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This paper focuses on the geographical imagining and agency of colonised people by exploring particular accounts in the life-experience manuscript of Tan Malaka (1897-1949), a displaced Indonesian “radical”, who found himself in Shanghai in January 1932 and engulfed in the semi state of war between China and Japan. It traces the ways in which this adventure in Shanghai both shaped and was shaped by how this “hero of national independence” confronted colonialism and the nationalist agitations in Jakarta in the 1940s. It, thus, traces the ways in which the landscape and contradictions in the social space of the (colonial) city heightened the consciousness of people in the colonial world, transforming the way they thought about their social and political identities.