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.