Exploring idea and media while developing skills is always an interesting challenge in the middle grades. Often, the daunting task of having to draw a self-portrait turns some students away, so the author set out to create portraits with realistic likenesses while incorporating an exploration of multiple materials and allowing an expressive quality to weave its way into the work. In this article, the author describes how her students proportionally enlarged 8" x 10" self-portraits onto larger sizes of paper. (Contains 1 online resource.)