AbstractThis article details the work experiences of small‐scale smugglers at the Mexico‐Guatemala border and how they give meaning to their work by redefining contraband as legitimate “business.” Through their daily practices, border residents distinguish between the “legal” flows of the everyday goods they smuggle and “illicit” flows of drugs, arms, and migrants. I apply a practice theory perspective to illustrate how everyday work practices deemed illegitimate by statist ideologies can lead to a reevaluation of hegemonic notions of “work.” Through their daily extralegal activities, border residents challenge conventional assessments of work and redefine neoliberal market logics that otherwise exclude them. Furthermore, I argue that a reflexive engagement with the ethnographic process provides insight into our own work principles and praxis. I reflect on my experience as an American female working among mostly male smugglers, leading to a critical reformulation not only of dominant definitions of legality, but of the politics and ethics of what is considered legitimate and worthwhile work.