This chapter begins with the strategic decision-making issues for successful applications of the business reinvention methodology and discusses how businesses can decide proper strategic plans in accord with contextual situations for proper application of the methodology. This chapter models the examinations of contextual situations to assess missing components (the when and where) of the 5W1H given the methodology already addresses the who, what, why (i.e., the value design), and how (i.e., the ecosystem design and the operational design). Subsequently, this chapter reinforces the book's vision of collective wellbeing toward economic quality and growth by connecting the vision to a modern economic conception of Doughnut Economics, or the idea that “a healthy economy should be designed to thrive.” Meanwhile, this chapter suggests the proper mindset and behaviors required for different business reinvention roles, which are required for successfully applying the business reinvention methodology to create the wanted results in a cost-effective and timely manner. These business reinvention roles could be regarded as creative leaders who have qualities like inviting disruptive innovation, being comfortable with ambiguity, and changing the enterprise. Finally, the emerging research opportunities and the conclusion are also discussed.