Obering is a native of Birmingham, Alabama and joined the Air Force in 1973 after completing the Reserve Officer Training Corps (ROTC) program at University of Notre Dame as a distinguished graduate. Obering received his pilot wings in 1975 and flew operational assignments in the F-4E; he was later assigned to the Space Shuttle program and participated in 15 space shuttle launches as a NASA orbiter project engineer and was responsible for integrating firing room launch operations. Obering has also been assigned to tours with the Air Force Inspector General, the Defense Mapping Agency and Electronic Systems Center.