Never Retire: The Myth of the Perfect Time to Move Abroad—Or Do Other Big Things
“Someday” is usually just comfort in disguise.
Sometimes the waiting is the hardest part. But only for people who actually decide to do things.
For others, waiting is usually just comfort in disguise. That line would not have made a Tom Petty classic—and it’s certainly no way to live life.
There’s always a reason to not do something big now. Sometimes the reason is real. But sometimes—the reason is an excuse.
The myth is that there is a perfect time to do big things. There isn’t.
What there is—and this is the part people miss—is a window where the discomfort of staying put finally outweighs the discomfort of making the move. As in: I know if I don’t do this, I’ll regret it for the rest of my life. That’s the only “perfect time” you’re going to get.
And the funny thing is, that moment doesn’t erase fear. If anything, it heightens it. Because you realize what you’re about to do: step away from what’s familiar.
Trade known comforts for unknown terrain. Risk failure. Risk being misunderstood. Risk feeling out of place—or like a dummy who used to be smart, funny, and quick on his feet before the move. Sometimes for a long while.
That’s what moving abroad really is. Not just logistics and spreadsheets. But choosing to step away from the comfort of what you know and into the unfamiliar—even when you’re convinced it’s the better life.
If it feels scary, that doesn’t mean you’re doing it wrong. It means you’re finally doing it.
But here’s where people get stuck. They think fear is a stop sign. In reality, it’s more like a green light: a signal you’re entering territory that actually matters.
So the question isn’t “is this the perfect time?” It’s “how do I move forward even though it feels risky?”
That’s the practical part—and the part I’ll break down behind the paywall.
How to separate excuses from legitimate reasons to wait.
How to know if your “window” has actually arrived.
What discomforts are normal in the first year abroad—and how to plan for them.
Why waiting for certainty can guarantee regret.
Because the Never Retire principle isn’t about waiting for life to line up—it’s about building the structure that makes life worth living, even when it feels scary to start.
There’s never a perfect time to move abroad—or do anything else that matters. There’s only the moment when staying put feels more costly than stepping into the unknown. That’s the signal. And if it scares you, that’s how you know you’re finally doing it right.