This comparative psychobiographical study provides an in-depth exploration of meaning in the lives of two extraordinary individuals, Helen Suzman and Beyers Naudé. A comparison of the construction of meaning, as an important aspect of wellness within the holistic wellness model, is given for these South African anti-apartheid activists. Suzman (1917–2009) dedicated her career to opposing apartheid policy as a parliamentary politician. Naudé (1915–2004) was a renowned public figure dedicated to social justice in his role as a theologian. The holistic wellness model views the Neo-Adlerian life task of spirituality as crucial to ascribing meaning to life events, acknowledging multiple potential sources of meaning. The differences and similarities pertaining to the domains of meaning-making of these two subjects are explored. The subjects, who differed regarding biographical variables, were found to share a common sense of purpose within the same socio-political milieu. The study findings confirm that commitment to diverse sources of meaning and generativity are central to meaningfulness. This comparative psychobiographical study contributes to the eugraphic exploration of the meaning-making processes of these exemplary individuals.