The liberal arts tradition portrays Prudence as a woman holding a mirror. To be prudent leaders, we must know ourselves and be humble enough to come to terms with our own limitations. We are often our most substantial obstacle to prudence. Our ability to make sound, prudent decisions is fraught with sin, pride, and a myriad of other influences, many of which we are blind to. Without falling into the traps of self-authentication, self-justification, or unabashed self-interest, we must know that who we are is how we lead.