This study investigates the experiences of women reentering the workforce after extended child-rearing leave, focusing on how organizations, leaders, and society as a whole can better support their transition. Through qualitative interviews with women that reentered the workforce after a minimum one-year leave, the research identifies the multitude of challenges faced including imposter syndrome, identity integration, connection and belonging, and work-life balance. The findings highlight the critical role of organizational policies, leadership practices, and societal attitudes in facilitating successful workforce reentry. Supportive measures, including flexible work arrangements, targeted reskilling programs, and inclusive workplace cultures, are shown to significantly enhance women's reintegration and professional development. Additionally, the study emphasizes the importance of empathy and mentorship in fostering a supportive environment. Recommendations are provided for organizations and policymakers to create more equitable and supportive frameworks, ultimately contributing to greater gender equality in the workforce. This research contributes to the broader understanding of the interplay between individual experiences and societal factors in shaping women's workforce reentry.