People in today’s society are living in constantly changing environments where they are confronted with complex and occasionally unexpected problems. Previously learned practices do not provide adequate competencies to cope with these situations. Creative collaboration (Romero, Hyvönen, & Barbera; 2012) is one of the competencies required for successfully tackling challenges across the life span. Older adults (N=8), aged 60-82 years old, took part in the project called Creative Hut, where the purpose was to provide prerequisites for active ageing by using tablet technologies creatively and collaboratively. In this paper creative collaboration is explored in problem-solving situations where people have to choose strategies to self-regulate their learning (Zimmermann, 2008). The results of structured interviews showed that participants had specific interests; they set goals for themselves and developed strategies of self- and co-regulated learning to use tablet technologies. In particular, we found that 1) collaboration with peers and relatives is a key for solving problems and 2) note-taking is useful for deepening of understanding. Other successful strategies were 3) constant working and learning with the technology, 4) trial and error strategies and 5) phone calls to service providers.