Although Natsume Sōseki (1867–1916) enjoys worldwide fame as a novelist, his work as a first-class kanshi 漢詩 (classical Chinese poetry) poet remains largely unknown to Western audiences. This article focuses on Sōseki's kanshi of 1916 and his pursuit of the Dao toward the end of his life. Contextualized in both the turbulence of Meiji Japan (1868–1912) and the Chinese poetic and philosophical traditions, this piece offers a comprehensive overview of the thematic and formal features of Sōseki's 1916 kanshi. Perpetually torn between the pursuit of secular success and the freedom and tranquility of the life of pure thought, Sōseki infused his kanshi with visions of the Confucian, Buddhist, and Daoist Dao. To him, kanshi offered a highly personal medium for complex philosophical inquiry, an outlet for psychological distress as well as modern concerns, and at the same time represented a tradition from the past that he tried desperately to hold on to in the tide of change. In many ways, the inner struggles of Sōseki offer a glimpse into the collective tormented psychology and spiritual crisis of Meiji intellectuals. His short, illness-plagued, yet prolific life presents nothing less than a crystallization of Meiji Japan in the throes of drastic transformation.