Gwendolyn began her experience in education as a middle school social studies teacher. After two years, she taught high school English for eight years. During her high school teaching tenure, Gwendolyn was also the faculty advisor to the student literary magazine. The magazine won four awards for excellence and broke previous records for sales and participation. She also taught creative writing and advised students on how to publish their work. After teaching English, Gwendolyn went back to school and received a school librarian certification. She became an elementary school librarian. Prior to working in public school and after becoming a school librarian, Gwendolyn taught college-level English and literature courses at a community college.