Printed under his name in the class "will" published with his Salisbury, Maryland, high school yearbook was, "Jack Shilkret leaves running." From an early age, Jack fantasized about what life was like outside Salisbury. He had no idea where he would go after high school. All he knew is that he wanted to leave. In a sometimes amusing, sometimes poignant retelling of his transition from high school student to high school psychology teacher and then community college professor, Jack shares vivid images of life in Salisbury and Annapolis, Maryland. After chronicling his childhood during the fifties and eventual move to attend the University of Maryland to major in psychology. Jack includes a brief description of his college experiences which led to his transformation from student to high school teacher. His girlfriend Ruthie suggests that he switch his majors to Social Studies Education. The hire interview at Annapolis High School prove to be that the defining half hour that led to a successful career of fifty years as a high school teacher and later a community college professor. My Two High Schools details a retired educator's path from high school student into the world of academia where he taught students for over fifty years.