Recent paradigms have highlighted the capacity of returnee migrants to generate developmental impacts on their countries of origin through investment of their capital. This group of migrants could contribute remotely through various channels of engagement, such as knowledge and skills transfers, financial remittances, diaspora direct investments, entrepreneurial undertakings, and diaspora networks. This case study evaluates strategies that a motivated returnee entrepreneur employed in establishing and managing her business activities in her country of origin. The case also investigates obstacles she encounters. At a crossroad, the entrepreneur is contemplating her next move, utilising her personal and entrepreneurial experiences. The choices are threefold: to remain, to retreat, or to readjust.