In this article, Rosa Bruno-Jofre and Jon Igelmo Zaldivar examine Ivan Illich's own critique of "Deschooling Society", and his subsequent revised critique of educational institutions and understanding of education, within the context of both his personal intellectual journey and the general epistemological shift that started to take shape in the early 1980s. Bruno-Jofre and Zaldivar consider how, over time, Illich refocused his quest on examining the roots (origin) of modern certitudes (such as those related to education) and explored how human beings are integrated into the systems generated by those "certainties." Illich engaged himself in historical analysis rather than providing responses to specific contemporary problems, while maintaining an interest in the relation between the present and the past. Under the metaphors of the word, the page, and the screen, he identified three great mutations in Western social imaginaries and the reconstruction of the individual self. Bruno-Jofre and Zaldivar argue that while his written work, including "Deschooling Society", generally had an apophatic character, his critique of education, particularly in the late 1980s and 1990s, is intertwined with his analysis of the parable of the Good Samaritan and his belief that modernity is an outcome of corrupted Christianity. (Contains 58 footnotes.)