We are all social animals, and thus, a well-lived life cannot be separated from the cultural context in which individuals define and accomplish a good life. Reflecting this, attempts have been made to understand the link between culture and flourishing (broadly defined). Much of this work relied on individualism-collectivism (I-C) as an analytic tool. It produced descriptive knowledge on how I-C is associated with various indices of flourishing across nations. Though informative, this sort of comparative study suffers from inconsistent findings, suggesting that asking whether one form of culture is better than the other may be too simplistic and even dangerous. Indeed, an emerging conclusion from previous research on the culture-flourishing link is that, in an extreme form, neither individualism nor collectivism is desirable. More importantly, a simple dichotomy between I-C does not adequately capture the dynamic changes in highly industrialized Asian countries where people must negotiate their experiences between the traditional collectivistic values and the Western notion of independence. Building on a synergy model of I-C (Choi, 2016; Choi, Seo, Cho, & Bechtoldt, 2017), we propose that a combination of collectivistic values and independent self-views promotes individuals' functioning in the social world, thereby having a positive impact on their mental and physical health. We present data from organizational surveys involving Korean employees and specify the underlying psychological mechanisms of the proposed combinatorial effect. We also present our analyses of the World Values Survey (Wave 6, 2010-2014), which tested our predictions across clusters of individualistic and collectivistic countries. We discuss the implications of our findings in promoting conditions for individual and collective flourishing. We also discuss directions for future research in health psychology and other related fields.