The radical changes of our environment under the influence of information technology require an adaptive approach between programmers and designers to enable lay participation and interaction with it. Satin is an application builder for mobile devices that enables end-users without programming skills to create and share their own apps (http://www.satinproject.eu/). Using shortcomings discovered in its design and development as a basis, we use the foundational principles and process behind the design of the Satin interface to illustrate that apart from following user centered design, designers also need to consider the constraints and influences of the design space they operate within. When designing a product, the systems and paradigms within which designers act, in this case information infrastructure and work practices, inevitably affect the solution space in which the final designs and products will be searched for. This often results in a limited impact or intelligibility of the initial goals. The design of innovative, collaborative user centered solutions requires designers to work not only on the final product, but also to challenge and evolve the foundations and underlying infrastructures that determine the possibilities of that specific design space. We conclude the paper by emphasizing the need for development of ways of working on the design of interactive systems that are informed by a holistic stance based on day-to-day experience and behavior as a guiding principle for technological development.