The notion of learner pathways has assumed considerable policy interest in many countries as they seek ways of enhancing seamlessness within their educational systems. In contemporary society, where job boundaries are blurring, there is need to consider many types and directions of pathways between educational sectors throughout lifetimes. Focus has been mostly on transition from Vocational Education and Training to Higher Education. The road "less travelled" lies in the opposite direction, and far less is known about this pathway. This article analyses how adult learners experience this pathway, appropriating the concept of "boundary-crossing" in interpreting these experiences. It draws on information from surveys and interviews in two different countries. Singaporean (n=101) and Australian respondents (n=190) had graduated from both sectors, and were therefore in a uniquely informed position to reflect on their experiences. Findings provide insight into relationships between these sectors. (Contains 2 tables and 1 figure.)