Information systems design has long been concerned with improving utility, efficiency and effectiveness - a markedly rational functionalist perspective. Applying a broader view of design paradigms reveals that information systems have a generative capacity, which enables reframing and recasting reality to enable human action based and support multiple values. Viewing Design Science Research through the lens of pragmatist philosophy reveals that broadening the ontological foundations for design theory and evaluation can increase our understanding of how people actually interact with technology to achieve ideographic goals. The secondary design of information technologies and community-based Geographic Information Systems are offered as examples for which demonstrates a pragmatic perspective enriches design directives