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.