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  • Writer's pictureElaine Berberich

Piloting in the Air and on the Water

“If birds can glide for long periods of time, then… why can’t I?” – Orville Wright.


In 2023, almost everyone has flown on a commercial plane, and jet travel is an accepted way of life. Some are white-knuckled flyers, and some love every moment of seeing the world below and the clouds above. Fairfield Harbour is home to many who have experienced air travel from the military, taken flying lessons, and been on charter flights such as flying over the Grand Canyon or Machu Picchu. The critical person on any flight is the pilot, and Fairfield Harbour is home to two residents who spent their professional lives flying jets for commercial airlines. Scott Cleveland and Dave Phipps were bitten by the flying bug as teenagers and made it their career.


Dave Phipps soloed at age 16 and got his private pilot’s license at 17, even before he had his driver’s license. Scott Cleveland took his first flying lesson as a junior in high school.

Dave and Scott described the process of becoming a pilot in detail. Both went the civilian route as opposed to being trained in the military. In the 1980s, a majority of pilots had training in the military. Today, it is estimated that about one-third of airline pilots are trained in the military, and the others obtain their experience through the civilian route. The process is first taking flying lessons and soloing and then accumulating hours and building up enough hours( estimated at 3000) to obtain an interview with a commercial airline. Both pilots stressed how important it was to “get a break” and be able to be hired by an airline and that pilots took the first available one. Today, there is a higher pilot demand, so it is easier to get an interview. Dave Phipps started accumulating his hours as a flight instructor and charter pilot, and one of his first jobs was flying sick Native Americans from reservations to the US Public Health Service in the desert Southwest. Scott Cleveland started out flying air mail and air freight, and after obtaining his hours, he flew for North Central and, after several mergers, flew for Northwest, which merged with Delta. He retired from Delta, and his longest route was flying a 747 from Detroit to Shanghai. Scott pointed out that since a pilot does not have to live at their assigned base, he lived with Darlene and their family in the Dallas-Ft. Worth area.


Dave Phipps’s professional flying career spanned 42 total years. His break came when he was hired as a co-pilot for a four-engine Lockheed Electra and flew tourists from Denver, Colorado, to various destinations. With that experience, he joined the airlines and flew different planes, including the Airbus A330, and finished his career on the new Airbus A321, flying between Hawaii and the US mainland. He flew for Midwest Airlines and then Hawaiian Airlines. He also spent about a third of his career in various flight operations training and management roles and oversaw the introduction of the Airbus 321. He hasn’t been able to give up flying yet and owns and operates a small twin-engine plane for pleasure flying.


Both pilots are accomplished boaters as well and moved to Fairfield Harbour to enjoy the water. There are many similarities between piloting a plane and a boat. Scott Cleveland felt they are alike because they involve leadership, having plans to prepare for any emergency, and always being ready for challenging situations. He and Darlene started power boating at lakes in Texas and then moved on to a different type of water on the Neuse after retirement.

Dave and Paula Phipps started boating on Lake Michigan, and Dave bought their first boat…a plywood-hulled Trojan powerboat, at an auction, much to the consternation of Paula, who was expecting their first child any day! They owned and operated boats there for 25 years before moving to FH and downsizing to a trawler for retirement and exploring the East Coast. Dave felt that with piloting in water and air, you’re totally responsible for the safety of your passengers and crew and knowledge of emergency procedures is essential. Dave pointed out, “when you encounter adverse weather in an aircraft, you’ll generally get through it in a matter of minutes; In a boat, you can have bad weather for days!”


Both had memorable experiences from their careers with the airlines. One of Scott’s most memorable was meeting Darlene, who was a customer service agent with the airlines, and marrying her in 1998. He was also in the air when 9/11 happened and described this as a “crazy” experience he will never forget. He was flying from Indianapolis to Minneapolis in crystal clear skies when he was told he had to make an emergency unplanned landing in Milwaukee as directed by the FAA. Pilots were not told what was happening until they landed and discovered what had happened on this tragic day. Scott and the crew were grounded for four days until the situation was resolved. He describes flying through the Northern Lights on the way to China as an” incredible sight.” He also recalled memories of doing charter flights for most of the NBA teams under luxurious conditions with passengers including Kobe Bryant, Phil Jackson, Michael Jordan, and Shaquille O’Neal. Among his “famous” passengers also included the incomparable Dolly Parton, who made a point of stopping by the cockpit and chatting for a while.


Dave remembered seeing passengers and families greeting loved ones and seeing loved ones leave with tears in their eyes and waving goodbye, which was a reminder of how precious his cargo was. He experienced three engine failures, which he described as “irregularities rather than emergencies” because the crew had practiced so much for this situation. He also recalled a flight where he flew around the world in seven days to pick up a new aircraft, and upon returning home after flying through all those time zones, he was a “wet rag” for days.


Scott and Dave had similar thoughts when asked about personality traits that make for a successful airline career in the pilot’s seat. First was having the perseverance and determination to get into the business. The best pilots can think quickly under pressure and have a mental model of all that is happening around them at all times in an environment that is constantly changing. They also need interpersonal skills to work with various personalities in small spaces. Surrounding yourself with options and being prepared for any challenge is critical, whether you are driving a car, piloting a plane, or manning the helm of a boat. Fairfield Harbour has a wide tapestry of professions, and we are indeed lucky to have these pilots in our midst.


After landing on his retirement flight, Dave Phipps posing with some of his cabin crew.

Flying a light twin engine aircraft for pleasure

Darlene with Scott on retirement flight

In Flight with Captain Cleveland

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