The Didascalicon of Hugh of St. Victor encourages the study of many disciplines in order for the soul to acquire knowledge that aids in the restoration of human nature. However, according to Hugh's epistemology much of the acquired knowledge depends upon sensory qualities internalized as images which distract the soul and cause it to degenerate from its original unity. This essay explores the tension between Hugh's educational optimism and Hugh's epistemological pessimism. After considering and rejecting two unsuccessful strategies the soul might pursue for avoiding degeneration and distraction, we shall utilize Hugh's non-representational conception of cognition to develop a plausible intellectual strategy. We shall also build upon some of Hugh's remarks about music to sketch a model of self-knowledge as a kind of proportionality in the soul.