Individuals with a history of gang membership face unique difficulties when transitioning out of gang participation and to alternative work. This transition can be of personal and social benefit but requires support to ensure that it is successful. Unfortunately, vocational supports for former gang members often overlook the psychological perspectives that are necessary for their career well-being. Our aim is to shed light on the common barriers former gang members face during their career transition, exploring the socio-environmental factors, identity development, and discrimination that many former gang members must overcome in a North American context. We also review major theories that promote the career well-being of former gang members and provide recommendations for counselling interventions to support their career transitions.