John grew up in Dallas and graduated with Bachelor of Arts and Bachelor of Journalism degrees from the University of Texas at Austin. After graduation he headed straight to New York to pursue a career in advertising. He landed a job at the former Ted Bates Company and afterwards moved on to be Western Public Relations Manager for Air France In Los Angeles. Moving back to New York, this time with a wife and daughter, he became US Advertising Director for Air France, where he eventually launched numerous national and international campaigns, including one to introduce the supersonic Concorde aircraft on the North Atlantic.
John and his wife, Diantha, were first introduced to Litchfield County by New York friends who had a home on North Street in Litchfield. When the Bowlings decided that they no longer needed New York 24/7, they returned to Litchfield to make it their home. John and his business partner, Jim Hiltz established their own real estate brokerage, Hiltz & Bowling, which operated for 13 years before merging with E.J. Murphy Realty, LLC in 2013.