What the research on regret actually shows about the decisions people wish they’d made differently — and why it’s almost never the ones they expect

Here’s a statistic that stopped me cold: 76% of people’s biggest regrets involve things they didn’t do, not things they did. After 34 years of teaching high school English and counseling students through their first big life decisions, I thought I understood regret pretty well. Turns out, I had it backwards too.

We spend so much energy trying to make the “right” choice, analyzing every angle, weighing pros and cons until our heads spin. But the research on regret reveals something unexpected: the decisions that haunt us most aren’t usually the ones we agonized over. They’re the ones we never made at all.

The overthinking trap that creates more regret

You’d think careful deliberation would protect us from regret, right? That’s what I always told my students when they were choosing colleges or career paths. Take your time, I’d say. Think it through.

But here’s where it gets interesting. James R. Langabeer, Ph.D., Ed.D., explains that “Extended deliberation encourages mental simulation. We imagine what life would look like if we chose Option A or B instead of Option C or D.”

This mental simulation sounds helpful, but it actually sets us up for disappointment. When we spend weeks or months imagining how perfect one path could be, reality can’t possibly measure up. The fantasy version we created during all that deliberation becomes the standard we judge our actual choice against.

I saw this play out countless times in my teaching career. The students who agonized most over which college to attend were often the ones calling me freshman year, wondering if they’d made a terrible mistake. Meanwhile, the kids who went with their gut? They were usually too busy enjoying their new life to second-guess themselves.

The research backs this up. When we overthink, we don’t just consider practical factors. We start creating elaborate stories about how each choice will transform our entire future. Then when normal life continues being, well, normal, we feel like we must have chosen wrong.

Why your brain remembers the wrong regrets

Think about a decision you regretted five years ago. Got it? Now here’s the thing: there’s a good chance that regret has faded or even disappeared entirely. But I bet there’s something you didn’t do five years ago that still bothers you.

Our brains have a fascinating quirk when it comes to processing regret. Actions we take, even bad ones, tend to generate immediate regret that peaks quickly then fades. We adapt, we rationalize, we find silver linings. That terrible job you took? At least you learned what you don’t want. That relationship that went nowhere? Hey, you gave it a shot.

But inaction? That lingers. And it grows.

When I retired in 2022 after 34 years in education, I felt this acutely. Sure, I had moments where I questioned specific choices I’d made in my career. Should I have pursued that principal position? Was I too harsh on that troubled student back in 2003?

But what really got to me were the opportunities I’d let pass by. The sabbatical I never took. The novel I never tried to write during summer breaks. The colleague I never told how much their mentorship meant to me before they retired.

These regrets of inaction have a different quality. They don’t fade with time; they actually intensify. Because while we can explain away our mistakes, we can never know what might have happened if we’d been brave enough to try.

The education myth about perfect decisions

Paula Davis writes, “Regret is a powerfully strong emotion that most people have felt, despite all of the self-help advice stating that regret is foolish and that it should be avoided.”

She’s absolutely right, and I think our education system accidentally reinforces this impossible standard. We teach kids that there’s always a “best” answer, that careful planning prevents problems, that smart people don’t make mistakes.

I spent years doing exactly this in my English classroom. Essay assignments with clear rubrics. Test questions with definitive answers. The implicit message? If you’re smart enough and work hard enough, you can avoid failure.

But life doesn’t work that way, does it? The students who challenged me most, the ones who questioned everything and made what seemed like terrible choices, often taught me the most profound lessons about resilience and growth.

One student comes to mind who dropped out of her full-ride scholarship program to start a business. Everyone thought she was making a huge mistake. Ten years later, she’s thriving, not despite that “wrong” choice but because of what it taught her about trusting herself.

How retirement changed my understanding of regret

Retirement hit me like a freight train. I’d prepared financially but not emotionally for the identity crisis that followed. Who was I without lesson plans and parent conferences?

In those first disorienting months, I found myself cataloging regrets from my teaching career. But here’s what surprised me: the things I thought I’d regret most barely registered. That time I completely botched teaching “Romeo and Juliet”? Funny story now. The parent who complained about my grading system? Can barely remember their name.

What did sting were the chances I didn’t take. The teaching exchange program I talked myself out of. The doctorate program I was “too busy” to pursue. The students I didn’t push harder because I didn’t want to be “that teacher.”

This shift in perspective made me realize something crucial. We spend so much time trying to avoid making the wrong choice that we often make no choice at all. And that non-decision? That’s what really haunts us.

What actually prevents regret (hint: it’s not what you think)

After watching hundreds of students navigate major life decisions and now watching my fellow retirees grapple with their own regrets, I’ve noticed something. The people with the fewest regrets aren’t the ones who made perfect choices. They’re the ones who made choices, period.

They tried things. They failed sometimes. They changed course when needed. But they didn’t stand frozen at the crossroads, paralyzed by the possibility of choosing wrong.

This doesn’t mean being reckless. It means recognizing that most decisions are reversible, most mistakes are survivable, and most regrets fade if you actually did something rather than nothing.

When my grandmother lived with us during her final years, she shared something that stuck with me. At 89, she said her only real regrets were the conversations she didn’t have, the trips she didn’t take, the reconciliations she didn’t attempt. Not one single regret was about something she’d actually done.

Moving forward without the weight

So what do we do with this knowledge? How do we avoid accumulating regrets that will haunt us decades from now?

First, recognize that the decision you’re agonizing over probably won’t be the source of lasting regret you think it will be. If you’re actively choosing something, anything, you’re already ahead of the game.

Second, pay attention to what you’re not choosing. What are you putting off? What are you too scared to try? Those are the real danger zones for future regret.

Finally, understand that regret itself isn’t the enemy. It’s a teacher, showing us what matters to us, what we value, what we want to prioritize moving forward.

I mentioned in a previous post on DMNews how retirement forced me to reckon with who I really am versus who I thought I should be. This reckoning with regret is part of that same journey.

The research on regret doesn’t tell us to be fearless or reckless. It tells us that our biggest enemy isn’t making the wrong choice. It’s making no choice at all.

What opportunity have you been putting off that deserves your attention today?