Should I stay or stay go? The power of knowing when to walk away

16 January, 2023

Grit isn’t always the best answer. Sometimes quitting at the right time can lead to success.

You gotta know when to hold ‘em, know when to fold ‘em, know when to walk away, and know when to run”, Kenny Rogers in the Gambler

A recent episode on the new season of Shark Tank India captured an unusual moment of vulnerability. Ganesh Balakrishnan, the co-founder of Flatheads Shoes and someone who I have known and admired for many years, opened his heart on national television and talked about the struggles faced by his venture. He got some tough feedback from the sharks. While he had come on the platform to raise funds, the conversation with the sharks gave him a different perspective and in spite of getting an offer, he decided to walk away. His courage, honesty and humility won the hearts of millions and sparked an outpouring of support on social media.

When Ganesh voiced his thoughts about quitting, it got me thinking. Quitting is usually viewed as something negative, but there are times when it might be exactly the right approach. So, this week, my message focuses on the power of knowing when to walk away. How to know when to stick and persevere on something? Or when to quit? And what are some steps we can take to quit in a healthy, constructive way?

Traditionally, the idea of quitting has been seen as defeatist. Ideas like “winners never quit and quitters never win” or “it’s always too early to quit” are deeply ingrained in most of us. Conversely, we tend to valorise those who persist until the end, even when it’s irrational, counterproductive or downright dangerous. Case in point: athletes who continue to play despite being seriously injured, thus risking their future careers, are often celebrated as heroes.

My deep-dive on this subject led me to an insightful book – Quit: The Power of Knowing When to Walk Away. Written by professional poker player and decision scientist Annie Duke, this book asserts that, in certain situations, relentlessly sticking to something can actually hold us back. This applies across various dimensions of life, from jobs to relationships. As Duke explains:

In professional poker – my former field – knowing when to quit is a survival skill that separates elite players from the rest of the pack. Yet, despite the obvious virtues of folding a bad hand, in most areas of life human beings tend to extol perseverance… But is grit a virtue when we stay too long in bad relationships, bad jobs, and bad careers?

There are times when quitting could be the better course of action. Stepping away from something that isn’t working can allow you to find something that does. It can free up your time and resources, and enable you to move in a direction you find more worthwhile. Duke sums it well:

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

It’s important to remember that the goals we set at the start of any journey are fixed entities. They don’t take into account our learnings along the way, or new information that might surface at a later time. This means we sometimes end up working towards objectives that no longer serve us – or may even be detrimental to us.

Why do we stay on in such situations? There are several possible answers. Firstly, unhappiness can have a paralyzing effect. It can feel easier to stay put than to take the huge step of leaving. Then there is the fear that quitting will undermine your reputation and derail your trajectory. People in toxic workplaces, for example, often feel like they have no option but to stay.

Cognitive biases also play a key role. For instance, the status quo bias: when comparing two options, people overwhelmingly stick with the option representing the status quo, even when it is clearly worse than the option representing change. There is also the sunk-cost fallacy, which essentially translates as: “quitting would mean a waste of all the time and effort I’ve put into this, so I might as well continue”. Finally, there is the endowment effect: when we “own” something, we tend to ascribe greater value to it, often irrationally. People tend to dig their heels into a losing position because it has become core to their identity.

In an interview with The New York Times, Duke sums up her perspective on the usefulness of quitting: 

Anytime that you decide to start something, you’re making that decision under conditions of uncertainty… What this means is that after you start something, you’re going to discover new information. That information can be about whether you’re happy. It could also be information about your own changing values: “I thought I wanted this, but now I realize that I want this other thing.” 

The option to quit is what allows you to do something about it.

How can you tell when it’s truly time to move on? Here are five signs to look out for:

1. Lack of joy or fulfilment.

Everyone has bad days and challenging periods – that’s part of the deal. The important thing to ask yourself is: How do I feel about the bigger picture? Am I passionate about what I am doing? Does it engage me and fulfil me? If you don’t have an inspiring vision of the future with what you are in, it could be a sign that you need to make a change.

