Work holds great meaning and benefits beyond just monetary gain for people with intellectual disabilities. It gives these individuals the opportunity to engage in meaningful occupation. The purpose of the study was to explore challenges that people with intellectual disabilities (PWID) experience when adapting to their worker roles in the open labor market. The study used grounded theory as the research design. Five male participants and two key informants participated in the study. Two semi structured interviews were conducted with each one of the seven participants (five PWID and two key informants). Three core concepts emerged: 1) Unforeseen challenges of change; 2) A well-planned work preparation program enables success and 3) Crossing the bridge into the workplace: "Do I belong here?" This indicated that with sufficient external support, PWID are able to gain a sense of social belonging and develop the necessary skills to cope with challenges that arise in the workplace when PWID transition from protective/sheltered workshops to the open labor market. The findings of the study also indicated that work preparation programs and supportive employment approaches helped PWID transition to the open labor market.