This document provides a summary of a keynote address given at the World Usability Day in Milan, Italy in 2019. The speaker discusses how digital transformation has changed the way people live and work over the past 30 years since they were a student in Milan. The speaker outlines three stages of digital transformation: 1) digitization of analog artifacts, 2) digitalization of processes, and 3) systemic transformation of entire industries. Examples discussed include how music, grocery shopping, and other daily activities have been transformed. The speaker argues that "we" must think more critically about who benefits from new technologies and how they impact various populations around the world differently.