In response to the article by Mathew and Hopkins, also in this volume, the author discusses the case study of the Boston Graduate School of Psychoanalysis which celebrated its 50^th anniversary in 2023. Parsing out what is entailed in training to become a psychoanalyst at this particular institute, the author deconstructs the “impossibility” of the profession and the rigorous nature of process-oriented training. Program learning outcomes (PLO's) are broken down by the author so as to address specific skills the students will acquire and the complexity in pursuing these goals in relation to the self-discovery that is inextricably linked to the work.