On June 30, 2018, the founders of Mkhiwa Trust, Johannesburg, South Africa, considered their dilemma of deepening their impact in South Africa, using education as a key vehicle to bring about systemic change. The case highlights the evolution of their mutual support throughout their careers. The tragic death of their young son had far-reaching implications for the couple and their business interests, their career aspirations and the focus of many of their future business and philanthropic initiatives. It also defined a number of choices taken by the couple since then. The story of these individual leaders, who support each other in their businesses, illustrates the power of a couple as servant leaders.