This article aims to recover the foundational importance of training in ascesis for Christian education. For early Christian pedagogues such as Basil of Caesarea and John Chrysostom, education was seen not so much as the transmission of information as it was an invitation to a life of virtue and faith; to this end they especially encouraged teaching that would promote an ascetical lifestyle and therefore greater communion with God. By examining two key patristic texts connecting pedagogy and asceticism, this article outlines an approach that can enable modern Christian teachers to engage their students with ascetical practices that will contribute to their spiritual formation and counter-cultural witness.