Tom shares a conversation with his brother, Andy, while on a backpacking trip in the Grayson Highlands of Virginia. They talk about how the comforts of modern living can trap you in a cycle of discontent. Andy presents his theory that most people default to following the path of least resistance - the comfortable, easy path - and that the best way to break out of it is to challenge yourself with something that scares you a little bit. He shares stories from his 15-year career as an outdoor professional and how his meandering path has ultimately led him through jobs in education and law enforcement before taking a leap of faith to his dream job of farming.