Many self-studies focus on an individual or several teacher educators. Although there have been self-studies undertaken by teacher education administrators, there is relatively little research that focuses specifically on an administrator's program development work in teacher education. This self-study examines one teacher education administrator's program development work over a period of 18 years and in two institutions. Data come from entries from a professional journal kept during those years. A framework consisting of emergent categories and sub-categories was developed for analysis. Initial findings suggest there are both a complexity of roles and multiple roles that are influenced by outside forces. The scale and complexity of undertaking a long-term self-study surfaced in understanding the scope of the work, deciding on a framework for data analysis, allowing time and place for making personal connections and meaning, and sharing the work with others. Next steps are discussed for this study and for future multi-year self-studies that involve multiple roles. (Contains 1 table.)