This paper is about chronic illness and its impact on the chronically ill and their loved ones who live through the illness and the eventual death. A new concept is introduced, the concept of “passing”: physically ill people may pass as healthy even though they are physically ill. In addition to a discussion about why people choose to pass, two major paradoxes are considered. One concerns the paradox that results from “passing.” The paradox is that while the falseness of “passing” keeps the self alive, it also deadens it before death. Specifically, “passing” enables the person with a physical illness to keep his well self alive with others, but results in one feeling dead, disconnected, detached, and inauthentic, before death. The second paradox involves the pressure on the chronically ill person to be heroically agentic in fighting the illness and overcoming it and, also, the pressure for this same person to be totally submissive and compliant with treatment. While in analytic treatment, the ill person can be helped to access authentic emotions and aliveness and to feel the power of authenticity.