This article chronicles events in the author's secondary education literacy course when she asked students to write in a descriptive, analytical, and reflective way about the experiences that led them to teaching. The stakes were high, and so was the confusion about what it means to write reflectively and how to link such writing to teacher education standards. This forced the author to study her own efforts to encourage reflective practice to discover where the gaps in understanding had occurred and how those gaps might be reduced. The author realized that the only way to know if understanding has occurred is to ask the right questions and then be prepared to adjust her practice accordingly.