Homeless by Choice: Redefining My Why

In this soul-spilling solo episode, I get honest from a borrowed cabin (and even more borrowed fishing hat) about why I gave up my home, comforts, and stability to chase a 40+ day goal on the Appalachian Trail. This isn’t just about trying to set an FKT—this is about redefining why we go after anything in life. I break down what it means to pursue something uncertain, unplug from the chaos, and find the rawest form of purpose in a world drowning in notifications, optics, and comparison traps. From unexpected homelessness to deep reflections on fear, failure, self-worth, and the primal joy of moving through wild places, this episode is a deep dive into what motivates me—and maybe what can motivate you too. No pretense. No performance. Just truth, vulnerability, and a reminder that trying is enough. Plus: gear talk, sponsor love, and why I might be cramping somewhere on the AT as you listen. Brought to you by: Janji. (wearing the AFO Ultra Shorts right now) Garage Grown Gear CS Instant Coffee Chapters 00:00 Introduction and Personal Journey 03:14 The Importance of Defining Your Why 06:05 Embracing the Challenge of the Appalachian Trail 08:49 Finding Pride in Personal Goals 12:08 Overcoming Fear and Embracing the Unknown Support the show: patreon.com/freeoutside Subscribe to Substack: http://freeoutside.substack.com Support this content on patreon: HTTP://patreon.com/freeoutside Buy my book "Free Outside" on Amazon: https://amzn.to/39LpoSF Email me to buy a signed copy of my book, "Free Outside" at [email protected] Watch the movie about setting the record on the Colorado Trail: https://tubitv.com/movies/100019916/free-outside Website: www.Freeoutside.com Instagram: thefreeoutside facebook: www.facebook.com/freeoutside