Learning to Love Grey Skies (And Why That Might Be the Problem)

Lately, I’ve been sitting with a thought that won’t leave me alone.

There is so much we could do right in life when we have the chance… and yet, we choose wrong.

Not always in big, dramatic ways. Not usually with malicious intent. More often, wrong is built quietly—from selfish desires we don’t want to name or fears we’d rather not confront. Fear of conflict. Fear of loss. Fear of what choosing right might actually cost us.

When we stand at the crossroads where right is possible, it’s rarely crystal clear. Wrong has a way of rolling in first. It clouds things. Creates grey skies. Brings rain. And suddenly, the path that once felt obvious feels slippery, inconvenient, or exhausting.

What I keep coming back to is this: Most of the time, we can get out of the rain.

But the work it requires—honesty, courage, humility, disruption—often feels harder than simply learning to live with grey skies.

So we adapt.

We tell ourselves this is just how life is now. We normalize discomfort. We romanticize endurance. We call resignation “acceptance” and convince ourselves that loving grey skies is a sign of maturity or strength.

But here’s the harder truth I’m wrestling with:

Learning to love grey skies can be another wrong choice.

Not because endurance isn’t admirable—it is. But because prolonged compromise dulls discernment. When we stay too long in the rain, right and wrong don’t disappear… they blur. The contrast fades. The compass weakens.

And eventually, we stop asking if this is right and settle for whether it’s manageable.

Midlife has a way of exposing this. Maybe because we’ve lived long enough to recognize patterns. Or because we’re tired of carrying umbrellas for storms we didn’t create. Or because somewhere deep down, we remember blue skies—and we miss them. Or maybe we never gave ourselves the chance to see any other sky at all.

This isn’t about perfection. Or judging past choices. Or pretending that choosing right is always clean or painless.

It’s about noticing when survival has quietly replaced alignment.

Because just because we can survive in the rain doesn’t mean we were meant to live there.

And maybe midlife—this reflective, honest, sometimes uncomfortable chapter—is less about learning to love grey skies… and more about remembering that stepping out of the rain is still possible.

Even now.