Robert Jon Meyer Shipley was born in Toronto on February 26, 1948, the youngest of three children to Miriam Irene (Smith) and Captain Vernon Meyer Shipley (captain in the Pay Corps and served as paymaster at the Royal Military College). Shortly after his birth, the family moved to Kingston (1952) and later to London (1959).

Robert J. M. Shipley got an Honours BA from the University of Western Ontario in History and Philosophy in 1972. Between 1972 and 1976 he was an officer of the Canadian Armed Forces serving in Calgary, Chilliwack, Halifax, Atlantic Canada, the Caribbean, Europe, and London (Ontario). In 1976, Shipley was released from the Armed Forces and became a freelance writer, publishing articles in different media (sometimes under the pseudonym Jon Meyer) and receiving several research grants for his work on Canadian history and heritage. During this time, Robert Shipley also worked as an editor, wrote and published poetry and theatre plays, taught courses on writing in schools throughout Ontario, and illustrated many of his own articles and publications. In the late 1970s and early 1980s, Shipley’s work focused on corporate and community histories, political speeches, planning studies, and tourist promotions, and publishing history and fiction books.

Shipley’s paintings were selected in the Western Ontario Jury Show; were displayed in galleries in Halifax, Toronto, and London; and appeared regularly in Perception Magazine. In 1978, he travelled to Cyprus to illustrate a book about Canadian soldiers on UN peacekeeping duty titled The 8th Hussar: Cyprus 1978-1979.
Between 1984 and 1987, Robert Shipley worked as the administrator at the Welland Canals Preservation Association (WCPA) and, in 1987, he became the senior developer consultant for the Welland Canals Society. In the late 1980s, Shipley’s work focused on cultural heritage, heritage-based tourism, and community development.

In 1990, Shipley began his Ph.D. studies at the University of Waterloo, becoming an active associate of the University’s Heritage Resources Centre (HRC). Shipley received his doctorate in 1997 with his dissertation Visioning in strategic planning : theory, practice and evaluation, and joined the University of Waterloo's Faculty of Environment as Professor and Associate Director of the School of Planning. While at the University of Waterloo, Shipley conducted international research on cultural heritage issues and published dozens of articles, book chapters and consulting reports. In 2003, he became the director at the HRC. As an academic, Shipley was a guest lecturer at Michigan State University, the University of Western Ontario, Brock University and Niagara College.

Robert Shipley retired in 2016 and, in 2018, he received the National Trust for Canada’s Governors’’ Award.

In 1983, Shipley married Pamela Fielding. The couple had a son, Ceilidh Jamieson Meyer, in 1985. The couple divorced in the 1990s. In the 1990s, Shipley met who would become his second wife, Dana Švihlová.

During his professional years, Robert Shipley published numerous books, including, among others:

• Relation ships (1984),
• To mark our place : a history of Canadian war memorials (1987),
• St. Catharines, garden on the canal : an illustrated history (1987),
• The girl who got stuck in the… mud (1987),
• Written with Fred A. Addis and part of the Great Lakes Album series: Paddle wheelers (1990), Schooners (1990), Propellers (1992), and Wrecks and disasters (1992),
• Exploring the value of heritage properties (1992),
• On leaving Bai Di Cheng : the culture of China’s Yangzi Gorges with Caroline Walker, Ruth Lor Malloy, and Fu Kailin (1993),
• Editor of The first 50 years by the Faculty of Environment at the University of Waterloo (2019).