After the American Civil War, she began to sell works she painted, which included portraits of many African-American freedmen and freedwomen.

[2] When Jane, one of the older Weeden daughters, was attending college in Tuskegee, Alabama, the mother moved the rest of the family there.

Her images included pictures of many freed African Americans who worked as servants for her and friends' families.

[3] While she painted, she listened to their accounts of their lives and of folktales, and later adapted some of these as poems, which she wrote in the black dialect.

[3] She also painted a portrait of Saint Bartley Harris, a prominent African American pastor in Huntsville, Alabama.

[5] Some of her poems were written in the black dialect, now known as African-American English, as she was inspired by stories and folktales told to her by her subjects when they were sitting for portraits.

[3] Between 1866 and 1896, Weeden also contributed numerous essays and short stories to the Presbyterian Christian Observer, under the pseudonym of "Flake White."