Five Questions to Ask Yourself Before You Quit

How to prepare yourself for the stress of transition

Posted Feb 13, 2014

Yes, the adage tells you that “winners never quit and quitters never win” but the truth is that, at one point or another in our lives, most of us will have to let go of a relationship, a job, an endeavor dear to our hearts, or a goal and move on. Transitions are a fact of life. How well we manage a given transition and the act of reinventing ourselves depends on many things—among them, habits of mind, personality, and mind-set, as my book Mastering the Art of Quitting explains in detail—but before you make a move, you need to ask yourself the following five questions. Answer them honestly and you’ll have a better idea of what this period of transition is going to feel like for you, and what problems and opportunities it will present.    

 1. Am I good at anticipating how I’ll feel and react? 

Most of us are actually pretty bad at predicting our behaviors and thoughts because the problem with tomorrow is that it hasn’t happened yet. In addition, numerous experiments show that people tend to believe that their best and most idealized selves will show up when the going gets tough. I’ve mentioned this study in another post but it’s worth repeating because it’s a dynamite example.  Psychologists Julia Woodzicka and  Marianne LaFrance asked women ages 18-21 to predict how they would react if  they found themselves being harassed by a very intrusive and rude male interviewer in his early thirties. Most of the participants were sure that they’d be proactive and take charge—telling the guy off or even walking out. But when the researchers had the same women take part in what they believed was an actual interview for a lab position under the same circumstances that had been described theoretically, they acted very differently than they’d anticipated. They were much, much meeker and accepting.

We all tend to think about the future in an over-simplified way, both in terms of our own responses and the situation itself, whether we’re anticipating dealing with bosses, spouses, friends, acquaintances, or strangers. We don’t take into account that we might feel ambivalent in the moment, or that the situation might end up being less straightforward than we anticipated.   

When you think about how you’ll feel once you’ve quit that relationship, paint a picture that includes feelings of sadness and regret, not just the joys of liberation and starting over. Ditto on that job you’re so sick of; you’ll probably feel some relief but it’s likely to be mixed in with anxiety about where you’re going next and how you’re going to get there. The bottom line is to do what you can to imagine the future in a nuanced, in-depth way; just thinking positively or being overly optimistic will actually leave you unprepared for how difficult the transition is likely to be.

2.  How conservative am I?

This question isn’t about politics but whether or not you focus on what you’ve already invested in whatever it is—your work, a relationship, an endeavor, a long-term goal—you’re thinking about quitting. Even though we all like to think of ourselves as creative risk-takers, the truth is that, as the work of Daniel Kahneman and Amos Twersky showed, human beings are universally loss-averse and far more motivated to avoid a loss than they are enticed by the possibility of gain. If you tend to think in terms of what you’ve sunk into the situation (that’s why it’s called the  “sunk-cost fallacy”), the likelihood is that you’re going to have a lot of trouble leaving it and, if you do manage to get your foot out the door, you’ve going to be stewing about what you’ve lost. Know this about yourself to begin with, and work on reframing your thoughts to focus on the possibilities inherent in the future you haven’t yet encountered.

3.  How do I define myself?

Studies show that the more central whatever it is that you’re planning to leave is to your sense of self, the greater the recovery time and uncertainty once you do quit. According to the work of psychologist Patricia Linville, the people who handle stress best and do better in times of transition are those who have more complex definitions of self; they are more buffered from negative emotional fallout when they have to quit something or are fired because they have other positive and continuing definitions of self which sustain them during times of stress.

Getting a bead on how you define yourself needs to be done first so that you can better anticipate the sense of upheaval you may experience. This profound sense of dislocation can happen even when you’ve chosen to switch paths, as the late William Bridges, author of the book Transitions, discovered after he willingly gave up his career as a college professor and could no longer answer the question “What do you do?” directly. It doesn’t matter whether the definition you’re relinquishing is professor or sales manager, stock trader or lawyer, Dan’s wife or Susan’s husband; what matters is how central it is to your sense of self. The closer what you’re leaving is to your core, the greater your sense of free fall will be.

