This chapter examines the career of the novelist and advice columnist Walther von Hollander during the Third Reich, setting it in the context of his longer career before and after Nazism and in particular his prominence as an advice columnist in post-war West Germany. It argues that von Hollander’s books and letters to his readers during the Nazi period contained an ambivalent mix of messages. On one hand, he promoted the idea that individual personal happiness could be achieved during self-optimisation and conscious effort applied to personal relationships. This notion, characteristic of contemporary Western societies, was not specific to Nazism. On the other hand, his advice was also tinged with elements of Nazi ideology that promised to dissolve and eradicate the disappointments associated with individuality through an orientation towards the wider community and the nation.