The Regrets That Cut Deepest Aren't About Money

It's not the money. It's not the house you didn't buy or the job you didn't take.
For many older adults, the biggest heartaches — the ones that still sting decades later — have everything to do with family.
One day, the phone stops ringing. A wedding invitation never comes. You think there's still time to fix it... until there isn't. This is the regret that lingers deepest — letting a relationship slip into silence, thinking there'd be a better moment to speak up.
So, what are the regrets older Americans most often carry about family — and what can you do to avoid them?
Stopped Talking Over Something Small
Estrangement doesn't usually happen in one dramatic moment. Often, it starts with a disagreement or hurt feelings that never get resolved. Over time, silence hardens into distance.
According to Cornell gerontologist Karl Pillemer, many of the most anguished older adults he interviewed for his book "30 Lessons for Living" were estranged from their children or siblings and felt it was just too late to make amends, according to TODAY.
They didn't regret the fight as much as they regretted their own pride. That one child they stopped speaking to? Even when their other children stayed close, the loss of that one connection haunted them.
"The kinds of things that seemed worth saying 'My way or the highway' when you were 40 and they were 18 usually never seem worth it at 80," Pillemer says. If there's even a sliver of possibility to reconcile, reach out. A letter, a voicemail, a birthday card — something.
Not Telling Them How Much You Love Them
For some, the regret isn't estrangement — it's emotional distance. Many men, in particular, told Pillemer they wished they'd told their family what they felt. "Unless you believe in séances, you can't go back and ask for forgiveness, apologize, express gratitude, or even get information from somebody who has died," Pillemer said, as reported by TODAY.
Once someone is gone, there's no second chance to say what you meant to say. So, say it now. The text you think about sending, the praise you keep in your head, the apology you've been holding off — say it. There's never going to be a perfect time. But silence is what you'll regret.
Missed Too Much Trying to Get Ahead
Career pressure often collides with family life, and many older adults wish they'd chosen more balance.
In one story shared by Mindbodygreen.com, a man who traveled for work missed most of his daughter's childhood. By the time he was ready to be present, she had grown distant. He never forgave himself.
Even with love still intact, that lost time is something you can't get back.
So, stop always putting work first. Take the vacation. Leave work at work when you can. Be fully present — especially for milestones that only happen once. No one wishes they had spent more time on emails.
Thinking You Have More Time
40% of Baby Boomers surveyed by Talker Research said their biggest regret was not spending more time with family and friends, Newsweek reports.
Regret often shows up not because of what was done — but what wasn't.
Make time for your family, even if it's imperfect. A weekly phone call, Sunday lunch, or spontaneous visit can become the moments your family cherishes most. You don't need a big event to make a big memory.
Letting Your Ego Win
Regret, psychologist Eric Zillmer explained to Newsweek, "is a negative emotion that often hangs around longer than it should. Indeed, as one gets older, one accumulates and carries these cognitions around like an unwanted backpack full of weight: 'I should have' or 'If only I had.'"
We wait for the other person to call first. We stand our ground in a standoff no one is winning. But what's the real cost?
Be willing to be first. To apologize. To forgive. To let go of needing to be "right." Choosing presence, connection, and appreciation now can help you let go of what could've been.
What You'll Remember Most
When 90-somethings were asked about their happiest memories, the answer wasn't money, status, or success. It was time spent with family: raising kids, laughing at dinner, holding someone's hand.
Take the time to make those kinds of memories.
References: How to live life without major regrets: 8 lessons from older Americans | Older Americans Share Their Biggest Life Regrets | The 9 Most Common Regrets People Have At The End Of Life | What do 90-somethings regret most? Here's what I learned about how to live a happy, regret-free life