This volume explores existential questions within the following three thematic fields: first, experiences of anxiety and despair as related to the question of what these phenomena show about freedom and its difficulties; second, hermeneutical theories as related to the question of how we can develop an existential hermeneutics that can account for the ambiguities of self-understanding between transparency and opacity, and, third, selfhood between self-understanding and self-alienation as a focal point of existential psycho(patho)logy. What can disturbances to or breakdowns in self-understanding teach us about personhood? Making visible one's own blindness by articulating the shadows of our knowledge and abilities is at the core of a negativistic approach to existential questions discussed in a dialogue between philosophical anthropology, phenomenology, theology, psychoanalysis, and psychiatry.