Universal Design for Learning (UDL) has gained significant momentum in Higher Education (HE) over the last decade in North America. It offers considerable potential to achieve the inclusion of diverse students in the HE classroom. It is a unique approach, first because it shifts the instructor mindset away from medical model practices, and second because it allows the development of inclusive practices that address the needs of the full spectrum of diverse learners. As a result of this growing interest, there have been implementation efforts within a wide range of disciplines and settings in post-secondary education. The time has come, however, to identify the challenges that remain, to seek appropriate solutions, and to develop strategic direction to shape UDL adoption for the next decade. This paper draws on phenomenological data collected by the author on his own practice through a process of auto-ethnography. This data emerges from three dimensions of the author's practice: his past role as manager of an accessibility unit, as well as his current role as UDL consultant within HE, and faculty member exploring UDL in his own teaching. The chapter identifies remaining challenges, explores solutions, and frames a vision for what UDL development might look like in HE over the next decade.