Indian spiritual autobiographies pivot on the idea of spiritual enlightenment: by transcending the ego, the self puts an end to the cycle of reincarnation. On the one hand these works reflect an individual experience, and on the other hand they mirror the society and culture that forms its background. In this paper I examine two “enlightened” autobiographies, Paramhansa Yogananda’s Autobiography of a Yogi (1946) and Osho Rajneesh’s Glimpses of a Golden Childhood (1984), from the viewpoints of ideational content and rhetoric, in order to show the difference between Yogananda’s sacred outlook, which G.K. Shandya interprets from a post-colonial vantage point, and Osho’s secular spiritual perspective, which has a cross-cultural character and includes key aspects of the Western worldview. In the field of spiritual life writing no less than in general, the movement from the cultural moment of 1946 to 1984 reflects the modernization of the Indian tradition and consists in a change of emphasis from hierarchy to individualism. Though little known to the average reader, Rajneesh’s autobiography is noteworthy as it represents an original reinterpretation of spiritual enlightenment from the viewpoint of Western individualism. Conversely, Autobiography of a Yogi (1945) is a staple of Indian spirituality, and privileges cultural continuity and tradition. Apart from their artistic merit, the interest of these books lies a) in the paradox that they are purportedly written by self-realized and hence “egoless” authors, and b) in the fact that they belong to a period in which the process of decolonization came to fruition, and India took a stance with regard to the scientific and individualistic outlook that constitutes “secular modernity.” As for method, my framework draws on Modernization of the Indian Tradition, in which Yogendra Singh analyses social change along the lines of a culturological conception. In this perspective, what matters is not only reality per se, but also the subjective representation of ideas of reality. The focus is on how Indian minds have adapted to the revelation of Western culture: Autobiography of a Yogi and Glimpses of a Golden Childhood are important examples of adaptive reaction because they represent the viewpoints of pivotal figures of the Indian tradition: the gurus. Accordingly, I interpret Osho’s work and Yogananda’s work, respectively, in the light of what Singh calls “Modernization” and “Indian Renaissance.”