This chapter studies the internal debate within the advertising profession during the formative years of the neoliberal shift, 1980–2000. This period also coincided with a transformation of the advertising business, as smaller agencies multiplied in the aftermath of de-cartelization. This transformation also meant a feminization of business leadership, although the majority of the leaders—especially in larger firms—were still men. In the chapter, both the shaping of femininity within the profession and how these notions spilled over into ideas of making sense of the commercial landscape are scrutinized. Additionally, how female entrepreneurship was connected to notions of self-making is analysed. The results show that women’s qualities were described as essentially different from male counterparts, but still assets in a consumer-oriented, commercial business. Unlike classical self-made men, they were portrayed as more collective in nature but still more hard-working than their male colleagues in a gender-unequal labour market. A supposedly female, softer, non-authoritarian leadership and women’s dual roles as advertising professionals and consumers were framed as well-needed characteristics when facing the market-oriented future.