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While the workplace custom of working long hours has been known to exacerbate gender inequality, few have investigated the organizational mechanisms by which long working hours translate into and reinforce the power and status differences between men and women in the workplace. Drawing on 64 in-depth interviews with workers at financial and cosmetics companies in Japan, this article examines three circumstances in which a culture of long working hours is disadvantageous for women workers, and the consequences of those circumstances: (a) managers in Japanese firms, reinforcing gender stereotypes, prioritize work over personal and family lives; (b) non-career-track women experience depressed aspirations in relation to long working hours and young women express a wish to opt out due to the incompatibility of work with family life; and (c) workers who are mothers deal with extra unpaid family work, stress such as guilt from leaving work early, salary reduction and concerns over their limited chances for promotion. The article argues that the norm of working long hours not only exacerbates the structural inequality of gender but also shapes employed women's career paths into the dichotomized patterns of either emulating workplace masculinity or opting out. [ABSTRACT FROM AUTHOR]