Most Boomers I know would rather discuss their colonoscopy results than admit to the regrets that keep them awake at 3 AM.
I discovered this during a retirement party last year where six of us stood around making small talk about golf handicaps and grandchildren.
The conversation stayed safely on the surface until someone’s third drink loosened the truth. “I should have taken that job in Seattle,” one friend said quietly. The room went silent. Then, one by one, the admissions started flowing.
After thirty years of watching how people navigate status and reputation, I understand why we keep these regrets buried.
Admitting them feels like confessing failure, especially for a generation raised to project strength and certainty.
But here’s what I’ve learned at 64: The regrets we refuse to acknowledge are the ones that shape our remaining years most powerfully.
These nine regrets surface repeatedly in private conversations, therapy sessions, and those rare moments when defenses drop. They’re not unique to every Boomer, but they’re common enough that you’ll likely recognize several.
1) Choosing money over meaning for too long
The mortgage needed paying. The kids needed college funds. The safe job with good benefits made sense.
Most Boomers I know spent decades in careers that paid well but drained their souls, always planning to pursue their real interests “someday.”
That someday rarely came, or it came too late. A former colleague recently told me he spent 35 years in insurance while dreaming of teaching high school history.
By the time he retired, he felt too old and disconnected to start. The regret isn’t about the money earned—it’s about the decades spent doing work that never felt like it mattered.
The cruel irony is that many of us discovered our financial needs were less extreme than we believed. We traded decades for security we might have achieved with less sacrifice.
2) Not standing up to their parents
This one catches people off guard, but it’s surprisingly common. Many Boomers never had the hard conversations with their parents about childhood wounds, unfair treatment, or family dysfunction.
They kept the peace, played the dutiful child, and waited for the “right time” that never came.
Now those parents are gone, and the chance for resolution died with them. The weight of unspoken truths and unresolved conflicts doesn’t disappear with death—it often intensifies.
I’ve watched friends struggle with this particular ghost, angry at themselves for choosing comfort over confrontation when it still mattered.
3) Sacrificing their marriage for their career
I got married at 35, later than many peers, because work consumed my prime years. I thought I was being smart, establishing myself first.
Looking back, I see how many of us made our spouses compete with our careers for attention—and the career usually won.
We missed dinners, arrived late to anniversaries, and checked emails during family vacations. We told ourselves we were providing, being responsible.
But provision isn’t just financial. Many Boomer divorces stem from decades of emotional absence disguised as professional dedication. Those who stayed married often face retirement with a stranger across the breakfast table.
4) Being too hard on their kids
Boomer parents often operated from a playbook of high expectations and conditional approval.
We pushed our children toward conventional success, measuring their worth by grades, degrees, and job titles. We thought we were preparing them for a competitive world.
Many of us now watch our adult children struggle with anxiety, perfectionism, and the inability to feel good enough.
The distance in these relationships isn’t always about geography. It’s about years of criticism disguised as guidance, standards that communicated love was something to be earned.
The regret comes when you realize your kids succeeded professionally but never learned they were valuable just for existing.
5) Not taking care of their bodies
We treated our bodies like machines that would run forever on neglect and willpower. Skipped checkups because we were too busy. Ignored warning signs because addressing them meant admitting vulnerability. Pushed through pain that should have sent us to doctors.
Now we’re paying the compound interest on decades of deferred maintenance. Friends face health crises that earlier intervention might have prevented or minimized.
The regret isn’t just about the current limitations—it’s about all the activities with grandchildren we can’t do, the retirement dreams that require physical capacity we no longer have.
6) Letting friendships die
Career moves, family obligations, and simple neglect killed more friendships than any actual conflicts did. We assumed these relationships would survive on autopilot while we focused on “more important” things. We were wrong.
Making friends after 60 is like dating with arthritis—possible but significantly harder. The shared history that makes friendship effortless can’t be manufactured.
Many Boomers face retirement with plenty of acquaintances but few real friends, having traded depth for networking contacts who disappeared the moment the business cards became irrelevant.
7) Playing it safe with investments and opportunities
Not just financial investments, though those matter too. I mean the failure to invest in experiences, learning, and calculated risks when we had the energy and flexibility to recover from failures.
We chose the safe path repeatedly, avoiding discomfort and potential embarrassment.
A friend recently said his biggest regret was never starting the restaurant he dreamed about for twenty years. He had the money, the concept, even a potential partner. But the risk seemed too great.
Now he eats at other people’s restaurants wondering what might have been. The safety we chose often became a prison of our own making.
8) Not learning to say no
We said yes to every committee, every overtime request, every family obligation that came our way. We thought it made us valuable, indispensable.
Instead, it made us exhausted and resentful. We gave away our time like it was infinite, discovering too late that it was our scarcest resource.
The inability to set boundaries meant living other people’s priorities instead of our own. In retirement, I keep returning to one question in my notebook: “What am I optimizing for now?” I wish I’d asked it forty years ago.
9) Waiting too long to examine their beliefs
Many Boomers inherited their worldviews wholesale from their parents and communities, never stopping to question whether these beliefs actually served them.
Political affiliations, religious dogma, ideas about success, gender roles, and what constitutes a good life—all accepted without examination.
The regret comes when you realize you lived someone else’s life, followed rules that didn’t align with your actual values.
Some discover this in time to course-correct. Others realize it only in retrospect, seeing how these unexamined beliefs limited their choices and damaged relationships.
Closing thoughts
These regrets share a common thread: They’re all about choosing the comfortable, expected path over the authentic one. We optimized for approval, security, and the absence of conflict instead of meaning, connection, and growth.
The hardest truth I’ve learned is that you can’t negotiate someone out of what they’re committed to misunderstanding—including yourself.
These regrets persist because we spent decades misunderstanding what actually mattered, mistaking busy for important, achievement for worth.
If you’re reading this and recognize yourself, remember that acknowledging regret isn’t wallowing—it’s the first step toward different choices.
The question isn’t whether you have regrets, but whether you’ll let them teach you something while there’s still time to apply the lessons.
