Few studies have been conducted to take an in-depth look at the role and experience of a new middle school assistant principal. Advantageous timing provided the opportunity for the author to conduct this research study examining his experience as a first-year assistant principal. The guiding question for this autoethnography was What can be learned from the experiences of a first-year assistant principal that can be used to improve the administrative certification program and training of future assistant principals ? Autoethnography is employed as a methodology to portray the experience and understanding of the participant/observer in comparison to his training and preparation to become the assistant principal of a middle-level school. Data were gathered from personal journal entries both verbally recorded and written by the author during this year and a half period. Other data sources included school discipline records, behavior files, and incident reports recorded during the experience as well as those leading up to this experience. This study describes the preparation experienced by the author from his time as a middle school and high school classroom teacher, through the certification process, and into his acceptance of his first administrative position at a semi rural, medium size, sixth- and seventh-grade intermediate school. This study takes a critical look at the author\u27s perceived understanding of students, discipline, and his preparation to become an educational leader. The author\u27s own experience forced him to question his views and readiness while bringing to light needed reforms and understandings to the world of an assistant principal