The Schooling of a 21st Century Principal traces my journey to the principalship, a career goal nowhere to be found on my bucket list. I took the reins knowing that my middle school faced some daunting tasks; however, I would soon discover that it was the extraordinary events, changes, and challenges of a new millennium that would present the greatest arc of learning on the job. I led my building using a collaborative team approach, a style that sustained me in my first year during the dark days of 9/11 and throughout our school's exponential growth, evolving student needs, and radical reforms. This compelling and unique memoir offers a personal and rare inside glimpse into the expansive and formidable roles and responsibilities principals face in a world of shifting social norms, rising expectations, demoralized teachers, technology dependence, cyberbullying, school shootings, and mounting student mental health distress.