If you spend your life waiting for the next eruption of anger from your mum, or your dad announcing another rule that you’d broken, you end up not knowing what to do: the uncertainty of what’s going to happen next fills you with fear. So I was incredibly insecure, scared of my own shadow. On top of that, I thought I was somehow responsible for the state of my parents’ marriage, because a lot of their rows would be about me. My father would tell me off, my mother would intervene, and there would be a huge argument about how I was being brought up. It didn’t make me feel very good about myself, which manifested in a lack of confidence in my appearance that lasted well into adulthood. For years and years, I couldn’t bear to look at myself in the mirror. I really hated what I saw: I was too fat, I was too short, my face just looked weird, my hair would never do what I wanted it to, including not prematurely fall out. The other lasting effect was a fear of confrontation. That went on for decades. I stayed in bad business relationships and bad personal relationships because I didn’t want to rock the boat.

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.

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.

One of the useful—and difficult—things about experiments is that they sometimes tell us that we were wrong, that we actually don’t love or can’t make a living from what we thought we wanted to do. That’s when it comes time to close doors. It’s harder than you might think.

Unexpected events often provoke insights that allow progress toward a solution after a period of being stuck. They allow us to reframe our stories. For John, the revelation was not that he should become a writer. It was that he could not live in two worlds and that he would have to come to terms with letting go of the old identity that was slowing him down. John had never stopped to challenge his basic assumption that he could maintain his old social and financial status while moving into a realm that would allow him greater artistic expression.