Hi Reader

In praise of not having a clue yet

Two new client conversations this week, and between them they had a to-do list for retirement that made my head spin.

The first, I’ll call him Martin, retired two months ago. When I asked what he’s going to do with himself, here’s the actual list. Acting. French tutoring. Teaching business studies. Selling heli-ski trips. I’m not making any of that up, and neither was he. Four completely different lives, all on the table, none of them started.

The second, I'll call him Chris, is winding down and reeled off his own version. Mentoring university students. Photography for a jazz festival. Charity work around neurodiversity. Again, all live, all possible, none of them nailed down.

And here’s the interesting bit, both of them said all this slightly apologetically. Like it was a problem. Like the fact they hadn’t picked one and committed was a sign they hadn’t done retirement properly. As if I was going to lean across the table and go, “Martin, you’re 56, you really should know by now whether it’s acting or teaching.”

I did the opposite. I told them it was the healthiest thing I’d heard all week.

The tyranny of having it sorted

There’s this idea floating around that a good retirement is one you’ve got figured out in advance. You’re meant to walk out of your leaving do clutching a fully-formed 'Plan For The Next Chapter'. The allotment. The novel. The move to Portugal. One clear answer, decided, committed, underway by the second Monday.

And if you haven’t got that, if all you’ve got is a vague pile of maybes, you feel like you’re failing before you’ve even started.

This is rubbish. Complete rubbish.

Because think about where it comes from. It comes from work. For decades you lived in a world that demanded a plan, a target, a deliverable, a decision by Friday. Vagueness was a weakness. “I’m not sure yet” was not an acceptable answer in a meeting. So you got very, very good at picking a direction and committing to it, and you’ve carried that instinct straight into retirement, where it doesn’t belong at all.

You’ve retired from the job. You haven’t retired from the mindset that says you must have the answer, and you must have it now, and not having it means something’s wrong with you.

A pile of maybes is not a problem. It’s the whole point.

Here’s what I actually think is going on when someone like Martin or Chris lists four possible lives.

That’s not indecision, it's possibility. These are people who spent decades locked into one narrow track suddenly standing in an open field going, “hang on, I could go anywhere.” The four maybes aren’t a sign they're lost. They’re a sign they're finally free.

The mistake is thinking the job now is to hurry up and narrow it down. To pick one, commit, and get your single new identity sorted so you can tell people at parties what you “do” now.

But you don’t have to, and rushing it is how you get it wrong.

Here’s the thing about all these maybes, you genuinely cannot know which ones are any good until you try them. Martin has no idea if he’ll love acting or hate it. It might be the best thing he’s ever done. It might be a church hall full of people he can’t stand, and he’s out after two sessions. He can’t think his way to the answer, he can only try his way there.

So the smartest possible approach isn’t to pick the winner in advance, it’s to audition. Try the acting. Do a term of the tutoring. Take the photography gig. Treat the whole first year or two as a casting session, not a final answer. Say yes to a few, keep the ones that light you up, drop the ones that don’t, and feel no guilt whatsoever about the ones you drop.

The pile of maybes isn’t the problem to be solved. Working through the pile IS the retirement. That’s the good bit. That’s the freedom you spent forty years paying for.

Why the maybes matter more than the money

I’ll tell you what actually worries me, and it isn’t Martin or Chris with there four lives.

It’s the person who walks in with none, no maybes at all. Nothing bubbling. Just a pension, a finish date, and a completely blank space where the curiosity should be. That’s the one I want to gently poke, because a blank space is a lot harder to work with than a messy, overflowing, undecided list.

Martin and Chris are going to be fine, and not because their numbers are good, though they're ok. They’re going to be fine because they’re still curious. They’ve still got things they want to try. They’re standing at the start of this thing with their list full of maybes, and that pile is worth more than another hundred grand in the pension, because it’s the raw material of a life that’s actually interesting to live.

The money buys you the open field, the maybes are what you do with it. You can have all the money in the world, but if you arrive with an empty pile, you’ve got a very well-funded blank space and not much else.

The question

So if you’re heading towards this, or you’re in it and feeling a bit useless because you haven’t “found your thing” yet, here’s what I’d offer.

Stop demanding an answer of yourself. You don’t need one. Not yet, maybe not ever, not a single tidy one anyway.

What have you got in your pile of maybes? What are the things bubbling away in the background that you’ve never had the time or the permission to try? Write them down. All of them, however daft, however contradictory. Acting and heli-skiing and French tutoring, the lot.

And then, instead of trying to pick the right one, just start working through them. Audition them. Give them a go. Keep what sings, bin what doesn’t, and let the answer reveal itself slowly, the way real answers actually do, by living, not by deciding.

You spent forty years having to know. You’re allowed to spend the next few gloriously, curiously, productively not having a clue.

That’s not you failing at retirement, that’s you finally doing it right.

P.S. - What’s in your pile of maybes? Hit reply and tell me the daftest one, the thing you’d secretly love to try but have never admitted out loud. Mine involves doing a improv comedy gig!! Go on, show me yours.