Although a growing literature explores occupational identity, or the overlap between "who we are" and "what we do," this literature has not fully considered how occupational identity may interact with technological change. In this paper, we explore this interaction, asking how an occupation's identity shapes and is shaped by its interactions with a new technology. We focus, specifically, on the relationship between librarians and Internet search. Drawing on an analysis of 22 years of articles from library journals, we demonstrate how and why librarians initially discounted Internet search and differentiated themselves from it. We argue that these responses were associated with a "paradox of expertise," by which librarians failed to innovate with one of the most important information technologies in history, despite their identity as masters of information. Later, however, we demonstrate how librarians engaged with this same technology, drawing upon it to redefine their occupational identity. Our findings demonstrate how occupational identity conditions the interpretation of a technology, while also showing how these interpretations can change with ongoing interactions. We also illustrate how occupational identity itself can change in response to new technology. Finally, we elaborate upon why expert insiders may not actually be best positioned to pursue emerging technologies.