Currently, very little qualitative research exists that addresses the experiences of women administrators, let alone the professional and personal struggles of women superintendents in small, rural schools. Therefore, the purpose of this qualitative study was to reveal the stories of women superintendents in small, rural schools as well as to describe how their careers affected their personal lives while working in the “good old boy system.” Understanding cultural and educational diversity exists among all schools, small, rural schools, in particular, have characteristics and attitudes that are unique to their size and location, and specific to their own school and community. Oppressive behaviors and practices exist, and at times, even blatant acts of discrimination occurred to these women. And though they were able to endure these struggles and remain successful in their careers, they often experienced changes in their personal lives and within themselves due to their unique positions of being a superintendent in a small, rural school. Through the use of narrative nonfiction, the stories of four women superintendents in small, rural schools were shared.