Hull entered the University of Michigan in 1890 after high school and received a teacher's degree in 1894.
She then entered Southern Illinois Normal College and graduated salutatorian with another degree in 1895.
Her first job was as principal of the high school at Henry, Illinois, in 1895.
She worked there for almost two years and then was a history teacher at the high school in Bloomington starting in late 1896 and through the winter of 1897.
Hull then resigned her position and moved to Milwaukee in the summer of 1897 and became a teacher at the West Side high school in the history department.

Hull recalled in a 1942 radio interview that one day MacArthur's mother brought her son, Douglas, to Hull's school to get some quick lessons in 1897.
At the time Hull was a lead instructor at the Milwaukee high school, so she became his history tutor and an assistant coach for other subjects.
She was a key influence in MacArthur's passing the West Point entrance examination because of the lesson preparations she did.

MacArthur and his mother were then living at the exclusive Plankinton House Hotel to establish a temporary residence in Milwaukee, Wisconsin.
It was two miles away (3.2 km) from the high school and MacArthur had to walk the distance each school day for several months while being tutored by Hull.
She recalled one day that MacArthur worked on one of her specially prepared practice exam questionnaires for over three hours and ultimately turned in a paper that received a 99% grade.

Because of Hull's coaching and special teaching, MacArthur was then so well prepared that he passed the West Point examinations ahead of all others by at least fifteen percent, scoring 93.3% overall.
The next highest score of the entries was 77.9 percent.

There were 750 points total for the examinations and MacArthur received 700 of them.
There were a dozen others that were competing for the congressional cadet-ship appointment to West Point.
Because of his preparedness MacArthur was the one selected by Milwaukee congressman Theobald Otjen to receive the honor to be the one selected from his district for entrance to the United States Military Academy.
Hull entered the University of Michigan in 1890 after high school and received a teacher's degree in 1894. She then entered Southern Illinois Normal College and graduated salutatorian with another degree in 1895. Her first job was as principal of the high school at Henry, Illinois, in 1895. She worked there for almost two years and then was a history teacher at the high school in Bloomington starting in late 1896 and through the winter of 1897. Hull then resigned her position and moved to Milwaukee in the summer of 1897 and became a teacher at the West Side high school in the history department. 
Hull recalled in a 1942 radio interview that one day MacArthur's mother brought her son, Douglas, to Hull's school to get some quick lessons in 1897. At the time Hull was a lead instructor at the Milwaukee high school, so she became his history tutor and an assistant coach for other subjects. She was a key influence in MacArthur's passing the West Point entrance examination because of the lesson preparations she did.
MacArthur and his mother were then living at the exclusive Plankinton House Hotel to establish a temporary residence in Milwaukee, Wisconsin. It was two miles away (3.2 km) from the high school and MacArthur had to walk the distance each school day for several months while being tutored by Hull. She recalled one day that MacArthur worked on one of her specially prepared practice exam questionnaires for over three hours and ultimately turned in a paper that received a 99% grade. 
Because of Hull's coaching and special teaching, MacArthur was then so well prepared that he passed the West Point examinations ahead of all others by at least fifteen percent, scoring 93.3% overall. The next highest score of the entries was 77.9 percent. 
There were 750 points total for the examinations and MacArthur received 700 of them. There were a dozen others that were competing for the congressional cadet-ship appointment to West Point. Because of his preparedness MacArthur was the one selected by Milwaukee congressman Theobald Otjen to receive the honor to be the one selected from his district for entrance to the United States Military Academy.
Gertrude Hull