The COVID-19 pandemic, natural disasters, and political and social movements have required each of us to pause. Collectively they signal a unique moment in our history, and we argue that they provide us with an opportunity to consider what matters most as we move forward. Using poetic representation and Brené Brown's guideposts for wholehearted living as a framework, we offer a series of provocation for readers to consider the role of wholeheartedness and wellbeing in education.