Twenty years ago, I began a project to learn about the professional and personal lives of 130 deans of women who were practicing in their careers between 1903 and 1922, and who laid the foundations of what is now called student affairs. The collective group shows both trends and diversity in the identities, professional lives, and personal choices among these women, many of whom have been considered by previous scholars who have studied the dean of women role. Yet, by looking at a wider number of early deans, the exceptions to these presumed trends challenge and complicate our understanding of how these women experienced, practiced, and built the profession over a century ago.