This article contributes to the growing research into the structural inequalities characterising the cultural industries by investigating the lived experience of older cultural workers. By drawing on 22 in-depth interviews with experienced advertising creatives it explores how ageism manifests itself in the creative departments of advertising agencies and how older creatives negotiate their professional identities in response to ageist representations, discourses and practices. By focusing on one of the so far mostly neglected inequality regimes prevalent in the cultural industries, this research adds to recent attempts to empirically explicate the formation of entrepreneurial subjectivities of cultural workers and the ‘psychic life of neoliberalism’. In all, the accounts provided by older advertising creatives paint a complex but also a consistent picture of entrenched ageist work cultures, which require considerable efforts on the part of older practitioners to successfully navigate. They do this by adopting an attitude we describe as resigned resilience. This notion encapsulates the ambivalence expressed by these older creatives towards their prospects in the industry and adds nuance to overly simple portrayals of the entrepreneurial subjectivities of cultural workers.