The purpose of this article is threefold: to offer a vision of human flourishing in the academy premised upon 'living in truth', embracing lived experience and being in relation; to explore counterfactual thinking across the life-course, from the period of compulsory schooling to the end of life, with the emphasis on the latter; and to critique the practice of drawing upon philosophy to provide an interpretative framework through which to address the arts, drawing upon the work of Cora Diamond. The movement towards death is explored through three vignettes, focusing on the lived experience of three 'characters' facing the prospect of their imminent demise: the philosopher Richard Rorty, the English television dramatist and screenwriter Dennis Potter and a consultant physician (the father of one of the authors). Drawing upon the work of the historian Timothy Snyder, the relevance of the claim made by Vaclav Havel that 'essence precedes existence' is explored in relation to the climate of the contemporary education system. The primacy of essence over existence is also a key feature of the vignettes of the lives of the three players that form the centrepiece of the article. These enable us to 'think without thinking', which is perhaps a counterfactual claim "par excellence."