Transformational wisdom must undergird transformational politics to achieve the benefits of living in a democratic civil society. The purpose of transformational politics is to maintain social cohesion while adapting to changing circumstances in order to achieve eudaimonic outcomes. However, the reality of agonism presents the challenge of dealing with incommensurable values, beliefs, and desires. Failure to do so can lead us back to a Hobbesian authoritarian society. After outlining the nature of civil society and of democracy, which are fundamental to achieving wise transformational politics, the chapter outlines the contemporary factors that are causing the demise of the Enlightenment ideal. These are the systemic social pathologies of alexithymia, pleonexia, and akrasia.