To be a school principal is a complicated task that demands strength and commitment, especially if this is such a famous school as Moscow “School of Self-Determination.” The author, who is the head of this school, shares with the reader a number of primary ideas and principles of how to build a truly educational and democratic environment for students and teachers, how to involve everyone in the process of co-management, and how to make dialogue an essential part of school communication. The article provides challenges for educators interested in creating a genuine school oriented towards students’ academic achievements and their personality and character formation.