In this chapter, Machiavelli presents himself as a “master of reading”, reflecting a deep intellectual identity shaped by his commitment to reading and interpretation. Through his correspondence, particularly with Vettori and Guicciardini, Machiavelli’s unique approach to reading becomes clear. He considers reading not merely as an act but also as an experiential, interpretative process that parallels real-world observation. Unlike conventional thinkers, Machiavelli resists strict adherence to classical texts, instead embracing a method that values re-reading and critical engagement to reveal hidden meanings. His perspective implies that interpretation is vital to understanding reality, as seen in his critique of both historical and scriptural misinterpretations. He promotes reading “with discernment” to uncover deeper truths, questioning traditional interpretations, and aligning more closely with practices seen in religious and intellectual circles of his time. Ultimately, Machiavelli’s reading strategy advocates intellectual freedom and challenges canonical views, pushing for interpretations that accommodate complex, often contradictory aspects of human experience.