Tom Rademacher wishes someone had handed him this sort of book along with his teaching degree: a clear-eyed, frank, boots-on-the ground account of what he was getting into. But first he had to write it. And as 2014’s Minnesota Teacher of the Year, Rademacher knows what he’s talking about. Less a how-to manual than a tribute to an impossible and impossibly rewarding profession, It Won’t Be Easy captures the experience of teaching in all its messy glory.
The book follows a year of teaching, with each chapter tackling a different aspect of the job. Pulling no punches (and resisting no punch lines), he writes about establishing yourself in a new building; teaching meaningful classes, keeping students a priority; investigating how race, gender, and identity affect your work; and why it’s a good idea to keep an extra pair of pants at school. Along the way he answers the inevitable and the unanticipated questions, from what to do with Google to how to tell if you’re really a terrible teacher, to why “Keep your head down” might well be the worst advice for a new teacher.
Though directed at prospective and newer teachers, It Won’t Be Easy is mercifully short on jargon and long on practical wisdom, accessible to anyone-teacher, student, parent, pundit-who is interested in a behind-the-curtain look at teaching and willing to understand that, while there are no simple answers, there is power in learning to ask the right questions.

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.