#157 - John Calabrese, Ultra Runner, Dad and Caregiver

In this episode, we dive deep with John Calabrese—ultrarunner, Navy veteran, caregiver, and single dad. From military life during 9/11 to battling addiction and finding new purpose through caregiving and the ultrarunning community, John shares raw, funny, and deeply moving insights on what it means to survive, adapt, and keep showing up.He opens up about parenting through guilt, hallucinating Pikachu during 100-mile races, and why running won’t fix you—but it might introduce you to the people who can help. Whether you’ve been through a divorce, battled addiction, or just want to understand why some of us chase pain on purpose, this episode is a testament to resilience, real talk, and rediscovering peace one mile at a time. Plus: Why the Barkley Fall Classic is both ridiculous and irresistible, how caregiving changed his life, and why sleep might be the real finish line.John’s IG: https://www.instagram.com/breezytrailhead/SQ Socks: https://stupidquestions.show/pages/sq-merch SQ Newsletter: https://stupidquestions.show/pages/newsletter-signup