I am often asked, "How do you decide where you're going next?"
The truth is, there isn't a simple answer. It's equal parts spreadsheet and spontaneity. Put another way, it's the merging of science and art.
For years, I've kept a Google Sheet with five to seven destinations I wanted to visit. Each tab has estimated airfare, hotels, local transportation costs, and a rough daily budget. Every few months I update flight prices, tweak hotel costs, and see which destinations become more—or less—affordable.
This is a throwback spreadsheet. I wish prices still looked like this.
Sri Lanka has been on that spreadsheet for years but has eluded me more than once. Someday I'll take the train across the Nine Arches Bridge.
As an educator, most of my travel happens during the summer, so by spring it’s decision time. I’m not necessarily looking for the cheapest trip. I’m looking for the most adventure for my dollar. That's where the spreadsheet—and my numerical madness—come in.
That's also how I ended up in Barbados last summer: driving on the left side of the road, snorkeling with green sea turtles, and somehow eating an unhealthy number of hot dogs. (That's a story for another day.)
But not every trip starts with a spreadsheet. Some of the best adventures begin because you stay open to opportunities.
When a friend and colleague asks over lunch if you want to help run a basketball camp in Israel, you say yes. When another colleague tells you about an incredible professional development experience they led in Guatemala, you casually invite yourself along the next time they go.
There's an art to creating the invitation.
I don't mean inviting yourself where you aren't wanted. I mean letting people know you're interested. Saying, "If you ever do that again, I'd love to come." Sometimes people assume you're too busy, or that travel isn't your thing, or they simply don't think to ask. A simple sentence lets them know you're game.
More often than not, the worst they can say is no. But sometimes they say yes.
Those weren't places I had planned years in advance. They became part of the journey because I was willing to raise my hand before anyone asked. I've realized that deciding where to go next isn't just about chasing cheap flights or checking countries off a list. Sometimes it's careful planning. Sometimes it's pure serendipity.
The trick is making room for both.
Looking back, almost every memorable trip I've taken started one of those two ways: months of careful planning or a conversation I almost didn't have. Maybe the real answer isn't where to go next. It's staying prepared enough—and open enough—to take advantage of the opportunities when they show up.
