The purpose of the study was to explore the transitions of two individuals within a twinship from Grade R through to Grade 2, and to offer an in-depth description of their transition experiences and perspectives. The transitions were investigated with a focus on variables such as stress, stressors, emotions, coping and life skills. The inquiry was conducted as an interpretive case study. The participants were two monozygotic boys within a twinship, their mother and their Grade R, Grade 1 and Grade 2 teachers. The findings suggest that the transition was predominantly uncomplicated from Grade R through to Grade 2, and that the transition to Grade 2 was more stressful than that to Grade 1. The findings also indicate that although the life skills taught by the researchers helped the boys to cope with negative stressors, their personal support structures were probably the most important factors in easing their transitions from Grade R through to Grade 2. The life skills learned mostly helped the two children to deal effectively with bullies, to contract and maintain satisfying friendships, and to control their personal emotions.