Students demonstrate their understanding of art by drawing upon many aspects of their being. Art products are based, in part, upon the student's cognition of the subject, context, techniques, and materials. In addition to the cognitive aspect of art production, the student is also drawing upon his or her creativity, motor skills, emotions, life experiences, personal aesthetic, personal communication skills, and more. In this article, the author discusses how art educators can determine the worthiness of a given work of student art or his or her progress over the course of a school year. As an art teacher, the author is experimenting with methods to evaluate student work so as to be true to the idea that art by its very nature is a personal expression. What she has yet to determine is how to do that while somehow having that evaluation reflect on the efficacy of her teaching. That is the challenge that art teachers face.