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You’ll Regret Everything in Life, No Matter What

BYYassine Hariss

September 7, 2026

As a professional overthinker — whose brain seems physically incapable of making a decision without immediately coming up with seventeen reasons why it might be the wrong one — I’ve spent an embarrassing amount of my life trying to make choices I won’t regret. Where to live, what to do, who to love, when to leave, when to stay, when to just shut up and see what happens. Every decision somehow turns into an endless loop of buts, ifs, and maybes. It’s like if I think about something for long enough, I’ll eventually land on the one option with zero downsides and absolutely no chance of me lying awake at 2 a.m. wondering whether I’ve just completely messed my life up. And it only took me nearly three decades to realize that I’ve been looking for something that doesn’t exist.

Because, as annoying as it is to admit, I’m starting to believe that we’re going to regret pretty much everything in life, at least a little bit. Not because every decision you make will be wrong, but because choosing one thing almost always means giving up another. And no matter how happy you are with what you picked, your brain has a funny way of wandering back to whatever you left behind and asking: but what if?

Move to a new city and you’ll miss home. Stay home and you’ll wonder who you could have become somewhere else. Leave the job you hate and you’ll panic about whether you’ve made a terrible mistake. Stay because it’s safe and you’ll wonder why you didn’t have the guts to leave. Winning clearly isn’t an option for my anxiety-crippled mind. But that’s what I’m also learning to understand: you’ll regret almost everything in life, no matter what. But why?

As it turns out, it’s a question Søren Kierkegaard asked himself almost two centuries before I started losing sleep over unanswered WhatsApps and questionable career decisions. In Either/Or, published in 1843, the Danish philosopher takes this idea to an almost comical extreme: marry and you’ll regret it; don’t marry and you’ll regret that too. Laugh at the world, regret it. Cry about it, same problem. Whatever direction you take, there is always another direction sitting somewhere in the back of your mind looking suspiciously appealing.

Admittedly, Kierkegaard’s argument is a little more complicated than “everything sucks, good luck.” The point isn’t that every choice is wrong, or that we should all give up deciding anything and spend the rest of our lives standing motionless in supermarket aisles. It’s that there is something inherently uncomfortable about choosing. The second you commit to one possibility, you abandon countless others. And those abandoned possibilities don’t just magically disappear, they become fantasies; romanticized versions of a reality you never know would’ve happened the way you’ve imaginined them.

We compare the life we actually have, complete with its boring mornings, awkward conversations, disappointments, bills, mistakes, and bad days, with a life that exists entirely inside our heads. Of course the imaginary one wins. We’ve given it absolutely none of reality’s inconveniences. Maybe, then, I’ve been asking myself the wrong question all these years. Instead of Which decision am I least likely to regret?, perhaps the more useful question is Which regret am I willing to live with?

Because every serious choice involves some kind of loss. Even getting exactly what you wanted can leave you mourning the person you might have become had you wanted something else. There’s something strangely comforting about that. Regret stops being this flashing warning sign telling you that you’ve ruined everything and starts looking more like proof that you actually made a choice; a decision involving all the ups, downs, gains and losses that choosing anything inevitably entails.

And I think that’s the part I’ve been getting wrong. I’ve spent years treating regret as something I could outsmart if I just thought hard enough beforehand, as though somewhere beneath the seventeen tabs open in my brain there was a perfect answer waiting to be found. But maybe growing up is partly realizing that there isn’t. There are just different lives, each with their own pleasures, disappointments, and versions of what if? Kierkegaard was right: marry, don’t marry, laugh, cry, you’ll probably regret all of it at some point. So you might as well choose something because you’re going to wonder what if? either way.

At least this way, you’ll have actually lived something worth wondering about.

You’ll Regret Everything in Life, No Matter What

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