Planning your exit, or evolution: coaching for retirement or reinvention

The conversations I'm having in November tend to be different from the rest of the year. The light is shorter. The energy is starting to turn inward. And clients in their late fifties and sixties — and increasingly, in their forties — are asking a version of the same question: am I planning to leave this, or am I planning to evolve into the next thing?

The two are not the same. And mistaking one for the other is one of the most common, most quietly painful mistakes I see.

Career reinvention isn't always a leap

The model in our heads — encouraged by every career-change book and most LinkedIn posts — is that you exit Career A and arrive in Career B. There's a moment of leaving and a moment of arriving, and somewhere in between, a brave decision.

Real career reinvention rarely looks like that. It's more often a slow sideways drift — a project here, a board role there, a piece of writing, a non-executive position, a mentoring relationship that gradually becomes a practice. The leap, when it appears, is usually the formalisation of a transition that already happened.

Three honest pictures of 'exit'

The clean retirement. Some people genuinely want to stop. The work has been a long, satisfying chapter and they're ready for the next one to be about something else entirely. Coaching for this group is mostly about giving themselves permission, and avoiding the regret-shaped trap of staying because they don't know what else to be.

The reinvention disguised as exit. Most common in my practice. People say I'm thinking about retiring when what they actually mean is I'm exhausted by this version of the work and don't yet know what the next version looks like. Career reinvention coaching, here, is largely about untangling the two.

The evolution that doesn't need a leap. Sometimes the answer is to stay, but renegotiate. Less of one thing, more of another, slightly different terms. Surprisingly often, the people you're working with are willing to have that conversation — they were just waiting for you to start it.

A question worth living with

What would I most regret not having tried, by the time I'm seventy-five? It's a slow question. Don't rush the answer. The career transitioners I see do this well are the ones who let it sit for a few weeks before doing anything with it.

If you're at a turning point and want a calm hour to think it through with someone, book a free 45-minute call.