Chris Jester: "Common People Do Uncommon Things"

Chris Jester didn’t start out as a sailor. He started as a planner—on a traditional path, building a career inside structured systems, doing what made sense. But underneath that was a quieter pull toward something else: travel, freedom, and a life that felt more aligned with how he actually wanted to spend his time.That tension came to a head around 30. Chris and his wife made a decision most people only talk about—they walked away. They sold what they had, left their jobs, and set out to travel the world. When that plan was immediately disrupted by an unexpected pregnancy, they didn’t retreat back to safety. They adjusted. They kept going. And in that decision, something shifted—from planning life to actually living it.Over time, that mindset became a way of operating. Chris built a business around sailing, but more importantly, around helping people experience something they’ve been putting off. His philosophy is simple: extraordinary lives aren’t reserved for extraordinary people. They’re built by ordinary people willing to take a different path, set bigger goals, and follow through on them.At a time when many people feel stuck between stability and something more meaningful, this conversation offers a grounded reminder: you don’t need to wait for permission. The life you’re imagining is often on the other side of a decision you’re avoiding.What You’ll Learn• Why major life shifts often happen around moments of tension or transition• How taking risks can lead to clarity, not chaos• The role of travel in expanding perspective and identity• Why kids adapt faster than adults—and what that reveals about fear• How entrepreneurship and lifestyle design are deeply connected• The concept of “big, hairy, audacious goals” and why they matter• How to think about your life trajectory at key inflection points• Why “just doing it” is often more important than overplanningAbout Chris JesterChris Jester is an entrepreneur and co-founder of SailTime, a company that helps people access sailing and boating without the traditional cost and ownership barriers. Over the past two decades, he has built multiple businesses while designing a life centered around travel, family, and experience. His work reflects a belief that meaningful living comes from intentional choices, not default paths.About Extraordinary StoriesExtraordinary Stories explores the ideas, people, and experiences that shape extraordinary lives.Hosts Forbes Shannon, Christine Butler, and Aaron Bare sit down with entrepreneurs, thinkers, creators, and leaders to uncover the moments that changed how they see the world.