Schein proposed his career anchor construct more than 40 years ago. The purpose of our research is to use current career theory perspectives to reconceptualize and develop a measure that is grounded in the career anchor framework but better reflects the boundaryless nature of careers today. We conducted two studies in which we develop and validate a measure of career orientation by examining its internal structure (Study 1) and external validity within a nomological network of conceptually related variables (Study 2). Results suggest that career orientation is best represented by a six-dimension factor structure: entrepreneurial creativity, security, managerial competence, lifestyle, technical competence, and service to a cause. Five of the six factors that emerged were correlated as expected with proactive personality, ambition, career self-management behaviors, mentoring relationships, and workplace attitudes, providing support for our conceptualization and measure of career orientation. The implications for both theory and practice are discussed.