This paper examines Hermann Hesse's penultimate novel, "The Journey to the East", from an educational point of view. Hesse was a man of the West who turned to the idea of "the East" in seeking to understand himself and his society. While highly critical of elements of Western modernism, Hesse nonetheless viewed "the East" through Western lenses and drew inspiration from other Western thinkers. At the end of "The Journey to the East", the main character, H.H., believes he has found the solution to his despair. This paper argues that he has not, at least not in the fullest sense Hesse came to see was possible. H.H. relies too heavily on faith and abandons reason too quickly in seeking to become "absorbed" into the Other that he regards as his higher self. An answer to H.H.'s existential angst can be found in Hesse's final novel, "The Glass Bead Game", where educational growth through the development of a critical, questioning, inquiring attitude is a central theme.