The morning after my husband asked me that question, I had a sort of epiphany. I realized that I already had enough money to take a risk. What was holding me back was not financial security; it was plain fear that I might not be good at what I thought I’d be happy doing. I concluded that I might as well change now because I was dying to do something else and it would not get any easier with time. The next day—a year and a half ago—I quit.

We like to think that we can leap directly from a desire for change to a single insight or decision that will complete our reinvention. As a result, we remain naive about the long, essential testing period when our actions transform (or fail to transform) fuzzy, undefined possibilities into concrete choices we can evaluate.

Endings are tougher and take longer than we think. No matter how unhappy we may be in a job, most of us continue to revisit the possibility of making it work because the present role is necessarily tied to a possible self—an image, outdated though it may be, of whom we once wanted to become. June’s academic identity, for example, kept reasserting itself throughout the entire transition period, even after she had handed in her resignation. “My department was family, a dysfunctional one,” June says, “but one I was an intimate part of, one I joined at age seventeen when I went to college.” For her, leaving academia meant not just giving up a long-term career objective but also an image of who she should become that important people in her life, including her mentor, harbored. The emotions she felt when she found the pile of draft articles that would have assured her professorial future show just how much giving up a possible self—even one that has become a burden or lost its appeal—marks a real loss.

A working identity, however, is not merely what we do and with whom; it lies also in the unfolding story of our lives. Throughout a career transition, the narratives we craft to describe why we are changing (and what remains the same) also help us try on possibilities. June’s attempts at explaining herself—why she wanted to make such a seemingly “crazy” career change, why a potential employer should take a chance on her, why she was attracted to a company she had never heard of a day before—were at first provisional, sometimes clumsy ways of redefining herself. But each time she wrote a cover letter, went through an interview, or updated friends and family on her progress, she better defined what was exciting to her, and in each public declaration of her intent to change careers, she committed herself further.

Experience reveals barriers to change that we can rarely identify at the outset of a career transition, no matter how much self-reflection we do. What we see as feasible and appealing is always constrained by the limitations of our experience.