Objectives The study examined the predictive strengths of self-esteem, and positive and negative self-compassion for hedonic and eudaimonic well-being as well as assessed the relative mediating roles of positive and negative self-compassion for the relationships among self-esteem, and hedonic and eudaimonic well-being. Design A correlational design was employed through which self-esteem, self-compassion, and hedonic and eudaimonic well-being were measured. Methods One hundred thirty-four male (M = 25.11, SD = 1.66) and 138 female (M = 21.89, SD = 1.87) participants were chosen by a convenient sampling. Results The findings evinced that there were significant positive correlations among self-esteem, positive self-compassion, and hedonic and eudaimonic well-being while negative self-compassion exhibited small positive correlations with both the well-being measures (criterion). The regression analyses showed that self-esteem and positive self-compassion reflected significant predictive strengths for hedonic as well as eudaimonic well-being while negative self-compassion did not. This was also true for the social and psychological aspects of well-being. The beta values reflected that positive self-compassion did show a higher contribution for both the well-being measures as compared to self-esteem. Conclusions The findings evinced that positive, not negative, self-compassion mediated the relationship between self-esteem and hedonic well-being as well as self-esteem and eudaimonic well-being. Moreover, self-esteem and self-compassion have predictive strengths for both kinds of well-being. The findings showed the relevance of self-esteem and self-compassion to underscore well-being. The implications and directions for future researchers have been discussed. Practitioner points Contrary to the earlier findings suggesting self-esteem and self-compassion carrying relevance to explicate performance and well-being of people with individualistic and collectivistic cultures, respectively, the findings of this study suggest both the constructs to be useful to understand the well-being of people with both the values belonging especially to the fast-changing societies like India. The study also suggests reconceptualization and empirical verification of self-compassion that will make it more effective for enhancing and promoting interventions for positive life outcomes.