The Solo Travel Playbook

Jason Kyser is a travel writer and pre-trip planning coach who helps nervous first-timers replace "someday" with a departure date. For ten years he worked in event logistics, building the detailed operational plans behind conferences and large-scale productions, where he learned an unglamorous truth: the events that look effortless are the ones with the most preparation behind them.

That insight followed him into travel. His own first solo trip—a ten-day journey through Portugal he'd postponed three times—was supposed to prove he wasn't the traveling kind. Instead, it revealed that his anxiety had never really been about the road; it was about the unknown. The planning system he built for that trip became the foundation of The Solo Travel Playbook, and his writing since then has focused on one conviction: confidence is something you construct, step by step, long before you leave.

Jason has since solo-traveled to more than twenty countries, developed planning workshops for first-time travelers, and built a popular newsletter for people who want to see the world but keep talking themselves out of it. His approach is practical and warm: research reduces fear, preparation builds momentum, and a good plan is what makes spontaneity possible.

He lives in Portland, Oregon, with a perpetually half-packed carry-on and a map of his next destination taped to the fridge. When he's not writing, he's usually practicing what he preaches—alone at a café counter, ordering with confidence in a language he's still learning.