Despite a surge in global gender equity initiatives, women in India continue to face barriers that undermine their sustained career engagement, particularly in male-dominated sectors. This study offers a nuanced, multi-level investigation into how individual, organizational, and societal factors collectively shape women’s engagement in their careers. Using a two-phase research design, the first phase (n = 147) quantitatively assesses career engagement levels among female employees, while the second phase (n = 32) employs qualitative interviews to explore the lived experiences of women with low engagement. Leveraging a double-loop gendered framework, this study reveals how patriarchal norms, caregiving responsibilities, and implicit biases within leadership structures disrupt women’s career progress. Grounded in India’s socio-cultural landscape, this research provides actionable insights to foster inclusive networks, align policies with experiential insights, and build sustainable career pathways for women professionals.