Chapter 5, “The Wilderness,” continues the metaphor developed through the first few chapters. After the “valley,” in which an individual suffers a prolonged period of deep and transformative suffering, comes a self-propelled journey into the wilderness. This is a wilderness that needs to be traversed before ascending the second mountain. Brooks believes that poets have perennially referred to a three-step process of moral growth toward the advent of wisdom: a period of suffering in which the ego-self is disrupted followed by an isolated period of deep self-reflection that then, finally, yields the insight of second-mountain communitarian zeal and love.

Brooks does not assume the period of self-reflection will spontaneously happen. An individual must actively go out into the wilderness. “The right thing to do when you are in moments of suffering,” Brooks writes, “is to stand erect in the suffering” (38). This resoluteness is the path forward. Brooks believes that the solitude imposed on the individual at this stage of their journey yields a different perspective on time, which he calls “kairos time” (40). This period is defined not by the active pursuit of a goal but rather by the resolve to listen to what life is asking of one and a growing appreciation for the fact of life.