Before entering the culinary field, John Woolley spent 10 years as an aviator with the US Marine Corps. After leaving active duty he became the chief pilot of an executive helicopter charter company in New York City. After graduating from Johnson & Wales University, Woolley began his culinary career at the Ritz-Carlton Hotels in Boston and Palm Beach before moving to Baltimore, MD, where he worked first as a sous chef and later as the executive chef in the dining operations for MBNA Bank. Woolley relocated to Washington DC where he continued to work as an executive chef in the corporate dining arena for companies that included Electronic Data Systems, the Federal Reserve, the American Red Cross, the International Monetary Fund, the National Counter-Terrorism Center and the Central Intelligence Agency.
Woolley also taught at Baltimore International College, Anne Arundel Community College, and University of Maryland. In 2005, he moved to North Carolina and taught culinary classes at Carteret Community College in Morehead City.