Psychoanalytic clinicians are experienced in weathering the intense feelings that arise with terminations. However, the final good-bye when the therapist retires is unchartered territory. This essay offers a two-fold reflection on the process, based primarily on the author’s experience as a retiring psychotherapist, but also including her perspective as a patient whose own therapist retired. The author will discuss the complex clinical, philosophical, and ethical issues associated with this forced ending, examining her experience through a series of detailed clinical examples. Describing an approach to retirement that sometimes remained within the conventions of the particular analytic frame in which she was trained and sometimes deviated from that frame, she candidly assesses clinical decisions she deems, in retrospect, to have been mistakes, as well as those that served her patients well.