The complete philosophical works of Arthur Schopenhauer are explored through a comprehensive psychological reading that intends to highlight the holistic theories of human nature that amount to a pessimistic and metaphysical worldview. A thorough analysis of Schopenhauer’s philosophical concepts, theories, and ideas is conducted in order to construct a clear understanding of his worldview and avoid a reductionsitic approach to a holistic philosophy. From this I initiate a novel theoretical groundwork derived from Schopenhauer’s philosophy that I have termed a “negative psychology”. I argue that this negative psychology provides a robust understanding of human nature and has applicability in several domains of psychology such as theory of human nature, education, and therapy.