This article examines how former prisoners of color conceptualize their political, social, and economic futures and how these conceptualizations relate to the racialized social structural obstacles encountered upon reentry and decisions to re-engage criminal labor. I find that, presented with similar post-prison challenges, excarcerated men take several approaches when reentering society. I argue that the differences among their approaches lie in their varying interpretations of how they can act as individuals against and within their social structural limitations. Their decisions to rejoin or forfeit participation in criminal economies are thus shaped by experiences confronting the limitations of material conditions but also emerge from their critiques of racialized structures.