The authors review the ancient mentoring relationship in Homer's Odyss
ey and the mentoring discourse of Socrates. These relationships illust
rate the art of inspiring a searching quality in the subject and the a
ngst of the struggle that accompanies perplexity amid unknowing. The d
evelopmental stages of the mentor and resident in psychiatric training
are reviewed. A spectrum of teaching interventions are discussed as t
hey might be perceived by the student. Finally, Plato's ''Allegory of
the Cave'' is used as a metaphor for the art of Enlightenment and angs
t of learning and teaching in the mentoring relationship.