Jesus didn’t promise his early disciples a life of luxury and ease. Instead, he told them they would have to let go of pretty much everything in order to follow him. The early monastics pared their life down to the barest of essentials out in the deserts of Egypt and Syria. Beloved St. Francis of Assisi let go of his prospects as a middle-class Italian cloth merchant and pledged his allegiance to Lady Poverty instead. Why? Why does letting go seem to be such a necessary element in the equation of transformational spirituality? One answer is as simple as it is painful: because if life inevitably entails loss, and if true spirituality is about fully embracing the (often messy) reality of life, then any authentic spiritual path must make room for loss. Otherwise, spirituality really is just an opiate for the masses or a form of bypass, leading us away from life’s mystery rather than into the heart of it.