Diaries kept during wartime employ an everyday, casual style to describe extraordinary events. At the same time, they narrate everyday life under a non-everyday situation. How, then, can we understand the heavy burdens of the sociopolitical structure under the Japanese colonial rule and wartime mobilization, which will be found in the delicate balance between ordinariness and non-ordinariness in the wartime diary? This article, through the analysis of a Japanese woman's diary from 1944 attempts to explore the possibility of a critique from the viewpoint of Japanese imperial history and colonial rule. How the writer of the diary recalls the war and the colonial experience normally depends on her structural ＂position＂, such as gender, political orientation, and generation. First, in regard to gender, how should we evaluate diaries written by Japanese women at home which, in contrast to those written by men on the battlefield and including much information about the war, tend to focus on daily events rather than war itself? Second, from the view of political orientation, what is an appropriate attitude for a student of Taiwanese social history when handling the personal narratives of Japanese imperial rule that were written at home in Taiwan under the colonial rule of Japan? Third, from the view of generation, how should family members approach the diary, or the students of family history interrelate or combine the memory of war and the colonial experience found within it? How should we understand and relocate ourselves between family records and so-called ＂historical materials,＂ as well as between politic situations and generations? Through the intricate relations between the diary and surrounding conditions, the writer and the reader, the ruler and the subordinate, the pre-war and the post-war, we will uncover a new style of critique and dialogue between everyday personal life and war.