Leaving the life of the streets involves personal and social considerations. This paper explores the social dynamics of desistance from crime – what it means to leave behind one’s gang as well as the larger gang landscape – and how these processes have changed in Chicago over a period of eroding structure among its gangs. Through conducting 45 interviews with current and formerly gang affiliated individuals and drawing upon over two years of ethnographic observations in Chicago, I generate a conceptual framework describing variation in gang exit strategies and suggest forms of support that could help individuals navigate the desistance process. This paper argues that desisting within a social system defined by increasingly “blurry” gang boundaries has made it easier to leave one’s immediate group while introducing new and understudied challenges corresponding to leaving the wider gang landscape – specifically making it more difficult to signal exit to many potential rivals and navigating ever changing territorial boundaries. This shift in criminal network structure in Chicago has given rise to new exit strategies used to maneuver this precarious gang landscape, some of which may be mistaken for anti-social behaviors: avoidance/isolation, situational awareness, locus of control, and calculated risk taking. In cases where leaving the life is primarily constrained by one’s inability to leave the gang or wider gang landscape rather than personal motivation or job supply, the relevant policy lever may not be changing individual preferences or expanding social programs so much as offering assistance against potential threats.