The Arc of Age, Up Close

Regrets, reflections, and the long arc of aging. Written at 60. Read, posted at 70.

The Long Ride Essentials with Greg Pallone

Note to Reader: I wrote this just before my 60th birthday - 10 years ago - before even thinking about writing about aging. It was never posted, but I found it ten years later, unedited, and posted it as I found it — a letter to myself that I never sent. It reads differently at 70. That is probably why I kept it.

I’m 60. I don’t feel old so much as time-aware. The calendar feels different now. Some days, the pliable clay of my life feels set, as if it’s too late to reshape what still needs reshaping. That’s usually when regret drifts in — not to scold me, but to nudge me.

Many of us love to quote Paul Anka’s lyric, made famous by Sinatra: ‘I did it my way.’ It sounds like a victory over regret. But if I’m honest, I have a few regrets. A few small ones — the language I never learned, the trip I kept postponing. And a few bigger ones — the safe career path I chose over the riskier one that lit me up, the creative itch I didn’t scratch, the friend I didn’t call back.

What stings most, I’ve noticed, isn’t what I did. It’s what I failed to do.

—

Psychology offers a useful way to understand that ache. A Cornell study describes three versions of the self we all carry. The actual self — who I am today. The ought self — who I think I should be, shaped by duty and the rules I grew up with. And the ideal self — who I want to become, the life I dare to imagine.

When researchers asked seniors about their biggest regrets, roughly three-quarters cited the ideal self: the dream left on the shelf, not the obligations they failed to fulfil.

That aligns with my experience. In the moment, I’ve regretted many actions. Over time, those regrets soften. I can usually find a lesson or a relationship that grew from the mess.

Inaction doesn’t give you much to work with. A door you never open teaches you little. It lingers like an unfinished prologue.

—

The transition from full-time work to whatever comes next brings this into sharp relief. For decades, my life ran close to the ought self: show up, meet deadlines, pay the bills, be responsible. When you start to think about stepping back from work, the questions change. Less ‘did I do what I was supposed to?’ and more ‘am I becoming who I hoped I’d be?’ That shift can be disorienting. It’s also a gift.

Jane Fonda said something that helps orient me: ‘The way to live, especially in the latter part of your life, is to envision how you want to die.’ Not morbid. Clarifying. Most of us hope to leave this world reconciled and connected, at peace with the story we chose to live. To get there, we must do some work now, while time is still on our side.

—

What I have learned along the way to 70.

Here’s what’s helping me bridge the gap today — between the ought self and the ideal self — without throwing prudence out the window:

— Name a north star, not a bucket list. Write one line that starts: ‘I’m the kind of person who…’ Identity first, activities follow.

— Make reversible bets. Audit a class before enrolling. Volunteer short before committing long. Reversibility quiets the fear of getting it wrong.

— Shrink the change. A 20-minute writing session. A one-week trip before planning a month abroad. Starting small builds momentum.

— Work in 90-day seasons. Forever is paralyzing; a season is doable. Review at the end. What gave energy? What dragged?

— Practice repair and release. Apologise without conditions. Say thank you while you can. Where repair isn’t possible, practice release: write the unsent letter, give the words a home.

— Find adjacent routes. Some doors are closed. I won’t become a studio musician at 70. But I can play for a small audience. I may not move to Italy, but I can spend a month there — or bring Italy to my kitchen every Thursday with a new recipe and a few friends. If the main door’s shut, look for the ones beside it.

—

Part of this work is reinterpreting the past. I don’t want to whitewash my choices, but I do want to see them in full. That ‘sensible’ career I stuck with? It paid for my kids’ education, taught me patience, and introduced me to people who became family. None of that erases the ache of the creative person I didn’t become. It widens the story.

Regret isn’t proof that I failed. It’s proof that I can tell the difference between the life I lived and the one I still want. The key is not letting it harden into self-reproach. I’m trying to use it as a compass.

I used to stare into the rearview mirror, counting wrong turns. Lately, I watch the road ahead.

I’ll sing my own verse of ‘My Way,’ quieter, maybe, humbler, for sure — but still mine.

This is The Long Ride — Essentials: an abridged version of the original essay, ‘The Arc of Age, Up Close,’ originally published April 2, 2026 — the first piece on The Long Ride, written at 60 and posted unedited at 69. The full version, including the complete list of reflections and the original author’s note, is on Substack, The Long Ride.