Clifford Graduated from the University of Wyoming College of Law in 1987. During that year, he was hired as a Deputy County and Prosecuting Attorney for Sweetwater County.

In 1991, Clifford became an Assistant City Attorney in Rock Springs, Wyoming, a position he held for fifteen years.

After a short period as a Judicial Clerk for both District Court Judges, Clifford began working for the Sweetwater County Attorney's Office in 2007, as the Civil Deputy.