This chapter focuses on the personal, social, and historical contexts that shaped Donna Sinclair’s career as a feminist historian. The story of Sinclair’s trek to the 2013 Prelinger Award took root in a divorce that left the former army wife alone with three small children. Returning to school reshaped her identity, provided purpose, and led to her life’s work as an oral and public historian, educator, and social justice advocate. In this essay, Sinclair engages in the self-scrutiny that oral historians so often ask of their narrators. As recommended by Antonia Castaňeda, she digs into “the silences, gaps, and interstitial spaces” of experience to examine her journey to the Prelinger and beyond.