From the Howling Twenties to Redemption with Wing Williams

#198 - A story of wild trails, darker nights, and a love that wouldn’t let go. I sat down with author and long-distance hiker Wing Williams to unpack his “howling twenties,” the constant motion that took him across 49 states, and the quiet rituals that hid a growing addiction. From Mount Washington to the Appalachian Trail and the Pacific Crest Trail, Wing explains how the woods taught him endurance and community while alcohol promised relief from an unseen torment he now names as spiritual warfare.What follows is a candid look at rock bottom: seizures, medical detox, and the moment pride finally broke into surrender. Wing shares why asking for help is the bravest first step, how family showed up when it counted, and why spiritual and medical support must work together when alcohol has become a lifeline and a trap. We also explore the stark difference between hiking with a bottle and living strong in sobriety, the loneliness of being misunderstood, and the humble daily practices that keep recovery honest.Cinereal, Wing’s new memoir, threads these pieces into a story about addiction, faith, and redemption that is both gritty and life-giving. You’ll hear practical insights on recognizing early warning signs of dependency, how long trails like the AT and PCT become blueprints for resilience, and what it means to rebuild identity on purpose instead of performance. If you’ve ever felt lost in the silence after the summit, this conversation offers a handhold: hope is real, healing is possible, and you don’t have to walk alone.If this episode moved you, tap follow, leave a quick review to help others find the show, and share it with a friend who needs to hear that redemption is still on the table.To learn more about Wing and his book check out wingwilliams.com and give him a follow on Instagram @cinerealememoir.Want to be a guest on Journey with Jake? Send me a message on PodMatch, here: https://www.podmatch.com/hostdetailpreview/journeywithjake Xploreum connects you with authentic wilderness expeditions led by trusted local experts. Browse real adventures, book directly with experienced guides, and get $200 off your first trip using code HumanAdventure2026 at xploreum.io/humanadventure.