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Unhooking From Certainty with Megan O'Malley

Welcome to Twice 5 Miles Radio. I’m your host, James Navé. Today, my guest is Megan O’Malley—coach, speaker, and soon-to-be TEDx Asheville presenter—whose work explores our cultural addiction to certainty, control, and the subtle ways “should” shapes our lives. In this wide-ranging conversation, Megan reflects on what it means to surrender without collapsing, to choose agency over fear, and to cultivate wisdom in an age of information overload. We talk about verification, intuition, and the messy middle of creativity—where innovation actually begins. Megan candidly shares her own journey through divorce, career shifts, and personal loss, and how those experiences are shaping her upcoming TED Talk on unhooking from certainty so we can access deeper creativity and connection. Along the way, we wrestle with big questions: How do we know what to believe? What’s the difference between control and agency? Is “should” a tyrant—or a tool? And what does it really mean to embrace the mess? This is a thoughtful, soulful conversation about creative evolution, spiritual intelligence, and the courage to stand in not-knowing long enough for something new to emerge.