This paper describes the results of qualitative and exploratory research into the transition to and experiences of the working world of graduates from a Chilean technical-professional higher education institution, whose student body is mainly made up of first-generation higher education students. The study includes eight in-depth and six group interviews, with a total of 33 graduates taking part. The results reveal the different obstacles graduates face as far as their career development is concerned, as well as the personal and strategic resources and actions they have used in their transition to the labor market. Among these perceived obstacles, the fact that society does not particularly value their work, long hours, low salaries and even gender and class violence particularly stand out. The study ends with practical recommendations so higher education institutions can actively support the transition of their graduates into the labor market.