This paper offers a close reading of two distinctive autobiographical texts by psychoanalysts Helene Deutsch and Margaret S. Mahler, situating them within the broader context of women's self-writing in the history of psychoanalytic literature. It argues that revisiting their memoirs can shed new light on psychoanalytic understandings of autobiography and allows for a deeper reflection on the dynamics of psychoanalytic work during the early years of the Freudian movement. Both Deutsch and Mahler witnessed the establishment of psychoanalytic hierarchies and training standards that diverged significantly from contemporary models. By bringing their memoirs into conversation, this paper invites a deeper inquiry into the varied ways analytic dyads were historically formed and subjectively experienced within Freudianism.