In what sense can we grant the fundamental technological disruption as described by Bernard Stiegler (2019) a proximity and relationship to the self-diagnosed hypochondria suffered by G. W. F. Hegel? The question informs the struggle and question of what knowledge is, and therefore the formation of Bildung (liberal learning or culture), which are shared themes and key issues in both thinkers. The question will serve to inform the meaning of crisis both in terms of personal crisis and philosophical crisis of Hegel as well as the modern psychical and societal sense of crisis. Despite their different contexts and different philosophical traditions, Hegel and Stiegler are both offering a philosophy of youth, a philosophy of age, and a response to the crisis found in the development of conscious being. Both then are vital thinkers for discussing the trials and tribulations of contemporary youth. With this in mind, a comparison is made between the empty subjectivity of young Hegel’s hypochondria and the very disruption of desire itself among contemporary youth who can no longer envisage a future. The question is whether Hegel’s hypochondria is comparable to the nihilism and alienation of young people who Stiegler describes as suffering from a profound loss of belief in the future. The conclusion speculates on whether the current technological era has distorted the process of individuation to such an extent that the necessity of psychological passage through forms of youthful hypochondria and alienation has been superseded by an altogether different mode of automatization.