Given its fluid nature, wisdom in the sapiential corpus of the Hebrew Bible is notoriously difficult to conceptualize, much less define. There is no one-size-fits-all definition. Nevertheless, the field of “virtue ethics” offers a useful approach for highlighting the defining contours of wisdom in Proverbs, Job, and Ecclesiastes. This essay explores these books according to three main features of virtue ethics: (1) the efficacy of virtue, (2) the shape of eudaimonia, and (3) the narrativity of the moral self. Whereas a virtue-based ethical approach is a natural fit for Proverbs, it encounters limitations in Job and Ecclesiastes, highlighting thereby their radical distinctiveness vis-à-vis Proverbs. While Job ultimately champions an ethics of encounter over an ethics of virtue, Ecclesiastes adopts a peculiarly hedonic orientation. Nevertheless, virtue ethics remains a useful hermeneutical tool for identifying the sapiential distinctions and commonalities across all three books within the broad scope of wisdom, which has all to do with living “well,” however that is to be defined.