Note to Reader: I found this old blog from ten years ago, just before my 60th birthday. I never published it. I was going to edit it for this week’s article, but decided to leave it as is and post it now, unedited, except for an update: I’m nearly finished a letter to my younger self, and hopefully it will be more interesting for my younger followers. 70. It reads like a letter to myself.
I’m 60. I don’t feel old so much as time-aware. The calendar feels different now. Some days, the pliable clay form of my life feels set, as if it’s too late to reshape what still needs to be reshaped. That’s usually when regret drifts in—not to scold me, but to nudge me.
Many of us in this cohort love to quote Paul Anka’s lyric from “My Way”, Frank Sinatra made famous: “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 guitar lessons that failed me, 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 didn’t do.
Psychology offers a simple way to explain that ache. A Cornell study describes three versions of the self we all juggle. There’s the actual self—who I am today. The ought self, who I think I should be, is 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 regret, roughly three-quarters pointed to the ideal self: the dream left on the shelf, not the obligations they failed to meet.
That tracks with my experience so far. In the moment, I’ve regretted plenty of actions—things I said, friends I’ve disappointed, or risks I took that didn’t feel right or pan out. But over time, those regrets soften, and I can usually find a lesson, or a relationship that grew from the mess - a silver lining.
But know this: inaction doesn’t give you much to work with. A door you never open doesn’t teach you much. It hangs around like an unfinished prologue.
The transition from full-time work to whatever comes next throws this into sharp relief. For decades, my life ran close to the ought self: show up, meet deadlines, pay the bills, be responsible. Important stuff. Then, when you start to think about stepping back from work, the questions change. It’s less “Did I do what I was supposed to?” and “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 but clarifying. Most of us hope to leave this world reconciled and connected, surrounded by people we love, 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: mend fences, say the unspoken things, follow a few threads from our ideal selves that we’ve ignored.
The good news is that this phase of life (you can call it retirement if you want to) isn’t a short coda anymore. It can stretch two or three decades. That’s not leftover time; it’s a whole chapter- another book! As we age and feel time’s edges, research shows we naturally lean toward meaning, close relationships, and authenticity. That doesn’t mean chasing every abandoned dream. It means picking a few that matter and acting on them, gently and consistently.
UPDATE: What I have learned along the way to 70.
Here’s what’s helping me bridge the gap today at 69, between my ought self and my ideal self without tossing prudence out the window as I now move into my seventies (yikes):
- Name a north star, not a bucket list. A bucket list can become a pressure cooker. Instead, write one line that starts, “I’m the kind of person who…” Maybe it’s “who makes things with my hands,” “who mentors,” or “who learns and shares beauty.” Then I choose one or two projects that fit that sentence. Identity first, activities follow second.
- Make reversible bets. Not every decision is a cliff. Many are two-way doors. Audit a class before enrolling. Volunteer on a short project before taking on a leadership role. Try consulting part-time before declaring a new career. Reversibility quiets the fear of getting it wrong and gets me moving.
- Shrink the change. Big dreams can collapse under their own weight. So, start a short, like 20-minute writing session tomorrow morning. A one-week vacation before planning a month abroad. One 30-minute music lesson. Starting small builds momentum.
- Work in 90-day seasons. Forever is paralyzing; a season is doable. Pick one aspiration, set a 90-day container with modest outcomes, and review at the end. What gave me energy? What dragged? Renew, pivot, or stop. Seasons make the ideal self feel real and achievable.
- Build a small circle. Tell one or two people what you’re doing and ask them to check in. Join a class or a group, so you’re not doing it alone—book club, revolving cooking night, walking club. Companionship turns discipline into habit.
- Lean into generativity. Look for ways to pass something forward: tutoring a student, mentoring a younger colleague, recording family stories, or coaching. It doesn’t need to be grand. It reminds me that my life spills over into other lives.
- Practice repair and release. Some regrets involve hurt I caused or ties I let fray. I try to apologize without conditions, start hard conversations, and say thank you while I can. And where repair isn’t possible, I now practice release: write the unsent letter, give the words a home. Regret needs ritual.
- Find adjacent routes and possibilities. Some doors are closed. I won’t become a studio musician at 70. But I can play for a small audience at the long-term care home. I may not write the book I once imagined, but I can advise someone who will. 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.
- Be kind to yourself. Fear of looking foolish stops more action than lack of time. Self-compassion isn’t lowering the bar; it’s accepting that the learning curve looks wobbly at any age.
Part of this work is reinterpreting the past. I don’t want to whitewash my choices, but I do want to see them whole. That “sensible” career I stuck with? It paid for my kids’ education. It taught me patience. It introduced me to friends and colleagues who became family. None of that erases the ache of the creative person I didn’t become. It widens the story. And now, with time still ahead, I get to choose again.
It’s tempting to wish we’d lived without regret. I’ve stopped wishing that. Regret isn’t proof I failed; it’s proof I can tell the difference between the life I lived and the life I still want. The key is not letting regret harden into self-reproach. I’m trying to use it as a compass—pointing toward the conversations to start, the places to go, the skills to try, the kindness to offer.
I used to stare in the rearview mirror, counting wrong turns. Lately, I watch the road opening ahead. Cornell says the regret that lingers is the unlived ideal; Jane Fonda says to live so the ending is gentle. I’m taking both to heart. I’m swapping “maybe later” for “start now,” trading perfection for presence.
I’ll sing my own verse of “My Way,” quieter maybe, humbler for sure—but still mine. And if I’m lucky, years from now, I’ll feel a hand in mine and a calm in my chest, and I’ll know: I made repairs. I followed wonder. I told the truth. The ache of what-if became the steadier light of, I am.