This study developed and validated the Higher Education-to-Work Transition Barriers Scale (HEWTBS) to assess students’ perceived barriers when transitioning to work. Conducted in Switzerland and Togo, two culturally and economically distinct countries, it resulted in two versions: HEWTBS-CH (Switzerland) and HEWTBS-TG (Togo). The first phase involved interviews with 13 students and surveys of 617 higher education students to identify relevant items and barrier structures for each context. In the second phase, data from 452 participants were used to confirm the scale structures and analyze their relations to career decision-making difficulties, satisfaction with studies, and self-perceived employability. Despite starting with the same item pool, the selected items and structures varied between countries, showing the influence of context. The scales demonstrated good reliability and relevance in their respective contexts, with important implications for counseling, research, and future studies.