In Xenophon’s Memorabilia, Socrates discusses with Aristippus how a leader should behave. Basically, leaders need to be trained to postpone their own somatic or corporal desires and prioritize those of the community or society. Aristippus agrees with Socrates, but he presents a different philosophical model, a hedonistic one, in which the best life is the life of those who are not involved in politics. Mainly, in his Hiero, but also in the Cyropaedia, Xenophon developed an argument against Aristippus’s theoretical stance. In doing so, Xenophon introduces the notion of virtuous psychological pleasures related to leadership—the pleasure of helping others (philanthropia), and the pleasure of being respected or honored (philotimia) that comes when good leaders help their community or society. But, as is shown in Cyropaedia, Xenophon is realistic—leading well is hard work, and very few people are willing to commit themselves to such an endeavor. Xenophon’s Simonides presents an alternative view to Hiero, the tyrant who became a good leader: If someone is willing to sacrifice to the community or society, eventually it will pay off, thus inverting Aristippus’ non-political stance. In sum, we are confronted with two opposite positions, where Xenophon offers a sound argument for taking the hard work of being a leader.