Today we’d like to introduce you to Kourtney Gillespie.
Hi Kourtney, please kick things off for us with an introduction to yourself and your story.
I have always been close to aviation, I was even born less than six miles from my local airport. I was born and raised in Sarasota, Florida. When I was about 5 years old I have a very vague memory of my parents taking me to airshows and I would be so memorized with what I was seeing, almost to the point of being in a trance.
When Sarasota schools used to encourage “take your child to work day”, I would always participate. Usually, I would go work with my dad, as he was employed with the city of Sarasota, but one year I decided to join my younger cousin and tag along to go work with his step-father. He was employed as a ramp agent at our local airport. I was nine years old at the time and have never set foot in an airport, let alone on an actual airplane.
Everything was so exciting to us whether it was cleaning the airplane at night, reorganizing the magazines in between flights, or watching the ramp agents marshal the airplanes in and out of the gate. Most impactful for me, that day, was when we were allowed to sit on the tug as it pushed back aircraft.
Every time the ramp agent unlatched the tug and began backing away from the aircraft, I would smile and excitedly wave at the pilots, and to my absolute joy, they would return the smile and wave back to me. That was my very first impression of pilots. I thought they were all very friendly people.
Working in and around airplanes for the first time that day took my curiosity to the next level. Prior to that day, I would stop and stare as airplanes would fly over my house to land at the airport, but now I was starting to name the companies that owned the airplane and was starting to distinguish their different features.
Before I even began to dream I could ever be a pilot, I counted myself out. I never saw anyone fly an airplane that looked like me so I thought it was pointless to even dream that I could be sitting in the left seat waving at another little girl who was sitting on a tug.
Three years passed and I was beginning to think about other careers. For a 12-year-old, I thought being a dentist by day and rock guitarist by night was my path until my mother decided she would send my older cousin and sister up to Ohio to cheer my brother on in a big rival college football game. My sister ended up not wanting to go and that decision changed my life.
When I was 12 years old, I took my first flight to Columbus, Ohio. Since I had never traveled by any means other than a car, imagine my surprise when a commercial airliner pulled up to my departure gate painted to resemble Shamu the SeaWorld whale! When I stepped aboard my Shamu flight, I was greeted by an amorous interior, which featured romantic hues of purple throughout the cabin.
But what truly made the atmosphere special was the hysterical flight attendants and the excited passengers chanting about the upcoming football game. As I took my seat, I was so intoxicated by all the multicolored lights and stadium chanting that I had not realized time slowed. Yes, it was as soon as I heard the engines spool up for take-off, that I discovered the magic of flight, but more importantly, I knew with absolute clarity what my calling was. I will become the captain of a Boeing 747 flying cargo, from the United States to South Korea.
Ultimately, I dove into the aviation industry because flying gave me a total sense of freedom while still having the soothing element of the home. It was a feeling I never knew I was craving, and I am still chasing it to this day. Simply, I chose to become a pilot because every day I do not fly, I long to be.
All things considered, it has been 16 years since my first flight and I still pursue aviation with the same enthusiasm, today. In my pursuit of flight, I graduated from Embry-Riddle Aeronautical University – Daytona Beach, where I received my bachelor’s in Air Traffic Management and minored in Aviation Law. In addition to my degree, I went from being a Private Pilot to a Certified Flight Instructor – Instrument (CFII) in one year at the Luke Weather’s Flight Academy located in Olive Branch Mississippi.
I am currently flight instructing at the academy and am on track to transition to jets later this summer. In my spare time, I volunteer for organizations I am involved in, such as; the Organization of Black Aerospace Professionals (OBAP), and Sister of the Skies (SOS). I also take great pleasure in mentoring young women who are trying to navigate their flight training.
Would you say it’s been a smooth road, and if not what are some of the biggest challenges you’ve faced along the way?
I was fortunate enough to have parents that supported my dream of becoming a pilot. My parents did what they could but flying is extremely expensive. In order to attend Embry-Riddle Aeronautical University, I had to pull out student loans. While in school, I was employed by the University as a Student Ambassador and a Peer Mentor. When you are 17 and signing a major financial contract, you tend to skim over the finer details.
After graduation, my student loan payment peaked at $1,500/month, for six months after graduation. I was instantly unable to afford flying lessons and settled into a job as a lifeguard for the time being. Over the years, I worked numerous jobs, sometimes simultaneously. I worked as a 911 dispatcher, a substitute teacher, a lifeguard, and even an aviation analyst. Finally, in 2019 I just had enough. I was working as an aviation analyst and the job called for me to speak with working pilots over the phone.
