The author, a first-year candidate in psychoanalytic training, reflects on his personal history including aspects of the coming-out process, his first time in psychotherapy, his initial rejection of psychoanalytic theory and technique because of how it has been used to pathologize gay folk, and his decision later in his career to pursue analytic training for the depth of understanding it provides. He considers the work of Ken Corbett—specifically his analysis of the gay male’s passivity in relation to other men—and applies it to his own relationship to the psychoanalytic world. Throughout the article, the author reflects on perceptions of belonging personally and professionally.