At the age of 48, I left a management job with the Federal government to pursue a full-time airline pilot career. At the age of 49, I accepted a job to fly transatlantic routes for a major U.S. airline and have been doing so since 2023. It was a difficult decision, as most advice I received was to stay with my well-paying government job because it offered good pay, stability, and solid retirement benefits.
Furthermore, I was told that pursuing an airline pilot job was a difficult career path due to typically low entry-level pay that lasted for years, if not decades. In addition, the quality of life as a junior pilot was poor because you normally work weekends, holidays, and odd hours. I frequently met pilots who were unhappy in their jobs. I recall talking to aviation industry experts who told me things like, “Being an airline pilot is chasing the ‘sexy’ part of the industry, but being a cargo pilot is where the money is.”
As I researched cargo jobs, I discovered that while FedEx and UPS paid well, most of those pilots flew pure redeye flights (night flying). It is said that FedEx and UPS pilot pension plans are overfunded because many of them pass away at a younger age due to sleep disorders. Several studies have shown a strong correlation between night flying and significant health problems.
Additionally, the cost to complete all the necessary flight training is nearly the same as it would be to become a doctor or lawyer. Yet, I was faced with a career that may or may not pay off my student loans due to its instability and unpredictability. The airline industry is fraught with failures, layoffs, furloughs, and all the challenges mentioned in the preceding paragraphs. While in college, I could not financially justify the cost of flight training. I managed to attain a private pilot’s license, but that was only the first step in a long progression of necessary pilot ratings required to reach the Airline Transport Pilot (ATP) license.
As a result, I sought a career in aviation, but not as a pilot. In college, I worked full-time as an air freight forwarder (cargo). I also “threw bags” for Frontier Airlines. Later, I became an airline ticket counter supervisor and eventually went to Trans World Airlines (TWA) as a pricing analyst. At TWA, I also learned yield management. After TWA, I accepted a job as Director of Revenue Management for a travel agency that owned the website Air4Less.com. I received an offer to work for Virgin Atlantic Airways in sales in the Boston area, which I took.
I was riding on a Virgin Atlantic Boeing 747 to London on September 11, 2001, and was stuck in London for a couple of days while U.S. airspace was closed. After Virgin Atlantic, I moved to the West Coast and became an Air Service Consultant, helping small communities attain improved commercial air service. Then in 2007, I accepted a position with the U.S. Federal Aviation Administration (FAA). I spent 13 years working for the FAA, where I supported Air Traffic, then worked as an Airport Inspector, and eventually became the Manager of Airport Safety and Standards for the New England Region Office of Airports. I frequently tell people I’m a “jack of all trades, master of none.” All the while, I kept flying small planes with my private pilot’s license.
Between 1993, when I first received my private pilot’s license, and 2019, I had reached approximately 300 flight hours. Flying was expensive, and therefore I only did what I could afford. Fortunately, as I reached management at the FAA, I was able to afford additional flight training, so I pursued my instrument rating. I also lucked out in that a friend of mine gave me the keys to his airplane and said, “Fly it, I can’t right now as I don’t have a medical.” I was able to get an extra 100+ hours for essentially the cost of gas. Next, I found a consolidated course for both a Commercial rating and Certified Flight Instructor (CFI) rating. In less than two months, I was able to get both ratings. Then, in March of 2020, I pursued my multi-engine rating and had a goal of leaving my government job in April in order to build enough flight time.
As I started the multi-engine training with my good friend Dustin Rodriguez, COVID began to shut down the world. We were unable to finish the training as a result, and I returned home, feeling lucky that I had a government job while many people were worried about keeping theirs.
Over the next few months, I observed airlines offer early retirements and thin out their ranks to survive the unprecedented global pandemic. I realized that, in time, as we (hopefully) exited the pandemic, the pilot shortage would be at an all-time high. I had nearly 500 hours but knew I had to get an additional 1,000 hours to get to a regional airline. Once able, I started flight instructing, and I applied for charter jobs and positions with aircraft operators that could operate under less stringent airline transport regulations. This included applying at Cape Air and Southern Airways Express, among others. Despite the low pay offered by these companies, they allowed me to build valuable flight hours necessary to move into better-paying pilot jobs.
The Phone Call
My wife and I discussed the prospect that if I received a call for one of these opportunities, it would be time to leave my safe and secure government job and take the leap of faith. Fortunately, I had saved some money to get through at least a year of lower pay. More importantly, my wife supported me and the family, as she also held a very good job.
Then, in December 2020, as I was returning from the funeral of a friend I had worked with both at TWA and an Air Service Consulting firm, I received a call. I was in the Des Moines airport terminal waiting for my flight home. It was Julie, from Southern Airways Express. She said they were bringing their first class back for training since before COVID had shut everything down. She told me they had invited back people whose training classes were canceled due to COVID, but one of the pilots decided to bow out. She had one opening, with class starting in a couple of weeks, and she needed a quick “yes” from me or she would invite the next candidate on her list. And so began my flying career.
The Mighty Caravan
Southern Airways Express operates nine-passenger Cessna Caravan flights throughout small cities in the U.S. to major airline hubs. Several of their routes are subsidized via the U.S. Essential Air Service (EAS) program. They also owned and operated Mokulele Airlines in Hawaii. I started my ground school training at their original headquarters in Palm Coast, FL, in January 2021—not a bad place to be during the winter in New England. While I was the eldest pilot in the group, I made some of the best friends I’ve ever had. After ground school, they sent us to Maui, Hawaii, for the flight training portion and check rides. Yep, another great place to be during the winter.
