Last updated September 12, 2026 · Editorial policy
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.
What the research on regret actually finds
There is a consistent finding in the psychology of regret that bears directly on this. In the short term, people mostly regret the things they did — the money spent, the awkward decision, the trip that went wrong. But when researchers asked people to look back over a longer horizon, the balance reversed: regrets of inaction came to dominate, and they lasted longer.
The explanation offered is that actions have a bounded cost. You know what the bad trip cost you, you tell the story, it becomes funny, and the mind closes the file. Inactions do not close. The trip you did not take has no outcome, so it stays open and keeps accumulating an imagined version of itself that gets better every year. That asymmetry is the whole argument against “someday”, and it is not a motivational slogan — it is what the data on regret keeps showing.
The cost of a deferred trip is not only money
Deferring reads as a neutral act, which is why it is so easy. Nothing is spent, nothing is lost, the option stays on the shelf. But options in travel decay, and they decay in ways that do not announce themselves.
Some decay physically: the trek, the dive, the multi-day walk at altitude all have a window that closes quietly, usually earlier than people assume. Some decay socially — the trip with a specific person, at a specific stage of both your lives, is not the same trip five years later even if you both still want it. Some decay in the destination itself: places get more expensive, more crowded, more restricted, and a few get harder to reach or close entirely. And some decay in your own life shape, as jobs, mortgages, children and ageing parents narrow the length of absence that is possible. None of these appear on the ledger when you postpone, which is exactly the problem.
How to turn someday into a date
The practical move is to convert an intention into a constraint, because intentions lose to whatever is urgent and constraints do not. In descending order of how well they work: book something non-refundable, book something refundable, tell someone specific you are going and when, put the dates in the shared calendar at work, and finally write it on a list. Only the first two reliably survive contact with an ordinary year.
Two smaller things also help. Pick the date before you pick the details — itineraries expand to fill any amount of planning, and a great many trips die in the research phase rather than the decision phase. And take the smaller version rather than none: four days in the nearest version of the thing you want beats a perfectly planned three weeks that never leaves the document. The trips people regret are almost never the ones that turned out shorter or rougher than planned.
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Written by
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.
