It is 2020 and, still, many teams, products, and services across sectors yield inaccessible, inequitable, or otherwise problematic designed experiences. Why does this happen? What can we do about it? In this talk, I will share how this truth manifested in my own work, which focuses on designing technologies for learning in cross-cultural contexts, and present a new approach, culturally disruptive design, for how to critically (re)engage our research, teaching, and design work. Culturally disruptive design requires us to identify and disrupt tensions in underlying knowledge systems, values, and beliefs, which leads to self-discoveries and innovation. To illustrate these points, I will share empirical examples from two projects: (1) a partnership with the Northwestern Band of the Shoshone Nation in which youth and Elders are working together to design a place-based storytelling experience at the Bear River Massacre site, and (2) a partnership of Indigenous and non-Indigenous, researchers designers, and educators in which we are collaboratively redesigning sixth grade curriculum across disciplines to develop students cultural competence.