This chapter serves as an in-depth introduction to the critical examination of Ivan Illich’s contributions to the discourse on higher education and societal norms. It delves into Illich’s profound critique of institutionalized education systems, emphasizing his call for a shift towards a more learner-centric model that empowers individuals to foster personal intellectual growth. The chapter also scrutinizes the enduring relevance of Illich’s ideas, especially in the context of sweeping transformations in higher education that have been accelerated by technological advancements like artificial intelligence. It raises pressing questions about whether society has made any strides in assimilating Illich’s transformative propositions, and it argues for a comprehensive re-evaluation of traditional educational values, norms, and institutional arrangements. The chapter sets the groundwork for subsequent discussions on how artificial intelligence interfaces with Illich’s notions of human flourishing and conviviality, all framed within a broader theoretical context of learning and social change.