The present study investigated theoretically and empirically derived similarities and differences between the constructs of enduring happiness and self-esteem. Participants (N = 621), retired employees ages 51-95, completed standardized measures of affect, personality, psychosocial characteristics, physical health, and demographics. The relations between each of the two target variables (happiness and self-esteem) and the full set of remaining variables were assessed through a series of successive statistical analyses: (1) simple Pearson's correlations, (2) partial correlations, and (3) hierarchical regression analyses. The results revealed that happiness and self-esteem, while highly correlated (r = 0.58), presented unique patterns of relations with the other measured variables. The best predictors of happiness were the following: mood and temperamental traits (i.e., extraversion and neuroticism), social relationships (lack of loneliness and satisfaction with friendships), purpose in life, and global life satisfaction. By contrast, self-esteem was best predicted by dispositions related to agency and motivation (i.e., optimism and lack of hopelessness). Implications for the understanding of happiness and self-esteem are discussed.