This article examines the underlying modern-day assumptions about curricular objectives and the meaning of education by inviting readers to consider the ancient, historical relationship between shamanism, shamanic experience, teaching, and education. Where academic literature on this topic most commonly points to the similarities between teachers and shamans, this article focuses rather on more compelling affinities between shaman-apprentices and our own teenage students, as well as on the associated problem of there being so few shaman-teachers who might lead students on their own shamanic soul-journeys. Finally, connecting shamanic "techniques of ecstasy" to the philosophic "art of dying," I suggest that our best hope of offering our students a truly transformational education is to ourselves embark upon such philosophic journeys after self-knowledge; only by engaging in the shamanic-philosophic "art of dying" might we serve as genuine guides for the shaman-apprentices who await instruction and are eager for shamanic descent or "katabasis".