Under the tutelage of Gregory the Great and John Webster, the virtuous life of the Christian entails learning how to steady oneself in three ways: 1) by the reality of Christ and his gospel, 2) how to act in its wake, and 3) how to refuse the charms and threats of other false realities. The ministry of the pastor involves many tasks, yet arguably close to the center, if not central altogether, is shepherding the flock entrusted to him to imitate God in Christ to whom they are united. In order to accomplish this, the pastor must first address himself so that he may have the “skill in applying knowledge to some useful purpose.” What Calvin describes here is the virtue of prudence and is what is needed for the pastor to faithfully shepherd the flock entrusted to him. Stemming from his union with Christ, this essay argues that the pastor’s ability to shepherd is determined by his ability to discern the true and best end, and choose the effective and best means to attain that end. In the sphere of pastoral ministry, this essay considers what gives cause for prudence and the end of prudence. Limiting the scope, sins of speech and the beatific vision will serve as examples of the causes and end, respectively.