Most people over-plan trips into anxiety or under-plan into chaos. Josh and Ashley Negron share what 17 years of travel — from a snowed-in Colorado cabin to Italy and Alaska — actually taught them.

Travel is one of the things people most want to do more of and feel least equipped to plan well. In this episode, Josh and Ashley break down how they've made travel a real, recurring priority: how they budget for it every month, how they navigate two completely different planning personalities, and the hard lessons from trips that went sideways.

The core insight is simple but easy to miss — identify the purpose of a trip before planning anything. A rest trip and an adventure trip require completely different approaches, and blurring that line is where most travel stress originates. They also get into why over-planning can turn an e ...