This paper highlights five challenges to the accepted wisdom in career development theory and practice. It presents the chaos theory of careers and argues that the chaos theory provides a more complete and authentic account of human behaviour. The paper argues that positivism, reductionism and assumptions of linearity are inappropriate for capturing career behaviour. Equally, predicting effect from cause is difficult and often impossible given the complexities of modern life. This paper calls for career development theory to accept a broader purview and concludes that ignoring other aspects of life both limits and undermines the utility of narrowly defined theories. Traditional notions of logic, rationality and objectivity are called into question. Finally, it is argued that chaos theory provides a natural connection between science and spirituality.