I have been thinking more about the partner who became indignant when I suggested he might experience uncertainty in retirement. It isn’t what he had planned for his next stage that stays with me - time with his children, travel, charity work - but rather the weight he placed on it. My strong feeling was that he needed the plan to be enough. And perhaps that's the issue.

I've been reading Didier Eribon's book about old age, loss and identity. One passage stopped me, not because it's about death - though it is - but because it captures something I see regularly in career transitions. Eribon writes: "We are not quite the same person depending on whom we are with: a relative, a close friend, a colleague from work." Our identity, he argues, is plural and composite - constituted through relationships and the roles we play with different people. When those relationships end, we lose not just the person but the role itself. And with it, part of who we are. Applied to professional life, this explains something I've noticed but struggled to name. When people leave long careers - particularly senior roles in firms or organisations - they don't just lose a job title. They lose the version of themselves that existed in relation to colleagues, clients, the organisation itself.

I ran a workshop recently on preparing for retirement from equity partnership. One of the participants, a partner close to retirement from the partnership, became indignant when I suggested he might experience uncertainty in the transition. As he explained, he had a plan. He knew exactly what he was going to do. His certainty was absolute. I found his certainty puzzling. Not because his plans weren't sensible. They were. But because having a plan for what you'll do is different from knowing how you'll experience the transition.

“The time you enjoy wasting is not wasted time.” Bertrand Russell*

In my last Reflection I asked: useful to whom? The question behind the question was really about measurement, and who gets to do it. Russell’s observation takes that somewhere else. It doesn’t ask whether time is useful. Rather it asks whether it is enjoyed. Which is a rather different standard.

When people step back from full-time work, they often struggle with whether they're using their time "usefully." I hear it regularly. Sometimes from clients, sometimes from friends who've made the transition. The guilt isn't about being idle (though that may come into it). Rather, it's about not being useful enough. But useful to whom?

I read Enuma Okora's column in the FT this week (behind the FT Paywall). One paragraph stopped me:

"I have a friend who, whenever I ask how he's doing, takes a moment before answering. Often he'll then express two seemingly conflicting feelings. 'A part of me is feeling grounded and engaged but another part of me is also feeling anxious because I'm concerned about [xyz].' I've grown to admire his willingness to sit with multiple realities, and even to begin practising it myself."

That willingness to hold contradictions, to say "both things are true" without rushing to resolve them, is rare. We aren’t always comfortable with it. We would much prefer coherence.

I left my law firm nearly twelve years ago. It was the right decision. I had work lined up, consulting opportunities were emerging, and trustee roles were accumulating. On paper, the transition looked straightforward; in practice, it wasn't quite so simple. The difficulty wasn't the work itself. Rather it was the gap between knowing I'd made the right choice and feeling comfortable with it. Knowing you've earned the right to step back doesn't make stepping back immediately comfortable.

I still write longhand when I want to think something through carefully. Not from habit, and not from sentiment. The pencil does something the laptop cannot replicate: the pace, the weight of commitment, the absence of a delete key. I have kept the pencil because I know, from direct experience, what I lose when I put it down.

Oliver Burkeman, writing in his newsletter The Imperfectionist, reaches back to a book title that stopped me: Rabbi Alan Lew's This Is Real and You Are Completely Unprepared. Burkeman's point, characteristically, is not to alarm. Uncertainty, he argues, is not a temporary inconvenience. It is our basic state of existence. We are never ready. Not really. And waiting until we are ready is, in the end, just another way of not beginning.

Some ten years ago I wrote a short post about the tension between Urgent and Important. I was then Chair of Trustees at Bridge Support, and I framed my role as encouraging the Executive Team to stay focused on the Important - the strategic work that could all too easily be displaced by firefighting.

My perspective has shifted.