How to Know When to Quit

It’s a realization that can come with many signals. For me, it was a persistent sensation of vertigo — as though I were falling while standing still — at a job I was thinking of leaving. For many of us, it’s an ineffable emotion around a relationship, a habit, or a situation that might not be giving us what we need.

Sometimes it’s someone close to us, telling us what they think we need to hear: It’s time to quit. And maybe we resolve to do just that: leave the job, end the romance, pull back from a pattern that doesn’t feel right.

But then, as soon as the next day, the doubts start to build. Is this the right thing to do? What if things get worse? Am I thinking clearly?

It often turns out that quitting is one of the hardest things we can do.

“There are a lot of reasons we stick around when we shouldn’t,” says ­Annie Duke, author of Quit: The Power of Knowing When to Walk Away. “We’ve sunk costs and resources into the situation we don’t want to lose. There’s endowment, which is when we value something like a job or an idea more highly than one we don’t possess. And there’s status-quo bias, when we feel an aversion to the possible loss or regret from switching more keenly” than the discomfort of the current situation.

In other words, the deck can be stacked against us when we try to weigh what we have today versus how things might be if we were to make a change. It’s a tendency reinforced by our language and our social norms: “Hanging in there” and “sticking with it” are positive values, while “being a quitter” is equated with a lack of willpower.

“The actual word ‘quitting’ is such a problem, with all the baggage it carries,” says executive coach Marilee Adams, PhD, author of Change Your Questions, Change Your Life (see “Lines of Inquiry” for more on Adams’s work). “Instead, in retrospect, it can be a decision to leave something for a positive reason. The word ‘quitting’ implies there’s something wrong happening, and that may not actually be true.”

And here’s the crucial point: Quitting is hard, it’s scary, and it’s not always the answer. But sometimes it can be a constructive act that leads to greater personal growth and opportunity. The key lies in how well we’re able to assess our circumstances, and whether we’re able to be honest with ourselves about what’s happening.

Balancing Values With Change

In her research on quitting, Duke has concluded that we often take too long to make the decision. “The problem is that we don’t quit until we’re certain that we have to,” says the former professional poker player. “And by then, we’re past the point at which we should have.”

Duke cites a story about a 1996 Mount Everest expedition during which climbers perished long after they sensibly should have turned back. We can all recall times in our own lives, and those of friends and loved ones, when the value of “stay the course” outlived its usefulness.

“Let’s say somebody is running a marathon, and they’re a very good runner,” Adams notes. “But now they’re injured. If they keep going, they might even win the race, but they might suffer permanent damage. Is it quitting if they stop, or is it taking a long-term view of their health?”

A good first step is starting to see the world in terms of opportunities rather than possible calamities. This is the kind of visualization that Duke frames as counter to our fallback nature.

“We have an aversion to uncertainty, so we stick with something we’re super unhappy with because we prefer it to the unknown. Once we’re set on a path, we tend not to see what else is available.”

“We have an aversion to uncertainty, so we stick with something we’re super unhappy with because we prefer it to the unknown,” she explains. “Once we’re set on a path, we tend not to see what else is available.”

Sometimes our loyalties — to a person, an idea, or an institution — can cloud our ability to recognize other possibilities around us. But we can train ourselves to acknowledge that we can be open to other opportunities without betraying our current colleagues or denigrating the status quo. Someone might love their job, for instance, but still stay in touch with employment recruiters, Duke explains.

It’s also important to distinguish between momentary hardship and a more structural need for change. Making the choice to quit will be more rewarding if it’s based on a clear-eyed assessment of our own motivations.

In an episode of the We Can Do Hard Things podcast, cohost Amanda Doyle identifies the heart of the question: “Do I want to become free of this thing because this thing is hard for me?” she asks. “Or do I want to become free of this thing because this thing is not for me, it is wrong for me?”

Once we’ve understood that we need a change, these are the tough questions. It’s also worth remembering that humans tend to think in binaries: good or bad, right or wrong. But gray areas can be fertile ground for personal growth.

Often, we avoid making a change because we fear we might become unhappier as a result, rather than changing direction with the understanding that — whatever happens — it simply represents the continuing unfolding of possibility and opportunities for transformation.

To help clarify your thinking, Adams says, ask yourself a few crucial questions about your values and how they might have changed over time:

“What were my goals when I started this job, or this marriage, and how did my goals at that time reflect my values and my desires?” she says. “Now, down the road into the present time, what are my goals now? And how do they reflect my current values and ­desires? Given who I am now, and what I know now, would I make the same choice? If yes, why? And if no, why?”

When we’re able to take stock based on our values and self-awareness, we can make a conscious choice to stay where we are for the right reasons or to make a positive change from a position of strength. In the same podcast, Doyle offers a fascinating fact: “The Latin origin of the word ‘quit’ is quietus,” she points out. “And it actually means ‘to set free.’”

To sustain what gives us strength and to surrender what doesn’t: This seems like a good definition of freedom.

Find a Quitting Coach

Annie Duke, author of Quit: The Power of Knowing When to Walk Away, describes that moment when you’re talking to a friend who seems to need a change. “People will say, ‘I’m thinking about changing jobs.’ But you see them a few weeks later, and they still haven’t made a decision.”

Then she adds a twist. “Here’s the key to that story: You do it, too. That’s what we all need to realize. We can see it so clearly in other people, but [we] don’t think that we might be doing the exact same thing.”

Duke’s strategy: Find a “quitting coach,” someone you trust to offer unfiltered input. “You need someone to tell you when what you’re doing is no longer worthwhile. Sometimes our friends have been looking at us and thinking it already.”

This can be reciprocal. The two of you can make an agreement, whether it’s in your personal lives or a business setting, to give honest opinions with the understanding that hurt feelings will be left out of the mix.

If we’re going to make a big change, an outside perspective can be the sort of handhold that makes it possible.

This article originally appeared as “Quitting time” in the July/August 2022 issue of Experience Life.