John B. Cheeseman '92
MS, Guidance and Counseling
For John Cheeseman, it all started with his parents – people of strong, Midwestern stock who launched his life in ’39 amid the cornfields of Illinois. With a firm parental push, John came east in the mid-50’s to a boys’ boarding school – the Wooster School in Danbury – where he rapidly learned how to write sentences, paraphrase Shakespeare and eat quickly! Wooster provided a disciplined, Spartan existence which set the direction for his life. After graduation in 1957, he went to Princeton University where he enjoyed English literature and specialized in the writings of Ernest Hemingway, graduating in 1961 with an AB degree in English.
During his first decade out of college, Cheeseman was devoted largely to industrial writing for International Harvester, attending graduate school in Psychology at San Francisco State, a year in Mexico studying Spanish and Central American history, and worked in two journalism jobs – one in D.C. as a reporter for Broadcasting Magazine covering the Federal Communications Commission and Capitol Hill; and the other as a wire service reporter for the City News Bureau in Chicago working police beat and City Hall with Mayor Richard J. Daley. The Democratic National Convention in ’68, when “the whole world was watching”, was his last journalistic assignment. Soon thereafter, he joined the world of independent schools, first at Lake Forest Academy, a coed boarding school in Illinois, and, since 1974, here in Danbury at Wooster, his old alma mater, now a K-12 coed day school. At various times during his 35 years in education he has been a football coach, a dorm master, a teacher of English, Spanish, history and journalism, a girls’ softball coach, the Director of Studies and College Guidance, the Director of Development and Admissions, and, in 1996, he was appointed Wooster’s seventh Headmaster.
Inspired by his wife and colleagues, Cheeseman pursued a graduate degree at Western Connecticut State University during four years of challenging courses which culminated in an M.S. in Community Counseling in 1992. In recent years, he devoted time to professional counseling with Raymond Psychological Associates in Ridgefield, and also served as Board Officer for the Regional Hospice of Western Connecticut which provided strong support, during a time of crisis, for himself and one of his parents.
Cheeseman retired as Wooster’s Headmaster in July, 2003, and now enjoys his
wife’s full-time company, building rock walls on his Candlewood Lake
property, cavorting with the grandkids and preparing for the next adventure.