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Cathleen Cushing Duff has had an extensive work experience with various organizations. Cathleen Cushing started their career in 1972 as a Correspondent for Foster Parents Plan of Canada where they worked until 1975. In 1975, they joined YMCA-YWCA of Northeast Avalon/ Newfoundland as a Public Relations Director. In 1976, they started their own company, Cushing, where they served as the President. In 1993, they became the President of the International Reprographic Association, and in 2002, they became the Director and Past President of Chicago Family Business Council. In 2007, Cathleen joined ReproMAX as the Director and served as the Chairperson of the Board of Directors until 2010.

Cathleen Cushing Duff obtained their Bachelor of Arts (BA) degree in English Language and Literature, General from the University of Toronto - University of St. Michael's College, graduating in 1972. Prior to attending university, they completed their high school education at Regina Dominican from 1964 to 1968. Additionally, there is no available information about their education before high school.