The COVID-19 outbreak resulted in higher anxiety levels, in which cyberchondria played a significant role. However, little is known about the factors that helped individuals maintain their wellbeing amid the pandemic. The current chapter presents selected results from three surveys carried out with school leaders in Ireland in relation to their source of stress, and factors that helped them cope with the COVID-19 crisis. The first survey took place a week after the COVID-19-related school closure (study 1, N = 2,864). The second survey took place two months after the school closure (study 2, N = 939). The third survey took place three months after the school re-opening (study 3, N = 861). Participants were asked about their source of stress and the actions they took to maintain wellbeing. Similarities and differences were identified across all three samples using thematic analysis. Unique factors associated with specific stages of the pandemic were identified. This chapter discusses implications in relation to the policy and practice of school leaders during the school closure.