Shortly after the Pandemic began in 2020, I wrote two blog posts: the first was about what children should master to cope with an uncertain, turbulent, and dangerous future; the second discussed how better methods of assessment were needed to provide a compass for this journey of learning. Walter McKenzie kindly offered to publish this combined, updated, and extended reflection that builds on those two posts. My thoughts have evolved in the past five years, a chaotic period of profound worldwide discontinuities: the culmination of the pandemic, the advent of generative AI, and the rise of authoritarianism across the globe. That said, my fundamental assertion is unaltered: Learning is a journey, not a destination and, like all travel. the settings through which one passes shape what is important to master.