I asked 40 boomers what they regret most about their life—and the same 3 answers kept showing up – VegOut

When I started talking to people in their sixties and seventies about life regrets, I expected a wide range of answers. Some told me about careers they never pursued, places they wished they had visited, or relationships they wished had lasted.

But what surprised me was how often the same three themes came up. Out of forty different conversations, these regrets surfaced again and again.

And here’s the thing—none of them were about material possessions, flashy achievements, or even financial mistakes. They were about deeper, human things. The kinds of things that quietly shape the quality of our lives without us always noticing.

Let’s unpack what I heard—and what we can learn from it before it’s too late.

Not spending enough time with loved ones

Almost everyone I spoke with brought this up in some way. Some regretted working long hours while their kids were growing up. Others talked about friendships they let drift away because they were “too busy.” A few mentioned parents who passed before they had the chance to say what they really felt.

It wasn’t that they didn’t love these people. It was that life’s noise drowned out the signals. Work deadlines, bills, obligations—all of it seemed urgent at the time. Only later did they see how fleeting those moments were.

One woman told me she still remembers the look on her daughter’s face at a high school play when she glanced out into the audience and didn’t see her mom there. “I thought I was doing the right thing by finishing a big project at work,” she said, “but I’d give anything to have been in that seat.”

Psychologists have long noted that relationships are one of the biggest predictors of long-term happiness. As Harvard researcher Robert Waldinger put it: “The clearest message from the 75-year study is this: good relationships keep us happier and healthier.”

Boomers confirmed this over and over again. What they missed wasn’t the stuff they owned, it was the dinners they skipped, the birthdays they phoned in, the simple conversations that never happened.

It made me think about how I sometimes catch myself saying, “I’ll call them next week” or “We’ll make plans later.” Later has a way of slipping away.

And when later finally arrives, it’s often too late.

Letting fear hold them back

The second regret surprised me in how consistently it appeared. People didn’t talk about being afraid of the dark or of spiders. They talked about being afraid to take chances.

One man told me he stayed in the same job for 35 years because it felt “safe,” even though he dreamed of starting his own business.

Another woman confessed she always wanted to move abroad but was afraid she wouldn’t handle it. Someone else said they stayed in an unhappy marriage for decades because they were terrified of being alone.

These weren’t irrational fears—they were deeply human. But fear, left unchecked, became a cage. And in their seventies, they could see clearly that the bars weren’t as strong as they once seemed.

A retired teacher put it this way: “I kept thinking, what if I fail? But now I realize the real failure was never trying. Failure at least teaches you something. Regret just weighs you down.”

As Rudá Iandê writes in Laughing in the Face of Chaos, “Fear only has as much power as the importance you give it.” Many boomers I spoke with wished they had learned that lesson earlier.

What struck me was how often they said the regrets weren’t about failing. They didn’t regret the things they tried and messed up. They regretted the things they never even attempted.

That’s a lesson I tucked away for myself: comfort is nice, but it rarely leads to growth. If fear is steering the ship, chances are you’ll miss the horizon you were meant to sail toward.

Not taking care of their health earlier

The third regret came from people who were now facing health challenges—some minor, some life-altering. Almost all of them admitted they hadn’t thought much about their health when they were younger.

They worked too much, skipped exercise, smoked, drank heavily, or just assumed their bodies would always bounce back. Now, in hindsight, they wished they’d done the boring, unglamorous things—more sleep, regular checkups, daily walks, balanced meals.

One woman shared that she used to joke about “living off coffee and adrenaline.” Now, she wishes she had treated rest as a priority rather than a weakness.

And it wasn’t only physical health. Several mentioned mental health—saying they brushed off depression or anxiety instead of addressing it early. “If I had gone to therapy in my thirties, I could have saved myself decades of unnecessary struggle,” one man admitted.

Experts back this up. According to the CDC, many of the most common chronic illnesses—heart disease, type 2 diabetes, even some cancers—are heavily influenced by lifestyle choices. Prevention matters more than we like to admit.

Hearing boomers talk about this made me rethink my own excuses for skipping workouts or staying up too late. The small choices add up, and one day, they stop being small.

The connecting thread between these regrets

What fascinated me was how much overlap there was in these stories. They came from people with very different lives—teachers, business owners, parents, people who had traveled the world and people who had never left their hometown.

Yet the regrets circled back to the same three truths:

• People matter more than productivity.

• Fear is a thief if you let it run your life.

• Health is a long game, not something you can fix at the last minute.

When you boil it down, these aren’t flashy lessons. They’re simple, almost obvious. But simple doesn’t mean easy.

I think that’s why regret exists—it shows us where we ignored what we knew deep down. And it offers us a second chance if we’re willing to listen.

What I learned from listening to them

At first, I thought these conversations would feel heavy, even depressing. But what surprised me was how hopeful many of the boomers sounded. They weren’t sharing these regrets to wallow in sadness. They were offering them almost like advice.

One man told me, “You younger folks don’t have to repeat our mistakes. We already tested them for you. Trust me—love harder, take the leap, and take care of your body. The rest will sort itself out.”

That hit me. We spend so much time searching for life hacks and productivity tips when the wisdom we need is often right in front of us—sitting across the table in the stories of people who’ve already walked the path.

It also reminded me of a conversation I had years ago with my grandmother. She told me she didn’t regret the years of financial hardship or the missed vacations.

What she regretted was not telling her sister she loved her more often. At the time, I brushed it off. Now, after talking with dozens more boomers, I realize how universal that feeling is.

Taking the wisdom forward

So, what do we do with this information? It’s one thing to nod along, another to let it change how we live.

For me, it means actually picking up the phone and calling a friend instead of scrolling past their photos. It means choosing the run over the couch more often, not because I “should” but because future-me will be grateful. It means asking myself whether I’m making a choice out of fear—or possibility.

The boomers I spoke to didn’t share their regrets to dwell on the past. Most were remarkably at peace with their lives. But they wanted younger generations to see clearly what often takes decades to learn.

One man summed it up perfectly: “If you get these three things right, everything else is just details.”

Final thought

We can’t live a regret-free life—no one can. But we can let the regrets of others guide us. And if forty boomers all point to the same lessons, maybe those are the ones worth paying attention to.

Because the truth is, time is moving whether we notice it or not. The question isn’t whether we’ll have regrets—the question is which ones we’ll have. And today, we still have the power to choose.