Four case studies were developed of women who were promoted to high school principalships in a public school district in Virginia, 1970 __ 2000. Using qualitative research methods, data were obtained through interviews, school system documents, and written media. The software package Ethnograph was used to code and analyze interview data. Three themes resulted from cross-case analysis: school district policies, school district culture, and women's career aspirations. Grounded in data from coding and analysis, a theory evolved that changes that occurred over time opened leadership opportunities for these four women, changes that emerged from society's pressure to the institution of education, then the individual. Further research is needed to corroborate this theory of change that impacted women's careers in education administration.