Quitting has a bad reputation but decision-making consultant Annie Duke argues in favour of cutting your losses to get ahead. By Jo Bennett.

On a bright but typically windy day in northern Nepal on May 6, 1996, three mountaineers, Stuart Hutchison, John Taske and Lou Kasischke, entered the mess at Mount Everest Base Camp.

They were there to join a group huddle, headed by New Zealand expedition leader Rob Hall. The wind at that time of year was always ferocious, but there was an upcoming window of calm for their summit attempt a few days later. In the climbers’ HQ, Hall drilled into his clients the importance of their agreed “turnaround time” at 1pm.

This is the specified time climbers must begin their descent off the mountain and back to camp, regardless of how close they are to the summit, to avoid hypothermia, frostbite, disorientation, exhaustion and a lack of oxygen, among countless other problems that plague climbers on descent, the deadliest section of a climb for any mountaineer.

Just after midnight on May 10, the climbers left Camp Four for their summit attempt. As they approached the Southeast Ridge in an area referred to as the “death zone”, it was 11am, and a storm was brewing on the horizon. Despite being within three hours of the world’s highest peak, having spent more than US$70,000 and countless hours in training, they quit. Within a few hours, a blizzard had engulfed the mountain, and four of those from the mess briefing earlier that week, including Hall, died, making it one of the deadliest days in Everest’s history.

In Quit: The power of knowing when to walk away, Annie Duke, an expert decision-making consultant and world-champion poker player, uses this pivotal moment faced by Hutchison, Taske and Kasischke to illustrate how quitting is a powerful decision-making tool but one with a reputation problem.

We might not associate one of the world’s best poker players with quitting but, speaking to the Listener from her home in Philadelphia, Duke says “quit” and “grit” are simply two sides of the same coin, and when employed correctly, they are both strategically potent.

“We think about the decision to quit as the decision, but we don’t think about staying as a decision. This is something called omission commission bias, or the failure to act versus acting. When we’ve already started something – say we’re already in a job or we’re in a relationship – we don’t think about it as an action to stay in it,” she says.

As a society, we really hate quitting. The heroes of our stories are all lauded for their perseverance and their ability to “stick it out”. Angela Duckworth’s lecture “Grit: The power of passion and perseverance” (later a bestselling book) is one of the most-watched TED talks of all time, and Forbes chose “resilience” as its word of the year in 2021. But, just as perseverance can sometimes show great character and strength, Duke says sticking to something past its use-by date can also earmark stubbornness and an inability to read clear signals when a situation is not working.

“Why don’t we rehabilitate the word so that people can understand it’s just as virtuous to quit when the time is right as to stick to it? We don’t need to lionise sticking through hard things. What we need to lionise is sticking to things that are worthwhile and quitting everything else.”

The recent phenomenon of “quiet quitting” went viral last year after a career coach on TikTok used the term to describe doing the bare minimum of work to get the job done, forgoing any extras or overtime. It sparked hundreds of think pieces all over the world, clearly striking a nerve in a burnt-out post-pandemic workforce. Duke says quiet quitting has nothing to do with quitting, and only serves to highlight how much we don’t like to do it.

Why do we hate quitting?

Part of our ingrained dislike of quitting is our discomfort with uncertainty, she says. If we stay put in a job or a relationship, we have a fairly good idea of how the next 12 months might look, even if it’s bad. When we quit, we cast ourselves into the unknown. She tells the story of a client who loved her job as an ER doctor and was then promoted to an upper administrative position.

The extra work was impinging on her family life and making her miserable. She was offered a job in insurance with a healthier work-life balance but was struggling to quit a job she had once loved, and worried about the risk of being unhappy in a new role. When Duke asked the doctor what the probability was that she would be happy in her current job in a year’s time, her answer was 0 per cent. When asked the probability of her happiness at her new job, it was 50:50. Rather than focus on the negatives of leaving her job, Duke asked her to look at the comparison. Is a 50 per cent chance of happiness not worth the risk?

Two cognitive issues often play out when we consider quitting. We tend to overvalue the emotional side of loss and regret, and we also get tangled up in what we have already invested. Duke points to behavioural scientist Daniel Kahneman’s term “loss aversion”. His studies revealed that, when coming to a decision, people tend to put more weight on the potential emotional impact of loss or regret, and less on the benefits they’d reap from their choice.

We can also find it harder to walk away when we consider the resources we’ve already put into our careers, relationships, or material items. Duke describes how common this is at the poker table: there’s always one player who can’t quit despite having a losing hand, because they’ve already invested too much. Economist Richard Thaler calls this the “sunk-cost fallacy” and it’s why we sometimes choose to finish a film we find boring because we’ve already paid for the ticket, or continue in an unhappy marriage.

