Although professionals begin their physical education teaching career in an urban setting with excitement and pride, many of them choose to leave urban schools in their first five years of teaching and seek employment in the suburbs or in rural settings or even abandon the teaching field altogether to pursue a different profession. While searching for an explanation, it may be helpful to explore the viewpoints of experienced urban teachers. Their thoughts could help new professionals to experience the long-term rewards of teaching urban physical education. This article describes four considerations of teaching physical education in urban settings that can help teachers succeed: know the challenges, acknowledge successful beliefs and practices, value teacher-directed instruction, and maintain a professional demeanor.