Literacy education is always a potentially problematic undertaking, one that shifts people's relationships among themselves, with bodies of transmitted knowledge and with structures of political control (Collins & Blot, 2003; Lee, 2004; Mazrui, 1990). The teaching of writing and composition in early 20th-century Japan presented a number of unique challenges, centered on the complexity of the writing system and the historical diglossia that had separated the spoken and written forms of the language for centuries. In this article, the author compares the responses of Makiguchi Tsunesaburo (1871–1944) and Ashida Enosuke (1873–1951) to these challenges. Where Ashida promoted the idea of writing as a spontaneous expression of the “self,” Makiguchi encouraged a more deliberate, conscious and “scientific” approach to the teaching of writing, one that encouraged more interactive and socialized understanding of language and the self-other relations it embodies. These approaches are compared against the background of the role assigned to language learning and teaching in defining the contours of an emerging national “self.”