Mrs. Sheppard has a B.A. in Latin from the College of William and Mary and a M.Ed. from George Mason University as a reading specialist. She taught Latin at Spotsylvania High School for nine years and has taught home-schooled students for three years. She has taught online for one year and has been the director of Challenge II for Classical Conversations Fredericksburg campus for three years. She studied in Rome in 2003 as part of the American Academy of Rome's Classical Summer School.