Despite decades of global efforts to promote gender equality, progress in women’s leadership remains limited. According to the World Economic Forum’s Global Gender Gap Report, around 68.8% of the global gender gap has been closed. However, at the current pace, achieving full gender parity is expected to take over a century—approximately 123 years [1]. While significant gains have been made in health and education, major disparities persist in economic participation and leadership—areas most closely tied to power and advancement within organizations. Importantly, no country has yet achieved full gender equality, highlighting the deep-rooted structural and cultural barriers that continue to limit women’s access to leadership roles.

Gender equality outcomes also vary widely by region. European and North American economies consistently perform best, having closed more than 75% of their gender gaps [1]. These regions benefit from transparent promotion systems, gender-sensitive legal frameworks, and broader societal acceptance of women in leadership. In contrast, many Asian countries—including Japan, South Korea, and several in Southeast Asia—continue to lag behind, despite achieving near parity in education and health [2]. This gap reveals one of the most persistent paradoxes in global gender data: although women in Asia are highly educated, they remain underrepresented in organizational leadership. Recent developments in Japan may appear to indicate meaningful progress. Institutional reforms, such as initiatives to promote gender diversity and increase women’s political participation, have started to reshape formal expectations in organizations [2]. Most notably, the election of Japan’s first female prime minister in 2025 marked a historic and symbolic moment, suggesting that even deeply traditional societies may be entering a phase of institutional change.

However, symbolic progress does not always translate into structural change. Long-term labor data show that despite a steady pipeline of highly educated women and a stable female labor force participation rate of around 40%, the share of women in managerial roles in Japan has increased only slightly—from 30.2% in 2003 to 35.4% in 2023 [3]. Moreover, recent improvements in global gender indices have been driven mainly by advances in education, health, and political inclusion, rather than by significant changes in how organizations support leadership development. These patterns suggest that the mechanisms distributing authority, visibility, and promotion remain largely unchanged. This continued stagnation reveals the limitations of common metaphors like the sticky floor, glass ceiling, and glass cliff. While useful for identifying specific barriers, these concepts fail to explain the consistently flat trend in women’s leadership representation over time. If inequality were driven mainly by isolated obstacles, substantial progress would likely follow once those were addressed. Instead, the data suggest that gendered disadvantages operate continuously across the career journey, not just at key transition points.

Together, these global trends, regional disparities, and persistent organizational stagnation suggest that gender inequality in leadership is not best understood as a set of isolated barriers. Rather, they reflect a system of uneven career momentum, where the same organizational structures produce different outcomes for men and women. In response, this paper introduces the tailwind–headwind framework, which integrates cultural, structural, and psychological dynamics to explain how men accumulate career momentum, while women encounter ongoing resistance throughout their leadership paths. By viewing leadership careers as layered, dynamic processes rather than isolated transitions, the framework provides a clearer explanation for the persistent underrepresentation of women in leadership. It also offers a solid foundation for future research across organizational and institutional settings by clarifying why gender gaps in career advancement persist even within the same systems.