Cicily has taught writing off and on since the 1970s: composition, grant writing, research writing, and developmental English. She has taught at Purdue University, Western New England College, American International College, Springfield Technical Community College, and Kaplan University.

Her preferred method of teaching, which she has been allowed to implement to varying degrees by the institutions where she has taught, has been to dispense with attendance, quizzes, tests, and grades. Students in her classes write and revise, revise, revise, until everyone is satisfied with the result. At required mid-term and end-of-term conferences, students assign themselves a term grade, using all the versions of their manuscripts to defend it. In all of her years of teaching, she has only disputed one grade, from a student who handed in all of his work after grades had closed, missed the required conferences, and nevertheless demanded an A.