Recently, psychoanalysts have begun to write about the ways in which trauma and loss in their lives have affected their work. However, there has been nothing published about that subject in the life of a psychoanalytic candidate. This article is an exploration of the ways in which a family tragedy that occurred during my candidacy affected my psyche, my training, and my work. It was particularly poignant that my trauma reignited issues of trauma and loss in my two analytic cases, both of whom had a history of trauma and loss. The structure and guidance provided by my analysis and supervision during this time were comforting and healing, and enabled me to continue to work confidently with patients.