Somewhere there’s a version of you that booked the ticket. Took the leave. Said yes when the friend asked you to come to Patagonia, or Japan, or just the coast for a long weekend. You think about that version more than you’d admit out loud.
We talk endlessly about where to go. We almost never talk about the trips we quietly let die — the ones that expired not because we decided against them, but because we never decided at all.
The math of “someday”
“Someday” assumes the window stays open. It doesn’t. The window narrows in ways you don’t notice year to year: money frees up but knees get older, friends scatter, parents age, jobs get heavier, the easy travel companion gets a mortgage and a baby. The trip that would have been effortless at 26 becomes a logistical campaign at 38.
None of this is an argument for reckless yes-to-everything. It’s an argument against the quiet, default no — the one you make by not answering.
We regret the trips we didn’t take
Here’s the uncomfortable pattern: over time, people rarely regret the trips that went wrong. The disaster trip becomes the best story at dinner. What lingers is the trip that never happened — the clean, frictionless what-if that you can’t turn into a story, because nothing happened. Action fades into anecdote. Inaction calcifies into regret.
There is no perfect time
The perfect time — when work is calm, money is plentiful, and everyone you love is free — does not arrive. Waiting for it is the single most reliable way to never go. The goal isn’t to take every trip. It’s to stop letting the ones that matter expire by accident.
If you’re tired of chasing the obvious places anyway, our where to go instead guide is a gentler starting point — and if the “dream trip” pressure is part of what’s stalling you, read you’re allowed to not love your dream trip.
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John Morrison is the founder and lead travel writer at Packzup. Over the past decade he has explored destinations across Africa, the Americas, Asia, Europe, the Middle East, and Oceania — always self-funded, never on a press trip.