New York Times bestseller – "Thrilling, tender, utterly absorbing . . . Every chapter shimmered with truth." –Cheryl Strayed From travel writer Jedidiah Jenkins comes a long-awaited memoir of adventure, struggle, and lessons learned while bicycling the 14,000 miles from Oregon to Patagonia. On the eve of turning thirty, terrified of being funneled into a life he didn't choose, Jedidiah Jenkins quit his dream job and spent the next sixteen months cycling from Oregon to Patagonia. He chronicled the trip on Instagram, where his photos and profound reflections on life soon attracted hundreds of thousands of followers and got him featured by National Geographic and The Paris Review. In this unflinchingly honest memoir, Jed narrates the adventure that started it all: the people and places he encountered on his way to the bottom of the world, and the internal journey that prompted it. As he traverses cities, mountains, and inner boundaries, Jenkins grapples with the questions of what it means to be an adult, his struggle to reconcile his sexual identity with his conservative Christian upbringing, and his belief in travel as a way to "wake us up" to life back home. A soul-stirring read for the wanderer in each of us, To Shake the Sleeping Self is an unforgettable reflection on adventure, identity, and a life lived without regret.