In this article, the author discusses what acclaimed teacher educator Magdalene Lampert called a "practical dilemma" (1985, p. 181) about managing the classroom. As a Montessori teacher, the author taught with the belief that children need to be independent and empowered. The idea of commanding them to sit, or telling them what to do and where to do it, was not even in the realm of possibility, especially at a school where the author felt expected to portray the ideal image of a Montessori teacher. The author had been trying desperately to redirect, engage, and entice the students to do anything but run in circles--to no avail. The dilemma was made worse by the presence of a student teacher and observers; there was immense pressure to perform, to prove that she was a quality Montessori teacher, but the situation called that into question. The author felt uncertain, insecure, and ultimately pushed to tears. Emotions such as uncertainty, guilt, and stress need to be managed at some point and in some way. In addition to teachers finding self-care that works for them, the classroom dilemma also needs to be addressed. The idea of Montessori teachers today need to be prepared for challenges that may not have been directly addressed in Montessori curriculum. Developing an ability to experiment with different strategies to meet the needs of the students and environment should be included in Montessori teacher preparation and identity.