This presentation aims to explore and understand the identities of the karayuki-san who became sex workers across the Pacific Rim in the late 19th and early 20th centuries, arguing that the karayuki-san were an integral part of the process and experience of modernization in Japan. The karayuki-san have been seen as both soldiers of the empire and the bane of its modern existence as a great nation, yet these strands of thinking have been strewn across the discussion about these women and were used in constructing one dimensional discussions about these women. The approach taken in this presentation is to bring together these disparate strands of thinking, which yields both a broad history of the karayuki-san and a multi-dimensional understanding of their identities as women, sex workers, and persons swept by modernity. The resulting analysis finds that the karayuki-san were ascribed a number of imagined identities, which built upon their real identity which lied at the core, and these identities evolved as Japan progressed farther along the road of modernization.