The present study aims to explore occupational engagement during expected and unexpected transitions in life, as well as to understand how self-identity and meaning, situated in the context, is created and recreated through the daily occupations. We use case examples of children with disabilities, adults with acquired brain injury, older adults with stroke and people with serious somatic illness, undergoing rehabilitation. The cases are drawn from previously performed studies by each of the authors. In the present study, a secondary analysis of data was conducted based on an abductive approach and theories of self-identity and transaction, to illustrate how changes in everyday life occupations made sense. Three themes emerged that structure the discussion; Disruption of a former self, Pursuing normality, and Reconstructing daily occupations and routines. Our discussion illustrates how different life transitions can be demanding and how people, situated in the context, revise and create new meaning and self-identity through their occupations. This discussion is relevant to occupational science and occupational therapy as well as to health promotional work more generally.