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8 Ways You Can Tell That It's the Right Time to Quit

Expert advice for making tough decisions about relationships, jobs, and dreams.

Key points

  • Despite cultural mantras that "quitters never win," quitting something that is no longer serving you is often a healthy decision.
  • Cognitive barriers like the sunk cost fallacy, intermittent reinforcement, and others can keep people stuck in unhealthy jobs or relationships.
  • When you do decide to quit, mentally preparing for strong emotions and the upcoming transition can help you cope with the change.
Peter Bernick/Shutterstock

It will surprise no one that the “right time” question is the one every interviewer always asks me about Mastering the Art of Quitting. Imagine how easy and unstressed life and decision-making would be if there were a foolproof formula, a one-size-fits-all strategy for knowing absolutely and positively when to bail on something—a relationship, a job, a goal, a venture, a life path. You’d be able to put an end to almost all angst, 4 a.m. pacing, and the endless discussions with yourself and trusted others, and light out for the territories, to borrow a phrase from Mark Twain.

I’m always sorry to disappoint, but there is no magic answer. There is, alas, only one person who can decide with any certainty when the “right” time to quit is at hand—and that's you. No waffling or weaseling; you need to know as much as you can about yourself to make the best decision.

But here is a bit of good news: Figuring out the right time can be made easier by considering the following, all drawn from research. Use these to troubleshoot your thoughts and behaviors:

  • Your brain is the biggest obstacle. I know you’ve been raised on a steady diet of lessons on grit and perseverance, but the truth is that the culture is really preaching to the choir. Yes, there are lazy people, slackers, and folks who don’t step up, but generally, human beings are hardwired to hang in, not to leave or quit. All those adages—like “Winners never quit, and quitters never win”—aren’t really necessary. What’s hard for human beings is letting go. We are, as the Nobel Prize-winning work of Amos Tversky and Daniel Kahneman famously showed, a conservative and loss-aversive bunch.
  • How you think provides the super-glue that keeps you stuck. You can thank our ancient forebears because there wasn’t an evolutionary advantage to have the Paleolithic hunter crawl into his cave if he didn’t bag the caribou or to give up if he failed to ford a raging river the first time. Many of our habits of mind derive from a time in human history when the challenges of life were largely physical and perseverance tended to pay off. Even though that was then and this is now, our brains simply haven’t caught up.

Once you’ve focused on the fact that you’re much more likely to stay long past the expiration date than you are to leave the party too early, you need to take a close look at the habits of mind that are blurring your vision and making you think you should wait just a little bit longer and see how things turn out.

Here’s a list of some of the most common biases in thought that keep us stuck:

1. You’re focused on the time and energy you’ve already invested.

Its fancy name is the sunk cost fallacy, and it’s universal. You start thinking about leaving a relationship or a job, and all you can think of is the time you’ve already put into it. Of course, this isn’t rational thinking: if the relationship no longer makes you happy, or going to work fills you with dread, staying even longer won’t help you cope with the time you now consider wasted or lost. But people do it anyway, all the time. This fallacy has you focused on time already spent—which is by definition irretrievable—and keeps you from imagining where you might find yourself in the future.

2. Your eyes are trained on positive cues.

A combination of biases—being overly optimistic and loss averse—make for a heady cocktail that, combined with intermittent reinforcement, act as the granddaddy of all super-glues. If the words “intermittent reinforcement” vaguely remind you of Psych 101, you’re spot on; B.F. Skinner discovered that when rats, pushing a lever for food, were rewarded some of the time (as opposed to on all occasions or none), they would try even harder for longer. Well, fellow rats, this is precisely the predicament we find ourselves in. The one day the boss says something that, for once, doesn’t cut you off at the knees, or the time your beloved actually does something you’ve been begging him or her to do, suddenly you’re no longer heading for the door but settling in for a spell and totally sure that everything will work out. Uh-huh. It’s another blob of adhesive that makes us think the time to bail isn’t now and keeps us hanging on.

3. Being thwarted makes the heart grow fonder.

Remember the Greek myth about Tantalus, from which our word “tantalizing” derives? The gods punished him by having him stand under a tree, its fruit just out of reach, and close to flowing waters which receded every time he tried to quench his thirst. Well, it turns out that when we realize we’re likely to fail at a relationship or job or other endeavor, we begin to see that goal as even more valuable than it was initially. Yes, it does explain all those torch songs—such as “The Man/Gal That Got Away”—but it’s yet another habit of mind that keeps our feet (and our minds) firmly anchored to the ground we’re standing on.

4. FOMO—and the fear of making a mistake.

FOMO, or fear of missing out, isn’t a scientific term, but it's handy here.

Some people are naturally better at quitting and more confident about when to let go than others so you’ll have to spend some time figuring out which camp you fall into. People who are largely motivated by challenges gear up to meet them and do relatively little second-guessing; this group is what the work of Andrew Elliot and Todd Thrash deems to be motivated by “approach” goals and temperament. These people are better at getting unstuck and moving forward. On the other hand, there are people who look at the landscape of life and largely see a series of mistakes to be avoided; they are motivated by “avoidance” goals. They’re not comfortable taking risks, are even more conservative in terms of loss, and are motivated by fear of failure. Keep in mind that we’re all motivated by approach and avoidance at various times; think about how you would generally classify yourself and be as honest as you can.

