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This paper explores Pareyson’s constant drive toward an ontological dimension, despite the presence of a “dialectic of tension” that shifts heterogeneously throughout his entire work. To support this thesis, we first demonstrate how his philosophy, while rooted in Gentile’s actualism, functions as a critique of Hegelianism, aligning itself with the tradition of Italian personalism and the legacy of European existentialism. Within Pareyson’s ontological personalism, the person’s intimate existential bond with truth is not restricted to a theoretical framework based on a “dialectic of necessity”; rather, it is characterized by a participatory relationship with being. By showing that the foundation of his philosophy of action lies in the specific phenomenological structure of “initiative,” we argue that this dialectic of tension culminates in an ontology of freedom: a concept that, until the very end, preserves its ethical and anthropological essence alongside its purely speculative value.