I asked 30 Gen Xers what they regret most in life—and the same 4 answers came up again and again

A few weeks ago, I sat down with thirty Gen Xers—people born in that 1965–1980 pocket who have lived through landlines, mixtapes, and the first iPhones.

Some are parents. Some are caretaking their own parents. Many are leading teams at work and quietly shouldering more than they admit.

I asked each of them a simple question: When you look back, what do you regret most?

The answers were vulnerable and surprisingly consistent. No matter their job title or zip code, four themes surfaced again and again.

If you’re a self-observer like me—curious, practical, always iterating—consider this a mirror and a map. Nothing here is about shame.

It’s about noticing patterns so we can choose differently today.

Before we dive in, a quick note: I’ve mentioned Rudá Iandê’s Laughing in the Face of Chaos before. His insights helped me make sense of these conversations, especially around the body and authenticity.

One line kept echoing while I listened to people’s stories: “Everything that you conceive of as 'you'—your personality, your memories, your hopes and dreams—is a product of the miraculous creature that is your body.”

That’s where we’ll start.

1. Waiting to care for their bodies until something broke

No one phrased it like a fitness goal. It was more sobering than that. “I ignored the small alarms,” one dad told me. “The tight chest on stairwells. The ‘I’ll sleep this weekend’ routine. Then the big alarm hit.”

That quote from Rudá above wouldn’t leave me alone because it reframes the whole conversation. Your body isn’t a vehicle you park in the garage until the weekend.

It’s the source of your mind, your creativity, your patience with your kids, your decision-making at work. It’s not separate from who you are.

When I’m trail running, I notice how quickly my thoughts and moods change after ten minutes of moving. It’s not heroic. It’s maintenance.

And that’s the shift most of the people I spoke to wished they’d made earlier—not a crash diet or a January detox, but small, boring, consistent signals of respect:

• Going to bed on time more nights than not. 
• Walking after dinner instead of scrolling. 
• Annual check-ups even when nothing hurts. 
• Lifting a modest amount of weight to keep joints and bones happy. 
• Saying “no” to the extra drink because tomorrow matters.

A simple move for this week: Pick one signal of respect and attach it to something you already do. After your morning coffee, take a ten-minute walk. After you brush your teeth, stretch your back and hips. If you love trackers, great. If you don’t, skip them. What matters is repetition, not perfection. Remember: you’re not “working out.” You’re taking care of the thing that makes everything else possible.

2. Choosing work over moments with the people they love

Here’s the regret that drew the longest silences. Not because everyone hates their jobs—many like theirs—but because the tradeoffs were invisible while they were happening.

A mom of two said, “I told myself I was doing it for them. The hours, the travel, the constant ‘just one more email.’ Then one day the house was quiet and I realized I’d missed the middle—the ordinary dinners, the dumb jokes, the Tuesday night walks.”

I get this one. Earlier in my career as a financial analyst, I prided myself on being the go-to person. It felt responsible. But being the hero at work sometimes meant being a ghost at home. I had to learn that “urgent” and “important” aren’t synonyms.

If this is hitting a nerve, try this tiny experiment:

• Name your “Hour That Matters.” Choose one hour on a weekday that is sacred. Dinner, bedtime, pickup, a call with your parents—whatever. Put it in your calendar with the same force you’d protect a client meeting. 
• Make your boundary boring and clear. “I’m offline at 6–7 PM.” No apology. No paragraph. 
• Replace guilt with presence. During that hour, you’re there. Not perfect. Not performative. Just there.

Will you still disappoint people sometimes? Absolutely.

And, as Iandê notes elsewhere in his book, being human means you’ll disappoint others and be disappointed in return; part of our work is accepting that tradeoff with kindness.

The point isn’t to erase conflict. It’s to choose what you will regret least ten years from now.

A question to carry: If nothing changes, what ordinary moments will future-me wish I hadn’t bargained away?

3. Staying too long in the wrong jobs and relationships

I heard this in whispers first. Then it got louder. People described slow-drip stuckness: a job that was “fine” but siphoned their energy, a relationship that dulled them instead of growing them, a city that made everything harder but felt too intimidating to leave.

Why do we stay? Fear is an honest answer. So is sunk-cost bias—we’ve invested so much time, so we keep doubling down.

