As we elaborated earlier, measuring community sustainability is a diffi cult process that is prone to subjectivism and lack of systemic rigour. In response to these kinds of problems there has been a tendency to move towards overly rigid and positivist mechanisms of enquiry. Moreover, measuring community sustainability tends to suffer from a fundamental tension that arises in developing a generally applicable mechanism of research that at the same time is able to handle local differences and requirements. The tension is redoubled when the surveys are used in various settings that cross the Global South and Global North. In this chapter, the development of a ‘social life’ questionnaire within the Circles of Sustainability approach is critically narrated. The fi rst version of 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 fi rst 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 this chapter, to begin to overcome profound structural limitations. The questionnaire appended at the end of the chapter is the outcome of that work.