Using "a day in the life" format, this session looks at how digital tools have shaped and reshaped the work of faculty, students, and administrators. Specifically, it looks at the typical software a faculty member, a staff member, and a student might use in one typical day in 1998, 2003, 2008, 2013, 2018, and 2023. In doing so, this session provides a reflection on the evolving impact of digital tools in the life of higher education, the triumphs and challenges along the way, and reflects on which digital tools were flashes in the pan and which ones have become institutionalized and part of everyday life.