Rohr deepens his theme on the importance of suffering in his examination of loss and its role in initiation. While modern culture may interpret loss as a terrible setback, Rohr argues that such experiences are the beginning of people’s most important journeys: The initiation into the second half of life. According to Rohr, being challenged by an obstacle or loss forces people to release their ego and begin to operate on the soul level. He feels that this process is reflected in cultural rituals and myths around the world. He explains, “Every initiation rite I studied worldwide was always about dying before you die. When you first discharge your loyal soldier, it will feel like a loss of faith or loss of self. But it is only the death of the false self and is often the very birth of the soul” (31). He urges readers to refuse to remain stagnant, and to instead embrace letting go of what feels familiar when challenged to go beyond one’s comfort zone.

Rohr depicts paradoxes and contradictions as an inherent part of life which only mature thinkers can really grasp. By rejecting the reality of paradoxes, people stay trapped in the dualistic, rigid thinking characteristic of the first half of life. This can lend itself to judgmental and exclusionary thinking. He argues, “Our Western dualistic minds do not process paradoxes very well. Without a contemplative mind, we do not know how to hold creative tensions. We are better at rushing to judgment and demanding a complete resolution to things […] This is not the way of wisdom” (23). As such, Rohr encourages the reader to recognize the many paradoxes of life, Jesus’s teachings, and their own spiritual journey. He urges readers to cultivate more tolerance of mystery and nuance instead of demanding black-and-white answers.

The author laments that many people, Christians included, too easily become entrenched in rigid belief systems which encourage tribal or fundamentalist perspectives. He feels that this leads people further from God’s message of radical acceptance, forgiveness, and inclusion. He connects exclusionary thinking to the cultural conditioning that many people receive that prompts them to prioritize their own religion, country, or other group over the communal whole. He explains, “It takes a huge push, much self-doubt, and some degree of separation for people to find their own soul and their own destiny […] To move beyond family-of-origin stuff, local church stuff, cultural stuff, or flag-and-country stuff is a path that few of us follow positively and with integrity” (52). By rejecting this rigid thinking, Rohr believes that people will be better able to extend acceptance and compassion to everyone, emulating Jesus’s example. He therefore urges readers to reflect upon what rigid habits of thought they might be clinging to out of habit, urging them to reassess and think for themselves even though it may mean letting go of some old habits and beliefs.