This chapter provides a snapshot of issues museums face today (volatility, uncertainty, complexity, and ambiguity), with emphasis on changing demographics, visitor expectations for personalization and multi-sensory experiences, and the shifting philanthropic landscape that increasingly depends on individual giving. It posits how art museums must position their offerings and programs to meet the expectations of new, younger donors and granting agencies, while also keeping traditional donors engaged. Interpreting their collections in light of the public zeitgeist – both locally and nationally – will become increasingly important, especially as patrons feel the urgency to address acute societal needs such as social justice and diversity. Finally, the chapter contends that museum boards and staff – including their professional fundraisers – must become more diverse and adept at using technology if they are to court a growing donor audience of diverse digital natives successfully.