The Thought Behind The Route

The Thoughtful Route started as a tool for my own travels.

I wanted a simple way to keep everything I needed in one place: routes, lodging, confirmations, food stops, hikes, driving times, and all the little details that are easy to forget once you're on the road.

Over time, those itineraries became more than just a checklist.

I realized the route itself was part of the experience. The roads you choose, the pace of the trip, the coffee stop before a hike, the extra hour spent in a place you weren't expecting to love. Those small decisions often become the moments you remember most.

The goal was always the same: create a simple itinerary that fit on a single sheet of paper. I'd print it front and back, fold it up, and carry it in my pocket throughout the trip. The itinerary below is one of those originals from an Oregon trip in 2023, complete with handwritten notes and updates made along the way.

I kept refining my itineraries, making them easier to use, easier to update, and easier to share. Looking back, it's probably no surprise. I've spent more than twenty years organizing information, solving problems, and building tools that help people make better decisions.

Eventually, friends and family started asking me to plan their trips.

The Thoughtful Route grew naturally from there.