The first term of any preservice teacher education program can be challenging for students in many ways, and learning to read and write in a scholarly way is one potential challenge. This article chronicles events in my secondary education literacy course when I asked students to write in a descriptive, analytical, and reflective way about the experiences that led them to teaching. The assignment was to be forwarded to potential cooperating teachers seeking interns in their classrooms. 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 me to study my own efforts to encourage reflective practice to discover where the gaps in understanding had occurred and how those gaps might be reduced. The self-study experience was enlightening, and I now realize that I can assume nothing about student understanding. The only way to know if understanding has occurred is to ask the right questions and then be prepared to adjust my practice accordingly.