In the face of imminent death, the 6th-century Roman philosopher Boethius, once a man of fame, power, and fortune, sought to understand the nature of evil and what is valuable in life from the confinement of a prison cell. In his final work, The Consolation of Philosophy, Boethius develops a pedagogical dialogue between the prisoner and the personification of philosophy to contemplate concerning matters of existence. The author creates this dialogue between characters to think clearly and critically in a time of heightened emotion due to the unjust circumstances of his imprisonment. An explicit goal of this essay is to demonstrate the effectiveness of the specific tools Lady Philosophy employs in her instruction and argumentation as she guides the student-prisoner to overcome his self-pity and meditate on broad concepts of humanity. This paper will explore ideas of teaching and instruction by way of analyzing the characterization, form, and rhetorical conventions in Boethius’ famous treatise. This interpretation reveals that the text can be read as a broad teaching tool to model a sort of inner dialogue or self-examination that, despite a conflict, is mindful, resilient, and actively contemplative.