Complex sentence: Barr became a teacher and eventual headmaster of the Central School of Windsor, Ontario, from which position he began to contribute short stories-often based on personal experiences-to the "Detroit Free Press".
Split into simpler sentences: Barr became a teacher and eventual headmaster of the Central School of Windsor, Ontario. Wjile he had that job he began to contribute short stories-often based on personal experiences-to the "Detroit Free Press".