ABSTRACTThis essay offers a Kierkegaardian analysis of and response to the harmful effects of destabilization that can be caused by engaging with certain technological media. It argues that the intellectual technological ethic that is at work in social media platforms reflects two types of despair discussed in Søren Kierkegaard's Sickness Unto Death. It advises using a Kierkegaard‐inspired Socratic rhetorical strategy of communication that ironically employs technology for depicting this despair and awakening individuals to its presence in their lives. Moreover, this essay suggests that the edifying themes of “misery” and “guilt” can be communicated indirectly and thereby offer one intervention that could possibly help the current technological age move from the immediate aesthetic sphere of existence to the religious sphere. Considering the important role of upbuilding in Kierkegaard's oeuvre, the final portion explores how even someone who does not identify with a religious tradition or community may encounter what Kierkegaard terms the paradox of the eternal in time in ways that foster the development of authentic selfhood.