When confronted with the ineffable, poets turn to metaphor. Similarly, philosophers of education often employ metaphors and analogies to explain the functions of education (e.g., schools are families, machines, prisons, etc.), and, more specifically, the role of educators. Teachers have been described as prophets, liberators, and midwives, which, on the surface, suggests that the profession of education involves a range of meanings and interpretations. This may also indicate that there is an unspeakable quality to the phenomenon of education. These metaphors, while cognitively clear, are conceptually opaque. What does it mean for education, or for educators, that discussion of this work so often turns to analogy? Moreover, what can be made of the varied meanings of these metaphors? To answer these questions, this paper will consider several key pedagogical metaphors: the teacher as prophet, liberator, text, physician, and entertainer. These educational metaphors present a philosophical challenge. Language, especially figurative language, that philosophers of education employ betray conceptual preferences. Reflecting on each of these metaphors reveals the insights and limitations of each concept as a tool for philosophically investigating education. However, looking over these metaphors will lead to the conclusion that education, like theology, must take an apophatic turn to penetrate its deepest mysteries. The apophatic exercise, familiar to mystics and theologians, seeks understanding from negation. While each of these metaphors will illuminate teaching in some way, denying these metaphors, paradoxically, will reveal even more.