A senior psychotherapist's decision to retire her clinical practice is explored through the lens of attachment theory and psychoanalytic practice traditions. When burnout is differentiated from longings and challenges of age, an older yet healthy therapist can approach retirement as a normal rite of passage. Doing so allows patients a positive termination experience, which allows healing from past traumatic endings and empowerment through shared grief, participatory transfer arrangements, and a farewell without burden of concern for the clinician's well-being. Case vignettes illuminate countertransference conundrums and enactments particular to therapist-initiated termination as they present themselves in a field of practice where constancy is the professed road to healing. In the service of treatment excellence, and informed support for elder analysts and therapists, this article urges debate and further discussion among clinicians of a certain age and those who are consultants to them going forward.