4. How do I manage uncertainty?

Whether you are motivated by approach or avoidance is going to determine how sanguine you’re going to feel and how well you’re going to do when you’ve quit or have been fired from one thing and there’s no plan B in sight. It could equally be in the area of work or relationship.

You need to take an honest inventory of your motivations. If the arc of your career or love life has been distinguished by avoiding failure—choosing the most reliable path, or the least challenging, or the one that involves the least amount of risk—starting over is going to be harder for you than it will for someone who is comfortable with making mistakes. The work of Andrew J. Elliott and Todd M. Thrash suggests that “approach” and “avoidance” are key aspects of personality. Avoiding failure will, for example, keep you persisting at a task that is doomed to failure, as one study by Heather C. Lench and Linda J. Levin showed. After testing people for approach and avoidance motivation, the researchers gave the participants three sets of seven anagrams to solve in a timed test; the first set was unsolvable. People motivated by approach quit working on the set when they realized persistence wouldn’t pay off; those motivated to avoid failure kept going, and got both stuck and more agitated.

Try to assess yourself honestly; you’re not helping yourself by overstatement or fudging. What motivates you: Fear of failure or the possibility of success? When you hit a snag or obstacle, how flexible are you? Can you change directions or is your default always to stay the course? Take some time and look back over your past experiences and analyze what motivated you and when; you will learn a lot about yourself and how skilled you will be during a transition.

5. How do I manage stress?

The playing field isn’t level, alas, and some of us are better at coping with stress and pressure than others. Make no bones about it: Leaving one thing you know and directing your energies to the unknown future are very stressful. Psychologists have determined that there are two kinds of coping styles, one called “action-oriented” and the other “state-oriented.” These traits may explain why two people with similar goals, talents, and abilities may experience very different outcomes—with one flailing and the other successfully navigating his or her way through the inevitable twists and turns of life. If life were a simple upward trajectory, human beings wouldn’t need to be able to manage their thoughts and feelings.

Action-oriented people manage their emotions effectively, don’t get easily sidetracked, don’t rely on external cues for motivation, and are able to act decisively. If things start to so south, the action-oriented put thoughts of failure out of their minds and focus on what they can do to get their goals met and the obstacles overcome. The state-oriented need structure and deadlines to get going, are sensitive to and need external cues, tend to procrastinate, and have trouble managing negative thoughts. When things go wrong, they tend to get swept up in rumination and second-guessing. 

There are ways of improving how you manage your thoughts and emotions but knowing whether you fall into one category or the other will help you prepare for the inevitable stress and strains of transition. Keep in mind that all of life is just a series of transitions. And that, as Lao Tzu put it, “The journey of a thousand miles begins with a single step.”

Copyright © 2014  Peg Streep


READ MY NEW BOOK AND LEARN MORE: Mastering the Art of Quitting: Why It Matters in Life, Love, and Work

Kahneman, Daniel and Amos Twersky, “Prospect Theory: An Analysis of Decision Under Risk,” Econometrica. 45, no. 1 (March, 1979), 263-291.

Woodzicka, Julia and Marianne La France, “Real versus Imagined Gender Harassment,” Journal of Social Issues, 57, no.1 (2001):15-39.

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

Bridges, William.  Transitions: Making Sense of Life’s Changes. New York: Da Capo Press, 2004.

Eliott, Andrew and Todd M. Thrash, “ Approach and Avoidance Temperament as Basic Dimensions of Personality,” Journal of Personality, 78, no.2 (June 2010): 865-906.

Lench, Heather C. and Linda J. Levin, “Goals and Responses to Failure: Knowing When to Hold Them and When to Fold Them, “ Motivation and Emotion, 32 (2008), 129-140.

Jostmann, Nils B. and Sander l. Koole, “ When Persistence is Futile: A Functional Analysis of Action Orientation and Goal Disengagement,” in The Psychology of Goals, edited by Gordon B. Moskowitz and Heidi Grant. (New York: Guildford Press, 2009), 337-366.