2. Consistently failing to achieve targets could point to one of three underlying issues. One, you simply don’t enjoy your work and are stagnating. Two, there is a mismatch between your role and your skills. Three, you’re overwhelmed and lack the support you need. If the situation doesn’t improve despite your efforts, then moving on could be the right decision.

3. Lack of appreciation.

Are you feeling under-valued? Are you getting excluded or not being given the right opportunities? Do you feel that you are not being respected enough? If so, you might not be set up to succeed.

4. Negative changes in self.

Being in the wrong setting can change you for the worse. Some people become irritable and quick-tempered, others turn self-centred, yet others might find themselves gossiping and complaining like never before. If you think that your behaviour has undergone a negative change due to your circumstances, it could be a sign that something needs to change.

5. Frequent thoughts of quitting.

If you find yourself repeatedly thinking about an exit, that’s a pretty strong indicator. If you’re persuading yourself to stick it out for a few more years, do consider the opportunity cost: could that time be better spent pursuing an alternative path?

Quitting is a life choice that we should approach thoughtfully and systematically. Here are seven suggestions to help you know when to quit – and to do so gracefully:

1. Thinking in Expected Value.

For the stick versus quit decision, you need to make an educated guess on the probability that the outcome will be favourable and the probability that the outcome will be bad. What you need to do is to identify the range of possible reasonable outcomes. Duke advocates thinking in expected value:

The first step is to ask, ‘Does the course of action I am considering (either a new course of action or continuing what you’re already doing) have a positive expected value’? The second step is to compare the 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 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 that the thing I’m currently doing’?

Obviously, this kind of mental travel is hard to do, since we don’t have all the facts, but it is worth trying to make a reasonable guess.

2. Set kill criteria.

It can be hard to think clearly and make good decisions when we’re fully immersed in a situation. Which is why Duke suggests setting “kill criteria” when you start a new journey, be it a job or some other pursuit. Ask yourself: what are the signals that would tell me it’s time to quit? Create very clear definitions for yourself. E.g., “If I find myself unhappy at work for over six months, I will walk away” or “If my doctor advises me to cease training due to injury, I will stop”. These will serve as valuable reminders down the road.

3. Get a quitting coach.

Consider asking a close friend or mentor to serve as your “quitting coach”. Duke advises choosing someone who has your long-term best interests at heart and whose judgment you trust. Explicitly give this person the freedom to tell you when they think you’re stuck in a bad situation – even if it hurts your feelings.

4. Beat the bias.

One way to undercut cognitive biases like sunk-cost fallacy is to ask yourself: “Knowing what I know now, would I take this job if it was offered to me today?” Essentially, the idea is to ask yourself to approach the decision afresh – without the weight of time and effort already invested.

5. Understand the risks.

Leaving something in the heat of the moment can be costly. Before you quit, assess all the downsides – professional, financial, reputational and emotional – and make your peace with them. Do keep in mind that if you quit too quickly at work, too often, companies will start seeing you as a serial job-hopper – making you an undesirable hire.

6. Look to the future.

It isn’t always necessary to know exactly what you want to do next before quitting (depending, of course, on your financial and personal circumstances). However, it’s certainly wise to have a rough idea of your future plans. What excites you? What do you want to explore? It’s easier to leave when you know what you’re moving towards.

7. Quit well.

There’s quitting – and then there’s quitting, complete with drama, fireworks and burned bridges. The latter is definitely not how you want to leave: it reflects poorly on you and can blemish your credibility. Try to exit in a dignified manner.

Quitting isn’t always a negative action. Don’t view it as a failure. In fact, in certain situations, it can be the braver, more empowering choice. Developing a thoughtful approach to walking away can help you cut your losses. Quitting at the right time in fact can help you win.

P.S. If you are interested in learning more on this topic, I recommend that you pick up the book “Quit: The Power of Knowing When to Walk Away”, by Annie Duke


Join the 8AM conversation