“Once we start doing something, we start to invest in it – training time, money, effort, attention; sometimes we even say our heart and soul,” says Duke. “But also, our identity starts to become wrapped up in the thing that we’re doing. So, if we walk away, we’ll feel like we’ve lost what we’ve put in – that it will have been wasted.

“The problem with this is that waste is not a backward-looking problem, it’s a forward-looking one. The stuff that’s already been put into it, it’s gone. The question is, should I put more into it going forward? What happens is that we convince ourselves to keep going at something that isn’t worthwhile, for fear of having wasted what we already put in. This creates more waste, which then makes it harder for us to quit in the future.

“The sunk-cost effect makes us all, in ways big and small, build a track from nowhere to nowhere, refusing to quit because we don’t want to lose what we’ve already spent.”

Escalation of commitment

Duke compares this accumulation of losses to a video game she used to play with her daughter, where the protagonist is given a giant adhesive ball called a katamari – Japanese for “clump”. As the katamari rolls along the landscape, it sticks itself to whatever is in its path, at first gathering thumb tacks and coins, then eventually buildings and mountains. A similar thing happens when we refuse to quit. Studies show that when people are already in the losses, they are much more likely to escalate their commitment to their chosen course of action.

Escalation of commitment is seen in the tale of the once-giant US retail store Sears. Faced with declining retail sales, it decided to double down on its commitment to retail, despite also having a thriving insurance business. Both eventually went out of business.

The lighting company Philips, on the other hand, when faced with declining lighting sales, acknowledged its burgeoning healthcare business and pivoted to make this its main enterprise. In 2021, Philips’ net income was more than €3 billion ($5 billion).

Duke says we think quitting slows us down when in fact it does the opposite – it gets us to our chosen path faster. But this usually works best if we make the decision while the going is still good, and we still have a choice.

“Quitting on time will usually feel like quitting too early,” she writes. “The moment that quitting objectively becomes the best choice, in practice, things generally won’t look particularly grim, even though the present does contain clues that can help you figure out how the future might unfold.

“The problem is, perhaps, because of our aversion to quitting, we tend to rationalise away the clues contained in the present that would allow us to see how bad things really are.”

What makes a good quitter?

To the uninitiated, championship poker seems like a solitary game – usually six or seven players sitting individually around an oval table, strategising in silence. Duke says this may appear true, but not if you want to be any good at it. She suggests watching the players with a journal or those visually remembering their “hands”. Most pro-players will join a peer group after each round to debrief and go over challenging parts of the game.

People who are good at quitting also bring in outside help and some even call in a “quitting coach”. Ron Conway is a well-known angel investor, regarded for his expertise in investing in the most successful tech companies, from Facebook to Airbnb. But, perhaps more interestingly, he’s also particularly good at helping failing start-ups recognise when it’s time to let go before going bankrupt. This is particularly helpful in an industry where 90 per cent of ventures fail.

Conway’s favoured approach is a four-step process to identify “kill criteria”. He begins by letting the start-up founders know they should consider quitting. When they inevitably push back, he agrees that they can turn the situation around. They then sit down together and make clear definitions of what success will look like in the future, and what the deadline is to meet these markers, calling this “kill criteria”.

If the founders don’t meet the agreed success markers by a certain date, this gives them clear data that it’s time to quit.

Duke suggests the best time to nail kill criteria is before entering into an agreement but it can also be done in the middle of a project, relationship or situation. If you can work out what your non-negotiables are and what your turnaround time is – whether that’s working out the loss limit on an investment, or an emotional state in a relationship – you can give yourself a deadline, or turnaround time, and hold yourself to it. Better yet, get yourself a “quit coach”, even if that’s a friend or a partner, to help you stay accountable.

“Be wary of goals and ‘intuition’, learn expected value and don’t build pedestals,” writes Duke.

Learning how to quit

In our achievement-driven world it’s rare to hear anyone point out the dark side of setting goals. Duke says that, while they can be helpful for motivation, creating inflexible “finish lines” in a world that’s constantly changing should come with a hefty warning: “may increase commitment of escalation”.

Goals also force us into one definition of success: pass and fail. But what do we lose when we subscribe to this way of thinking? Our climbers got most of the way up Mt Everest, something most people can never physically achieve. If we only see it in binary terms such as pass-fail, we erase all the success we’ve had along the way.

Instead of thinking of our careers and lives in separate silos, it can be helpful to see any investment – whether that’s a relationship, job or house – as a portfolio of shares. “What really matters is maximising 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.

“The best quitting strategy would be to examine all your holdings, not just the ones at the tails of your portfolio, and decide which were going to generate the least value going forward and sell those. That would maximise the value of the portfolio as a whole,” she writes.

