This article reflects on the Spanish Roma people’s aspiration dilemmas about their school-to-work transition (STWT). Study of the STWT of Roma young people casts light on the social and economic inequalities in Spanish society. Academic and occupational aspiration dilemmas reveal aspects of the interplay between structural-historical, societal, institutional and community-level factors that condition Roma people’s “capacity to aspire”, which Appadurai defines as a navigational capacity. Drawing on 31 interviews with Roma people living in a mid-sized Catalan city, we explore the following types of intermingled aspiration dilemmas: concrete vs. abstract, misaligned and insecure, misrecognised, interrupted, and postponed aspirations. We also unpack two cross-cutting aspects – young people’s capacity and strategies for navigating among aspiration-related resources and negotiating the meanings, terms, and conditions of aspiring school-to-work transition under multiple forms of pressure.