This paper discusses the meaning of the concept of ‘second-order observation’ used by Niklas Luhmann (1927–1998). Luhmann identifies second-order observation as a defining characteristic of modern world society. According to Luhmann, all social systems construct a social reality on the basis of the observation of observations. Rating agencies in the economy or the peer-review process in the academic system are examples of social mechanisms manifesting second-order observation. Social media also represent organized second-order observation. The paper suggests that in a society based on second-order observation, ‘genuine pretending’ is an adequate mode of existence. This notion is derived from the Daoist text Zhuangzi. It indicates a disassociation from social roles which allows their performers to exercise these roles with ease and, at the same time, maintain a state of sanity.