I asked 40 people over 85 what they'd do differently—every single one mentioned the same decade of their life

Last month, I sat down with 40 people over the age of 85 and asked them one simple question: "If you could go back and do one thing differently, what would it be?" I expected to hear a variety of answers about career choices, relationships, maybe even investment decisions (my financial analyst brain was showing). But here's what shocked me: without exception, every single person mentioned their thirties.

Not their twenties, when they were figuring things out. Not their forties or fifties, when many hit their stride professionally. Their thirties. The decade that, for most of them, slipped by while they were too busy to notice.

One woman, 87 years old with eyes that sparkled when she laughed, told me, "My thirties were when I was so focused on checking boxes that I forgot to ask if they were my boxes to check." That sentence has been rattling around in my head ever since.

The decade of shoulds

You know what your thirties feel like? They feel like standing in the middle of a crowded room where everyone is shouting instructions at you. Society tells you this is when you should have your career figured out. Your parents wonder about grandchildren. Your friends are buying houses, getting married, or doing both while you're still trying to figure out which city you want to live in.

I spent most of my thirties in boardrooms, analyzing spreadsheets and market trends. I was good at it, really good actually, but somewhere around 36, I started keeping a journal. Nothing fancy, just thoughts scribbled down between meetings. Looking back at those early entries now, I can see the pattern the people I interviewed were talking about. Page after page of "I should be grateful for this job" and "I should want this promotion" and "I should be satisfied."

The people I spoke with all described their thirties similarly. They were the years of maximum pressure and minimum self-reflection. One gentleman, a retired architect, said he designed hundreds of buildings in his thirties but never once designed the life he actually wanted to live.

The myth of having it all together

Here's what nobody tells you about your thirties: everyone else is faking it too. That colleague who seems to have the perfect work-life balance? She told me last week she cries in her car after dropping her kids at daycare. That friend with the Instagram-perfect marriage? They're in counseling, working through stuff just like everyone else.

The octogenarians I interviewed all wished they'd known this. They spent their thirties comparing their insides to everyone else's outsides, measuring their behind-the-scenes against other people's highlight reels. One woman said, "I spent that entire decade trying to keep up with people who, I found out later, were trying to keep up with me."

When I hit 37, I was making six figures, had the corner office, and felt completely empty. The Sunday night dread had become Tuesday morning dread, Thursday afternoon dread, and eventually just... dread. But I kept going because that's what responsible adults in their thirties do, right? We show up. We deliver. We don't rock the boat.

The relationships we sacrifice

Almost everyone I interviewed mentioned relationships when talking about their thirties. Not romantic ones necessarily, though those came up too. They talked about the friendships that withered while they worked late nights. The family dinners they missed. The conversations with their kids that got pushed to "later" until later became never.

One man, 91 years old and sharp as a tack, told me he could remember every detail of a business deal he closed in 1963 but couldn't remember his daughter's first word. "I was there," he said, "but I wasn't really there. My body was in the room, but my mind was already at the office."

This hit me hard because I see it happening all around me now. Friends who text less because they're buried in work. Couples who share a bed but not their thoughts anymore. Parents who know their kids' schedules but not their dreams. We're all so busy building our lives that we forget to live them.

The courage question

Here's the question that came up over and over in my interviews: "Why didn't I have the courage to change?"

Your thirties are when the stakes feel highest. You might have a mortgage, kids, responsibilities that make any change feel impossibly risky. The people I spoke with understood this, but they also understood something I'm only now learning: the risk of staying in the wrong life is greater than the risk of pursuing the right one.

At 38, I had what I now call my breakdown-breakthrough. One morning, I couldn't get out of bed. Not wouldn't, couldn't. My body had decided to hold an intervention. That forced pause made me realize I'd been sprinting through my thirties without ever asking where I was running to.

Three months later, I walked away from that six-figure salary. My colleagues thought I'd lost my mind. My parents were concerned. But you know what? That decision led me here, to writing, to trail running at dawn, to actually tasting my coffee instead of gulping it down while checking emails.

What they wish they'd known

The advice from my interviewees was remarkably consistent. They wished they'd known that their thirties weren't about having all the answers but about asking better questions. Questions like: Does this life fit who I'm becoming, or just who I used to be? Am I making decisions from fear or from purpose? What would I do if I knew I couldn't fail?

They wished they'd taken more risks, not fewer. Every single person had a "what if" story from their thirties. What if I'd taken that job in another country? What if I'd started that business? What if I'd had that difficult conversation? What if I'd chosen courage over comfort?

One woman summed it up beautifully: "Your thirties are not your final form. They're just one chapter in a very long book."

Final thoughts

If you're in your thirties right now, feeling that pressure, hearing all those "shoulds," wondering if you're doing it right, here's what 40 people with the gift of hindsight want you to know: slow down. Look around. Ask yourself the hard questions. The boxes you're checking, are they yours? The life you're building, do you actually want to live in it?

And if you're past your thirties, carrying regrets about that decade, remember what that 91-year-old man told me at the end of our conversation: "I can't change my thirties, but I can change my nineties. And that's what I'm doing now."

Tomorrow morning, I'll head out for my trail run, watching the sunrise paint the mountains orange. I'll think about these conversations, about the wisdom earned through years of living, about the thirties that shaped all of us in ways we're only beginning to understand. And I'll remind myself that every decade is a chance to course-correct, to choose courage, to stop shoulding all over ourselves and start living.

The people I interviewed taught me that your thirties don't define you. They're just the decade where you learn what definition means to you. And honestly? That lesson is worth more than any six-figure salary I walked away from.