In this paper we describe a case study in which we examine how to develop playful persuasive solutions to motivate older adults to maintain or increase their social and physical activities. By including various stakeholders (older adults, family, and care givers) and by designing for transitions in life we intend to create solutions that can be used by many different user groups. Based on a playful interaction framework and user studies we are designing playful persuasive solutions that incorporate social and physical activities as mutual motivators. Furthermore, the persuasive solutions should be relevant for the life transitions of losing partners or friends, of having to move to a care facility and of declining physical and cognitive capabilities. We describe our experiences with involving older adults in a design process. Finally, we present our initial concept the ‘Activator’, that provides awareness about upcoming activities and own performances and goals, and provides opportunities for older adults based on physical or social motivators to keep and extend their social circle, and to perform activities of lower and higher physical demand.