Self-directed learning denotes that the individual is in command of what should be learned and why it is important. In this study, guidelines for the design of Web 2.0 systems for supporting diabetic adolescents' every day learning needs are examined in light of theories about information behaviour and social learning. A Web 2.0 system was developed to support a community of practice and social learning structures were created to support building of relations between members on several levels in the community. The features of the system included access to participation in the culture of diabetes management practice, entry to information about the community and about what needs to be learned to be a full practitioner or respected member in the community, and free sharing of information, narratives and experience-based knowledge. After integration with the key elements derived from theories of information behaviour, a preliminary design guideline document was formulated.