Ivan Illich was a heavy critic of traditional schooling. His proposals were disregarded, perhaps too quickly, for various reasons. This paper, based on review research, aims to add to a current (re)reading of Illich, seeking to answer the following question: what is the relevance of Illich’s proposal for a successful education in an increasingly digitalised society? The results of this research allow concluding, on the one hand, that Illich’s proposal to replace strict schooling with (self)training networks in a society that is increasingly digitalised and linked by the internet may offer potential benefits, and it is worth, at least, of an in-depth analysis. On the other hand, provocative scholars that allow us to get out of any ideologically and socially delimited system have the merit of helping to provide instruments that enable a better understanding of the present and, consequently, a rationale for the options for the future. Ivan Illich is one of these scholars.