Adults who left school early are generally under-represented as participants in education later in life. However, some 'buck the trend' and this article examines the experiences and motivations of early school leavers in New Zealand and the UK, using information from two studies of adults on university-level courses. The findings from both these settings reveal remarkable similarities in a number of ways. The analysis shows that internal motivation is important, as are contextual factors, both cohort-based and relating to personal circumstances at specific life course stages. On the basis of an analysis of qualitative interview material, a typology is developed of different early school leavers, which links circumstances around school leaving with the processes of re-entry to education. The complexity of factors at work is discussed with reference to age, cohort and gender, using a life course perspective. It is suggested that a focus on those who 'succeed' against the odds constitutes a fruitful way forward in developing our understanding of what motivates adults to study.