This chapter presents an approach to deal with unexpected events by considering complexity, flexibility, maturity, autonomy, authority, as well as resource and context management. Humans always tried to extend their natural capabilities by designing tools appropriate for a job. The more tools have become available, the more complex human business has become. Modeling and simulation capabilities are ready to support both global and precise design infrastructures and functions. They enable the development of flexible applications that can provide quick results in uncertain environments. Designing for flexibility requires appropriate socio-cognitive representations. Flexibility is, therefore, associated with authority, responsibility, and domain capability. Authority can be given to a human or machine system or emerge from recognition. Design for flexibility in an increasingly complex world requires risk analysis, innovation, and dealing with the unexpected. Risk analysis uses methods, contributes to develop safety-effective systems, and performs risk-taking analyses based on various risk takers’ profiles.