This chapter addresses Nietzsche’s early exposure to pessimistic thought from the late 1860s to early 1870s, and aims to elucidate his philosophical articulation of pessimism as an individual and cultural problem to be solved. It argues against the view that Nietzsche was, at this time, a straightforward Schopenhauerian and pessimist. The chapter pays special attention to the ‘problem of quietism’, interpreting The Birth of Tragedy as concerned to speak to this problem, distinguishing Nietzsche’s strategy from competing strategies offered by the likes of Schopenhauer, Hartmann, Bahnsen, as well as pessimism’s opponents. After interpreting the notion of an artistic ‘justification’ as a solely pragmatic one for Nietzsche, the chapter ends with a discussion of the Untimely Meditations and Nietzsche’s evident early concern for the problem of suffering’s meaning.