A new position of Psychoanalyst Director was created at The Boston Psychoanalytic Society and Institute (BPSI), at a time of turmoil that catalyzed a period of organizational growth and change. I describe aspects of being a Director through the lens of my experience as the first psychoanalyst to hold the position at BPSI. I focus on a formative time before the role was created, where I learned the foundations of a Director role and ways of helping a psychoanalytic group change, move through polarizations to develop consensus, and work creatively. I then describe aspects of being a Director, including working as part of a leadership team, learning to be a transference figure, and serving the work of psychoanalytic education as an internal consultant. I highlight ways of leading that helped create an effective psychoanalytic organization focused on rigorous education, new initiatives, and a culture of psychoanalytic generativity.