The proliferation of digital connectivity and mobility continues to have a profound impact on remote and mobile work practices, collaborations and coworking spaces in urban environments. This chapter focuses on nomadic work patterns of designers, freelancers, hackers, and creative professionals, and explores the urban spaces that they occupy and navigate in order to go about their work. After a brief introduction on the changing use of office space and citywide work practices, we review current literature on the impact of digital connectivity and mobility on collaboration and coworking spaces. Two cases (the Centre for Social Innovation in Toronto, Canada, and The Edge, a digital culture centre at the State Library of Queensland in Brisbane, Australia) feature as examples of coworking and collaboration spaces affording nomadic work practices. The subsequent discussion of best practice designs of collaboration and coworking spaces focuses on three distinct themes: (i) the tension between universal versus specialized demands on space; (ii) the need for perpetual messiness, and; (iii) the entangled urban ecology of work spaces. Finally, we conclude by considering the configuration and promotion of nomadic and collaborative work practices especially by space managers and urban planners.