A focus of Government policy has been the need to ensure that those at the lower end of the labour market invest in their human capital through re-engaging with learning, which has been assumed to enable progress into better-paid employment. This article explores the problems created by "bad jobs" and the evidence for the existence of a set of mutually reinforcing factors that reduces the incentives acting on individuals in such work, and in many cases their employers, to participate and invest in education and training. Each of these factors, on their own, would be sufficient to cause problems at the lower end of the labour market. Acting in concert, as a mutually reinforcing matrix, they produce powerful reasons why many individuals perceive that the incentives to engage in work-related learning are weak. More broadly, our argument suggests that the fundamental causes of low pay and low-quality employment have been misdiagnosed and the subsequent public policy solution of up-skilling interventions is relatively ill-fitted to achieving the desired policy goals. Imaginative re-thinking on how policy might help those in low-wage, dead-end jobs is necessary. (Contains 3 notes.)