Robert A. Clendenin was born in Guilford County, North Carolina. He attended Bessemer High School, graduating in 1950. He received his bachelor’s degree from Appalachian State University in 1954 and his master’s degree in education in 1955, also from ASU. He returned to Greensboro and taught at his alma mater, Bessemer High School, for a year and a half. He was then drafted into the United State Army and was stationed in France for a year and a half.
Upon his discharge in 1958, Clendenin resumed teaching at Bessemer. In 1960 he was promoted to assistant principal, and the following year to principal of Bessemer High School. In 1963, Clendenin became principal of Bessemer Junior High School. Clendenin later served as principle of Aycock Middle School and transferred to Page High School in 1970. While at Page, Clendenin oversaw the court-ordered desegregation of the school.