Flexible work schedules and remote work (specifically the ability to work from home) have been framed as a benefit to workers, especially parents and caregivers. In the midst of a global pandemic, the ability to work from home proved to be life saving; in the United States essential workers bore a disproportionate rate of COVID infections and deaths largely because they were not able to stay home and self isolate while continuing to earn an income. Yet, even in times of crisis, a more critical lens needs to be placed on the framing of flexwork as a benefit. For most of 2020, university campuses across the United States remained closed and instruction moved from classrooms to homes. For faculty members with young children, the challenges of this transition were compounded by the additional responsibilities of parent-work, since most children were also learning from home and extended forms of childcare disappeared over night. For those who welcomed babies during this time, the weight of infant care alongside the loss of social support took a heavy toll. Individuals who were pregnant or gave birth during the pandemic encountered additional challenges to their physical and mental health, for example, managing postpartum care in isolation. The extreme challenges of this time have also proven illuminating, and we feel an urgency to reflect on what we have learned and how our collective experiences might prompt a call for institutional change. We bring together scholars who have been grappling with new forms of caregiving alongside their academic labors to begin the work of rebuilding a more inclusive and sustainable academy. This roundtable examines how the pandemic brought to light the ways gender, labor and caregiving intersect in the academic sphere. We will discuss the lessons we have learned about the academy and ourselves, and ask: How can we make up for the losses we experienced to our health, families, and professional identities? Moving forward, how might our experiences shape the way academics think about life-work balance, family and work, and where labor begins and ends? This Roundtable will be a virtual event.