Practical wisdom is a master character strength that is needed when specific virtues must be translated into concrete action. Although scholars have discussed practical wisdom since the time of Aristotle, empirical research on this master virtue has been hampered by problems involving conceptualization and measurement. The primary purpose of the current study is to assess the relationship between practical wisdom, self-esteem, and hope. This is accomplished by evaluating the relationships between self-esteem, hope, and a second-order confirmatory factor model which specifies that nine specific virtues (e.g., humility, compassion) are determined by a more abstract, higher-order construct that represents practical wisdom. This model is estimated with data from a recent nationwide survey of middle-aged and older adults. Two main findings emerge from the analyses. First, the data suggest that greater practical wisdom is associated with stronger feelings of self-worth and greater hope. Second, the findings reveal that the second-order factor model of fits the data well.