As a pilot, Katherine Stinson knew that to fly a loop, you have to turn things upside down. Stinson did just that — flipping the conventions of her era on their head when she became the first female pilot to fly the loop on July 18, 1915.

This wasn’t the only aviation record that Stinson would break:

• Stinson became the fourth woman to earn her pilot’s license in the United States on July 24, 1912. She qualified to earn her license at Cicero Flying Field in Chicago, where she later flew the loop.
• Stinson was the youngest licensed female aviator in the country in 1912, having trained for her license at 18, earning the nickname “The Flying Schoolgirl.” Stinson was said to be the first woman to earn a flight license in a Wright biplane.
• Stinson was also the first woman to fly at night.
• Stinson was the first female skywriter. While performing in Los Angeles, Stinson used her plane to skywrite “C-A-L,” for California.
• Stinson is credited as the first woman to fly over London.
• Stinson would also become the first woman pilot authorized to carry mail in the United States.

Her trailblazing, though, came close to never happening.

Stinson came from a family of aviators, but when she began flying, she was only trying to earn enough money to pursue a piano career. She soon found a passion for flight and became involved in the family business.

In 1913, Stinson and her mother incorporated the Stinson Aircraft Company, which Stinson later took over as president. Her family (including her sister Marjorie, who was also a pilot) began the Stinson School of Flying in San Antonio in 1915, and Stinson taught there—a fitting role for the former “Flying Schoolgirl.”