The transition from primary to secondary school can be a period of anxiety for many children. Although most schools have developed systems to ease this process, it has been argued that the emphasis is often on administrative and organisational procedures. In contrast, children and parents are typically more concerned with personal and social issues. It may be that such concerns have received insufficient attention in the past. This paper employs theoretical perspectives from the literature on resilience and self-esteem to examine key aspects of the process of transition from the perspective of the individual child. It is argued that for some children at least, transition can be legitimately considered "a challenge of living" because of the social and personal messages which are received from a range of experiences within a concentrated period of time. The nature and source of these messages are discussed, and some implications for practitioners suggested. It is argued that in order to help vulnerable individuals cope with, and even benefit from, the period of transition, we need to focus more on the way social and personal experiences are interpreted at this time.