Ollie, who used to hate weekends because they meant no school, was crying on the way to school almost every day. Sure, there were the slings and arrows of bullies and bad teachers, but, maybe worse, Ollie, a funny, anxious, smart kid, was gravely underchallenged and also struggling with identity and how to live totally as themselves. Ollie begged to switch to a new school with "kids like me," and so they made the change. Raising Ollie is dad Tom Rademacher's story (really, many stories) of that eventful and sometimes painful school year, parenting Ollie and relearning every day what it means to be a father and teacher. As Ollie-who is nonbinary and uses they/them pronouns-flourishes in their new school, Rademacher is making an eye-opening adjustment to a new school of his own, one that's whiter and more suburban than anywhere he has previously taught, with a history of racial tension that he tries to address and navigate. While Ollie is learning to finally feel comfortable at school, Rademacher increasingly sees how his own educational struggles, anxieties, and childhood upbringing are reflected in his teaching, writing, and parenting, as well as in Ollie's experience. He shows us how raising a kid changes everything-and how much raising a kid like Ollie can teach us about who we are and what we're doing in the world.