This article discusses the difficulty of establishing and maintaining emotional presence and connection when analysts work with their own difficulties of aging, illness and the prospect of death. In such situations the analyst is caught between the need to care for him or herself, as well as attending to the treatment needs of the patient. In this effort the analyst is challenged by the demands of heightened transferential inductions, as well as the stimulation of multiple subjective countertransferential states. The course can be an uncertain one and the angst which is so often inherent in such circumstances can be experienced as an intolerable darkness of night. Mitigating that darkness requires skill, fortitude, the help of others and the capacity for transcendence.