The life of an individual involves many transitions to new roles and new contexts. These include numerous educational transitions, from infants and young children entering early childhood services, through school transitions, to adults starting tertiary or work contexts. Each transition may offer both opportunities and challenges. In recent years "successful transitions" have gained national and international attention and have featured in many strategic plans and government policies. This paper considers the complexity of transition experiences through a critical exploration of individual, social and contextual issues associated with educational and life transitions.