Thinking metaphorically requires a reorganization of concepts. Reorganization is the essential ingredient for thinking metaphorically. The ability to conceptually reorganize becomes challenged as metaphors are created and comprehended since anomaly or absurdity must be reconciled with previous experiences structured differently. This ability can be characterized as cognitive flexibility and may be the ability that is most often charged to the students by the teaching artist. In this article, the author argues that visual metaphors should be more associated with metaphoric thinking than assigned to an object as a label. He makes an assumption that getting students to think metaphorically, to create new meaning, is crucial to the pedagogical pursuits of teaching artists. With this assumption in mind and to build the argument, he situates a particular class of metaphors, visual metaphors, within an historical and conceptual landscape that argues for their importance as a teaching vehicle for the creation of new meaning. Situating visual metaphors leads to investigating the use and meaning of metaphor in the visual arts and to its place in the teaching practices of artists.