A good portfolio – like a good life – is one loaded with opportunities and experiences. To avoid getting stuck in tunnel vision or “goal myopia”, as she puts it, Duke points to the way ants work in a colony. While some ants follow the pheromone trail, others are always scouting for new food sources.

Similarly, one part of us can stay on course, but there should always be a shadow self exploring our options. Keeping our options open is also a nifty quitting hack, because knowing there is a plan B can make it feel less daunting to quit when the time is right.

One thing winning poker players and talented quitters have in common is being able to think in expected value (or EV). Winning poker players aren’t trying to win a single hand whatever it takes. They know that only some hands can win enough of the time to make them worth pursuing. They take a long-range view, making decisions based on whether playing or folding has a greater expected value overall.

In lieu of a crystal ball, EV is the best way to cast into the future. Duke suggests calculating the expected value of a decision by identifying all of the possible outcomes – both good and bad – and working out what their probability is. If you multiply the probability of each outcome by how good or bad it might be, and then add them together, it gives the expected value.

“Ultimately, where you’re going – where we’re all going – is along whatever route will have the greatest expected value throughout our lives,” she writes. “That path is going to involve a lot of quitting. Contrary to popular belief, winners quit a lot. That’s how they win.”

Juggling monkeys

There’s another quitting method she takes from the world of tech start-ups. In a nutshell, it involves imagining you have a business idea to train monkeys how to juggle flaming torches while they stand on a pedestal in a public park. Pedestals have been around since ancient times, and most people could find a way to build one using a blueprint. Finding and training a juggling monkey is the tricky bit, the intractable obstacle.

In a relationship, for example, pedestal-building might be the house you have together, or that you look nice together. Training the juggling monkey would be the part you can’t breeze over.

Perhaps that’s the emotional attraction to your partner, or that you have fundamentally opposing values. If your relationship is full of pedestal-building, but the intractable obstacle still exists, quitting is usually your best bet.

Better yet, if you start a relationship or a project and realise before you begin that it’s full of pedestal-building, you can walk away before you invest time, money and energy into a losing equation.

“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 endeavours,” she writes.

Most of the decisions we agonise over are inherently emotional. Deciding when it’s time to retire, or to sell a beloved house, can trigger an avalanche of overwhelming thoughts and feelings. Duke agrees, but notes there are ways to manage it.

“Emotion enters into pretty much every decision that we make, and it particularly gets in the way of our decisions when we’re in what Kahneman would say is ‘the thick of it’. That’s when all the fear gets recruited and fear of regret and so on.

“To make better decisions, we’d like to make them at a time when we’re going to be less emotional about it. The best quitting decisions are made in advance.”

She’s quick to point out that emotions and values are two separate things. Emotions come and go but your values should act as a north star when deciding whether to quit.

“If I’m somebody who finds joy in my work and you’re somebody who finds joy in your family, we’re going to have very different ideas of what a good job is.

“So, you should allow your values to be guiding your decisions. But that’s different from emotion, in the sense of emotion being driven by fear, for example.

“I’m cool with emotion; I just think it shouldn’t be driving decisions except inasmuch as it has to do with your values, which you can intuit by things like, ‘Does this make me happy?’”

Gut instinct

Many people would regard poker players as having a good sixth sense and a close relationship with the mystery of luck and intuition. We’re also told to listen to our “gut” when making a hard choice, so how do these fit into Duke’s equation?

“I want to be clear that there is nothing magical about your gut,” she says. “Your gut is making decisions, ‘thinking’ about the same kinds of things that your rational brain would be, just not in an explicit way and [it’s] completely exposed to bias.

“What I say about gut is, look, sometimes your gut’s right. It’s some combination of experience and the way that you apply experience to the situation you’re considering.

“So, that can lead you into some pretty good places, but it can lead you into some pretty crappy places.

“How do we avoid that? Your gut is combing over your experiences and giving some estimations of what options are better for you, but in a way where we leave it implicit. So, let’s just take all of that and make it explicit, and then we can examine it.”

She refers to a navigation system such as Google Maps: we plug in our destination and work backwards from that to decide when to leave the house. It’s important to make decisions where our choices are explicit and free of bias if we want to stay on a happy path.

The analogy of poker and life is a cliché, but for good reason.

“Poker is a game of decision-making under conditions of uncertainty, where you can’t see your opponent’s card and there’s a lot of luck involved in the way things turn out. That should sound to you like every decision that you’ve ever made,” she says with a laugh.

Champion players don’t really care about losing one single hand of poker; what matters is that they maximise their expected value over the thousands of hands they play across their lifetime.

It’s what people mean when they refer to “one long game” – a game where those who’ve mastered the art of quitting usually find themselves on top.