Revision with unchanged content. A principal making the transition from one school to another experiences a new level of complexities and unique administrative challenges. This is a naturalistic study utilizing autoethnography as the research methodology which greatly facilitates an understanding of the processes of transition. Each school and each administrative district has its own unique culture and environment. In addition, the challenges of being an effective instructional leader, manager, and learner change as the overriding culture, and the demands on schools and educational curriculum change. These external demands, and the uniqueness of each subculture require the principal and administrator to be skilled and well-versed in multiple areas of organizational and instructional leadership. This study provides current and aspiring administrators with insight, tools, and a format for self-examination which each may employ in making an effective transition as well as to better-manage their current school or program.