This study applies Ecological Systems Theory to investigate how a configuration of complex interactions among socio-cultural structures, entrepreneurship education, and individual personality traits drives entrepreneurial career choices. Adopting an exploratory research design, the study draws on multiple in-depth interviews with key stakeholders in entrepreneurship education across five universities in four Sub-Saharan African countries. The findings reveal that the interplay between socio-cultural structures, entrepreneurship education, and individual agency significantly influences the likelihood of university students pursuing entrepreneurial careers. Unlike prior research, which often focuses on isolated contextual influences, this study advances the literature on contextual influences in entrepreneurship by presenting a holistic framework that integrates immediate social, broader societal, and individual personality dimensions as critical drivers of entrepreneurial career choices.