Welcome back to another Question of the Week here at The Confusing Middle!

This week’s question comes from Gregory Stock’s The Book of Questions, and it’s a heavy one. Not “heavier than last week’s Antarctic survival scenario” heavy — although that question did force me to confront some unflattering truths about my capacity for sustained human proximity. No, this one cuts a little deeper.

If you learned you were going to die in a few days, what regrets would you have? Which of them could you resolve if you were given another five years?

Take a moment with that.

I did. And I want to be honest about what came up when I sat with it — because I think the honest answer is more interesting than the tidy one.

First, a Clarification

I want to make a distinction that I think matters: there’s a difference between regret and wondering. A regret, to me, implies that I made a choice and I genuinely wish I’d made a different one. Wondering is more like standing at a fork you already passed and thinking, huh, I wonder where that other road went.

I bring this up because when I tried to answer this question seriously, most of what surfaced were “what ifs” — not regrets. And I’m not sure that’s a dodge. I think it’s accurate.

I’m generally pretty okay with my life. Not in a smug, “everything is perfect and I have no complaints” kind of way, but in a quieter, more honest way. I’ve made choices — sometimes by actively choosing, sometimes by choosing not to choose — and most of those choices have gotten me to a place I can live with. Pun intended and acknowledged.

But there are threads I pull on sometimes when I’m in a reflective mood. And since we’re answering hypothetical deathbed questions here, I might as well pull on a few of them in public.

The Big One

If I found out I had a few days left, I think the thing I’d keep coming back to is the question of whether I did enough to build a life with someone.

I’ve been single my entire adult life. I’ve also been comfortable with that — more comfortable, honestly, than I probably should have been, and I say that without a lot of self-recrimination. I’m an introvert. I recharge alone. I’ve spent more time than most people are willing to admit genuinely enjoying my own company. The bachelor life has suited me in a lot of ways, and I’m not going to pretend it hasn’t.

But there are these moments — usually late at night when Krypto is asleep at the foot of the bed and some movie is playing that I’m only half watching — where the “what if” shows up. What if, back in my twenties, I hadn’t been quite so timid when it came to relationships? What if I’d told that one girl I liked her? What if I’d actually noticed that the other one was flirting with me instead of standing there like a golden retriever who just heard a strange noise?

I wasn’t oblivious because I was indifferent. I was oblivious because I was scared, and being scared was easier to live with than the possibility of rejection. So I built some walls. Nothing dramatic — no origin story, no single moment that broke me. Just a slow, incremental construction project that started sometime around 1999 and ran well into my thirties. Good craftsmanship, as far as emotional fortifications go. Very sturdy.

Would I have ended up married? Would there be kids in this picture? Would I be divorced? Would I be happier or would I have traded one set of complications for another? I genuinely don’t know. That’s the maddening thing about “what ifs” — they don’t resolve. They just echo.

So is that a regret? I’m still not entirely sure. But I think on a hypothetical deathbed, I’d lie there wondering whether I’d let fear make too many of my decisions in that department, and that wondering would probably be uncomfortable enough to qualify.

The Smaller Ones

There are a few others that would surface, though I’d classify these more as “things I’d be embarrassed to admit I hadn’t done” than genuine regrets.

I spent five years at Bluefield College (now Bluefield University) studying Christian Studies and Behavioral Science. I graduated. And then I never really used those degrees in the way I imagine my younger self would have expected me to use them. At some point, I considered a path in elementary education — working directly with kids in a classroom, shaping little minds, learning which students were going to be the funny ones and which ones were going to run for class president someday. I never went down that road. I’ve worked with kids in other ways over the years, and I don’t think my professional life has been a waste. But occasionally I wonder what version of me exists in a parallel universe who stuck with that major and spent the last twenty years in a classroom, and whether he’s more tired than I am or less.

And then there are the books. I’ve always been a writer — this blog has been running for over twenty years, in one form or another, which is either impressive or a cry for help, depending on your perspective. But the books I really wanted to write, the ones that had been rattling around in my head for years? I waited a long time to start working on those in any serious way. Not because I didn’t have the time. Not because I didn’t have the ideas. Mostly because I kept telling myself I’d get to it later, and “later” has a way of arriving faster than you’d like. I’ve made up for some of that lost time more recently, but standing at the edge of a hypothetical five-day countdown, I think I’d feel the weight of all those years when the blank pages stayed blank.

Now for the Second Part

The question doesn’t stop at regrets. It asks which of them could be resolved if you were given five more years — and this is where it gets interesting.

The books? Resolvable. Absolutely resolvable. Five years is a lot of time to write, to finish things, to put words into the world that might outlast me. That one I’d grab with both hands.

The education path? That window has probably closed. I’m not going back to school for a teaching certification in my mid-forties, even in a five-year hypothetical. I’ve made peace with that particular road not taken, and I think I genuinely mean it.

The relationship thing? This is where I have to think harder.

The practical answer is that it’s never too late. People find each other at every age. I’m in my mid-forties, not my mid-nineties. If someone handed me five bonus years and said, go figure this out, the raw materials are arguably still there.

But here’s the thing I keep running into: is it actually a problem I want to solve? And should I even think of it that way — as a problem?

I’m not sure the emotional architecture I’ve spent the last quarter century building is as easy to renovate as the question implies. It’s not just about being willing to meet someone. It’s about being willing to let them stay — to stop treating solitude as the default setting and intimacy as the exception. That’s not a five-year project. That might be a forever project. Or it might be something that, under the right circumstances, goes faster than I’d expect.

I think what the five-year version of me might actually resolve isn’t the relationship itself — it’s the permission to stop treating the question as rhetorical. To take the walls down a few bricks at a time, on the off chance there’s something worth building on the other side of them.

Whether that results in a relationship or just a more honest version of my single life, I honestly don’t know.

But I’d rather spend five years finding out than spending a hypothetical deathbed still wondering.

What This Probably Says About Me

I’m aware that most of my “regrets” aren’t quite regrets. They’re cousins of regrets. They’re the softer, less committed version — the “I wonder” rather than the “I wish.” And I think that probably says something about the kind of person I am, or have been, when it comes to self-protection.

It’s hard to regret something you’ve worked very hard to not feel too strongly about.

But the question has a way of stripping that away. Faced with a few days left, I don’t think the emotional armor holds up quite so well. The “what ifs” stop feeling like idle musings and start feeling like the things I actually wanted and was too cautious to pursue.

So maybe the real thing to take away from this isn’t the list of regrets or the five-year resolution plan. Maybe it’s simpler than that.

Maybe it’s just: don’t wait until the hypothetical countdown to start being honest about what you want.

Your Turn

I want to know what comes up for you when you sit with this question. Not the polished, dinner-party version — the real one.

Are your regrets things you actually wish you’d done differently, or are they more like mine — softer “what ifs” that you’ve learned to live alongside? And the five-year question: does it feel like hope, or like pressure? Are there things you could resolve, if the time were real and the motivation were high enough?

Drop your thoughts in the comments. I’ll be down here sitting with mine — possibly with Krypto, who has no regrets, because he is a dog and he was born knowing something the rest of us have to work very hard to learn.

Until next week — this is Aaron, still here at The Confusing Middle, still figuring out what the hypothetical versions of my life say about the actual one.

Feature Photo by Norma Mortenson