The disruption of traditional teaching and learning strategies within the (post) COVID era has invited teachers to rethink education, evaluate what they have done so far, and reimagine what it means to be an educator in the 21st century. The need to reflect on 21st-century education has particularly been felt in the realm of the humanities (religion, literature, history, etc.). This essay seeks to compare the “textbooks” of the ancient world (Iliad, Odyssey, Aeneid, TNK) with modern textbooks and draw conclusions that can function as a critical lens for reflecting on modern teaching strategies for the humanities. I suggest that modern textbooks and teaching styles—without neglecting their benefits—have contributed to compromising the ideals of the humanistic and, more specifically, the Christian educational aim: developing critically and independently thinking individuals who live responsibly in their social context. This essay will, however, not remain critical of modern education but make suggestions informed by ancient textbooks to improve education in a world where remote and internet-based learning has become an integral part of 21st-century education.