The article explores how people born in Estonia in the 1970s contextualize their memories about their Soviet childhood in the context of school. Focusing on small group of people who grew up in the Soviet Estonia, we argue that in biographical narratives, school is treated as the representative of the Soviet regime. Nostalgic reminiscences from childhood embrace both commitment and resistance to the regime. The hegemonic framework of repression discourse is often flexibly stretched, embracing sometimes ironic stories of disobedience as resistance or commitment as play. Rather than opposing the official discourse, they create playful side-meanings about the era.