Despite their different contexts and different philosophical traditions, Hegel and Stiegler both offer a philosophy of youth, a philosophy of age, a philosophy of spirit, and because of this illuminate a particular response to the crisis found in the development of "Bewusst-sein" or conscious being. Both 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--a general melancholy or anxiety--and the very disruption of desire itself among contemporary youth who, in facing not only the stark realities of climate change and the Anthropocene, but also robotization, the breakdown of educational institutions and the ongoing deskilling of the workforce, "can no longer envisage a future." Both Hegel and Stiegler have been used in this article to contrast the passage of youth across the generations, the moment of crisis in youth and the senses and experiences of madness in two different epochs. The author examines both philosophers of spirit to think the role of philosophy as a discipline which thinks the future, which thinks of desire and hope for the future as something that emerges out of the madness and disruption of the present.