This paper examines young workers' beginning engagement in learning through work, placing it in the context of Australian policy on entry-level training. Eleven young people were followed through their first year of full-time work and the significant adults involved in their working and learning lives were also interviewed. The study demonstrates that the presence of a contract of training (an apprenticeship or traineeship) is a strong predictor of a young worker's propensity to regard the workplace as a learning environment. However, unsatisfactory interactions with employment or training providers can create disillusionment with policy interventions that are meant to assist. Moreover, the habit of learning through work is not only a function of policy and training frameworks, but is also affected by individuals' abilities to learn how to learn. The paper concludes by arguing that, for those young people starting work who are not in a contract of training, additional assistance may be required in order for them to continue the habit of lifelong learning in the new environment of work.