The gist of this book about career transitions is that you won’t find your new career by thinking hard about it, or by listing out your strengths and playing a matching game against existing industries and roles. Rather, successful career transitions (i.e., the ones that stick) emerge from a process of exploration and experimentation, a messy and non-linear experience in which new identities are tried on and adjusted while the old ones are alternately clung to and rejected. The book suffers from what I’ll call the HBR lens—that is, all the examples concern very affluent and privileged people, and none of the common systemic barriers (sexism, racism, ageism, etc.) are raised. That said, I think the case studies remain very instructive, and the strategic mindset here aligns with what I’ve observed of people from very different backgrounds who have made it through big transitions themselves. Transitions are iterative, experimental, wild, chaotic, opportunistic, joyful, and anxious periods, which, when observed in the midst of their unfolding, often seem like they are going nowhere; but that disorder has a point, in that it makes space for the trial and error necessary to learn where it is you want to go, and what it will mean for you when you get there.
In Working Identity, Herminia Ibarra argues that the process of transitioning from one career to another is both usually and necessarily messy and disordered, more like playing than like planning. During a transition, it can seem like nothing is happening, or too much is happening, or somehow both simultaneously. Often someone in the middle of a transition experiences a lot of pressure, both internally and from kin, to stop fucking around and get on with it. But that may be profoundly the wrong advice. Writes Ibarra:
We oscillate between “holding on” and “letting go,” between our desire to rigidly clutch the past and the impulse to rush exuberantly into the future. Over a period of months or even years, we move back and forth between these poles as we explore new roles and possibilities. Rather than being a sign of one’s lack of readiness, this moving back and forth is in fact the key to successful transitioning. It is how we stave off premature closure until we have fully explored alternatives.Ibarra, Working Identity, page 54
I think this point about “premature closure” is worth attending to. We have such a bias towards efficiency, towards optimization, that keeping open a messy process seems like an anti-pattern. But you can’t optimize exploration; you have to stay open to learning something unexpected, to turning around when you hit a dead end, to heading down a path you didn’t even know was there until you came upon it. That’s a space that is often deeply uncomfortable and anxiety-producing, and it can be maddening to live through it. But it’s the only way.