Virginia Woolf and Joan Didion challenge themselves as writers in their efforts to portray the emotional state of grief in their works Jacob’s Room (1922) and The Year of Magical Thinking (2005). Though they have their own styles of writing they both elaborate on the themes of self-experience and perception in ways that can be described as life-writing, and their works, both share similar features and at the same time belong in separate genres. Max Saunders’ work on life-writing serves as an applicable framework to discuss and show ways in which Woolf and Didion engage in life-writing. This essay explores the relationship between author and narrator from various layers of self-impression and into the subconscious of the bereaved. The rise of psychology, parallel with the modernist movement serves as an historical angle on the topic of self-impression and how the different domains such as literature, the arts and psychology share the same origin in philosophy. In the novels human emotion and the process of healing belong in medicine as well as in literary figuration. As critics have noted, there are forces of creativity in mourning and violent emotions can trigger creative states. Writing is a craftsmanship of many creative styles and Woolf and Didion explore their self-experience in their authorship.