Previous studies have indicated that young middle-class Japanese women’s stronger willingness to study English in the West can be attributed to Japan’s gender inequality and women’s longing for gender-equal Western societies. This literature-based study highlights an overlooked group of non-elite young Japanese women who make grassroots efforts to achieve upward mobility by studying English in Western English-speaking countries while participating in working holiday programs. Although socioeconomic and educational inequalities exist among international students, they are often invisible, particularly among the youth from developed countries such as Japan. This study provides new insights into the factors that influence unprivileged young Japanese women’s investment in studying English abroad. For example, women’s beliefs in the power of English skill development and overseas work experience are derived from the misconception dominant in Japan’s non-multilingual corporate world that anyone with self-acquired English skills can perform bilingual jobs, such as interpreting. This factor enables academic and commercial agents (e.g., women’s magazines and college prospectuses) to produce pro-women discourse that even non-elite young women can achieve career mobility by gaining English skills and overseas work experience. Implications are provided for international English education stakeholders positioned to emphasize global English promises while obscuring the reality of widening disparities. The gap between university-based elite researchers and non-elite research participants is also discussed as a challenge to the much-needed attempt to further examine the impact of global and localized English ideology on non-elite English learners’ grassroots efforts toward upward mobility.