This workshop includes reflections on the presenter’s experiences as the first openly lesbian candidate at an institute of the American Psychoanalytic Association. She will share lessons learned from her leadership role at the national and local level before and after the APsA’s 1991 decision to allow for the training of gay and lesbian psychoanalysts. She will then reflect on the current state of psychoanalysis and trans and non-binary genders. She will provide an introduction to trans and non-binary genders and an in-depth case presentation of her work with a transgender adolescent.