What If We Regret This?

The question that followed us everywhere — and the one that eventually set us free.

We heard it a lot when we told people we were retiring early and traveling full time:

“What if you regret it?”

It usually came from people who loved us. People projecting their own fear onto our version of freedom. Sometimes, we asked it ourselves — quietly, at night — after a long day of planning or in one of those “what are we doing?” moments.

But here’s the thing:
We didn’t run from that question. We lived with it.
We still do.

Because regret isn’t a one-time thing. It’s a companion.
The kind that tries to sneak into your luggage, even when you’ve packed light.

And freedom?
It doesn’t always look like a margarita on a beach.

…but also, sometimes margaritas on the beach!

Sometimes it looks like waking up in a place where no one knows your name… and realizing you have to rebuild everything.
Not just your life — your sense of who you are.

Here’s what I’ve learned:

The risk of regret is real, but the cost of never trying is bigger.

We didn’t retire early because we were fearless.
We retired because we were tired of not feeling.
Tired of performing success instead of practicing presence.

If you're standing on the edge of something — a new job, a new city, a new kind of life — the fear will come.

Let it.

Sit with it.
Ask it questions.
Pack it a carry-on, if you must.

But don’t let it drive

Every leap comes with a whisper of doubt — but regret feels smaller when the story is bigger. If you’d like to help keep us leaping: