The document introduces a design research approach called Envisioning Transitions. This approach was developed based on a case study called Connected Care that aimed to create design solutions for healthcare and wellbeing. One of the main challenges in healthcare is empowering people to change unhealthy lifestyle patterns and tackle chronic diseases. The Envisioning Transitions approach helps multidisciplinary teams understand lifestyle transitions over time through three levels - solutions, experiences, and socio-cultural changes - to develop meaningful and integrated healthcare solutions.