I asked 40 people in their 60s what they regret most about their life

A few months ago, I became obsessed with one simple question: What do people in their 60s regret most about their life?

It wasn’t out of morbid curiosity. I’ve just always believed that wisdom often comes from looking backward—and that regret, while painful, is one of the clearest teachers we have.

So, I started asking. Friends of friends. Readers who had written to me. A few strangers I met on flights between Singapore and Saigon. In total, forty people between the ages of 60 and 75 agreed to answer, on the condition that I’d keep them anonymous.

And when I read through their replies, I realized something striking: most of their regrets fell into the same three categories. Different lives, different stories—but the same emotional themes repeating over and over again.

1. “I spent too many years living by other people’s expectations.”

This came up so often it almost became a chorus.

“I became an accountant because my parents said it was stable.”
“I married the person my family approved of.”
“I stayed in a job I hated because it paid well.”

Again and again, people in their 60s told me they had built their lives around what would look good on the outside, not what felt true on the inside.

One man from Melbourne wrote, “I was so busy trying to make my parents proud that I never asked what would make me proud.” He said this realization didn’t come until he was 59, after his father had passed away.

In psychology, this is called extrinsic motivation—when our actions are driven by reward, approval, or fear of disapproval. It’s the opposite of living from intrinsic motivation: doing something because it genuinely matters to you.

In Buddhist philosophy, it’s a form of attachment. We cling to the image of who we think we should be, and in doing so, we lose touch with who we really are.

I’ll be honest—this one hit close to home. I spent years trying to meet invisible standards too. Not from my parents, but from the idea of “success” that I thought the world expected of me: build the business, buy the apartment, hit the numbers.

And yet, when you talk to people who’ve lived six decades or more, they’ll tell you that none of those metrics mean much if you didn’t enjoy the process of getting there. The older you get, the less you care about looking successful and the more you care about feeling at peace.

As one woman told me: “I wish I’d learned earlier that it’s okay to disappoint people who have the wrong expectations of you.”

2. “I didn’t take care of my health until it was too late.”

This regret was almost universal. Even people who had lived vibrant, fulfilling lives said they underestimated how quickly the body can change after 50.

“I thought I could eat and drink like I did in my 30s,” one man admitted. “By the time I hit 60, I was on medication for everything.”

Another woman, 67, said, “I was always too busy taking care of everyone else. My husband, my kids, my parents. I didn’t move my body. I didn’t rest. Now I’m trying to undo 30 years of neglect.”

It’s sobering, because you can’t buy back physical vitality. You can build wealth, patch up relationships, reinvent your career—but your body keeps the score.

Many of them weren’t talking about aesthetics or gym routines. They meant basic maintenance: sleep, walking, stretching, stress management, eating real food. The small, daily choices that seem insignificant in your 30s but compound massively by your 60s.

One retired teacher summed it up perfectly: “When you’re young, you trade health for money. When you’re old, you trade money for health. I wish I’d seen that trade sooner.”

This is where mindfulness really matters. In Buddhism, the body isn’t just a vessel—it’s part of consciousness itself. Every breath, every movement is a chance to wake up to the present moment. Taking care of your body isn’t vanity; it’s awareness in motion.

It reminded me of my own father, who’s now 77 and still fitter than most 40-year-olds. He walks every morning, lifts light weights, and gardens daily. He always says, “Your health is your independence. Protect it like your freedom depends on it—because it does.”

Listening to these stories, I realized that health regret isn’t really about aging—it’s about neglect. And the antidote isn’t complicated: move your body, rest deeply, eat clean, and don’t assume tomorrow will be as forgiving as today.

3. “I let fear stop me from doing what I really wanted.”

If the first two regrets were about pressure and neglect, this one was about hesitation.

People in their 60s told me about love they didn’t pursue, risks they didn’t take, words they never said. There was a heartbreaking consistency in the way they described it: “I was scared,” “I didn’t think I was good enough,” “I thought I had more time.”

One man, a retired engineer, told me he always dreamed of writing a novel but spent his entire life waiting for the right moment. “Now I’m 68,” he said. “And I’m just starting. I wish I hadn’t waited for permission that no one was ever going to give me.”

Another woman said she’d wanted to travel alone in her 30s, but fear of judgment and safety concerns stopped her. “Now I look back and think—I was so capable, and I didn’t even know it.”

There’s a famous quote that says: “You regret the things you didn’t do more than the things you did.” Every person I spoke with confirmed that.

But here’s the insight that stood out: most of them said fear doesn’t actually disappear with age—it just changes shape. When you’re young, you’re afraid of failure. When you’re older, you’re afraid of running out of time.

As one man put it bluntly: “Fear doesn’t leave you. You just learn that it’s never worth obeying.”

That line has stayed with me. Because it’s not courage that separates the fulfilled from the regretful—it’s action despite fear. It’s learning to move forward even when your hands are shaking.

In Buddhist teachings, this is called right effort—acting with clarity and compassion rather than paralysis or perfectionism. You don’t have to be fearless. You just have to take the next right step.

And the people who told me they had the fewest regrets? They weren’t the ones who never failed. They were the ones who tried anyway.

What surprised me most

I expected to hear more about relationships or money. But those only appeared as subplots. The main story was always about alignment—living out of sync with who they truly were.

One woman, 70, said, “I wish I’d realized earlier that life isn’t about finding yourself—it’s about choosing yourself every day.”

That, I think, is the quiet wisdom of age. You stop chasing what’s impressive, and you start valuing what’s authentic.

And maybe that’s what regret really is: not punishment, but an invitation. A reminder to return to yourself.

Three takeaways I’ll carry with me

1. Don’t wait for permission to live your own life.

No one else is going to tell you when it’s time to begin. Whether it’s a career change, a creative project, or setting boundaries with family, start now. Every person I spoke to wished they had been braver sooner.

2. Protect your energy like it’s sacred.

Because it is. Your health, attention, and emotional bandwidth are finite. Spend them on what truly matters. That’s not selfish—that’s wisdom.

3. Fear will always be there. Act anyway.

If you wait until you feel ready, you’ll be waiting your entire life. The secret isn’t eliminating fear—it’s realizing it doesn’t deserve the final say.

How I’m applying this now

After finishing these conversations, I made a few quiet changes in my own life. I started running more regularly, not to chase a pace but to celebrate movement. I stopped saying yes to every business opportunity that came my way. And I’ve begun writing more about what genuinely interests me, not what I think will perform best online.

I don’t want to wake up at 70 and realize I built a life that looked successful but didn’t feel fulfilling.

And if there’s one thread connecting everyone I interviewed, it’s this: time is generous, until it isn’t.

Final reflections

When I asked one woman if she’d do anything differently if she could go back, she smiled and said, “Of course. But then I wouldn’t be who I am now.”

I think that’s the healthiest way to hold regret—not as a burden, but as a teacher. Regret reminds us that our choices matter. It asks us to live consciously, not carelessly.

So if you’re reading this and you’re still in your 30s, 40s, or 50s—listen carefully to those who’ve gone before you. Not because they’re always right, but because they’ve had the time to see what truly lasts.

Stop performing your life for others. Start living it for yourself. Move your body. Call the person you love. Write the book, take the trip, forgive the friend. Don’t let fear or expectation dictate your story.

As one of my interviewees wrote at the end of her email: “Regret is just the echo of a life half-lived. Don’t let it be your soundtrack.”