The authors review the ancient mentoring relationship in Homer's Odyssey and the mentoring discourse of Socrates. These relationships illustrate the art of inspiring a searching quality in the subject and the angst of the struggle that accompanies perplexity and unknowing. The developmental stages of the mentor and resident in psychiatric training are reviewed. A spectrum of teaching interventions are discussed as they might be perceived by the student. Finally, Plato's "Allegory of the Cave" is used as a metaphor for the art of enlightenment and angst of learning and teaching in the mentoring relationship.