There is an overriding interest in measuring the well-being of communities and institutions: healthy (flourishing) individuals and groups perform “better” than those that are not. Capturing the facets of well-being is, however, not straightforward: it contains personal information with sometimes uncomfortable self-realizations associated to it. Yet, the benefit of such data is the ability to observe and react to imbalances of a community, i.e. it can facilitate community management. Due to its personal nature, the observation of well-being needs to leverage carefully considered constructs. To have a comprehensive look at the concept of individual well-being, we propose a gamified frame of reference within a social network platform to lower traditional entrance barriers for data collection and encourage continued usage. In our setting, participants can record aspects of their well-being as a part of their “normal” social network activities, as well as view trends of themselves and their community. To evaluate the feasibility of our approach, we present the results of an initial study conducted via Facebook.