Concern has been expressed within occupational science regarding the study of occupations defined as non-sanctioned and/or transgressive of a society’s moral and legal norms. Doing so is seen as an opportunity to shed light and delve deeper into the unknown aspects of these occupations. This study responds to that intent. Its purpose is to discuss the benefits and downsides of taking part in street racing in the city of Concepción, Chile. This is a banned occupation under the country’s legal framework that is considered transgressive, since it continues to be practiced despite prohibitions. The study used a qualitative methodology to gather data through semi-structured interviews with nine informants who functioned as competitors, organizers, and/or audiences. A thematic content analysis generated three main themes: emotions linked to taking part in street racing, a sense of community, and experiences of being discriminated against. This study’s contributions include discussing the experiences of people who conduct transgressive occupations in a context of occupational apartheid and identifying the emotions that trigger the street racing practice despite the risks. It also revealed strategies used by those involved to conduct this occupation in a safe manner while struggling to reduce social stigma and injustice, aspects that shed light on the dark side of an occupation considered legally transgressive.