Woolston worked as a teacher in the
Settlement movement in
New York City during the 1910s. She was on the editorial staff of the
Russell Sage Foundation, and editor of
The Woman Voter, a suffrage magazine. She was a regular contributor to ''
Harper's, The New Republic, Redbook, The Nation'', and other popular periodicals, often writing humorous observational essays about gender. In 1919, she wrote a satirical essay on the "marriage customs" of the women of
Heterodoxy, a feminist debating club she belonged to; it was partly modeled on Heterodite
Elsie Clews Parsons' serious study of family dynamics,
The Family. Her comic essays were collected in
The Delicatessen Husband and Other Essays (1926), illustrated by
Clarence Day. She also published a book on marital relations,
Love is a Challenge (1936), and another,
We, the Women (1938). ==Personal life==