This paper is developed from a report to the British Psychoanalytic Council (BPC) in 2016, ‘Recommendations for best practice for responsible retirement’. In expanding the thinking, some of the problems we can have in addressing the painful and difficult decisions we have to make about retirement whilst maintaining both an ethical and compassionate attitude to the topic are discussed. The paper explores potential conflicts that can arise between the needs of both the analyst and the patient in contemplating retirement and managing serious illness. It considers the role of clinical trustees in dealing with fitness to practice issues and with the aftermath of the death of the analyst. The role of our institutions in helping us when problems arise is discussed. Recommendations are made to assist moving forward to make the subject more open to thought and to overcome the resistances we have, both personal and institutional, conscious and unconscious, in accepting that this topic poses a challenge to most analysts and psychotherapists.