This roundtables feature alumnae from the Humanities Without Walls Pre-doctoral Summer Workshop, an intensive three-week interactive experience for PhD students in the humanities that is facilitated and curated by the Chicago Humanities Festival. The workshop is designed to help participants explore diverse future careers, particularly those outside of academia and/or the traditional tenure-track university system. Through a series of workshops, talks, and field trips, participants learn how to leverage their skills and training towards careers in the public humanities, the private sector, the non-profit world, arts administration, public media and many other fields. Each presenter will spend 10 minutes talking about their experience in the workshop and its impact on their thinking about their career. They will also reflect on the challenges and opportunities they faced in their home institutions as they navigated the terrain of career diversity during a turbulent time in the history of higher education.