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There have been a number of books on the Holy Man in Late Antiquity as well as works that discuss the monasticism in its traditional sense (i.e., as a communal movement associated with monasteries). However, while there has been some interest in the ways in which Greek and Roman philosophy influenced monastic ideas (e.g., Finn 2009; Hadot 1987), there has been no examination of asceticism in Ambrose’s De officiis, which was modeled on Cicero’s De officiis. My interest is the relevance of asceticism/early monasticism to the De officiis (c. AD 387) of St. Ambrose, Bishop of Milan (who was never a monk but rather an orator and consularis of the provinces of Liguria and Aemilia). I specifically examine the way in which Ambrose in De officiis 3.1-7 incorporated Stoic ideas about otium and the most honorable use of a “withdrawal” from public life, and how the wise man is free whatever his circumstances and is never really alone (Cic. Off. 3.1), and combined them with Cicero’s cardinal virtues and focus on the importance of the honorable in everyday life, and with Christian belief. But more importantly, the passage contains numerous standard themes associated with the new movements of asceticism and monasticism (especially Athanasius’s Life of St. Antony) and various ascetic ideals, i.e., its context is completely ascetic. By mixing these ideas together, Ambrose developed and promoted a form of ascetic and Christian everyday otium that consisted “withdrawal” that was not really isolation and of “being alone while not being alone,” i.e., prayer, meditation, poverty, temperance, faith, and the cardinal virtues in order to stimulate a concern for, and practice of, justice, charity, and the honorable (Amb., Off. 3.1-2, 7; 2.66, ed: Davidson 2001). Ambrose’s concern to elevate Christian asceticism by including classical concepts was based on others such as Clement of Alexandria but is an important attempt to rehabilitate monasticism intellectually because of the claim that monks were ignorant. His interest in inner asceticism is based on Origen (e.g., Homiles on Genesis 4.1-3); his concern that community is more important than solitude is similar to that of Basil of Caesarea and John Chrysostom. His focus on self-discipline is ascetic. But Ambrose is unique in combining all these elements together in one passage. Ambrose also importantly believed that such everyday asceticism is applicable to all people: he states that frugality, seriousness, and self-control are “seemly for people everywhere, and especially so for a person who occupies a position of honor” (Amb., Off. 2.67 trans. Davidson).