Seeking to draw parallels between the one and the whole, this work is as much a study of individual character as a critique of society and its institutions. Viewed through the lens of the enneagram, a personality system that divides people into nine character types, this analysis aligns each of the ailments and difficulties of the individual characters with the broader ills of the world. In addition to providing a discussion of the theological and psychological background of the enneagram, this work examines the interaction between the various ennea-types and theology's deadly sins. Each character type is presented in light of specific habits and behaviors that diminish a person's ability to give and receive unconditional love. The ensuing essay on the character of nations and cultures presents a commentary on the perennial flaws of modern society and the defective operation of social institutions and governments. Rather than proposing a political or revolutionary agenda as a solution, this text advocates a healing process that begins with individuals and associations of people as the ultimate means of effecting the habits of larger social spheres.