Her parents, Charles and Mary Emma Haywood, encouraged her creative abilities.

The same year, she was employed at the Friends Central School in Wynnewood, Pennsylvania as a third-grade teacher.

[2] In 1923, Haywood enrolled in the Pennsylvania Academy of Fine Arts with a scholarship and became interested in portrait painting.

Haywood worked on murals in the Philadelphia area during this time, some of which are still extant today.

She was inspired by Elizabeth Hamilton, juvenile department editor at Harcourt Brace to write about the experiences of American children.