While homeless youth are characterized by their risky behaviours we know little about how they conceptualize and manage risk in their everyday lives. This article will flesh out one aspect of a doctoral study that explored homeless youth’s conceptualizations of risk, by unearthing their self-regulation practices. Deploying an ethnographic lens, 18 youth were followed over a 1–4 year period to capture their risk perception and practices as they unfolded. The findings question the relevancy of the prominence of expert discourses in theories of risk. The study’s empirical findings run counter to the thesis that expert systems predominate in practices of self-regulation. In contrast, practices of self-regulation were not so much in response to expert discourses or social norms but were balanced by personal experience, intuition, and situated knowledges. Results provide valuable insights into the interplay of lay and expert knowledges in the construction of risk among an identified risky and at-risk group. Lessons can also be drawn for clinical practice and the relevancy of the expert role that social workers play in the lives of homeless youth.