Staff members in live-in positions often find themselves faced with a difficult choice: Leave their roles in search of a job that offers a better work/life balance or stay and hope their department is invested in making the changes necessary to support their staff. Live-in staff are in a unique position because the challenges they face in establishing work/life boundaries and confronting a constant sense of urgency permeate their jobs and are exacerbated by living where they work. Entry-level staff, often the ones who fill live-in roles, are the professionals who leave the field of student affairs at the greatest rate. How can residence life leaders make entry-level live-in roles feel more sustainable for their staff? In this study, researchers center the perspectives of seven live-in staff who attempt to re-imagine their roles. Findings show that there are greater organizational challenges related to a work culture characterized by a sense of urgency and lack of reflection. Participants' ideas for re-imagining the role are framed using a liberatory consciousness framework. [Discussion questions prepared by Ramon Izquierdo.]