For tens of thousands of years, teachers have used stories to promote learning. Today's teachers can do the same. In particular, we can employ Joseph Campbell's "monomyth"--with its stages of separation, initiation, and return--as a model for structuring learning experiences. Within the monomyth, one tempting role for teachers is the sage, but we should resist this temptation. Instead we should acknowledge, and benefit from, our role as tricksters. To do so is to accept and illuminate the dual responsibility of the teacher as both supporter and challenger.