This study explores gender-specific barriers to finding an ideal workplace in the Visegrád countries (Czech Republic, Hungary, Poland, and Slovakia), where similar historical and socioeconomic contexts shape labor market inequalities. Based on the relevant literature, women are disproportionately affected by challenges related to language proficiency, professional networks, and mobility. The research applied a quantitative methodology, including chi-square tests, multiple logistic regression, and cluster analysis, using SPSS Statistics software to analyze the survey data. Findings revealed significant gender disparities. Women report greater difficulties with language and mobility, particularly in Hungary and Slovakia, whereas men benefit more from strong professional connections. The cluster analysis identified three respondent groups: those hindered by language barriers, those with weak networks, and those facing limited mobility. International experience mitigates language challenges, and robust networks ease job search difficulties. In line with the ideals of a circular society, this study also explores how circularity, inclusiveness, and collaboration can help break down gender-based barriers in the labor market. The study’s novelty lies in its comparative regional focus and the integration of statistical methods to segment job-seeker profiles. These insights highlight the need for targeted policies that enhance language skills and foster professional networking opportunities, especially for women. By addressing these barriers, policymakers can better support gender equality in labor market access across Central Europe.