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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to revisit the possibility of making it work because the present role is necessarily tied to a possible self—an image, outdated though it may be, of whom we once wanted to become.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.