This project examined the many pictures of solids added to the margins of Macrobius's fifth-century Commentary on Cicero's Dream of Scipio in light of contemporary geometric practice around the turn of the first millennium. At this time, geometry was less a body of axioms and precepts to be demonstrated and memorized and more a tool that flexed and sharpened the mind, thus heightening the ability to comprehend worldly and divine things. This ability was not considered a native talent; it required teaching and practice. The definitions of geometry's so called elements—points, lines, planes, and solids—in the Commentary and elsewhere, provided opportunities for such practice, that is, for exercising the mind’s eye. Given this, the pictorial annotations added to these definitions are perhaps best understood as goads to the intellect and traces of an otherwise ephemeral activity. Picturing as Practice considered the graphic strategies adopted by annotators along side the didactic tactics and tools employed by medieval masters in the classroom seeking to cultivate the intellectual eye.