At 90, sitting somewhere beautiful

There's a question I come back to often — in my own life, and with clients.

Not because it's clever. Because it cuts through.

When you're 90, sitting somewhere beautiful, surrounded by people you love — and who love you — what do you want that version of you to thank you for?

It's not a bucket list exercise. It's a re-orientation.

Because when you look at your life from that vantage point, something quiet happens. The noise drops. The urgency softens. And what remains is usually far simpler than we expect.

Not more.

Just… clearer.

When I use this with clients — founders, creatives, people who've already built something meaningful — there's often a pause. Not because they don't know. But because they do. And they haven't been giving it much airtime.

What I've noticed is this.

Almost no one writes about revenue. Or status. Or scale.

They write about connection. Honesty. Time. Presence. And the feeling of having actually lived their life, not just managed it well.

A simple way to explore this

If you feel drawn to it, try this.

Find a quiet space. Imagine your 90-year-old self looking back on the life you've lived. Then, in their voice, write for ten minutes:

"I'm proud that I…"

"I wish I'd worried less about…"

"I'm grateful I kept choosing…"

"The moments that meant the most were…"

Don't overthink it. Don't try to get it right. Just write.

Then read it out loud.

There's something about hearing it that lands differently. Less mental. More… true.

If you want to take it one step further — pull out a single sentence from what you've written. A line that feels like it holds something real. That becomes your orientation line.

Not a goal. Not a plan. Just a direction you can return to.

Mine, for what it's worth

When I first did this, what came through was surprisingly simple:

"To appreciate life for everything it has to offer. To look back on it and be grateful for the joyful, contented and fulfilled life I've lived. To leave behind a happy and solid extended family I've helped to create and been a valued part of — and to be remembered fondly."

I remember noticing, even as I wrote it, there was nothing in there about titles. Or outcomes. Or anything I'd spent years chasing.

That didn't make those things wrong. But it did change their place.

What tends to shift

When you start orienting from this place, decisions simplify. Noise drops away. And you begin designing a life you don't need to escape from.

Not by doing less. By being more honest about what actually matters.

If this lands, I'd be curious — what might your 90-year-old self thank you for, that you're not fully choosing yet?

Best, Hugh

P.S. This doesn't reduce ambition. It just removes what isn't truly yours.

You've lived many versions of yourself in this lifetime. And there are many more still to come.

If this resonates and you'd like to explore further, you can book a discovery call here.