Chaos Is a Travel Strategy
Why the trips you don’t plan are the ones you remember
Ooops, mea culpa, so we missed a week. Why? Because I’ve been traveling. Obvious, right? Who woulda thunk? Which actually leads perfectly into the point that I want to talk about this week.
A few weeks ago, we talked about the idea of the “perfect trip” and how it doesn’t really exist. Perfect isn’t something you plan. Perfect is the trip you actually take, with all its imperfections, delays, surprises, and randomness. And sometimes, the best trips are the ones that barely resemble a plan at all.
As I posted earlier, I had a gap of about a month between trips recently. Not long enough to settle down and get “boring”, but long enough to get restless. So I did what any rational person would do… I booked 10 days bouncing around the Caribbean on small planes, mostly just to avgeek and see places I hadn’t been before.
Do I like heat and humidity? Not in the least. Still don’t. But you know what? I had a great time.
That trip reminded me of something simple that we all too often overlook in life: you don’t need the perfect conditions to have a great experience. You just need a reason to go…or at least a reason to get the gears in motion…
So, let me illustrate just a bit more what I mean. A few months back, I committed to a couple of events. Each one spaced out just enough that they could have easily been separate trips. But then the thought crept in: what if I just…connect them? And that’s how the next two months turned into one long, slightly ridiculous, very unplanned adventure.
So, this upcoming trip. It starts in Portugal, where more than 100 of the roughly 500 people who’ve been to every country are meeting for lunch. The largest gathering of “every country people” ever. But can I really go all the way to Portugal without finishing the regions of Spain and Portugal I still have left?
Of course not. So I’ll head over a couple of weeks early.
A week later, I’ve got a travel conference in Brazil. Conveniently, Portugal and Brazil are very well connected thanks to historical ties, so that part basically planned itself.
Then some friends mention they’re doing a 10-day trip after the conference. Easy decision. Then I start thinking…while I’m already in Brazil…why not hit a few more regions?
And that thought snowballed into this:
Eventually, that idea stretched all the way to the Amazon. Then Colombia. And beyond that…we’ll see. Did I “plan” any of this?
Not really. Am I excited for it?
Absolutely.
Will it be chaotic? Without a doubt.
Will things go wrong?
Most likely….But that’s kind of the point.
Because the trips you remember aren’t the ones that went exactly according to plan. They’re the ones where something unexpected happened. A place you almost didn’t go. A conversation you didn’t see coming. A detour that made no sense at the time but somehow became the highlight.
Like Abyei.
If you had asked me ahead of time whether I wanted to go there, I would have asked you where it was. And why I’d want to go there. Maybe overthought it. Maybe talked myself out of it.
Instead, I went…And it ended up being one of the most memorable experiences I’ve had.
Then…there’s St. Pierre and Miquelon.
A Europe trip fell through. Plans changed. Instead of forcing something else, I looked at a map and thought, “Why not here? Why not now?”
So I went….And then ended up doing Europe anyway.
You see, that’s the thing that happens when you stop “planning” and start “living.”
You can follow the standard script. Hit the same top 10 cities everyone else goes to. Optimize everything. Plan it perfectly. Or you can pay attention to the random ideas, the offhand suggestions, the places that weren’t even on your radar five minutes ago… and see where they lead.
Sometimes the best trips don’t come from a plan. They come from curiosity. From restlessness. From saying yes before you’ve had time to talk yourself out of it.
The Bottom Line
You don’t always need a perfect plan. Sometimes, throwing a few ideas at the wall and seeing what sticks creates something far more interesting than anything you could have designed in advance.
The trips you take on a whim, the ones that don’t quite make sense, the ones that feel a little chaotic…those are often the ones that stick with you the longest.
Over to You
What’s a trip you took that made absolutely no sense at the time… but ended up being unforgettable? And if something like that popped up tomorrow…would you say yes?