Little is known about the career development of youth with a history of criminal activity and the factors that influence their career development. The ability to secure employment is important in predicting successful outcomes for this population, but unfortunately youth who have been involved in crime are likely to face a myriad of obstacles to obtaining secure employment. This qualitative study used the enhanced critical incident technique to explore the incidents that 16 male and female youth with a history of criminal activity perceived as helping and hindering their short-term career goals and things that they did not experience but wish they had. Results revealed that criminally involved youth have career expectations of relatively low prestige and that their experiences with crime and the justice system have contributed to the development and achievement of these career goals in unique ways. The implications of these findings for career counseling and youth outreach programming are discussed.