[1] Gilchrist first began drawing as a young girl when she suffered from a debilitating bone disease, which prevented her from physical activities.
"[1] With her passion for art and practical advice from her father to find a more stable profession, Gilchrist enrolled at Eastern Illinois University.
[1] During her time teaching, Gilchrist enrolled at the University of Northern Iowa, eventually graduating with a Master of Art in Painting in 1979.
[1] Impressed by her depiction of normal African American families, Gilchrist gifted Greenfield slides of her work and a picture of herself.
Gilchrist's first published book was 1988's Children of Long Ago, written by Greenfield's mother Lessie Blanche (née Jones) Little.
[1] Her first authored book, Indigo and Moonlight Gold, captured a young African American girl's realization of the passage of time.
[9] Her second, Madelia, published in 1997, tells the story of a young African American girl who would rather get lost in her painting than attend her father's sermons in church.
[11][12] Many of the books she has worked on focus on the African-American experience over time and depict a diverse range of people, such as slaves in the United States, modern-day children participating in everyday activities,[13] and well-known figures such as Barack Obama[14] and Michael Jordan.
[1] Gilchrist is a prolific artist and illustrator in a variety of mediums, with praise given to her works in watercolor, pen, marker, pencil, gouache, and oil.
[4][17] Her work has also been recognized by the Cooperative Children's Book Center (CCBC) at the University of Wisconsin, the National Association for the Advancement of Colored People (NAACP), and Parents' Choice.
[2] Her body of work led to her induction into the Society of Illustrators in 2001 and the International Literary Hall of Fame for Writers of African Descent in 1999.