The present paper attempts to describe the routes we have traversed, the insights we have garnered, and the change of perspectives which have emerged during our decade-long study of expertise in information work with special attention to journalism. At the initial stage of the project we mainly, drew upon the information processing perspective, which focused upon the correspondence between mental representation and the outside world. Experts are distinguished from novices in terms of the quality of their representation. However, in the course of time we have gradually found the information processing approach dissatisf5iing. This led us to rethink the assumptions underlying the information processing approach, which we contend, may fail to capture the fluidity and flexibility of expertise. We have gradually come to the realization an epistemological re-evaluation, which takes into consideration of the embodied and distributed aspects of social interaction and knowledge may be needed to more fully account for the nature of expertise. At the same time our study of expertise has shifted attention to the expert's interaction with contexts rather than representation alone.