Using data on individuals from the National Income Dynamics Study (NIDS), this paper analyzes the relationship between intergenerational mobility and subjective well-being for two cohorts of South Africans. Subjective well-being has been measured using a multitude of factors, but the impact of changing economic mobility on reported life satisfaction has been less explored in the context of South Africa. Education and social mobility are the two mobility variables used to understand how changes in economic status relative to one’s parents affect self-reported well-being. This paper utilizes three methods of regression analysis for comparisons: cross-sectional, pooled cross-sectional, and panel (fixed effects and random effects methods). Estimates from each of these models indicate a positive effect of upward social mobility on reported well-being, however the effect is smaller for the apartheid cohort (older average age) compared to the post-apartheid cohort. The estimates for educational mobility give mixed results across the methods, so findings regarding the impact of educational mobility on reported well-being are less evident. These results suggest that improving one’s social mobility status positively impacts life satisfaction in South Africa, but that the magnitude of the effect is smaller for a post-apartheid generation of South Africans.