Background: Consideration of the patient’s perspective in healthcare is important because it may inform holistic and contextually relevant management strategies. Objectives: The purpose of this study was to explore patients’ experiences and perspectives about their chronic musculoskeletal (CMSK) pain and its management in the private healthcare sector in South Africa. This work was done as a pilot study to test, adapt and finalize an interview schedule. Methods: A descriptive, qualitative study was conducted. The sampling was purposive. Three patients with CMSK pain were recruited to participate in in-depth individual interviews. The interviews were recorded and transcribed ensuring confidentiality. Inductive, thematic content analyses of the transcripts were undertaken. Initial codes were assigned and a code book developed, which was applied to the transcripts to develop categories and themes. Results: Four themes emerged from the data: (1) the participants sought understanding about the pain’s origin and the reason for pain persistence; (2) pain impacted their lives in multiple ways; (3) the participants depended on healthcare providers (HCP) for guidance and support; and (4) they had the option of acceptance of chronic pain. Conclusion: The participants’ knowledge about their health condition had important implications as it influenced their perspectives on pain and its management. The pain presented the participants with several challenges, which included developing an understanding about pain and coping with the impact of pain in their lives. HCPs were perceived to play an important role in empowering or disempowering the participants.