Covid19 has forced many countries one can argue to undergo about ten years of digital transformation in one year. Something as basic as online learning, many countries, especially Small Developing States (SDI’s) in the Caribbean, have a hard time dealing with this. Both students and teachers alike are grossly underprepared for the “University of Zoom”. Then there is the over-focus on technology; we somewhat believe that digital transformation is all about the new technologies available to make life easier for all of us, however, it is much more than that. In the “Digital Transformation Playbook,” Professor David Rogers wrote that digital transformation is not about technology, but it is about strategy and a new way of thinking. He further went on to assert, that preparing for the digital age requires businesses and organizations to upgrade their strategic mindset more than their technology. Put simply, Digital transformation is about a shift in the mindset of the leadership of an organization.