While quality physical education teacher education requires recruits to be trained in the knowledge, skills, and dispositions necessary for effective teaching, research stemming from socialization theory and role theory indicates that this may not be adequate. Pre-service teachers also need to be made aware of organizational challenges they will face when transitioning into their first teaching position. These challenges stem from the ways in which recruits are socialized into physical education, and are related to the complex, sociopolitical structure of schooling. The purpose of this article is to provide a review of the organizational challenges faced by beginning physical education teachers and to present recommendations for how teacher training programs can better prepare pre-service teachers to meet these challenges. The discussion includes both general and specific strategies that can be implemented to provide pre-service teachers with the knowledge and skills necessary to enhance their ability to navigate life in the sociopolitical contexts of schools. Preparing students for the realities of school life should correspond with a decrease in reality shock and the washout effect.