This study investigates the following research questions in the Canadian and US contexts: 1) To what extent do those working at post-secondary institutions expect the future of post-secondary education to change over the next five years? 2) Do they feel ready for the changes that the future might bring? 3) Are they feeling optimistic or pessimistic about the future? In Spring 2023, Bay View Analytics and the Canadian Digital Learning Research Association (CDLRA) conducted US and Canadian survey studies to address these questions. Overall, the findings from both countries suggest that those working in post-secondary education expect the future to be different from the present and rate themselves as somewhat ready for these changes. Feelings of optimism and pessimism vary by country and may be explained by contextual factors unique to the differences between Canadian and US culture and policies; however, the qualitative analysis did not reveal any distinctive reasons for such differences. Overall, the findings clearly indicate that post-secondary education is well-poised for further digital transformation in the near future.