I’ve always thought the most memorable moments of a journey are the ones you don’t plan for. You can book the flight, pack the bag, map the route—but the conversation that lingers, the view that humbles you, the stranger who becomes a story—you can’t manufacture that. That’s serendipity’s domain. But here’s the catch: it won’t find you on your couch.
In 1984, I pedaled across Europe with no smartphone, no GPS, and no firm itinerary—just a bike, a vague sense of direction, and a willingness to be surprised. I met people I never would’ve encountered in a car or on a tour bus. I got lost, and in doing so, found places not listed in any guidebook. And once or twice, life seemed to place the right person next to me at precisely the right moment.
That wasn’t planning. That was proximity. Movement. Openness.
Serendipity doesn’t work on demand. It’s allergic to spreadsheets. But if you get yourself out there—on the road, in the world, in the company of others—it tends to show up. Not always, not predictably. But often enough to make it feel like a kind of quiet magic.
So no, you can’t summon it. But you can increase your odds. Show up. Say yes. Take the long way home.
And maybe, just maybe, the moment that makes your whole trip worth it will come walking around the corner—just when you’re least trying to find it.