A growing body of evidence indicates that the effectiveness of positive psychological interventions is contingent on a diverse set of individual characteristics, chiefly among them, one’s cultural context and background. Building an evidence base to support the selection of parameters most likely to promote individual well-being under such boundary conditions is a crucial step in the design of viable interventions. Towards that goal, we examined how gratitude disposition, self-esteem, and optimism relate to subjective (SWB) and psychological well-being (PWB) among Japanese individuals. Results revealed that while self-esteem was predominantly more strongly associated with SWB, gratitude disposition was more strongly associated with the PWB dimensions, in particular, personal growth, positive relations with others and purpose in life. These results suggest that though gratitude disposition and self-esteem can influence individual well-being at large, they likely play complementary roles as enablers of SWB and PWB in the examined cohort.