Unlearning To Fly: From Childhood Dreams To Cockpit Realities With Captain Russell Roberts

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Today, I sit down with Captain Russell Roberts — a seasoned pilot, author, and adventurer — where we explore his lifelong obsession with flight, beginning with his earliest memories upside down in a cockpit, to navigating the complex world of airline careers, toxic leadership, and personal identity.

Mr. Roberts shares stories from his memoir Unlearning to Fly, giving us insight into growing up in a chaotic household filled with big dreams, addiction, and religious upheaval. We talk about how his father’s addiction to alcohol and religion shaped his childhood, and how aviation became the one consistent thread holding his life together.

We also get into the heart of father-son dynamics, the painful loss of Christmas due to Jehovah's Witness conversion, and what it means to unlearn childhood conditioning in order to pursue your own truth. Mr. Roberts opens up about the heartbreak of missed opportunities — including the chance to own a regional airline — and the greater lesson of returning to your primary dream.

From toxic leadership in the airline industry to what it’s like landing planes in tropical storms with no backup airfields, this conversation dives deep into both the technical and emotional turbulence of a life in flight.

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