Following the Meiji Restoration in the late nineteenth century, Japan began a comprehensive program of ”modernization”. A tendency toward Europeanization was adopted in opposition to the conservative ideals of the Meiji era. Against such a background, Mori Ogai went abroad to study military sanitation systems in Germany from 1881 to 1884, and swung between the tide of modernity and feudalism. Prior to establishing his literary status in Japan, Mori Ogai had already published his diaries about western sailing and experiences studying abroad in volumes, such as ”Kosei-Nikki”, ”Doitsu-Nikki”, ”Taimu-Nikki”, and ”Kantou-Nichijou”. In his diaries, Mori Ogai adopted the Asian colonies of western empires as comparative subjects with which to illustrate the internal struggle of Japanese society. This paper focuses on Mori Ogai's two diaries, a record of his overseas voyage in ”Kosei-Nikki”, and his review of life in colonial Taiwan in ”Sosei-Nikki”. This work represents an attempt to elucidate the two overriding emotions of Japanese intellectuals concerning Japan's anticipated shift toward becoming a colonial empire and the fear of Japan itself becoming a ”colony” of other imperial powers. The goal of this paper is to explore the face of Japanese intellectual's self-positioning and views regarding colonial modernity and colonial Taiwan.