And then there’s identity: the story you’ve told yourself about who you are and how your life is “supposed” to look.

Let me ask you what I asked them: If you removed the sunk costs and the outside opinions, would you choose this again?

If your stomach drops, pay attention. That’s data.

Leaving doesn’t have to look like a movie scene with boxes by the door and dramatic speeches. Change loves small doors. Try micro-exits:

• Pilot projects at work. Before you torch your role, ask to spend 10% of your time on a different team or problem. Prove value, gather evidence, then negotiate. 
• Trial separations from habits. Not ready to break up with a city? Take a month-long work-from-anywhere and see how your nervous system responds. 
• One brave conversation. “Here’s what I need to feel alive in this relationship. Can we create this together?”

Fear doesn’t vanish when you do courageous things. It rides shotgun.

As Iandê puts it in another passage I love, fear is part of the human experience; treating it as a companion rather than an enemy changes how you drive.

A practice for the next 30 days: Each morning, ask: What is one tiny action that honors the life I’d choose again? Then do that before noon. Make the cost of staying slightly higher than the cost of experimenting.

4. Avoiding money on purpose—and paying more later

This was the most confessed-in-private regret. People told me they avoided money when they were younger because it felt confusing, boring, or judgmental.

Then life happened—kids, aging parents, layoffs, sudden expenses—and avoidance got expensive.

Here’s the liberating truth: you don’t need to be “good with money.” You need a repeatable, low-drama system. My analyst brain still loves a spreadsheet, but the system can be very simple.

Try this framework and adapt as needed:

1. Name your numbers. What does your life actually cost monthly? List rent/mortgage, utilities, groceries, transport, insurance, minimum debt payments, child/parent care, subscriptions. No shame—just clarity. 
2. Automate the basics. 
   • 3–6 months of expenses in a boring high-yield savings account (start with one month if that feels doable). 
   • Automatic transfer on payday into that account. 
   • Automatic contribution to a retirement account (401k/IRA/etc.). If a match exists, grab it first—it’s free money. 
3. Create a “Courage Budget.” Put a small, protected amount aside each month to fund experiments that move you toward a life you’d choose again—skills course, therapy, a few weeks between jobs, childcare so you can interview—whatever closes the gap between knowing and doing. 
4. Make debt visible and tactical. List balances, interest rates, and minimums. Choose one strategy—the snowball (smallest balance first) or the avalanche (highest rate first)—and automate extra payments on a single target. 
5. Decide your rich life rule. One sentence that keeps you honest: I spend extravagantly on X, and I cut mercilessly on Y. (For me: books and fresh food are “yes,” mindless subscriptions and status gear are “no.”)

Money will always have seasons. What matters is that you’re in a relationship with it. You’re talking. You’re making decisions on purpose. You’re not ghosting your future self.

A five-sentence script for hard money talks:
“I want us to feel secure and less stressed. Here’s what I see clearly and what I don’t. Can we look at the real numbers together this weekend? I’ll pull the list; you bring your priorities. Together we’ll decide one change we can live with this month.”

What these regrets have in common

Underneath each story was the same ache: I knew sooner than I acted.

Most people weren’t lacking information. They were waiting for permission, certainty, or a perfect moment that never arrived. That’s human. It’s also fixable.

Here’s the reframe I’m carrying from listening to these thirty lives: regret is a compass, not a punishment.

It points to what you value. If you listen without self-attack, regret can be one of the most constructive emotions you have.

And yes, the body keeps the score here, too. When you take a ten-minute walk, defend an hour that matters, make a micro-exit, or open your bank app, you’re not just checking a box—you’re shaping the conditions for a life that feels like yours. That’s integrity in action.

If you want one place to begin

• Choose one of the four areas that stung the most. 
• Write one sentence about what “better” would look like ninety days from now. 
• Take one awkward, unglamorous step today.

That’s it. No perfect plan. No life overhaul. Just momentum.

If you want deeper support around the inner noise that makes these changes hard, I found Rudá Iandê’s Laughing in the Face of Chaos grounding and surprisingly practical.

The book inspired me to examine where I was still negotiating with fear or perfectionism—and to choose presence instead.

We don’t get to rewind. But we do get to choose our next chapter. And that, in my experience, is more than enough.