The relentless evolution of opportunities and challenges presented by digital technologies, brings a corresponding business imperative for continuous digital transformation. But, the waves of disruptive change and the accompanying divergent choices they often present, can introduce unanticipated complications and uncertainties. We describe these as Digital Dilemmas. Businesses that understand the nature of these dilemmas and their options for resolution will be the ones that flourish on the journey to 2022 and beyond.