The forcing online of higher education classes should have constituted a major reckoning of pedagogical practices in universities, particularly in the humanities. Such a reckoning seems to have been muted by a focus on logistical concerns and by what might be called a false sense of preparedness within university departments. This study attempts to counter that general trend by taking seriously the cognitive and emotional demands of the online transition through a philosophical lens. This essay presents a phenomenological study of the abrupt transition from physical to online classes during the COVID-19 lockdown of universities. Reworking two central theses of Marshall McLuhan's (1994) study of media, the author proposes two dispositions as necessary to encountering the role of new media in the teaching of the humanities: a state of wilful unpreparedness and a state of artistic creativity. These in turn pose educational dilemmas that require changes to the relationship between teachers, students and the learning environment, wherein these relationships become subjects of conscious study by the participants. The article draws on a range of classroom experiences in which the instructor and students attempted such a study. In encountering the shock of the new media, a series of concepts emerge that can help promote an artistic approach towards the medium itself.