In this article, Margaret Conrad reflects on her four-decade career as a historian. She takes an autobiographical approach, tracing her interest in the past to an evangelical upbringing in rural Nova Scotia and the dramatic changes in post–Second World War Canada that begged historical reflection. On the leading edge of the baby boom, she benefitted from reforms in education that set her on the path to an academic career focusing on Atlantic Canadian history, Women’s Studies, and Digital Humanities. History, she argues, is always relevant, serving as a vehicle for wisdom and agency in a world where power struggles are contextualized by the past but the outcome never certain.