This article explores Poggio Bracciolini's letters to Niccolò Niccoli from a variety of perspectives: it looks at what imitation meant for Poggio, examines the letters’ commentary on the manuscript culture of the early Quattrocento, discusses Poggio's efforts to craft a personal voice, and traces the interplay of optimism and pessimism in the letters, an interplay common to humanist texts of this period. By bringing together these different perspectives, the article articulates the range of ways in which one scholar used his epistolary collection to shape his own persona, connect himself to Ciceronian precedents, and create norms and expectations for a developing intellectual community.