“Social Entrepreneurship” and “Social Innovation” are defined by their “ability to achieve large-scale transformation that enables others to copy the idea and distribute it through a number of imitations and implementations”. Arguments for consistent definitions are symptoms of a dominant episteme that tend to favour stability, transportability, and universality, and this knowledge paradigm has also created canons of Design. The scalability, again, a desirable characteristic of Social Innovation, requires things to be duplicated and distributed for larger, societal impact, based on the carousel of sameness. This chapter revisits the five existential conundrums that have accompanied the research in designing social innovation. Pragmatism in Design and Social Innovation can obsess over the HOW to instruct ways of achieving “alternatives”, and in so doing, promote replication or displacement. The chapter also presents an overview of the key concepts discussed in the subsequent chapters of this book.