If the previous two chapters were about regret through the rearview mirror, this chapter is about regret through the front windshield. Regret is a retrospective emotion. It springs into being when we look backward. But we can also use it prospectively and proactively—to gaze into the future, predict what we will regret, and then reorient our behavior based on our forecast. Sometimes that approach points us in a promising direction. Other times it can lead us astray. But if we understand both the upside and downside of anticipating regret, we can hone our strategy for pursuing the good life.