Although new understandings of career decision-making processes are emerging, the prevailing rhetoric points to careers imbued with new worker attributes--flexibility, job mobility, and constant upskilling. This discussion of the pragmatics of youth career decision making draws on a series of transition studies with Western Australian youths, many aspiring to enter the building trades. Here, career-related decisions were influenced by images of masculinity and aspirations for an on-the-job lifestyle of sociability and intersected with a confusing complex of impinging pragmatic decisions. In these trades, these youths sought challenge and fulfillment in their work and a degree of job security, at least during the training period. Their longer term career aspirations stood in stark contrast to contemporary conceptions and portrayals of the flexible, short-stay, new employee. The question as to how universally appropriate and even desirable might be the preparation of all to be new workers is considered.