This article introduces the reader to the articles contained in this special issue. It outlines how these studies contribute to our understanding of career development in light of the protean and boundaryless career era in which we now live. The articles contained in this special issue also raise questions that serve as a road map for future research. As a result of working on this special issue, we urge researchers to better clarify and differentiate among overlapping career-related concepts and to move career development research from a context-free approach to context-dependent one. Career development research that attempts to examine the connections between development in one’s organization, career, and life and the role played by career transitions would go a long way toward answering these questions raised.