In this book, depression is explored as a form of loss that manifests itself as an inability to connect with others, to narrate one’s own existence, to derive meaning from life experiences, and ultimately, to symbolically represent one’s inner world. This loss has the capacity to evolve into a chronic condition that can be seen as a form of subjective darkness. A hermeneutic, interpretative phenomenological approach is used that seeks to preserve the individual voices of each narrative, while embedding their stories in theoretical and current literature on depression. The clinical cases of five individuals are used to elucidate some common characteristics of depressive experience. Themes of loss, death, darkness, the intergenerational transmission of trauma, and unmetabolized pain are explored through a psychoanalytic lens that seeks to shed light on the underlying dynamics of chronic depression.