[1] After graduating from Harper High School, Boland moved with his family to Friendship, Wisconsin in 1955.
During the Berlin Crisis of 1961, Boland was assigned to the 32nd Infantry Division and stationed at Fort Lewis.
He flew the de Havilland Canada DHC-3 Otter in support of Special Forces operations.
After serving with the 1st Cavalry Division at Fort Hood, Boland attended the United States Army Command and General Staff College, graduating in 1975.
He remained in that position until 1980, when he began attending the United States Army War College, graduating the following year.
In 2012, Boland was a candidate for the United States House of Representatives from Wisconsin's 3rd congressional district, losing to incumbent Ron Kind.