When "You Can Always Do Better" Isn't Actually Good Advice

When "You Can Always Do Better" Isn't Actually Good Advice

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Publish Date:
November 1, 2026
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When "You Can Always Do Better" Isn't Actually Good Advice

 

Here's a question worth sitting with: if you could always theoretically find someone "better," does that mean you should keep looking?

That's the debate blowing up this week after "Call Her Daddy" host Alex Cooper reportedly suggested wives can always find better partners than the ones they've got. Riley Gaines and Kat Timpf both pushed back hard, and honestly? I get why.

I've spent the last several years building a life around freedom. Freedom to go where I want, do what I want, choose my own path without asking permission. Adventure Has No Age Limit isn't just a slogan I slap on a website — it's how I've actually lived since 2017. So you'd think I'd be the guy nodding along with "keep your options open, there's always something better out there."

I'm not.

Here's why. Freedom and commitment aren't opposites. People love to pretend they are, but they're not. The freedom to choose is exactly what makes a real choice mean something. If you pick a destination because it's the only one available, that's not adventure, that's just where you ended up. But if you've seen fifty countries and you still choose to go back to the same little town in Portugal because something about it fits you? That's a decision with weight behind it.

Relationships work the same way.

The idea that there's always a "better" partner out there assumes people are interchangeable upgrades, like phones or rental cars. Trade in the old model for the new one with more features. But is that actually how it works? Or is that just a comforting story we tell ourselves when things get hard, boring, or complicated?

I've made plenty of unconventional choices in my life. I left a conventional path to travel full-time well into my sixties, when most people are told to slow down, settle in, stop taking risks. People ask me all the time why I didn't just stay put, take the safe route, avoid the uncertainty. My answer is usually some version of: because staying put wasn't actually safer, it was just familiar.

But here's what I've learned chasing all that freedom. The things worth having — a destination you love, a skill you're building, a relationship you've invested years into — don't get better because you abandon them the second something shinier appears. They get better because you keep showing up. You adjust. You learn. You dig in when it's hard instead of bailing because theoretically there's a better option somewhere out there.

That's not the same as staying somewhere miserable out of obligation. I'm not arguing for that. I've walked away from plenty of things — jobs, routines, cities — because they stopped making sense for me. Independence means knowing when to leave. But it also means being honest about why you're considering leaving in the first place. Is it because the thing you have is genuinely broken? Or is it because "better" sounds exciting in theory, the way a place looks amazing in photos before you've actually been there?

I've been to destinations that were stunning on Instagram and forgettable in person. I've also been to spots that looked like nothing special until I'd spent three days there, talked to the locals, figured out what made the place tick. The value wasn't obvious from the outside. It showed up through time and attention.

People are like that too, I'd imagine. Easier to picture than to know, easier to swap out mentally than to actually understand.

So when someone suggests the grass is always greener, always better, always worth chasing — I'd ask: better by what measure? Compared to what you've actually built, or compared to a fantasy you haven't tested?

Riley Gaines and Kat Timpf aren't wrong to push back on that idea. Not because commitment means settling. But because real freedom isn't about always keeping one foot out the door. It's about choosing something, fully, and then having the guts to keep choosing it.

That's the real adventure. Not running from what you have in search of better. Building something better, together, with what you've already got.

What would you rather have: a thousand untested options, or one thing you actually know is good?

Source: 930 WFMD Free Talk

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