There is constant pressure on 20th-century psychoanalytic paradigms concerning gender and sexuality, leading to ambiguity in theoretical constructs of, and therapeutic approaches to, gender. The ongoing destructive notion that transgender people are inherently abnormal, perverse, and psychotic is an epistemological problem that warrants scrutiny and correction in the field of psychoanalysis. This article explores a nuanced set of transgender experiences juxtaposed with the author’s psychoanalytic encounters as therapist, analysand, and analyst-in-training, in an effort to elaborate on transgender subjectivities. Categories are woven, unraveled, and rewoven in the face of personal realities and the author’s relationship to gender over time.