This explores the narratives from three individuals in low-skilled employment in the UK. The interviewees reflected upon their experiences of learning from compulsory education and beyond and their pathways through education to employment. The narratives illustrate how with the support of significant others, resilience and proactivity, they can overcome negative influences and subjective barriers to learning. Their barriers to learning will be examined in terms of their impact on future pathways and aspirations. The discussion will conclude by examining the role of significant others, and the potential role of career professionals, in combatting negative experiences of learning in order to raise aspirations and support positive pathways.