This paper introduces "Career entrepreneurship," a rapidly spreading phenomenon in the global knowledge-driven economy. Career entrepreneurship involves taking an entrepreneurial approach to managing the authors' careers. It means doing things that seem "Illegitimate" to other people and contradict socially recognized and accepted sequences of work experiences in terms of age, education, or socio-economic progression. This kind of behavior challenges established norms about typical career development. The evidence presented in this paper suggests new possibilities for thinking about the way individuals invest in their careers, new insights for organizations interested in capturing the potential of career entrepreneurship, and new ideas for career and life coaches to support people embracing the phenomenon.