In Canada, like in many other countries, people working in the sex industry are subject to prohibitive regulation, stigma and pervasive moral judgement. At the same time, workplace and client demands, in concert with various modes of socio-economic marginalization, shape sex workers’ experiences of and access to work. However, sex workers are seldom recognized for overcoming these challenges as skilled workers. Moving beyond arguments about whether or not sex work is a legitimate form of labour, we argue for the recognition of sex workers’ entrepreneurial and security strategies as creative problem solving and in turn cognitive skill. We do so by drawing on two qualitative interview-based studies highlighting the intersectional experiences of female sex workers who modulate their appearance and behaviour to perform race, gender, class, culture and sexuality to succeed in the Canadian indoor sex industry.