is not the last hand they will ever play or at any particular day that they are playing is not the last day they will ever play. What matters is that they are maximising their expected value over all those days and all those hands. It is meant to help expert players overcome the sunk cost fallacy, expressed in poker as wanting to protect the money you have already invested in a single hand by not folding or not wanting to quit a game when you are in the losses.
If I were approaching this decision fresh, would I want to enter into this course of action?
It can be difficult to trick ourselves 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 does not mitigate the sunk cost effect the way you might intuitively think it would.
Monkeys and pedestals
Astro Teller, CEO of X, Google’s innovation hub uses the “monkeys-and-pedestals” as the mental model to approach problems and help you quit sooner.
To understand monkeys and pedestals, imagine that you’re trying to teach a monkey to juggle flaming torches while it stands on a pedestal in the town square. Two tasks are competing for your money, time, and attention: training the monkey and building the pedestal.
One is a possibly intractable obstacle. And the other is building the pedestal. The latter is part of the problem you know you can solve, like designing the perfect business card or logo. Building the pedestal is accumulating sunk costs that make it hard to quit even as you find out that you may not be able to train the monkey to juggle those torches. The hardest thing is training the monkey. Simply put, there is no point in building pedestals if you can’t solve for the monkey.
When faced with a complex, ambitious goal,
- identify the hard thing first;
- try to solve that as quickly as possible and
- beware of false progress.
Building pedestals creates the illusion that you are making progress towards your goal but doing the early stuff is a waste of time if the hard stuff is impossible. Advanced planning and precommitment contracts increase the chances you will quit sooner.
Tackle the monkey first, Astro Teller, Captain of Moonshots (CEO), X (formerly Google X)
The only way to get people to work on big, risky things — audacious ideas — and have them run at all the hardest parts of the problem first, is if you make that the path of least resistance for them. We work hard at X to make it safe to fail. Teams kill their ideas as soon as the evidence is on the table because they’re rewarded for it. They get applause from their peers. Hugs and high fives from their manager, me in particular. They get promoted for it. We have bonused every single person on teams that ended their projects, from teams as small as two to teams of more than 30. We believe in dreams at the moonshot factory.
But enthusiastic skepticism is not the enemy of boundless optimism. It’s optimism’s perfect partner. It unlocks the potential in every idea. We can create the future that’s in our dreams.
Extract: TED Talk – The unexpected benefit of celebrating failure | Astro Teller, 2016
Figure out the hard thing first
Try to solve that as quickly as possible
Beware of false progress
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; criteria for killing a project or changing your mind or cutting your losses. Kill criteria consist of information you learn that tells you the monkey is not trainable or that you are not sufficiently likely to reach your goal or signs that luck has gone against you. Essentially, kill criteria create a precommitment contract to quit.
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 in advance of what the signals in the market might be that would cause you to change your investment strategy.
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.
Taken together, the monkeys-and-pedestals mental model and kill criteria help us overcome our aversion to closing accounts in the losses.
- They both get you to go faster, which naturally limits the losses that you have to absorb when you quit. And the less you are down, the easier it is to walk away.
- When you set out clear kill criteria in advance and make a precommitment to walk away when you see those signals, you are more likely to follow through, even when you are losing. Anytime you can make a decision about cutting your losses in advance, you will do better at closing those mental accounts.
You own what you’ve bought and what you’ve thought: Endowment and status quo bias
Example: Andrew Wilkinson’s MetaLab’s Flow versus Asana
The endowment effect is a cognitive bias where we value something we own more than we would if we did not own it; people often demand more to give up an object than they would be willing to pay to acquire it.
We can be endowed to objects but also to our beliefs, ideas and decisions. Endowment is an obstacle to quitting because when we irrationally value things we own, we miscalculate their expected value. We might think that the company we started or the project we devised or the belief we have is worth more than it is. The effect is particularly strong if the thing you own you also built (also known as the IKEA effect).
The endowment and sunk cost effects live together in a way that amplifies the escalation of commitment. We prefer to stick with the status quo. It represents a mental account that we already have open, which has sunk costs associated with it, the time, money or effort that has already been put into the way we have been doing things. 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. We are warier of “causing” a bad outcome by acting than “letting it happen” through inaction. This phenomenon is part of omission-commission bias.
When you say, “I am just not ready to decide yet,” what you are saying is “For now, I am choosing the status quo.” We do not view the choice to stick with the status quo as a decision at all.
The hardest thing to quit is who you are: Identity and dissonance
Sears identified itself as a retailer that it divested its financial services empire when its retail business was not doing well. In the next two and half years after its announcement to divest in September 1992, it divested Allstate (raising $2b by selling 20% of its stake) and Dean Witter Discover through IPO and sold Coldwell Banker for $230m outright. Sears went bankrupt in 2018.
The financial services businesses it divested thrived. The market capitalisation of Allstate was $29.5b as of April 2023. Coldwell Banker merged with some other real estate companies and went public as Realogy Holdings in 2012 with a market capitalisation of $1.4b as of April 2023.
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 your identity is what you do, then what you do becomes hard to abandon, because it means quitting who you are.
When new information conflicts with a belief, we experience cognitive dissonance. Whether it is your actions or new and disconfirming information, when it comes to a battle between facts and changing your beliefs, the facts too often lose out.
