In this article, northeast Philadelphia teacher Daniel LaSalle describes the transition and struggle of leaving his past students and adjusting to a new school. He concludes that the highly contextualized knowledge of how to navigate, and be accepted in, a school culture is not something found in the latest journal articles or books on education. While teachers leave the profession and extracurriculars get cut due to the budget crisis, students suffer. They also suffer when trusted and favorite teachers leave their school for better job security elsewhere, and they begin a new school year even more hesitant to trust the unfamiliar face in front of them.