This article reflects on the experiences of a Fulbright scholar, drawing heavily on the collected writings from her Zimbabwean students. The story tells of the emerging identity of the first generation to be born in an independent Zimbabwe. The article explores the intersection of traditional culture, gender, and democracy that these students face and confronts some of the core educational issues in a postcolonial context. The article zeros in on work done with headmasters in Swaziland, confronting some of the challenges of educational change during a period of constitutional reform. Contemporary events intertwine with remembrances of things past, raising questions about the state of our own democracy.