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Despite much ignorance (deliberate and accidental) and neglect, pre-modern literature, philosophy, and theology continue to matter greatly for us today. The quest for human happiness is never-ending, and each generation seems to go through the same process. But instead of re-inventing the proverbial wheel, we can draw on most influential and meaningful observations made already in late antiquity and the Middle Ages regarding how to pursue a good and hence a happy life. This paper examines the relevant treatises by St. Augustine and Boethius (late antiquity), and a religious tale by Gautier de Coincy (early thirteenth century). Each one of them already discussed at great length and in most convincing manner how human beings can work their way through false concepts and illusions and reach a higher level of epistemology and spirituality, expressed through the terms “happiness” and “goodness.”