In our digital age of distance learning, disembodied teaching, and impersonal sermons mediated through a screen, there is a need for pastors and teachers to return to more personal and embodied forms of wisdom for forming souls. Many churches today value relevance over wisdom, mere information over holistic formation. We are nurturing cultures of consumerism and convenience in the church, and there is a need to make the church a Wisdom Culture once again. This doctoral thesis explores the interpersonal dynamics between sage and student in the ancient world. In particular, we examine Jesus among the Jewish rabbis, and Paul among the Greco-Roman philosophers. After building a case for embodied wisdom in education and formation today, and the need for pastors to reclaim the roles of sage, shepherd, and spiritual fathers/mothers, Jeremy offers one preeminent pedagogical practice from the ancient world—letter writing—as a dynamic way for pastors more personally engage and shepherd souls in church ministry today.