[1] Upon receiving her certificate she began teaching in the area, ultimately holding positions at twelve schools during her career as an educator.
[3] She stopped working in the 1890s due to a variety of frustrations; she felt that her salary was too low, and that it was difficult in general to teach in an impoverished rural district.
[5][6] During her time in Richmond Caldwell served on the Committees on Schools and Colleges, on Asylums and Prisons, and on Manufactures and Mechanic Arts.
[1] A staunch Democrat and ally of Governor of Virginia Harry F. Byrd, she assisted in the passage of a number of bills, including for education and for employment of the handicapped; she also was active in supporting bills to build the Blue Ridge Parkway and the Jackson Ferry Bridge.
[1] Caldwell did not run again in 1929, and returned to her hometown, where she devoted herself to welfare work,[1] serving for more than twenty years as a volunteer social worker.