From the analysis of the Wave 5 National Income Dynamics Study – Coronavirus Rapid Mobile Survey 2021 dataset, the study conducted in South Africa, we developed a model of analysis based on three dimensions, namely, subjective well-being, material living conditions, and importance attributed to education during the COVID-19 pandemic. A cross-sectional analysis of the data for Gauteng area indicates that the dimension of subjective well-being of families in South Africa—even in relation to the factors such as conditions of deprivation (e.g., hunger)—does not necessarily influence the importance the respondents attach to their children’s education, this as reflected in whether or not they send them to school when COVID-19 restrictions allowed for schools to come back to face-to-face teaching. Subjective well-being of parents and guardians is, however, a predictor of concern about their children’s education and future. Our working hypothesis is that, although there is little evidence that subjective well-being has a significant association with the respondents’ willingness for their children to continue their schooling, there is a significant indirect effect of subjective well-being—which is especially determined by the gender as well as of the living material conditions—and the greater or lesser importance that the respondents attribute to their children’s education. Likewise, and in more general terms, subjective well-being is clearly related to gender, with women having the lowest levels of subjective well-being.