When Southern Airways purchased Mokulele, it included a small flight training department that had a simulator. It was more cost-effective to send us to Hawaii and train in the company’s own facility rather than send us to one of the consulting facilities, like Flight Safety International.
As my classmates and I drooled over the Cessna Caravan and were impressed with the size and awesome sound of its turbine engine, we couldn’t wait to fly it. After spending several days in the simulator, we eventually got our turn to fly the real thing. We typically flew late at night, sometimes starting at 4 am, so the plane would be back in time for regularly scheduled passenger flights in the morning. It was a bit eerie flying over the Pacific Ocean at night with no horizon, but the thrill of flying the Caravan was incredible.
Nantucket, the “Gray Lady”
Upon passing my check ride and returning to New England, I was excited to be based in New Bedford, MA, flying the company’s Nantucket routes. New Bedford is only about a 35-minute drive from my home, and as most pilots will tell you, being home-based is the best. Unfortunately, the company had ceased the route during the COVID winter, and it wasn’t going to start again until April. In the meantime, they sent me on my first assignment to Hot Springs, AR. We would fly between Hot Springs and Dallas Fort Worth International Airport. I flew there several times between February and April. That is thunderstorm alley, and learning to dodge storms was part of the job.
I was fortunate because Southern Airways Express had a First Officer program that was approved by the FAA. This is unique in a plane like the Cessna Caravan, as it is certified as a single-pilot aircraft. Therefore, the company had to justify the need for a second pilot in the aircraft who was also allowed to log flight time as second-in-command. Certain requirements had to be met, and I’m extremely grateful SAE had this agreement with the FAA, as it allowed me to build my confidence flying in all sorts of weather conditions.
Once we started flying to Nantucket, I discovered why the island is called “the gray lady.” Nantucket is covered in low-level fog from Spring through June. We were landing and taking off in fog that had horizontal visibility of only 1,800 feet. It was eerie at first, but after doing it day in and day out for months, it became fun. I looked forward to getting the chance to shoot the approach down to minimums. However, had SAE not had the first officer program, I don’t think I could have done approaches like that solo when I first started.
I also enjoyed flying to Nantucket. I knew many of the airport employees from my previous job with the FAA, and I had the opportunity to chat with them. Some days, we’d have a four-hour layover on the island. I would go swimming at the beach or head into town for a nice lunch. The island is incredibly beautiful and has a rich whaling history.
Captain
In September, one of my classmates upgraded to Captain, and they sent him to Nantucket to help out. He and I had a great time flying together, and not long after that, in December, I returned to Hawaii with 1,200 flight hours, the threshold to upgrade to Captain. The 700 hours I had as a first officer gave me the confidence I needed to become a Captain. I spent the next 300 hours flying throughout the winter to and from Nantucket. Occasionally, they’d send me to Pennsylvania to fly some of our routes to and from Washington Dulles and Pittsburgh International Airport. I was grateful I had the opportunity to learn flying in icing conditions and impressed with the FAA regulations on how to do so. I always felt safe, as the rules were well written.
While I was a captain, my friend who had come to Nantucket was flying for Mokulele. I reached out to him and said that I’d love to come to Hawaii and fly the line there. He put me in touch with the base chief pilot, and I was able to arrange to fly the line in Hawaii for two days with some of their more experienced First Officers. I flew out to Hawaii on UPS. As a pilot, we can jumpseat on cargo flights. UPS flew a 747-800 from their hub in Louisville to Honolulu. Behind the flight deck, they have six first-class-style seats. Once in Hawaii, I met up with my classmate at his pad in Waimea on the Big Island. I had an amazing time island hopping and even spotted whales between Maui and Molokai. I would have paid to gain that experience, yet I was getting paid to do it.
Let’s Jet
Upon reaching 1,500 hours, I knew I had to keep moving. It was time to try and get to a regional airline. While the contract I had with SAE required me to stay for 12 months as a Captain (due to the expense of training me), I was willing to pay back the amount I owed. Even though it was several thousand dollars, it was worth it to me to keep moving and try to get to a major airline as quickly as possible. My next goal was to get to Republic Airlines.
There were several reasons why I wanted Republic. The most important was that they had a Boston base, so I could remain home-based. Additionally, many regional airlines had “flow-through” programs, which guaranteed pilots could eventually move up to major airlines like American, United, or Delta after a period of time. However, during the pilot shortage, this path sometimes inhibited pilots from progressing quickly. The regionals made these agreements to retain pilots longer and keep their operations running at lower costs.
However, these were unprecedented times. In the post-COVID environment, people had money and wanted to travel. As predicted, the airlines couldn’t hire pilots fast enough. Based on my experience in the industry, I knew I needed to keep moving “before the musical chairs” of pilot hiring stopped.
Once I was nearing the required 1,500 hours, I applied to Republic, and a few days later, I got the call from HR. I was in Nantucket on a long break and, to find privacy for the call, locked myself in a janitor’s closet while answering their questions. By May of 2022, I was in class at Republic. I’ll tell you more about that in my next article. Thanks for following along.