Andreas Reckwitz warns against a development towards a society where we try to avoid having to deal with negativity and ambiguity. This article argues that literature and literature didactics are important contributors to combat this alarming development. Working with literature may strengthen our ability to handle with adversity, ambiguity and negativity. This article gives a close reading of Franz Kafkaʾs Josephine the Singer, or The Mouse Folk (1924) as an example for a highly dense and multivocal literary text that challenges the pupil, the student or any other reader thinking about her or his way dealing with ambiguities, both in art and daily life.