This paper reports on a qualitative research project that explored the influence of basic skills on the school-to-work transitions of young adults. Large numbers of young people have poor skills yet it is a neglected area of study. We document how skill competencies act as barriers to learning and labour market opportunities, illustrating that some individuals are "reticent" about accessing opportunities and that individual decision-making and agency are important to transitions. The paper illustrates the relationships between decision-making and the structuring effects of prior learning experiences and indicates therefore how structural conditioning and agential processes are linked and together shape transition routes. (Contains 7 notes.)