To understand the experiences of educators during the 2020 extended school closures, we interviewed 40 teachers from across the country in public, charter, and private schools, at different grade levels and in different subject areas. Teachers articulated three main concerns about emergency remote schooling: (a) student motivation, (b) professional loss and burnout, and (c) exacerbated inequities. As the climate emergency makes school disruptions more common, school systems must learn from the tragic school closings under COVID-19 to prepare for an uncertain future. We propose five design considerations to build school systems with greater resilience for the long-term: center equity, focus on relationship-building, address student motivation, address staff motivation and burnout, and mitigate uncertainty.