The Map We Handed Them Doesn't Cover the Territory

Something I notice in conversations with senior professionals, more often than people tend to admit, is a particular kind of anxiety about their children's careers. Not the ordinary parental worry. Something with more edge to it. Almost a shame.

Their son is 24 and still working out what he wants to do. Their daughter took a role that doesn't fit neatly on a path to anywhere obvious. They've changed direction twice in three years, and the parent sitting across from me can't quite hide how uncomfortable that makes them feel.

What I find interesting is who these parents are. They are, almost without exception, experienced senior professionals. People who have built real careers. And a significant number of them have, at some point, found themselves in transition, trying to work out what they actually want next. They followed the map. They're not sure it took them somewhere they'd have chosen, if they'd been asked at the start.

And yet. They want the same map for their children.

The advice most of us grew up with was specific and confident. Don't move too often or you'll look like a job-hopper. Get into a good company and build depth. Stay long enough to be taken seriously. The logic was coherent for a world where organisations were stable enough to reward that kind of loyalty, and where a career in one sector, or one company, could last a working lifetime.

That world has largely gone.

The people who built careers under those rules know this better than anyone. They lived through the restructures, the pivots, the roles that disappeared mid-tenure. Many of them stayed anyway, because that's what you did, and because the alternative felt risky. Some of them thrived. Others are sitting in my office at 50 asking a question they probably should have asked at 35: what do I actually want to do?

I am not suggesting that the younger generation has it figured out. They don't, and pretending otherwise doesn't help them. What I am saying is that some of what looks like a failure to commit is something more useful than that. It is the process of finding out what works, through doing things rather than deciding in the abstract.

Self-knowledge is not something you arrive with. You build it through experience. You take a role and discover you are good at something you hadn't considered. You work for a manager whose style doesn't suit you, and you learn something precise about the kind of leadership environment where you do your best work. You move and find the new environment doesn't suit you, and that is not a failure. It is information. Expensive information, maybe, but real.

The people I work with who navigate career transition well tend to share one quality. They have a clear account of what they've learned from each thing they've done, including the things that didn't work. They are not embarrassed by the detours. They understand them.

The people who struggle are often the ones who stayed on a path because leaving it felt wrong, and who now find, somewhere in their fifties, that they can't quite explain why they made the choices they made, other than that they seemed like the right ones at the time.

A career that runs from 22 to 65 is forty-three years. The decisions made in the first five are not the whole story. They are barely the opening.

So when parents tell me, with that particular uncomfortable energy, that their child doesn't seem to be going in the right direction, I want to ask which direction they mean. And whether the path they have in mind is one they'd walk again themselves, knowing what they know now.

That's usually where the conversation gets interesting.