School is the crucial level for educating Montaigne’s well-made heads, aware that the significance of life and practice is innervated by errors and relationships. Education is citizenship, participation, and inclusion: fundamental questions that have now assumed even more strategic centrality, as schools and universities have once again become “agencies of selection” and no longer “agencies of emancipation”. Moreover, the crucial question of radically rethinking education continues to be limited to digital education, seen solely as skills and “know-how”. In spite of the exponential growth of connective opportunities, in which information and knowledge have become the main resources, society is as yet unable to guarantee that these networks generate fully communicative relationships, based on symmetrical relationships and authentic sharing. The sheer acceleration of processes, furthermore, has left little or no time for reflection, critical thinking, imagination or creativity, which are nourished precisely by contamination(s) between fields of knowledge, experiences, and socio-cultural landscapes. The (complex) organizations where young people will be employed are adaptive social systems, actual “organisms”; consequently, students must be educated (not indoctrinated!) to be capable of inhabiting and interacting with complexity, trained in unpredictability, open-minded thinking, imagining, and ultimately, in coping with the unexpected and the indeterminate.