Oh Wells Over What Ifs

What’s a personal mantra or philosophy you live by?

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What’s a personal mantra or philosophy you live by?

I’ve got one, and it’s short enough to fit on a sticky note: “I’d rather live a life of oh wells than what ifs.”

What it means. Both phrases are about regret, but they feel completely different.

An “oh well” is what you say when you tried something and it didn’t work out. You asked, you applied, you sent the text, you took the leap, and the answer was no, or it fell flat, or it went sideways. It stings for a minute, maybe a week, but then it’s over. You shrug, you learn something, and you move on.

A “what if” never ends. It’s the question that shows up at 2 a.m. years later: What if I’d said something? What if I’d gone? What if I’d just tried? There’s no closure, because you never got an answer. You only get to imagine the best possible version of what might have happened, and nothing real can compete with that.

Why I live this way

When I look back, the things I regret aren’t the failures. They’re the moments I stayed quiet, stayed comfortable, or talked myself out of something because I was scared of looking silly. The failures I’ve had make good stories now. The chances I didn’t take just sit there, unfinished. So when I’m stuck on a decision, I ask myself: If this goes badly, can I live with an “oh well”? And if I don’t try, will I be stuck with a “what if”? Most of the time, the answer makes the choice for me.

What it doesn’t mean

This isn’t a license to be reckless. I’m not saying jump into everything without thinking, ignore the risks, or never say no. Some leaps need a plan and a safety net. The mantra isn’t about skipping the thinking. It’s about not letting fear be the deciding vote. If I’ve weighed it honestly and I still want to say yes, I say yes.

The freedom in it

Living this way takes a lot of pressure off. I don’t have to get everything right. I just have to be willing to try, and “oh well” is a perfectly good outcome. It means I showed up.

So here’s my challenge to you: what’s something you’ve been circling around, waiting for the perfect moment or the guarantee that it’ll work out? Go find out. The worst case is an “oh well,” and I promise that’s easier to live with than wondering.

What’s your mantra? Tell me in the comments.

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