One study by Heather C. Lench and Linda J. Levine had participants self-report on whether they were approach- or avoidance-oriented, and then set them to the task of solving three sets of seven anagrams. Unbeknownst to the participants, the first anagram was unsolvable, and since the test was timed and you had to do the anagrams in order, giving up on that first anagram was crucial to success. Well, guess what? As the researchers hypothesized, the approach-oriented gave up and moved on, while the avoidance-oriented kept trying to solve the thing and got more agitated, too. A second experiment using the same scenario (the unsolvable anagram) confirmed the findings. Rather than relying on self-report, the goal was framed as “attain success” for half the group and as “avoid failure” for the other half. Those primed to avoid failure kept trying to solve that unsolvable anagram; instructed not to fail, they were so focused on not failing that they couldn’t recognize the thing couldn’t be solved. Ironic, no?

Sometimes, cultural wisdom aside, grit just results in banging your head against the wall.

4 Things You Should Do If You Want to Quit

So, if you’ve successfully tackled your habits of mind to the ground, what’s next on the agenda to ensure the timing and execution are optimal? Try the following:

1. Get a grip on your emotions.

The worst possible scenario is that you stay long enough that the situation—whether it’s in the area of relationship or work—reduces you to a quivering mass of reactivity. Don’t set yourself up for a “straw-that-broke-the-camel’s-back” moment because when you storm out the door, not only will it slam behind you (burned bridges, anyone?) but you will be taking a load of emotional and cognitive baggage with you. Many people end up trading one kind of stuck for another when they quit in this way. They are the people who end up wrecking their interviews for a new job by blurting out bad things about their former employers or going out on a first date and launching into lengthy diatribes about their ex-lovers or spouses. You really don’t want to end up there.

2. Motivate yourself.

Remember that quitting isn’t an end in and of itself; it’s a pathway to a new destination. Disengaging from a goal is a process that ends with engaging with a new one. Work on strengthening your motivation to get to that new place even as you consider letting go of the old one. (That’s another reason the “I’m outta here” style of quitting is so counter-productive; you’re slamming one door without a clue to where you might be going next.)

3. Plan and use “if/then” thinking.

The best way to get your brain off cruise control and stop those automatic biases is to make a plan that not only sets your new goal but anticipates possible setbacks and pitfalls along the way. Write your plan down—the research shows that it will help you articulate your thoughts with greater clarity. Map out the possible scenarios, and think them through. Mixing in a bit of realism and perhaps even pessimism to tamp down our tendency to overstate our abilities and to be overly optimistic is also a good idea.

4. Prepare for the stress of transition.

Just as there are those who are better at letting go than others, some are more skilled and confident managing the inevitable turbulence of major change, Again, self-knowledge is an important part of your transition tool kit; the best defense is knowing ahead of time how you’re likely to react. Research by Patricia Linville showed that people with a more complex sense of self and a more varied group of activities that defined their sense of self did better in times of transition and stress and recovered from setbacks more easily than those who primarily defined themselves by a single activity. If what you are thinking of quitting is central to your self-definition, you need to be prepared. For example, if your career and the rewards you’ve reaped from it are central to your sense of self, change will be harder than it would be for someone who is not mainly invested in that arena and defines him or herself by numerous roles in addition: parent, friend, community leader, gardener, golfer, etc.

Despite the cultural mantra, quitting an endeavor or relationship that is no longer making you happy, is failing and cannot be fixed, or no longer meets your needs is a healthy response as long as it’s the first step toward a new goal and destination.

Copyright © Peg Streep 2015.

Visit me on Facebook or read my book, Quitting: Why We Fear It and Why We Shouldn't—in Life, Love, and Work.

LinkedIn image: Deflector Image/Shutterstock


Kahneman, Daniel and Amos Tversky,”Prospect Theory: An Analysis of Decision Under Risk,” Econometrica (march, 1979), 47, no.2, 263-291.

Samuelson, William and Richard Zeckhauser, “The Status Quo Bias in Decision-Making,” Journal of Risk and Uncertainty (1986) 1, 7-57.

Jostman, Nils and Sander Koole, “When Persistence is Futile” in The Psychology of Goals, ed. Gordon Moskowitz and Heidi Grant (New York: Guilford Press, 2009), 337-366.

Eliot, Andrew and Todd Thrash, “Approach and Avoidance as Basic Dimensions of Personality,” Journal of Personality (June 2010), 78, no.3, 865-906.

Lench, Heather and Linda Levine, “Goals and Responses to Failure: Knowing When to Hold Them and When to Fold Them,” Motivation and Emotion, (2008),32, 127- 140.

Gollwitzer, Peter Heinz Heckhauser, and Heike Katajczak, “From Weighing to Willing: Approaching a Change Decision through Pre- or Post Decision Mentation,” Organizational Behavior and Human Decision Processes (1990).45, 44-65.

Linville, Patricia W, “Self-Complexity and Affective Extremity: Don’t Put All Your Cognitive Eggs in One Basket,” Social Cognition (1985), 4, no.1, 94-120.