Endsley was born into slavery in Jefferson, where she worked on a plantation.[2] In 1862, she married Moses Calloway, and the two moved to Rowlett.[2] The couple started out as sharecroppers, but eventually owned their own farm.[2] Together, they had eleven children.[2]
Endsley took over as the manager of the 100-acre family farm when her husband died in the late 1880s or early 1890s.[3] The farm was in Dallas County and had been assessed in 1882 to be worth $15,150 (~$423,390 in 2024).[3] Endlsley would take her own cotton to the local cotton gin, and defended her hard work from theft, even accidentally killing a white man who attempted to steal her cotton.[2] She was never prosecuted for striking the man; since another "white man who witnessed the accident apparently took the blame for it."[2] Endsley married three times after her first husband, all ending in divorce until she married H.E. Endsley in 1914.[2]
She sold her farm, retaining the timber rights on the land, and set up her own rail-yard coal and log business in Dallas.[2] Her sons, Joe, Lube and Emmett, helped her run the business, which became very lucrative.[2]
Endsley's home had the only telephone in the neighborhood for many years, and she allowed neighbors to use it.[2] She and others helped found the Macedonia Baptist Church, which eventually became a 5,000 member congregation called the Good Street Baptist Church.[2] She also started a lodge within the Household of Ruth in the 1920s.[2] Endsley and her daughter Maggie, reached out to the hungry and poor, especially during the Great Depression.[2]
Endsley died in her home on Collins Street in Dallas in 1933.[2] She was buried in Rowlett.[2]