Literature, issuing from a sense of wonderment about life and the world, involves a keen interest in major questions about human experiences and their patterns in the world. Therefore, a philosophical analysis of literature develops a reflective concern for life and makes suggestions for life-problems. It requires a careful and systematic reading of work of arts and a critical, logical examination of the arguments they put forth. It offers a chance to create and adopt seminal beliefs about human development, life and the world. Hermann Hesse, ‘a writer of man’s interior’ (Freedman, 1920, p.11) presents his hero- Siddhartha undertake self exploration within himself and into the world he lives. His life-course charts a particular pattern of human development. The philosophical analysis of the novel from educological point of view offers how Hesse’s thinking alludes to the interior of an individual journey than the exterior of it. The analysis in this book provides a deep revelation about all the aspect of human life.