Diversity emerges as a critical concern that spans all activities in software engineering (from design to verification, from deployment to runtime resilience) and appears in all sorts of domains, which rely on software intensive systems, from systems of systems to pervasive combinations of Internet of Things and Internet of Services. If these domains are apparently radically different, we envision a strong convergence of the scientific principles underpinning their construction and validation towards flexible and open yet dependable systems. In this paper, we discuss the software engineering challenges raised by these requirements for flexibility and openness, focusing on four dimensions of diversity: the diversity of functionalities required by the different customers; the diversity of languages used by the stakeholders involved in the construction of these systems; the diversity of runtime environments in which software has to run and adapt; the diversity of failures against which the system must be able to react. In particular, we want to emphasize the challenges for handling imposed diversity, as well as the opportunities to leverage chosen diversity. The main challenge is that software diversity imposes to integrate the fact that software must adapt to changes in the requirements and environment -- in all development phases and in unpredictable ways. Yet, exploiting and increasing software diversity is a great opportunity to allow the spontaneous exploration of alternative software solutions and proactively prepare for unforeseen changes. Concretely, we want to provide software engineers with the ability: to characterize an 'envelope' of possible variations; to compose 'envelopes' (to discover new macro envelopes in an opportunistic manner); to dynamically synthesize software inside a given envelop.