Stop Optimizing. Start Traveling.
Planning gets you there. Presence lets you experience it. ⭐⭐⭐
I have a dirty little secret I need to share: I love planning trips.
…but no, not like “normal” people love planning trips. Not just booking flights and hotels, but really planning them. Comparing airlines and potential routes. Reading about neighborhoods. Deciding whether three nights is enough or if I should make it four. My spreadsheets often have spreadsheets. I genuinely enjoy the process, and after traveling to every country in the world, I’d like to think I’ve gotten reasonably good at it.
And to be fair, planning matters. You should probably know how you’re getting there. Having somewhere to stay that first night is usually a wise move. A little research can keep you from missing something you’ve always dreamed of seeing. Logistics reduce stress, and less stress usually means a better trip.
But here’s the thing…once you’ve landed, made it through immigration, dropped your bags at the hotel, and stepped outside for that first moment of exploration, most of that planning is over. The flights have been flown. The hotel has been chosen. The itinerary has done its job.
That’s when the trip actually begins.
From that moment on, your experience is shaped less by the decisions you made months ago and more by variables you never could have controlled in the first place.
The weather. Your mood. The people you meet. The waiter who insists they no longer have that dish you’d heard so much about. The musician playing in the square you hadn’t intended to walk through and asking for change. The museum that’s unexpectedly closed. The conversation that starts because someone overhears you trying to order in their language and offers help. The wrong turn that ends up being exactly the right one.
Those variables are impossible to plan for.
They’re also the reason I travel.
I was reminded of this on my run this morning.
It was raining, so the sidewalks were full of umbrellas. What surprised me wasn’t the weather (it’s winter in Brazil after all) but how many people seemed completely disconnected from where they were. Heads down. Eyes fixed on their phones. Umbrellas tilted so low they couldn’t see more than a few feet ahead. Several times I had to dodge people who never once looked up. Had I been doing the same thing, we almost certainly would have collided.
As I was thinking about what I wanted to write today, it struck me that travel can be exactly like that.
We spend weeks planning a trip to somewhere extraordinary, then experience it while looking down at a screen. We worry about getting to the next attraction before we’ve really experienced the one we’re standing in. We obsess over checking things off a list while missing the life happening all around us.
Ferris Bueller understood this long before social media was ever a thing.
“Life moves pretty fast. If you don’t stop and look around once in a while, you could miss it.”
It’s a great line because it isn’t really about life. It’s about paying attention and being present.
Some things are impossible to miss. A giant crab overlooking the beach in Aracaju. An enormous iguana in the middle of a park in Macapá. A caterpillar the size of a bus. A tree in Lençóis that seems to have decided growing sideways was a perfectly reasonable life choice.
Those things don’t require much effort to notice…however, the moments that matter most usually do.
They’re the old men arguing over a game of chess in the park outside a bakery. The woman who hears you struggling through a few words of Portuguese and gently teaches you a better way to say it. The tiny neighborhood bar you duck into because it started raining. The family celebrating a birthday at the next table who somehow ends up inviting you for one too many rounds of celebratory cachaca.
None of those experiences appear on anyone’s “Top 10 Things to Do.”
Yet years later, after most of the trip is a distant memory, they’re always the stories I remember best.
I sometimes wonder if we’ve convinced ourselves that a perfectly planned trip is automatically a better trip. Maybe this is why some people are so enthralled by AI: the more you can plan and schedule (their reasoning goes) the “better” your trip is ultimately going to be.
A well-planned trip gets you to the right place. It makes the logistics smoother. It gives you confidence that you won’t miss something that’s genuinely important to you.
But after a certain point, more planning doesn’t improve the experience. More presence almost always does.
Looking up instead of down. Leaving room in the schedule to wander. Sitting in a park for half an hour without feeling guilty that you’re “wasting” time. Talking to the person next to you instead of checking what strangers on the internet think you should do next.
Travel isn’t a project to complete.
It’s an experience to notice.
So yes, keep planning. Book the flights. Reserve the hotel. Read enough that you understand where you’re going and why it matters. Then, when you get there, let go a little. Leave room for the variables.
Because the flights only get you to the destination.
The real trip begins after you arrive.
Thanks for another insightful post. Methinks think you could start a business helping people plan trips😀.
I agree that being present is so important, and also being flexible. So many times, we are en route somewhere on our planned itinerary, when we come across something which is not on the list, but we explore that and find that it was the most fun part of the day!
Keep these gems coming! 🙏🏾