Obtaining functional and inclusive societal organization is not a simple matter of ‘doing it’ by subscribing to winning formulae as there are many choices to be made in the process. Given that conceptual frameworks always guide thoughts, judgments and actions, how we relate to ‘sustainability’ specifically becomes relevant if we aim to achieve a more liveable society. It is increasingly appreciated how all societies contain ‘wicked problems’ or socio-cultural challenges that are multidimensional, hard to pin down and consequently extremely challenging to solve. This seminar engages with the consequent need to recognise this complexity by assembling three ‘brave’ takes on far-advanced problems bedevilling conventionally conceptualised paths towards sustainability. Arguing against oversimplification that comes from domination of polarizing concepts and unquestioned practices and rhetorics, the aim of this seminar is to foster explorations into new territories from which we may learn. This involves thinking differently, even if such thinking must sometimes both provoke and cauterise dissent, and revisit divergent ideological standpoints in order not to dismiss out-of-hand ways towards supposedly common goals.