Every time you rationalise away new information to cling to a belief, that belief becomes more tightly woven into the fabric of your identity. The act of rejecting the facts becomes circular. The more you discover conflicting information or your actions do not align with your beliefs, you are going to be even more motivated to stick to those beliefs.
How much harder it is to quit when we are worried about being judged by others. We get it in our heads that if we do not stick to our original choice, that will reflect negatively on us. We also want others to view us as consistent. We worry that if others see the inconsistency between our present and past decisions, beliefs or actions, they will judge us as being wrong, irrational, capricious and prone to mistakes. The irony is that this desire to be viewed as rational and consistent causes us to become less rational and consistent in the decisions we make. External validity increases the escalation of commitment. The tragedy of all this is that the way we imagine other people view us is often wrong. Those worries we projected onto others are just head trash we are carrying around.
The popularity of our belief is inversely correlated with your determination to fight for it no matter what (How to Change by Katy Milkman and John Beshears). The more extreme a position is, the more cognitive gymnastics we will do to defend it. The facts are more likely to persuade you away from the consensus opinion than a fringe view.
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.
Strong opinions, loosely (weakly) held
This framework, developed by technology forecaster and Stanford University professor Paul Saffo, enables us to make decisions or forecasts with incomplete information. Despite the lack of available information, you should develop a tentative hypothesis for what the decision or forecast should be. Then actively gather information that either supports or refutes the hypothesis. The important part is that if you uncover information that refutes the hypothesis, then change your hypothesis. Don’t cling to your original idea, decision, or forecast even in the face of contradictory information. In fact, actively seek the contradictory information — this provides you with data to iteratively improve the forecast, until you get to the right answer.
This is Saffo’s process:
“Allow your intuition to guide you to a conclusion, no matter how imperfect — this is the ‘strong opinion’ part. Then –and this is the ‘weakly held’ part– prove yourself wrong. Engage in creative doubt. Look for information that doesn’t fit, or indicators that pointing in an entirely different direction. Eventually your intuition will kick in and a new hypothesis will emerge out of the rubble, ready to be ruthlessly torn apart once again. You will be surprised by how quickly the sequence of faulty forecasts will deliver you to a useful result.”
Find someone who loves you but does not care about hurt feelings
Optimism causes you to overestimate both the likelihood and magnitude of success. That means that being overly optimistic will make you stick to things longer that are not worthwhile. Better to be well-calibrated.
Life is 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. A 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. They 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. Getting the most out of a quitting coach requires permission to speak the truth.
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.
Just knowing about the problem, doing a thought experiment of taking somebody else’s perspective and trying to see it from the outside, and looking in on yourself, is something you cannot do. Quitting is hard, too hard to do entirely on our own. We are riddled with lots of biases (sunk cost fallacy, endowment effect, status quo bias, loss aversion) which lead to escalation of commitment. Our identities are entwined in the things that we are doing. Our instinct is to want to protect that identity, making us stick to things even more.
Lessons from forced quitting
Be like ants: explore and exploit
While we are exploiting the opportunities now, we should keep looking for new opportunities. We will not know what may happen to the current opportunities; they may change and stop for reasons beyond us, thus, we need to look out for opportunities.
Being forced to quit forces you to start exploring new options and opportunities but you should start exploring before you are forced to. Exploration helps you to diversify your portfolio of skills, interests and opportunities.
Don’t wait to be forced to quit to start exploring alternatives
The myopia of goals
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. Grit is not always a virtue, 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.
Goals are pass-fail in nature. You either reach the finish line or you don’t and progress along the way matters very little. The finish lines are often arbitrary.
Fear of failing short makes us not want to start. We measure ourselves by whether we are short of the finish line. Don’t just measure whether you hit the goal, ask what you have achieved and learned along the way.
Set intermediate goals and prioritise goals that allow you to recognise progress along the way or acquire something valuable even if you do not reach the goal.
Inflexible goals are not a good fit for a flexible world. Our goals must be responsive to new information.
Creating more flexible goals is a way to address this. An “unless” is a powerful thing. Adding a few well-thought-out “unlesses” to our goals will help us achieve the flexibility that we are seeking, be more responsive to the changing landscape, and reduce escalation of commitment to losing causes.
With better 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.
It is a pretty rigid view of the world that defines success only as crossing the finish line. It is not just that we need to set more flexible goals. We also need to be more flexible in the way we evaluate success and failure. We should stop measuring how far we are from the finish but also give ourselves more credit for how far we are from where we started.
In general, when we quit, we fear two things:
- We have failed.
What exactly are we failing at? If you quit something that is no longer worth pursuing, that is not failure. That is a success.
Success means following a good decision process, not just crossing a finish line, especially if it is the wrong one to cross. That means appropriately following kill criteria, listening to our quitting coaches and recognising that the progress we have made along the way counts for a lot. - We have wasted our time, effort or money.
We tend to think about them in a backward-looking way. These are resources that are already spent, we cannot get them back. We need to start thinking about waste as a forward-looking problem. That means realising that spending another minute or another dollar or another but of effort on something that is no longer worthwhile is the real waste.
We need to rehabilitate the idea of quitting. Lots of hard things are worth purusing and grit is good for getting you to stick with it when it is right. But lots of hard things are not worth pursuing and the ability to walk away when it is right is also a skill worth developing.
Contrary to popular belief, winners quit alot. That is how they win.
Fallacies of “Once Bitten, Twice Shy” is about mostly about Annie Duke’s first book, How to Decide: Simple Tools for Making Better Choices.
