In this chapter, the development of a 'social life' questionnaire within the Circles of Sustainability approach is critically narrated. The questionnaire looked good and served our initial purpose, but beneath the surface the foundations of the questionnaire were naive and limited. The initial development was in many ways too ambitious, and the questionnaire was first rolled out at a time when we did not yet have the capacity to bring together cross-disciplinary skill sets. However, instead of suggesting that the project backtrack on its generalizing-particularizing ambitions, a series of steps were undertaken, described in the chapter, to begin to overcome profound structural limitations. The remaining common survey questions capture administrative and demographic variables the complete set is listed at the end of the chapter. It is clear that the first version of the survey showed potential but did not yet deliver as an adequate assessment instrument of community sustainability.