Low and high-skilled contractors are often positioned in an analogous way within the literature drawing attention to the benefits of highly skilled contracting in contrast to the precarious nature of low-skilled contracting. Highly skilled contractors are largely identified within the free agent view; as self-directed professionals who add significant value to client organisations. However, very little research has focused specifically on how highly skilled contractors identify themselves through the process of positioning. We present the findings of a qualitative study of 34 highly skilled contractors. We found that participants positioned themselves in three specific ways: as expert, outsider and stranger and theorise about why highly skilled contractors construct simultaneous but diverse positions of themselves. In doing so, we argue that developing a more thorough understanding of how highly skilled contractors identify themselves provides valuable insights for those tasked with managing different groups of workers in the one workplace.