Ormes drew and wrote throughout high school. She was arts editor for the 1929–1930 Monongahela High School Yearbook where her earliest efforts as a cartoonist can be seen in the lively caricatures of her school's students and teachers. It was during this period that she wrote a letter to the editor of the "Pittsburgh Courier", a weekly African-American newspaper that was published on Saturdays. The then-editor, Robert Vann, wrote back. This correspondence led to her first writing assignment—covering a boxing match. Her coverage of subsequent matches led to her becoming an avid fan of the sport.