The conversations that stick with you aren’t always the ones you plan.
Over the past year, I’ve had the privilege of talking with 50 people in their seventies and eighties. Friends from work, neighbors I’ve known for decades. Even a few regulars from my local café.
I asked them all the same question: If you could go back to 50, what would you stop doing?
Their answers surprised me. Nobody said they regretted their career choices or wished they’d made more money. Instead, they talked about habits, worries, and patterns they’d held onto far longer than they should have.
Here’s what I learned.
1) They’d stop worrying about what other people thought
This one came up so often I lost count.
Nearly every person I spoke with mentioned wasting years concerned about others’ opinions. They stayed in jobs they hated because leaving seemed irresponsible. They avoided hobbies that seemed “too young” or “too frivolous.” They held back opinions to keep the peace.
One woman told me she’d wanted to take painting classes at 52 but worried her friends would think it was silly. She finally enrolled at 68.
“I wasted 16 years worrying about something that never happened,” she said. “Nobody cared. They were all too busy with their own lives.”
Research by Cornell gerontologist Karl Pillemer backs this up. After interviewing over 1,000 older adults, he found that one of their deepest regrets was letting imagined judgment dictate their choices.
2) They’d stop postponing travel and experiences
“I’ll do it when I retire” is a dangerous sentence.
Almost everyone I spoke with expressed regret about delaying travel. They’d saved the money. They’d made the plans. Then they watched their health decline right when they finally had the time.
A former coworker told me he’d dreamed of hiking Patagonia his whole life. At 72, his knees won’t allow it.
“We kept saying ‘next year,'” he said. “Then next year kept not coming.”
The window for physical adventures closes faster than anyone expects. Your body at 50 is dramatically different from your body at 70, even if you feel fine at both ages.
3) They’d stop avoiding difficult conversations
Financial discussions with aging parents. Honest talks with spouses about retirement plans. Confronting adult children about concerning behavior.
Everyone I spoke with had stories about conversations they’d dodged at 50 that became crises by 70.
One man told me he’d avoided discussing his mother’s declining health with his siblings for years. When she fell and broke her hip, nobody had power of attorney. Nobody knew her wishes. The family fractured over the decisions that followed.
“I thought I was keeping the peace,” he said. “I was just delaying the inevitable and making it worse.”
4) They’d stop staying in relationships that weren’t working
This wasn’t just about marriages, though several people mentioned that too.
It was about friendships that had become one-sided. Professional relationships with colleagues who drained their energy. Family dynamics that felt obligatory rather than genuine.
A neighbor told me she’d spent her fifties maintaining a friendship from college purely out of guilt. They had nothing in common anymore, but she felt she owed the woman her loyalty.
“I finally let it fade at 64,” she said. “I should’ve done it 15 years earlier and made room for people who actually added something to my life.”
You have less time than you think. Spending it with people who make you smaller is a waste nobody at 70 looks back on fondly.
5) They’d stop putting their health last
I heard variations of this story dozens of times.
At 50, they felt invincible. A little extra weight didn’t matter. Skipping exercise was fine. That nagging pain could wait.
By 70, those small neglects had compounded into chronic conditions that limited everything they wanted to do.
Research from the University of Manitoba found that health problems are among the top regrets of older adults, particularly when those problems were preventable.
One woman put it bluntly: “I thought I’d die a little sooner if I didn’t exercise. Instead, I’m just spending 20 years feeling terrible while modern medicine keeps me alive.”
6) They’d stop working so much
Not a single person told me they wished they’d worked more.
Several told me they wished they’d worked less.
Men especially mentioned missing their children’s activities for meetings they couldn’t even remember. They skipped family dinners for projects that felt urgent at the time but meaningless in retrospect.
A guy from my book club said it best: “I spent 20 years climbing a ladder I didn’t even want to be on. My kids grew up. My marriage suffered. And for what? A title that meant nothing the day I retired.”
7) They’d stop letting grudges linger
Estrangements with siblings. Years of silence after a fight with an old friend. Resentments toward parents that outlived the parents themselves.
Everyone I spoke with carried deep regret about relationships they’d let die over things that seemed important at the time but trivial in hindsight.
One man hadn’t spoken to his brother in 15 years over a disagreement about their mother’s care. His brother died at 69. The regret, he told me, is worse than the anger ever was.
If reconciliation is possible, do it now. Pride is expensive, and by 70, the bill comes due.
8) They’d stop trying to control everything
This one surprised me.
So many folks mentioned spending their fifties micromanaging their adult children, trying to orchestrate outcomes at work, obsessing over things completely outside their control.
One woman told me she’d spent years anxious about her daughter’s career choices, constantly offering unsolicited advice and judgment. It damaged their relationship for years.
“She was going to live her own life anyway,” the woman said. “All I did was make her not want to share it with me.”
Learning to let go earlier would’ve saved them years of anxiety and preserved relationships that mattered.
Final thoughts
Talking with these folks reminded me of something I’ve come to appreciate more in my own sixties: time is the one resource you can’t get back.
At 50, you still have runway. Enough health to travel. Enough energy to rebuild relationships. Enough time to change course.
But only if you stop wasting it on things that won’t matter at 70.
The wisdom of age isn’t about avoiding regrets entirely. It’s about recognizing what’s worth your limited days and what’s just noise.
So if you’re anywhere near 50 and reading this, ask yourself: What am I holding onto that I’ll regret in 20 years?
Then stop.
