Africa faces numerous challenges such as retaining globally mobile talent and informal economies. Economic inequality leads developing countries to lose human capital, but research on staying strategies remains limited. This multiple-case study explores how Tanzanian medical doctors organise a sufficient income through parallel entrepreneurial activities with forms of light entrepreneurship. We present four strategies from intramural entrepreneurial strategy to extramural diversified entrepreneurial strategy that illustrates distinct contextual adaptations. These dual practices through parallel entrepreneurship enhance their stickiness to the context and profession, thus reducing brain drain. Such entrepreneurial strategies feed in towards upholding their primary profession, suggesting that informal entrepreneurial activity may advance overall sustainability of the society. However, parallel entrepreneurial activities require empowering capacity-building lenses and holistic policy approaches as they are linked to broader issues of local systemic viability and of talent retention in Africa. This study contributes to international migration-, human resources-, entrepreneurship- and sustainability management.