The work-family interface has been an area of increasing scholarly interest, especially within the second half of the 21st century. Researchers in this field have attempted to define and shape the manner in which the work and family components interact, resulting in a growing body of dyadic theorizations. At the same time, generational categorizations of employees on the basis of their ostensible peculiarities continues to fuel an entire corpus of workplace research, broadly informing curricula and establishing consultancy organizations designed to empower organizational leadership in managing different generations in the workplace. Both of these research trajectories are important in responding to the evolving concepts of work and family, but they largely frame a Western experience. The goal of this paper is to contextualize the two strands of discussion within an African context, providing an empirical examination into the ways in which digitization and rapid urbanization are radically shaping the understandings of work and family.