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In this ethnographic study we examine challenges faced by a recently renamed population: opportunity youth. Specifically, we explore how staff in a urban vocational training program negotiate a mismatch between participants’ aspirations and opportunities. Rather than “cooling-out” students’ aspirations (Clark, 1960), we find that staff encouraged participants to develop ambitious vocations, which boosted students’ motivation temporarily. However, staff did not pair this “heating up” with a strategic plan to help participants achieve those dreams. Ultimately, this practice demoralized some participants when they were unable to advance toward their (now inflated) goals. Our study highlights the critical importance of nurturing hope in opportunity youth as well as the insufficiency of this practice when it is not paired with viable career pathways.