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HBO and The Ringer's Bill Simmons hosts the most downloaded sports podcast of all time, with a rotating crew of celebrities, athletes, and media staples, as well as mainstays like Cousin Sal, Joe House, and a slew of other friends and family members who always happen to be suspiciously available.
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In this episode, I speak with Dylan Monaghan, engineer, pilot, linguist, digital nomad, and author of Singlethreading. Dylan’s life is a study in reinvention: from a childhood in the Virgin Islands to an elite school in White Plains, from the discipline of the U.S. Air Force to the creative freedom of Japan. His story moves across cultures and identities, and somehow he has stitched these chapters into a coherent, deeply intentional way of living.
We discuss the interplay between discipline and curiosity, and Dylan’s awakening to the idea that you are not your brain. He explains how the autonomous parts of the mind can be retrained and rewired, reshaping our perception of the world itself.
We end with a reflection on identity, legacy, and what remains when all the titles labels fall away.
Recorded on 9 October 2025.
Connect with Dylan on LinkedIn at linkedin.com/in/dylanmonaghan. Dylan's book, Singlethreading, is available on Amazon: amazon.com/Singlethreading-Just-Thing-Doing-More/dp/1961513013.
Instagram: @at.the.coalface
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