At the time he wrote Strange Life of Ivan Osokin, P.D. Ouspensky was already an acclaimed author and thinker, with such major works as Tertium Organum and The Fourth Dimension to his credit. In Ivan Osokin, Ouspensky sets out to explore the idea of 'eternal recurrence', the theory that most humans are condemned to an infinite repetition of a single lifetime, making the same mistakes and facing the same triumphs and tragedies each time.

The eponymous hero is a feckless youth, prone to pointless rebellion and easily bored. He changes little as he grows to manhood, wasting his future, squandering his inheritance and losing the woman he loves. In this parlous state, and contemplating suicide, Ivan Osokin meets a magician who agrees to send him back to attempt a conscious repetition of his life without mistakes, at the same time warning him that it will make not the slightest alteration to the outcome. Undaunted, Ivan Osokin undergoes the ritual and relives his earlier existence - with a strange and unexpected result.