There is much of value for educationists in the work of the great Russian novelist and thinker, Fyodor Dostoevsky. This paper explores a key theme in Dostoevsky’s later writings: the notion of a ‘Golden Age’. It compares the ideal depicted in Dostoevsky’s story ‘The Dream of a Ridiculous Man’ with the implied utopia of the classic Daoist work, the Daode jing. It is argued that these two texts can be helpful in understanding pivotal tensions—between reason and emotion, faith and doubt, happiness and suffering, and action and passivity—in educational development.