This paper is one of two which bring together leading educational researchers to consider some of the key challenges facing democracy and education during the twenty-first century, including rising social and economic inequality, political instability, and the existential threats of global pandemics and climate change. In this paper, key educational scholar-activists respond to the challenges and possibilities for democracy and education, with consideration of the importance of reimagining education as being for democracy. The questions asked in this paper have particular salience for educational leaders, who must be at the centre of any commitment to democratic education.