Wisdom: Apprenticing to the Unknown and Befriending Fate is a lucid account of such an apprenticeship. The work’s major theme is: You can’t get life right; and if you allow, life may get you right. Efforts to get life right—including the Spiritual Bypass, the Intellectual Bypass, the Psychological Processing Bypass, and the Trivia Bypass—are debunked as alleged detours around life’s mystery, unpredictability, and insecurity. The work offers a unique developmental model describing how wisdom evolves as we allow defeat to interrupt the ego’s claim to sovereignty, preparing us to reconcile life’s inevitable dominance. We can then begin to live the question: What is life asking of us? Further maturation of the apprenticeship happens as we live the question: How do we confirm what truly matters? The target audience is composed of those who refuse to believe that aging means accumulating years while slipping into mediocrity, massaged by cocktails and playing golf. My work continues to reveal a population approaching middle age who are disillusioned with dominant cultural understandings of aging. They want to believe that aging is not simply about escaping an unfulfilling career and experiencing mental and physical decline. This group will greatly benefit from the work’s lucid account of how to construct a personal epistemology, or what it means “to learn about how to know.” The text introduces the notion of good knowing, which avoids branding a fact with certainty. The reader is encouraged to commit to knowing the knower, in regard to biases and psychological defenses, welcoming ambiguity and ignorance. The target audience further encompasses those reaching retirement age who want to believe that their life experience is not limited to a series of personal and professional victories and defeats. Rather, they wish to leave behind a legacy as a final offering, embracing a life well-lived while feeling prepared to leave this earthly plane. The aging apprentice is inspired to acquire an artifact symbolic of some early driving force that rendered power in the name of adventure and ambition. Seven stages of development are examined, leading from the driving force of ambition to the driving force of discriminating wisdom. With less to prove, grace comes to the aging apprentice, interrupting a sense of urgency. Gratitude reconciles us with grace, morphing into the eyes of mercy, as the aging apprentice now knows the true name of home.