The term double awareness has been used in the context of advanced cancer to describe a person’s capacity to be engaged in the world while preparing for impending death. This phenomenon holds great import for psychotherapeutic interventions geared toward those coping with a fatal illness, but research on this phenomenon has only emerged recently. The aims of this article are (a) to describe the phenomenon of double awareness and (b) to present a developing, rational model of how double awareness might be cultivated in the process of a recently developed, integrative psychotherapy called “Managing Cancer And Living Meaningfully.” Task analysis method was used to guide construction of this rational model. The article integrates relevant knowledge from existential, experiential, humanistic, and psychodynamic psychotherapy related to the problem of advanced disease and impending mortality and offers a framework for future research on this important topic.