The chapter outlines the implications of two projects, namely the ‘Phi Books' (2008) and the ‘Digital Dreamhacker' (2011). These novel projects serve here as case studies for investigating new and challenging ways of advancing collaborative technologies, using in particular, Communities of Practice and insights gained from both embodiment and graph theory (social network analysis) as well as design. Both projects were developed collaboratively, between a computer programmer and a designer and a wider community of practice, consisting of other artists, writers, technologists and designers. The two systems that resulted also acted as methodologies, instigated by the authors with a view to facilitate, explore and comment on the act of collaboration. Both projects are multi-disciplinary, spanning ideas and techniques from mathematics and art, design and computer programming. The projects deploy custom-made software and fiction enmeshed structures, drawing upon methodologies that are embedded with dreams and stories while at the same time being informed by cutting-edge research into human behaviour and interaction design. The chapter will investigate how the projects deployed techniques and theoretical insights from social network analysis as well as motion capture technology and the wider concept of a Community of Practice, to extend and augment existing collaborative methods. The chapter draws upon Wenger et al (2002), as well as Siemens (2014) and Borgatti et al (2009), and will explore the idea of a new form of collective social and technological collaborative grammar, deploying gesture as well as Social Network Analysis. Moreover, the featured projects provide insights into the ways in which digital technology is changing society, and in turn, the important ways in which technology is embedded with the cultural and economic prerogatives of increasingly globalized cultures.