This life history research utilizes life story, a form of personal narrative, with a veteran teacher leader to understand what fosters and sustains teacher leaders. This research contributes to the literature by focusing on how the life story of one veteran educator, Dr. Nettie Webb, can inform possibilities rather than focusing on how personal narratives impede possibilities of change in the early years of teaching. I have selected Dr. Webb as an exemplar or instrumental case for her personal achievements as an African American woman located in the context of one Eastern United States community with cultural, institutional and historical commitments to valuing every citizen's contributions. The centrality of teaching across her career makes Dr. Webb uniquely positioned to inform the possibilities of teacher leadership in our current educational culture. Constructivist grounded theory strategies were used to analyze extensive in-depth conversational interviews, a subsequent dialogic interview on personal agency and a collection of career-spanning documents. Categories such as risk and feedback are explicated as implications for how we can foster and support the next generation of teacher leaders through the concept of personal agency. Praxis, the legacy of care and the culture of fear are discussed in the context of personal networks, professional learning communities and the historical norms of caution. Trustworthiness was established by multiple methods, including extensive member checking. The life story of an exemplary veteran teacher leader like Dr. Webb, a person committed to advocating for children in the context of the last five decades of social and educational reform, risks being lost. By capturing Dr. Nettie Webb's life work in print, it not only becomes an accessible memory of this woman and her work but a placeholder of possibility and a window to our educational and social history.