Hermann Hesse had three separate periods of Jungian psychoanalytic sessions during his lifetime whilst undergoing a mid-life crisis, i.e. 1916-1918, 1921 and 1925-1926. It appears that Hesse’s awareness of Jung’s thoughts and teachings helped Hesse to create narrative structures and contributed to the development of his writing approaches. Focusing on Hesse’s diary entries on his encounters with Jung, his sporadic letter correspondence with Jung and his book reviews of Jung’s psychoanalytic works, this paper will offer a closer look at how the lives of Hermann Hesse and Carl Gustav Jung were intertwined between the years 1916-1961 and how Jung influenced Hesse’s writings. I will also be exploring how Jung’s Liber Novus: The Red Book which dealt with Jung’s “confrontation with the unconscious” can be compared to the novels by Hesse that I am studying with respect to the theme of self-discovery.