In the mid-1940s, Taiwan underwent a change of ruling power from colonial Japan to the Kuomintang Party from China. Both governments implemented monolingualization on the Taiwanese population. In this article, we examine the situation translingual position in a historical aspect, dwelling in detail on the work of the outstanding Taiwanese poet Chen Qianwu. We come to several conclusions that may be useful to researchers in the field of translingual literature. 1. Taiwan’s translingual poets, born in the 1920s, found themselves in a situation of permanent code switching: using the local dialects of Hokkien and Hakka in everyday practice, they were trained in Japanese and used Japanese in a wider society. 2. Although the switch between one monolingual paradigm and another violated the creative result of translational authors, this did not exclude the experience of multilingual realities and interlingual influences that they experienced from the fragmentation of local identities, especially during the development and formation of Taiwanese linguistic consciousness. 3. The literary intermediaries between the paradigms were: the classical Chinese writing, brought with the first immigrants from China; vernacular Chinese writing, influenced by the New Literary Movement in the 1920s; Taiwanese writing based on the most common dialects, Hokkien and Hakka (the idea of speaking and writing in unison); Japanese writing, which was originally studied in school along with Chinese, but supplanted it. The switch from Japanese, the colonial official language, to Mandarin Chinese, the postcolonial official language, led to a so-called “translingual generation” of literary writers. While the switch from one monolingual paradigm to another disrupted the creative output of the “translingual generation”, it did not prevent these writers from developing a Taiwanese consciousness. As illustrated by the poet Chen Qianwu, language crossing experiences strengthened the translingual generation’s assertion of their local identities.