On the advice of Roosevelt's secretary, Malvina Thompson, Hickok then sought work in New York with public relations man and politician Grover Whalen. Shortly after Franklin Roosevelt's 1936 re-election, Hickok was hired by Whalen to do publicity for the 1939 New York World's Fair. Opportunities for female employees of the Fair were limited, and she found the work unrewarding compared to her reporting days. Hickok primarily worked on promoting the fair to young people, including arranging class trips. Because Hickok rented both a country home and an apartment, she often faced financial problems despite her good salary during these years, and Roosevelt occasionally sent her small gifts of money.