"The Sociological Imagination" is among the most recognized books in the history of American Sociology. Yet, the sociological imagination as such, a radical form of self-consciousness, is not commonly well understood nor easily acquired. This essay examines the challenges thus faced by instructors who seek to accurately impart what Mills meant by his famous neologism and the even stiffer challenge for those struggling to instill the sociological imagination in their students. Two pertinent examples of creative and probably productive pedagogy are discussed, Maurice R. Stein's "Sociology of Birth & Death" at Brandeis University and Brian Rich's senior seminar in sociology at Transylvania University. The essay concludes with advice for the instructor in pursuit of fidelity to Mills's original argument and guidance vis-a-vis the typical constraints encountered in today's classrooms. (Contains 5 footnotes.)