Youth involved in illegal street activities such as drug trafficking and violence are at high risk for school failure and other negative outcomes. Research often seeks to identify what is "wrong" with them, what makes them different from "normal" youth, but relatively few studies focus on variations in how youth engage in and make meaning of street activity as embedded within the contexts of their lives. In this article, Tara Brown examines how eighteen young adults in a predominantly Latina/o urban community experienced and understood their involvement in street activities. She draws on interview data from a participatory action research project that studied how and why participants were involved in street activities while they were attending K-12 schools. Framing street activities as adaptive responses aimed at well-being, she examines participants' involvement in relationship to their life circumstances, needs, and desires within the context of street life and proposes how youth may be similarly and differently oriented toward street activity. Ultimately, Brown argues that more complex understandings of youths' street involvement require deeper knowledge about its adaptive and varied nature, which can benefit educational researchers and practitioners in more effectively supporting these young people in achieving long-term well-being.