She taught first at Canisteo, New York, and in 1913 moved to Fulton, New York, where she taught American history at Fulton High School. It was here that she again met Syracuse classmate Nancy Cook, who taught arts and handicrafts at the same School. These two women become lifelong partners, spending almost their entire adult lives together, although Dickerman would also become involved in other lesbian relationships off and on. Her respect for Woodrow Wilson's vision overcame her strong antiwar sentiments and she and Cook both became active in the Red Cross. As Dickerman later recounted, she "really believed this was a war to end wars and make the world safe for democracy." In 1918, they both traveled to London to assist the women-staffed Endell Street Military Hospital and "scrub floors or perform whatever other chores were required." After their return she briefly entertained political aspirations but accepted the position of dean at the Trenton State College in Trenton, New Jersey in 1921. Unhappy there, she one year later joined the faculty at the Todhunter school. Cook who was now the executive secretary of the Women's Division of the State Democratic Committee would travel together with her in 1922 to Hyde Park where they would meet Eleanor Roosevelt. Their common dedication to politics, education, and progressive reform would lead to a friendship that some speculate to be romantic, and in the purchase of the Todhunter School in 1927 and the three women would share the Val-Kill property. Lorena Hickok took an active dislike to her and this started to unravel the relationship between the three. By 1936 Val-Kill Industries was disbanded. Dickerman and Cook continued to live in Stone Cottage until after Franklin D. Roosevelt's death in 1945. They sold all interest in the Val-Kill property to Eleanor in 1947 when they moved to New Canaan, Connecticut, where Dickerman became the educational programming director for the Marine Historical Association, which later became Mystic Seaport, the Museum of America and the Sea. She served as the museum's Director of Education, a post she held from 1946 until 1962. Dickerman was active in numerous organizations, including the American Association of University Women as president of the New York State Division. She died in Kennett Square, Pennsylvania and is buried next to Nancy Cook at Westfield Cemetery, Westfield, New York.
