Recent reports of out-of-school immigrant youth have brought attention to predominantly Mexican and Central American immigrant youth who immigrate to the United States and do not enroll in formal schooling (Fry, 2002; Hill and Hayes, 2007). Many arrive to the United States unaccompanied, joining their older, undocumented counterparts in becoming part of the undocumented labor queue (Esquivel, 2007). New York City is one of the more recent destinations for these immigrant youth, with Mexicans leading all immigrant groups in terms of the highest percentage of school-age youth not in school. This article examines how these youth understand their life stages, both pre-immigration in Mexico and post-immigration in New York City, as well as the behaviors and actions they undertake in both contexts that lead to earlier and more rapid transitions to adulthood across the transnational social space. Most often considering themselves adults, these youth remain outside of formal high schools to meet their own labor and life demands.