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This article constitutes a theoretical reflection from an educational perspective that places emphasis on the notion of inhabiting in the present technological society. The discussion is based on John Dewey's pragmatism, particularly on the idea of ​​technology resulting from the fundamental tenets of his conception of experience and aesthetics. A key element is the notion of habit, through which we manage our relationship with reality or inhabit it. Starting from an examination of technology in relation to the Deweyan notion of experience, the discussion moves towards the importance of the aesthetic dimension to come, finally, to some considerations on the meaning of habits in education and human existence.

This paper aims to analyse the notion of familiarity in Dewey’s pragmatism in order to show its important role as a tool for human beings to interpret the reality, manage it, and act within it. Starting from an examination of Deweyan transactional realism, the discourse focuses on familiarity and its related terms (such as “familiar,” “to familiarize,” but also opposites such as “unknown” or “strange”) in Dewey’s thought, to finally come to highlight its fundamental hermeneutic role. This might be useful to account for a subject of Deweyan thought not so deeply highlighted by scholarship and, at the same time, to show pragmatism’s closeness to hermeneutics regarding the relation between the human being and the real.