Working in the knowledge sector means dealing with increasing amounts of information, technology and people. Organizations as well as individuals in communities need to constantly maintain large repositories and networks of people, including colleagues, clients, experts, acquaintances and friends. This situation leads to complexity where person’s cognitive capability is insufficient when dealing with huge repositories of information and interaction. Viewing it as an individual problem has resulted in applications that highlight the need for structure and organization. We here define these applications in different levels where the first level is the office application generation, referring to “desktops” metaphors. The next generation, groupware applications, offers structure and process support for collaboration, but is still a rather limited “forum” metaphor. Our main argument is that current application generations and design metaphors are too limited when supporting the sharing of thoughts and associations in different community networks. We believe that a large portion of this problem is not related to information itself, but rather to processes of information categorization, navigation and interaction within and between communities. In our results we advocate the need for a new application generation and a new design metaphor, i.e. brainware applications based on “neural” metaphors. The result is a review of three application generations based on different design metaphors. We discuss several implications for a new design metaphor and suggest a design draft that supports boundary objects as means of knowledge sharing within and between communities.