This article addresses the discourse on career and technical education (CTE) from a multiperspectival approach to challenge the persisting academic-vocational divide. The author illustrates the paradoxical rhetoric in CTE, then shares a personal experience, and draws on ethnographic research to reveal a different understanding of enabling human capacity to support racially and culturally minoritized youth. In the end, the author suggests that a push beyond the language of investment and skills embedded in educational reform becomes all the more important in preparing youth for the future. Implications for practice, research, and policy toward possibilities in urban education are also discussed.