In this article I draw on Lauren Berlant's notion of ‘cruel optimism’ to identify and untangle how the prevailing sense of ‘optimism’ in education works against our common hope or collective striving for what is educational in education. In particular, I discuss how the ‘cruel optimism’ that invites individuals to constantly innovate and improve themselves through ever more learning leads ultimately to a sense of ‘presentism’, ‘privation’ and ‘loneliness’, which comes to threaten the role that education plays (or should play) in sustaining and forging a common world. Proposing that education is where the concern with ‘passing‐on’ (in all senses of the word) properly takes place, I discuss how education can tend to and pine towards something larger and more durable (the world) than the individual acquisition of knowledge and skills that serve immediate transient interests. As an exemplar of a place of ‘passing‐on’, I ask us to consider how education invites us to affirm the ‘living‐on’ of the question of what it might mean to live together after all: to forge, sustain and pledge something of significance in common (and across generations) amidst what is constantly passing away. In this sense, I seek to gesture to the possibility of hope (as opposed to a mere optimism) within education: a sensibility and affirmation for ‘passing‐on’ and ‘sur‐vivance’. Such a hope might help to address the cruel depravity and isolation affecting our time that is caught up in the ‘learnification of education’.