This chapter delves into Machiavelli’s concept of the “art of the state”, exploring his experience as a civil servant of the republic of Florence. This notion of the state reflects a medieval rather than modern reality: a territorial dominion in which Florence governs over subordinate communities. Florentine “libertas”, a republican ideal, remains a symbol of the city’s political imaginary, but in practice is accessible only to a limited elite. The chapter examines Machiavelli’s role as Secretary of the Second Chancery, positioned between the piazza and palazzo—the two poles of republican political discourse and imagination. Finally, it analyses Machiavelli’s strategy for building a public reputation within an environment of internal conflicts, where rumours and slander significantly impact careers and power relations.