This article is a republication, by permission, of a chapter of Arthur M. Melzer’s book Philosophy Between the Lines: The Lost History of Esoteric Writing (University of Chicago Press, 2014). The book explains four purposes or motives to esotericism: defense, protective, pedagogical, and political. The present article is devoted to pedagogical esotericism, in which a writer uses puzzles, riddles, contrarieties, conundrums, indirection, obscurity, and so forth, to induce the reader to richer understanding. Melzer writes: “Just as education must begin by addressing the student where he is, so, as he learns and changes, it must stay with him. The internal or dialectical critique of received opinion takes place not in a single stroke but in a series of successive approximations to the truth, each of which will seem in its time to be the final one.” And: “if the world is composed of appearance and reality, of a surface and a depth, then a book that consciously imitates that structure might best prepare one for comprehending the world.”