Abstract: Based on Gleb Uspensky’s cycle “Sketches of the Transitional Period”, this article analyzes the ethical-philosophical views of the writer upon national spirituality, Russian world and its future. Uspensky believed that the great mission of Russia consists in the desire to become a unifying spiritual center for the entire world civilization. However, due to its location in-between the West and the East. Russia is spiritually dying, and along with it in the global chaos and hostility of Western and Eastern civilizations, dies all of humanity. Russia’s position within the spiritual confrontation of East and West, the writer describes as "uncertain": Russia wants but is not able to impede the imminent spiritual demise of humanity. Such "uncertainty" contains the spiritual tragedy of Russia itself, which appears to be in a questionable situation with regards to its world goals and objectives. This article suggests a new approach towards understanding the cycle of G. I. Uspensky “Sketches of the Transitional Period”, based on peculiarity of his philosophical and ethical views associated with the idea of Russian messianism, its specialness in the context of the confrontation of Western and Eastern civilizations. The conducted systemic analysis of the cycle “Sketches of the Transitional Period” demonstrated that Uspensky comprehensively reflected the own understanding of spiritual tragedy of the Russian life, founded on a deep insight into the surrounding post-reform Russian reality of the 1850s-1880s. The revealed specificity of Uspensky’s worldview opens a new perspective for an overall scientific assessment of the later period of his works.