The scholarly consensus is that the early essays “Il mare dell’oggettività” and “La sfida al labirinto” are two of the most important Italo Calvino wrote on his literary poetics, influencing the metaphors and problematics of his entire corpus: the sea of objectivity, the labyrinth, chaotic flux, a rational cogito subjectivity, binary oppositions etc. The essays were made available to a general public in the collection Una pietra sopra in 1980, part of a selection of texts handpicked by Calvino himself. Curiously, the 1986 English translation titled The Uses of Literature does not contain these important and influential essays, making them unavailable to an Anglophone audience. These essays are here now translated, accompanied by a critical commentary by the translator about their relevance and importance to Calvino’s corpus. The problematics discussed in these essays would re-emerge, with remarkable consistency, in the metaphorical imagery Calvino deployed throughout his career. Nevertheless, Calvino evolves the problematics significantly throughout his career, almost inverting his original stance. Rather than this being an inversion, however, the translator argues that Calvino’s evolution represents a dialectical movement propelled by contradiction, and that therein lies the actual poetics or the stylized mode of thought that these essays inaugurated. Viewing the essays in this light renders them, and Calvino’s entire corpus, ripe for dialogic encounter and collision with otherwise parallel philosophical traditions and schools of thought.