Middle school teachers are not unique in their lack of time to contemplate their profession in any systematic way. Educators could benefit from journal-keeping as a means to reflect on their practice, their attitudes towards what they do in the classroom, and the obstacles they all face in teaching. This article presents excerpt from a teacher's journal exploring topics as gender issues in teaching, teaching methods, and curriculum concerns. Readings from this journal give insights into the dilemmas of teaching in a 21st century middle school.