The ancient Greek philosophers were bold in asking questions like “Who are you?” “What are we here for?” Young children often naturally ask these big or radical questions as a way of trying to understand the world (Hart, 2003; Matthews, 1980). But in schools, curricular demands and the emphasis on one right answer, often works against depth of exploration (Hart, 2001a). The result is that “neither teachers nor students are willing to undertake risks for understanding; instead they content themselves with correct answer compromises” (Gardner, 1991, p. 150). But pondering big and radical questions, what Tillich (1951) named ultimate concerns, has the capacity of opening to unexpected insight. Using the intellect in this way to go beyond intellectual understanding is described in a variety of traditions (see Rothberg, 1994). In the classroom we might pose and invite questions on: