This paper explores the interrelationship between patients' exercise of will to make advances in an analysis and their readiness to forgive their analysts for their human limitations. There is a thin line between idealization of the analyst, probably a necessary component of the process, and resentment of the analyst for his or her privilged position in the world and in the analytic situation itself. The patient's “progress” emerges as a kind of reparative gift, one that implicitly overcomes the patient's tendency to withhold such change out a sense of chronic, malignant envy. Particularly poignant in terms of its potential to elicit the patient's reparative concern is the situation in which the analyst is struggling with his or her mortality because of aging or life-threatening illness. In this essay two clinical vignettes are presented to illustrate some of the issues that this situation poses. One begins with an elderly patient appearing at the door of the analyst's (the author's) home the day of his return from the hospital after coronary bypass surgery. The other begins with an analyst who is terminally ill appearing at the door of a patient who is threatening suicide. The two stories are compared in terms of their implications for human agency, the exercise of will, and the coconstruction of meaning in the face of mortality in the analytic process.