This article considers David Brooks' recent "New York Times" bestseller, The "Road to Character", in light of Christian thinkers on the connection between virtue and suffering, specifically Dante and St John of the Cross. By putting Brooks in conversation with the Christian tradition, I show how his ideas, specifically his assertion that the mark of character is the willingness to encounter one's weaknesses, can be used by teachers concerned with cultivating virtue and character in their students. I argue that teaching to students' weaknesses, not only their strengths, is a significant way educators can cultivate virtue by helping students to understand their limitations. Students' growth in knowing their limitations and weaknesses is a kind of self-knowledge that points them inward ultimately to help them look beyond themselves and toward lives of service.