The term sustainable development is often criticized for having lost credibility due to a lack of clear-cut delineation. The same holds true for education designed to foster sustainable development often referred to as education for sustainable development (ESD). This contribution agrees that the term suffers from a want of meaning, but argues that the persistent hunt for a definition—i.e., a fixed generic description—produces rather than resolves this deficit. What sustainable development means is context and time dependent and is therefore necessarily ambiguous, open-ended and dynamic. Hence, the success of ESD depends on the paradoxical imperative of reducing vagueness while at the same time maintaining ambiguity. This paper explores how this can be established and proposes a process informed by the arts. Drawing from dialogic practices, site-specific theatre and a project conducted in a British village, this writing discusses elements that constitute a process of “context-based meaning finding”. It concludes that ESD essentially starts with and revolves around re-embedding SD in life and the act of living, engaging people in place through processes in which communities yield their own, context and time specific interpretations of sustainable development.