Despite increased academic attention paid to migration flows in Europe, the gendered nature of transnational migrant entrepreneurial journeys within the family business context remains under-researched. We address this gap by investigating how transnational spaces enable women to challenge the dominant ideas about their roles, and claim legitimacy by developing branches of their family business abroad. Reporting extensive longitudinal evidence collected over a seven-year period, we showcase four biographical narratives of women operating transnational family businesses in the UK, which originated in Eastern Europe. Adopting this novel longitudinal approach, we provide insights into how these transnational migrant women entrepreneurs exercise individual agency to overcome structural constraints by developing strategies which prioritize their own business aspirations without fully sacrificing their family ties.