Career theorists emphasize the importance of the development of career maturity in adolescents if they are to successfully negotiate the school-to-work transition. Transitions of deaf and hard of hearing adolescents may be especially problematic. The authors examine the implications of current labor market trends for young people, in particular those with hearing loss, and review data on employment outcomes for deaf and hard of hearing people. They discuss the environmental and attitudinal barriers that can influence the career outcomes of this population, consider the impact of hearing loss on adolescents' career maturity, and review the studies on this topic in the literature. The article focuses on the experiences of students with significant hearing loss who are educated in regular classes with the support of itinerant teachers, who communicate orally, and who may be defined as hard of hearing. Recommendations for research and practice are provided.