Michelle Hirschy, director of wellness, and Lucas Jacob, director of writing, communication, and media literacy at La Jolla Country Day School (CA), explore the challenges and opportunities of guiding students through today’s complex digital world. From the constant stream of online images and videos of war and terrorism to the rapid rise of AI tools and political extremism on social media, Hirschy and Jacob reflect on how their evolving roles intersect to support student well-being and media literacy. In this candid exchange, they share how schools can help students develop the skills and mindsets needed to engage with digital content critically, compassionately, and responsibly—while also supporting each other as sounding boards and collaborators in a rapidly shifting educational landscape.