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How I Learned When to Quit, the Really Hard Way

Lost and alone piloting a small plane, I screwed up, pondered death, and learned to reckon with failure

Robert Roy Britt
Wise & Well
Published in
13 min readJun 24, 2024

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Flying over unfamiliar mountainous terrain in Northern California on a hot summer afternoon, tossed about by developing thunderstorms in my tin can at 10,000 feet, alone, hopelessly lost and utterly unprepared for the challenge, I pondered, ever so briefly, piloting that little Cessna into a mountain rather than enduring for another minute the terrifying ride I’d gotten myself into, a perilous journey that seemed certain to end badly regardless. Either a powerful downdraft would slam me to the ground, or the clouds would envelop me in zero visibility, or the unbearable turbulence would shear the wings right off.

That was the moment when I realized why my Dad had been so worried about me. Given my arguably flighty nature and a tendency to take shortcuts to get things done, he guessed, but never said out loud, that I probably had no business trying to become a pilot.

That was also the moment I realized it’s OK to admit when you’re in way over your head, on a path in life that makes no sense given your skill set and temperament. When the endeavor you thought would be enjoyable becomes anything but. It was the moment I realized that sometimes…

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Robert Roy Britt
Wise & Well

Editor of Aha! and Wise & Well on Medium + the Writer's Guide at writersguide.substack.com. Author of Make Sleep Your Superpower: amazon.com/dp/B0BJBYFQCB