Why Does Every Choice Feel Like the Wrong One?

How I Ended Up Choosing Something That Didn’t Make Sense (And Why That Made Sense)

I came dangerously close to a full-blown existential crisis last week, because I couldn’t choose a 3-night vacation rental.

Not a breakup. Not a family emergency. Just... trying to plan a short trip to the mountains.

I wanted something peaceful. A view. A porch. Maybe a nice patio with enough space to barbecue with friends. That’s all.

But somewhere between tab 47 and tab 59, I lost my grip on what I was even looking for.

One house had a hot tub but no charm. One had charm but no sunlight. One looked amazing in photos but probably only from one angle. Another was perfect, except for this red leather couch you couldn’t unsee.

I kept thinking, “If I’m going to spend time and money, it better be worth it.”

So I kept going. Added more to my wishlist. Took breaks. Came back. Re-ranked. And then I found out that outside of Airbnb, there’s Vrbo, and even more sites with even more options.

By the end, I wasn’t planning a vacation. I was running a research project I didn’t sign up for.

---

It Reminded Me of Dating

Somewhere in that spiral of scrolling, comparing, second-guessing, the whole thing started to remind me of modern dating.

Too many options.
Too many invisible expectations.
A constant sense that whatever you’re looking at isn’t quite it.

You screen, you swipe, you keep another tab open. You try to define your type, refine your standards, adjust your filters. And just like that, what started as curiosity turns into a low-grade system of elimination.

Not bad, not bad, not bad—but maybe there’s something better.

The goal gets blurry. Is it to find someone who makes you feel something, or to find someone who fits the list? And is the list still yours? Or did it quietly evolve, based on what other people say they want? Based on what seems “high value” or emotionally mature or attractive on paper?

You see someone who makes you laugh, and immediately wonder if they’re secure enough, successful enough, intentional enough. You feel a pull toward someone, and then override it, because they don’t check a box you added last year after a bad experience.

It’s not just about indecision. It’s about friction. The internal kind. When desire and strategy quietly start working against each other.

---

Regret-Proof Living

It’s easy to laugh it off about getting anxious over vacation plans. But that kind of anxiety doesn’t come from nowhere.

It’s not just being indecisive. And it’s not about being picky, either.
It’s about trying to avoid that sinking feeling later, the regret, the second-guessing, the “I should’ve chosen differently.”

Even rest starts to feel like something that needs optimizing.
Because deep down, regret feels like failure, even when it’s just about mountain cabins and patio chairs.

At some point, I realized I wasn’t really looking for a house.
I was trying to avoid disappointment.
Trying to protect myself from that future version of me who might wish I’d picked something else.

The Dizziness of Modern Love

This isn’t the first time someone has felt overwhelmed by too much freedom.
Kierkegaard—19th-century philosopher, way before dating apps—had a word for it: dizziness.

He once described a kind of anxiety that isn’t fear of something specific. It’s the feeling of standing on the edge of infinite possibilities.

When nothing is chosen for you, everything is left to you, and the weight of that freedom makes you spin. He wrote about it during a time when people were just starting to ask if God wasn’t the only authority anymore. If tradition wasn’t the only road. If you could build your own life, instead of inheriting one. That was enough to shake the ground under his feet.

But Kierkegaard didn’t live in a world where you could filter through 300 “matches” within a two-kilometer radius. He felt that existential dizziness with just a few life paths opening up.

Now we feel it on a Sunday afternoons just trying to find a vacation stay.

So no, it’s not silly. It’s not dramatic.
It makes perfect sense that people today feel overwhelmed, choice paralysis.

Because how can you not be?

---

The Checklist Is a Trap

Love isn’t a side quest.
It’s the thing you build your life around.
And when something that big depends on a system that keeps you second-guessing, how could you not feel overwhelmed by the pressure to choose right?

So of course people come with checklists. One after another.
The must-haves, the nice-to-haves, the non-negotiables.
Your red flags, your deal breakers, your green flags, your ick list.
The categories multiply.
And behind each one is the hope that, if you just calibrate hard enough, they’ll lead you out of the woods of choice.

And you’ll get it right.

But the trap is this: the more vivid that ideal becomes, the harder it is for anyone real to live up to it.

You’ve already lived the future in your head.
What’s left for them to surprise you with?

Maybe that’s why those special moments—the ones that make your heart skip a beat—never arrive on schedule.

Remember that time someone just showed up in your life? Out of nowhere? Didn’t try to impress you. Didn’t fit the picture you had in your head. Maybe even broke a few of your rules.

But still, you couldn’t stop thinking about them.

There was something about them you couldn’t quite figure out.
Like, why this person? What did they even do?

And yet, there they were. Stuck in your mind.

What was that?
Why did that happen?

---

Risk Full-On

I don’t know.

But I do know I finally booked my vacation house.

I’d spent hours comparing options. I had my list. I ran filters, saved tabs, made rankings. But the one I picked? It didn’t meet half the criteria.

It just... stuck with me.

I don’t know why I’m drawn to this one.
Maybe it’s the patio.
Maybe it’s the weird choice of picture on the wall.
Maybe it’s something else that doesn’t quite add up, but makes me want to find out.

So I booked it.
It wasn’t perfect, or predictable, or polished.

But it snapped me out of the script.
Tore through the image I had in my head.

And somehow, that felt like enough to look forward to.