In this book, Aaron Simmons takes us on a trip to the mountains to reflect on the meaning of life. In a world too often defined by a quest for "success" that leaves us empty, alone, and anxious, Simmons seeks "faithfulness" outdoors with thinkers and artists from Aristotle to Kierkegaard, Sartre to Anne Lamott, and Kendrick Lamar to Donovan Woods. Simmons invites us to rethink what it means to make choices, take risks, be alone and silent while cultivating friendships, and to find our calling by facing our vulnerability. In the end, Simmons shows that faithfulness is more than a religious concept. It is about living a life of risk with direction.