Scattered across history and cultures, we encounter instances of people trying to limit or reject the expansion and application of mathematics. These actions, which we can refer to as “anti-mathematics”, are particularly common among artists of the modern era. This chapter tries to decipher, through a close reading of a large group of examples, the different motivations and desires that give rise to anti-mathematics across different contexts. The author argues that such actions are attempts at shielding particular ways of life from the encroachment of forces (economic, philosophical, and administrative) that use mathematics as their main instrument. In art, the pain and confusion caused by the uses of mathematics can be hurled back at those uses and expose their underlying violence. Anti-mathematics, however, does not only expose. It always creates new zones, new approaches, new products for thinking and life. The author finally connects these historical examples with the experience of children in contemporary schools and suggests that a study of anti-mathematics might be the key to developing an autonomous and rational relationship to the irrationality of mathematized reason.