Musculoskeletal pain impacts upon everyday life. A degree of chronicity may pose an increased risk of sickness absence. One of two rehabilitative interventions, "Tailored Physical Activity" or "Chronic Pain Self-Management Program", was offered to sick-listed citizens who experienced pain. The objectives of this paper were to: (1) Assess what factors are experienced as problematic for sick-listed citizens in everyday life with chronic pain, and (2) Evaluate the significance of two distinct rehabilitative interventions on the future everyday lives of sick-listed citizens. Seven semi-structured interviews with sick-listed citizens were analyzed using a phenomenological-hermeneutical approach. Results were discussed by applying the theoretical framework of Antonovsky's salutogenetic model and Yaloms principles for group psychology. The potential for development of citizen's coping is evaluated based on Roessler's notion of progression. The analysis revealed four main themes: (1) Living with pain and unemployment; (2) "Putting my foot down" and "asking for help"; (3) Significance of the group, including instructors, and; (4) Aspects significant to progression. Unemployment is a major life event that promotes stress and can be accompanied by problems related to depressed mood, acceptance of the life situation, feelings of not being useful, feelings of losing control and identity conflicts. Group characteristics that gave a significant basis for progression in the self-management program are both emotional and instrumental, while the physical training program offers a "here-and-now"-experience and motivation to participate. This study indicates that the self-management program could potentially improve coping while the physical activity program revealed one example of a means of progression.