With global reports of substantial mental health issues, there is an imperative to take seriously the criticisms of the traditional Western paradigm that entails the predominant epistemological and ontological assumptions about mental health. In this paper we argue that the historical development of concepts and theories related to self have created deeply embedded cultural legacies that are based on the ontological and epistemological assumptions of our individual and societal expectations about, and experiences of, wellbeing. Further, we will argue that ontological and epistemological assumptions in the Western paradigm concerning a fundamental ontological separation of selves from the world and of an intra-psychic divide mean that the way that the self is understood in relation to the experience of wellbeing is conceptually flawed. These embedded assumptions are demonstrated to be problematic by framing them in the double-bind scenario, whereby contradictory inputs create an irresolvable situation causing anxiety and confusion. Understanding the web of ontological and epistemological tangles and their consequent conceptual and lived ‘binds’ provides a framework within which to consider a paradigm shift in understanding the self in relation to critical thinking and the experience of wellbeing.