In this episode of The WHY Matters Podcast, we lace up our boots for a deeply human look into long-distance hiking, family bonds, and personal transformation. Jessica and her son Largo, share our experience hiking over 2,000 miles of the Appalachian Trail, all while juggling remote schooling, teenage growth, and the realities of life after a decade abroad.
From trail names to trail magic, we dive into what it really means to strip away the noise of modern life and walk, literally, into a slower, more connected way of being. This is a story of resilience, reinvention, and what happens when you step outside your comfort zone with the people who know you best. Whether you're dreaming of the thru-hike life, craving a digital detox, or curious what it’s like to spend half a year in the woods with your teenage kid, this episode is packed with honesty, insight, and a few laughs.
@01:54 Life After 68 Countries – How nomadic travel shaped their worldview
@06:20 School on the Trail – Balancing AP exams and miles
@10:47 Trail Names & Meaning – Meet “Sunshine” and “Captain”
@14:30 The Mental Game – What really gets you through 2,000 miles
@18:01 Family Dynamics – Lessons from a mom-son thru-hike
@22:45 Hiking With WiFi – Making compromises to make it happen
@26:12 Breaking the Mold – Why adventure can’t wait for retirement
@30:00 Final Thoughts – Would they do it again?
Ready to rethink adventure, effort, and what it means to come home? Press play.
Want more stories like this? Check out Zero to Travel for deep dives into nomadic living and purposeful exploration.
Leave us a voice message! Share your thoughts or questions at info@thewhymatterspodcast.com or call 424-442-9295.
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Come travel with us! Our company is owned (and 100% guided) by a family of four full-time travelers. Our passion is building bridges between cultures, fueling personal development, and expanding hearts and minds alongside a community of like-hearted individuals.
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10 years full-time travel with 2 world schooled kids, currently on a sailboat, writing about a travel lifestyle, education, equality & what it’s like to live an unconventional life.
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