When It Breaks follows award winning Special Education teacher Konrad Wert as he struggles with teacher burnout and reluctantly has to step away from the classroom. Upon leaving he turns to his side career of making folk music under the moniker Possessed by Paul James. Setting out on a cross-country tour with his family, he uses shows to advocate about special education and the difficulties teachers are facing in public education. As unexpected opportunities arise, he has to decide how his service is best used- as a teacher in the classroom or an advocate musician on the road.