How to Unplan
There was a time, not long ago, when booking flights felt like a form of self-care. I would sit with tabs open, measuring layovers like puzzle pieces, lining up departure times with sleep schedules and sunlight. The choices felt precise. Refined. A satisfying kind of order would settle after clicking the final button. The destination was chosen. The plan was made. Some small corner of the future had been neatly put away.
And yet, more and more, I notice how rarely life goes as planned.
It’s not subtle. Looking back on the past few months, three out of every four flights I book, I don’t take. I cancel them. Change them. Move them to a different day, or a different city altogether. The destinations shift. The timelines move. The ideas that once felt so certain become soft around the edges.
At first, it felt like a practical problem. Something to optimize. Better forecasting, clearer communication, more decisive decision-making. But something deeper kept nudging. An unease that this wasn’t about poor planning at all. This was about the need to plan in the first place.
There’s something seductive about having a plan. It gives the illusion of direction, of preparedness, of control. When a flight is booked, there’s less room for doubt. When dates are in calendars and confirmations in my inbox, I can tuck them away. A kind of quiet knowing: I’ve done it. The future is accounted for.
But it never is, really.
I used to believe planning was practical. Economical. That flights were cheaper when booked ahead, that being early meant being smart. It turns out, that’s not always true. Especially in places like Europe, where price protections exist and common routes are well-traveled. Waiting isn’t necessarily more expensive. Sometimes, it’s quite the opposite.
But even when it is more expensive, the trade-off has changed.
There’s a cost to locking my future self in, from the vantage point of today. To deciding where I’ll want to be, what I’ll want to do, before I get there. The emotions I use to justify my plans—the logic of saving money, of protecting my calendar—are often just that: justifications. I find myself talking logic to defend a deeper need for certainty.
And I’ve started to notice how emotional that need really is.
Oliver Burkeman, in “Four Thousand Weeks,” writes that planning is how we try to control the future. I keep returning to that phrase. It makes me smile, partly because of how innocently true it is, partly because of how absurd it becomes once seen clearly. Of course the future cannot be controlled. Not entirely. And more importantly—why would I want to?
What felt like effective travel planning slowly began to feel like something else entirely. A kind of performance. A script that became harder to follow as life’s tempo shifted. I began to wonder if the pattern was pointing to something deeper.
Maybe the canceled flights weren’t mistakes after all. Maybe they pointed to something right.
So much of the inner work I’ve done in the last decade—through meditation, therapy, personal reflection—has been about cultivating awareness. Presence. Closeness to reality. And that decisions made from presence will feel more grounded than decisions made from prediction.
Maybe all these changed plans are not a failure to commit, but a growing capacity to listen. A willingness to say yes to what is happening right now, rather than what was planned.
There are still moments when planning is necessary. Especially when involving others: family trips, group dinners, business meetings. When more people are involved, more coordination is needed. That’s real. But when it’s just me, or just my partner and I, that need softens.
There’s more room to respond to the present. More room to let the present shape the plan, rather than forcing the plan onto the present.
Sometimes that means booking a flight only a few days before leaving. Sometimes that means not booking at all. And sometimes it means changing something that, from a practical lens, "should" have worked, but from a deeper knowing, no longer does.
It might cost more in fees. That’s okay. It’s a small price to pay for closer alignment to my reality.
The shift, I’ve realized, is from control to freedom. Not freedom as chaos, but as responsiveness. Gentleness. Trust. The trust that life can be met in real time, not always prearranged. That clarity doesn’t always come months in advance. Sometimes it arrives on the morning of departure.
And in those moments, I’d rather be free than prepared.
The map still matters. But the roads that get drawn now are softer lines. They can be erased. Rewritten. Or simply walked, one breath at a time.
I don’t always know exactly when or where I’m going anymore. But I feel closer to wherever I am.
And that is how I learned to Unplan.
