To Shake the Sleeping Self: A Journey From Oregon to Patagonia, and a Quest for a Life With No Regret

Jedidiah Jenkins was a thirty-year-old law school graduate working at a nonprofit when he decided to quit his job and spend sixteen months bicycling from Oregon to Patagonia, the southern tip of South America. Raised in Nashville, Tennessee, by divorced parents who are both famous for walking across America in the 1970s and writing about the experience for National Geographic, Jenkins had spent his twenties following a safe, predictable path and felt a growing panic that time was slipping away. Beneath his career restlessness lay a deeper conflict: He was gay, raised in evangelical Christianity, and struggling to reconcile his sexuality with a faith tradition that condemned it. At twenty-seven, a coworker named Andrew who had cycled from New Jersey to Argentina inspired him with the idea for the trip. Jenkins announced the plan three years early to ensure social pressure would hold him accountable.

Jenkins did almost no physical training and only a week of Spanish study before departure. His mother insisted he not travel alone, and Weston, a charismatic, broke, philosophically intense acquaintance, invited himself along. On August 28, 2013, they dipped their bicycle tires into the ocean at Honeyman State Park in Florence, Oregon, the same beach where Jenkins's parents had finished their walk, and began riding south. They camped under bridges, ate lentils by campfires, and stayed with strangers who passed them along to friends down the coast. In Northern California, they rode through towering redwood forests and crossed the fog-shrouded Golden Gate Bridge. After Weston arranged a meeting with Instagram executives in San Francisco that felt unproductive, Instagram unexpectedly featured Jenkins on its official account, sending his following surging by tens of thousands and transforming the trip into a public narrative.

They continued south through Big Sur and Los Angeles, where a comfortable week with old friends tempted Jenkins to abandon the trip. After crossing the border into Tijuana, the Baja Peninsula proved punishing: extreme heat, dust storms, scarce water, and freezing nights. When Weston's front wheel bent in half, a kind stranger named Miguel took them into his modest home in a tomato-farming community. Jenkins recognized that Weston's frustrating choices had led them to this generous encounter. The peninsula's isolation plunged Jenkins into homesickness and fantasies of quitting.

Cycling through Baja's barren interior, Jenkins narrates his childhood realization of being gay at eight and his years of compensating through humor and deliberate weirdness. In high school, he found belonging among Christian athletes whose Bible study group provided acceptance, but the price was silence about his sexuality. He came out to friends before college, and each responded with love. He made a private deal with God: He would stay celibate unless God sent him a godly partner. At twenty-seven, he attended a meeting of Exodus International, an organization that claimed to change people's sexual orientation through prayer. The experience repelled him, and shortly after, he kissed a boy for the first time at twenty-eight.

After ferrying from Baja to the lush mainland, Jenkins and Weston confessed that they had both been miserable in the desert but had kept silent to avoid discouraging each other. In the surf town of Nexpa in Michoacán, a military operation against the Knights Templar, a local drug cartel, blockaded all roads and stranded them for ten days. In Mexico City, they stayed with local hosts and visited the National Museum of Anthropology, where Jenkins reflected on the history of Spanish conquest. Jenkins recalls a devastating phone call in which his mother called homosexuality an abomination, a conversation they had avoided ever since.

Jenkins flew home to Nashville for Christmas, then reunited with Weston in Nicaragua for New Year's after they agreed to skip Guatemala and El Salvador to stay on schedule. They traveled through Costa Rica and Panama, where conversations about money exposed a growing rift: Weston was nearly broke and framed his poverty as philosophy, while Jenkins resented subsidizing him. In Panama, Jenkins read about Harry Devert, a thirty-two-year-old American motorcyclist who had vanished in cartel territory in Mexico on a trip similar to his own. Unable to cross the Darién Gap, a roadless jungle between Panama and Colombia, they sailed through the San Blas Islands into South America.

In Colombia, Jenkins reluctantly tried psilocybin mushrooms on a mountaintop cattle farm outside Medellín and experienced a euphoric sense of interconnectedness. On a hike near Salento, Weston directly challenged Jenkins's Christian beliefs, asking whether he truly believed Jesus rose from the dead and calling him a coward hiding behind inherited tradition. Jenkins was shaken but not destroyed. His mother flew to Quito, Ecuador, for Easter with his brother Luke and sister-in-law Anna. They watched a Good Friday parade of penitents, and his mother, who had once told Jenkins that Catholics might not be truly saved, was deeply moved by their devotion. When Weston later flew to Hawaii for a wedding and missed his return flight, their partnership ended with a quiet fizzle of texts.

Six friends from Los Angeles flew to Cusco, Peru, to hike the Salkantay trek to Machu Picchu with Jenkins. On the trail, his friend Annabelle confessed she no longer called herself Christian, and Jenkins articulated his beliefs aloud and heard them falter. He interweaves the hiking narrative with the brutal history of Pizarro's conquest of the Incas, drawing parallels between religious imperialism and his own inherited faith. By the end of the trek, Jenkins tentatively adopted the label "mystic-Christian," a faith centered on mystery and experience rather than strict doctrine, feeling something in his old belief structure die and something new begin.

After Machu Picchu, friends Cyrus and Jordan joined Jenkins for a month of cycling through Bolivia and into Argentina before departing. Truly alone for the first time, Jenkins stayed with Laura, an architect in Salta, Argentina, restoring himself through domestic routine. He learned that Harry Devert's dismembered body had been found in Mexico, and the randomness of survival haunted him. His father visited in Mendoza, and friends Parker and Ronnie joined Jenkins for the push into Patagonia.

After Parker and Ronnie left, Jenkins crossed into Chile and began the Carretera Austral, a 700-mile gravel road through southern Chile, cycling alone past fjords, glacial lakes, and evergreen forests. Listening to a podcast about transgender identity, he recognized his own prejudice and underwent a quiet shift toward broader empathy. He reached El Chaltén, Argentina, at the base of Mount Fitz Roy, drank a beer at sunset, and felt calm completion rather than dramatic revelation. He never got on the bicycle again.

Jenkins bused south to Punta Arenas, Chile, where his mother and two friends met him. On his thirty-second birthday, his sixty-seven-year-old mother insisted on hiking the strenuous trail to the base of the Torres del Paine spires in Chilean Patagonia. Jenkins reached the glacial lake beneath the granite towers and felt the journey was complete: not a single epiphany but an accumulated erosion of old certainties and a new allegiance to truth over tradition. On the descent, in pouring rain and darkness, he found his mother still climbing upward; she had made her own summit. They hiked down together, Jenkins guiding with his phone flashlight. When she cried out in fear after losing sight of him, something primal activated in Jenkins: the need to protect the woman whose faith had both wounded and formed him. They reached the lodge after midnight, soaked and spent. His mother whispered that she was proud of him.

In an afterword written six years later, Jenkins reports that he has since fallen in love and had his heart broken. Weston lives in the mountains of North Carolina, and they talk often. His mother has been painting a picture of Torres del Paine for years, promising to give it to him when she finishes, though he suspects she never will. Jenkins states simply that he loves God, and "rarely provide[s] definitions" (317).