This article advocates an approach for teaching critical and contextual studies in secondary art education based on Wittgenstein's philosophy of language in relationship to meaning as use, custom, rule following, and physiognomy. The references to meaning form four metaphorical points on a compass for directing the will for making judgments about art. The metaphor is apt because a compass makes it possible for a relative novice to get around territory that otherwise would be difficult to navigate. The will-to-knowledge is directed at developing explanations, expressed in the third person, based on ponderable evidence of the context in which the art was made. The will-to-understanding is directed toward making sense of imponderable evidence, in which "I" witness, first-person forms of reporting are emphasized. These various points of view combine transpersonal explanations for contextual studies with personal understandings for critical studies. In this process of coming into understanding, the will is always directed and structured by Wittgenstein's idea of language operating as meaning as use, meaning as rule following, meaning as custom, and meaning as physiognomy, all of which build an understanding of art's complexity and the role that grammar plays in any intentional act when attempting to see it corrected. (Contains 54 notes.)