The convening centered on the design thinking question, “How might our institutions provide intentional and sustainable pathways to build 21st Century competencies and help all our graduates find meaningful employment in their desired career field?” UNCF 2nd Annual Career Pathways Initiative Convening not only provided a new way to look at how our institutions operate in a 21st century space but it also allowed reflection on the challenges HBCUs and PBIs–as well as higher education, in general–may encounter when implementing transformative initiatives.