Why does society make assumptions about what goes on in less affluent communities? Why are poorer communities so often assumed to be lacking: in creativity, in happiness, in possibilities? Does money equate to happiness? Is contentment an easy goal or a nuanced journey? What contributes to wellbeing, and how do we know we have it? I am an illustrator, poet and community worker, living and working in Oxgangs, a poorer area of Edinburgh. Seeing the shades of life that go on around me that often dispel notions of poverty as straightforward suffering, I am led to question, why am I happier here than in any other richer place I’ve lived? How come I have less than ever and am happier than I’ve ever been? What is it beyond owning things and having status that defines and enables true contentment? What is the value of wellbeing, and how do we quantify it?