Late 19th century imperial expansion constituted one of the hallmarks with a lasting impact on the international order. The exportation of new “modern”, “civilized” ideas became a global movement. Within this process of cultural transfer, one cannot fail to pay attention to the encounters between coloniser and colonised. Said otherwise, the manner in which Taiwan entered the global world was conditioned by its Japanese colonial experience (1895-1945). This colonial legacy continued to live on in the post-Japanese-colonial period, and still plays a significant role as to how Taiwanese society at present positions itself in the global world. In between the exportation of modern and new ideas, displacement from the Taiwan periphery to the Japanese center and subsequent cultural encounter, we may discern some of the commonalities which arise from sharing about the collapse of traditional ways to interpreting anew one’s own tradition and culture. As shall be demonstrated, through the passage of “becoming Japanese” and equalling modernity with Japaneseness, Taiwanese students and young professionals in Japan discovered and challenged the core of their identity in a cultural and social dialogue as framed and nurtured by the logic proper to early 20th century globalization. I have selected Taiwanese autobiographies or Memoirs as a particular genre of literary writings that enables us to disclose some features of Taiwan’s globalization process. Illustrations are drawn from the narratives of the following authors: Zhang Shenqie, Yang Zhaojia, Du Congming, and Chen Yisong.