I would feel so deflated because I would agonize about how these pilots were out there flying and I was inside a building answering their phone calls. That feeling began welling over, and one day, I woke up before work and started making phone calls. One call was to my long-time mentor and the other was to a man named Captain Albert Glenn. He and a few others started a flight school located at the Olive Branch Airport.
I let him know that I would find a way to get there. within two weeks, I quit my job, canceled my lease at my apartment, and moved back home so I can begin saving. I borrowed the absolute maximum amount of loans from my credit union and started planning.
When I look back, that was a seven-year financial hiatus. Let that sink in, after I received my private pilot’s license I was stagnant for seven years! I think a lot of people may experience this. Once you graduate from college, you feel like the world is yours to conquer until the student loans hit and employers are telling you, that your degree is too specialized, or even worse since you just graduated, you do not have enough experience for a decent paying job.
I want to be very candid when I say, this was soul-crushing, no matter how hard I tried to fight I could not seem to overcome that financial hurdle. I never wanted to be rich, I just desperately wanted to continue my education.
Overall, there were plenty of ventures I tried that ultimately failed. I was young and trying to figure it out. If I could go back in time, I would get a mentor sooner. It was very difficult to keep running into dead ends, but I use those experiences to help those I mentor, today. I learned two major lessons during those seven years.
In the first lesson, You must bet on yourself. For me, betting on myself meant borrowing the maximum amount I could and leaving my home, family, friends, car, and life behind, in order to move to a new state with a one-way ticket and a carry-on suitcase. It was challenging to do but you must be willing to be uncomfortable.
Shortly before arriving, I found out my housing situation fell through, which ultimately meant that I was homeless. For a little over a month, I lived in a hotel and got rides to the school from the hotel’s transportation, or other students at the school if they had time, if not I would walk.
When others see you bet on yourself they begin to believe in you too. Shortly after, The director of the school found some transportation for me to borrow and I was able to find some other students to share an apartment with.
The second lesson I learned was to be okay with failure. I failed plenty of times throughout the past 7 years. I looked at other people’s flight progress and it was hard not to compare myself to them. Failing is okay, so long as you fail forward.
If you find one route to aviation does not work for you, do not become despondent or even worse complacent. Regroup, get back to the drawing board, and fight for your dream.
Can you tell our readers more about what you do and what you think sets you apart from others?
I am a Flight Instructor. In a nutshell, it is my job to produce safe competent pilots. As an instructor, my first job is to learn my student and develop a plan that works best for them and their individual needs.
It is crucial that I make their learning environment engaging. The next phase is to teach my student how to be safe and stress the importance of having a solid foundation of knowledge. Next, is to teach them how to fly the airplane and challenge them to exceed the expectations of the FAA.
I am in an environment where a lot of other pilots will reach back and help others achieve their dreams. For a very long time, I believed that I had nothing to contribute to others since I was someone who was not yet at the major airlines. During my commercial training, I had a very impactful instructor that became my mentor.
My mentor (Patricia Grisham) was not in the airlines yet but she taught me so much about this industry and myself. I followed her footsteps and began mentoring and my mentees do tell me how much of a difference it makes for them. As I look at my mentees and students fly an airplane solo for the first time or achieve a new license I am always there beaming with so much pride.
I am a part of less than 1%. In America, black women comprise less than 1% of the pilot population. With that being said, I intend on being very intentional about spreading awareness to other women of color that we belong here too.
I am a very hardworking instructor and I can say the same for the other instructors at the Luke Weather’s Flight Academy. We all give our students our very best. What sets me apart from them is I think my students would say that I am pretty funny. I cannot remember ever having a flight lesson where we did not laugh at least once.
When I was a student, humor would really drive a point home for me, I think my students feel the same.
We all have a different way of looking at and defining success. How do you define success?
I define success as keeping my word to myself. I set out to be the captain of a wide-body jet over a decade ago, so when I am sitting in the left seat of one, I will feel like I have kept my promise to myself.
Part of that success will come from not only me becoming a captain of a wide-body jet, but also from putting those other women or people of color in the left seat of their dream airplane too.
It is also a life-long dream of mine to retire someday and start a center that combats homelessness in my hometown by addressing sexual assault trauma and mental illness.
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