This introduction presents an overview of the key concepts discussed in the subsequent chapters of this book. The book introduces readers to the enigmas of Charles H. Cooley's legacy. It is common for classics of sociology to become "old" in the eyes of new generations of scholars. It illustrates the idea of updating. The book also aims to concentrate on Cooley's critics, and their undermining of Cooley's reputation. It highlights the relevance of updating Cooley through a theoretical alignment with compatible thinkers. The book introduces an innovative methodological proposal—the "essentialist portraiture"—which is rooted in Cooley's idea of the larger mind. It discusses Cooley's method of sympathetic introspection for further application in current qualitative methodology. The book explores the most damaging critique to the looking-glass self theory: that it lacks a conceptualization of individual agency and that Cooley's organic perspective has an affinity with interpretations of the social world founded on the belief of a spiritual core in all human being.