This session draws on research into cognitive offloading: when it makes sense to let AI take over parts of our thinking, and when doing so undermines the deep processing required for genuine learning. I connect this research with practical observations from my time as Head of School at Hyper Island, as well as current research on learning and its implications for my work with AI skills development. One question keeps resurfacing: what should we learn to do ourselves, and what can we delegate to AI?