We have noted that the word “education” is derived from the combination of the Latin ex meaning “out of” and ducere meaning “to lead” and, therefore, has the literal meaning “to lead out of.” In class, we have noted that an “educator” is, taking the etymology of the word seriously, “one who leads out.” But who is being led out, out of what are they being led, and what are they being led to? These are important questions for those who would become educators and Plato’s “Allegory of the Cave” from Book VII of The Republic provides vivid, pertinent, and provocative insights into possible responses to these questions.