This paper explores the challenges facing educators in a time when modern technology, and especially modern social technology, has an increasingly powerful hold on our lives. The educational challenge does not primarily concern questions concerning the use of technology in the classroom, or as part of the learning environment, but a changeover in the whole social environment that marks our time. Taking guidance from Heidegger, Wittgenstein, Dewey and Nietzsche, the essay explores what we want the education of children to achieve, and how, if at all, this can be achieved in an age of modern social technology. The central argument is that the most basic educational goal of human flourishing cannot be achieved today as long as the main criteria of "best practice" in the classroom foreground pupil enjoyment rather than endurance of suffering. The paradox is that any call for the latter is now largely heard in a way cultivated by the culture of the former: namely, poorly and vulgarly, associated only with bullying authoritarianism, rather than the devoted care of teachers who want to awaken their pupils to self-responsibility.