It Can Be Done: The sky is the limit for med tech-turned-pilot

Photo of Airmen looking down at smoke bombs.

Then-1st Lt. Jesse Hildebrand, 93rd Bomb Squadron B-52 Stratofortress pilot (left), takes part in survival training in October 2003. Now the 343rd BS commander, Hildebrand enlisted in the Air Force Reserve as a medical technician before attending Officer Training School and becoming a pilot. (courtesy photo)

An Airman hugs his daughter as his wife looks on.

Lt. Col. Jesse Hildebrand, 343rd Bomb Squadron commander, looks over a B-52 Stratofortress with members of his family at Barksdale Air Force Base, Louisiana, in January. Hildebrand, who originally enlisted in the Air Force Reserve, used a wide range of resiliency skills to achieve his dream of becoming a pilot. (Senior Master Sgt. Ted Daigle)


Somebody said that it couldn’t be done

      But he with a chuckle replied

That 'maybe it couldn’t,' but he would be one

      Who wouldn’t say so till he’d tried.”


Lt. Col. Jesse Hildebrand smiled as he read the opening passage from Edgar Guest’s poem, “It Couldn’t Be Done.” The limerick is a favorite of the native Texan and it seems to capture his life’s philosophy in prose.

The new commander of the 307th Bomb Wing’s 343rd Bomb Squadron, Barksdale Air Force Base, Louisiana, has never been one to shy away from a challenge. His entire military career has been a series of missions into the unknown.

Hildebrand enlisted in the Air Force Reserve while still in college, entering service as a medical technician. But just joining the military was a practice in trial and error. Hildebrand did not come from a military family and he found himself navigating the myriad of options by himself.

“I went to every one of (the services) and the Air Force Reserve just seemed like the best fit,” said Hildebrand.

He quickly learned how to balance a full academic schedule with work and his military obligations. Before long, he became a noncommissioned officer. Still, he wasn’t satisfied. Something inside was pulling at him to try and do more.


A lightbulb moment


That tug grew stronger in the summer of 1999. Hildebrand was on orders at Sheppard Air Force Base, Texas, working as a medical technician. The constant parade of jets zooming across the skies of the pilot training base captured his attention and his imagination.

“I thought ‘Look at all those jets, I bet they need a lot of pilots,’ but what I didn’t know was they were just doing touch-and-go’s,” he said, laughing at the memory. “I didn’t realize I was seeing the same jets over and over!”

Hildebrand may have known little about Air Force aviation, but something had clicked. Those jets were a challenge in his eyes, a mountain he had to climb. The young staff sergeant was determined to become a pilot.

But the way ahead was far from clear. His path to flight school was marked with the same hazards as his initial entry into the military. Hildebrand had no experience flying, no family background in it and very little in the way of support.

What he did have was an attitude of determination. His rationale for wanting to become a pilot rings with the echoes of his favorite poem.

“I just wanted to see if I could do it,” he said, breaking into one of his big smiles and shrugging his shoulders.

Somebody said it couldn’t be done


Taking the same strategy he did to join the military, Hildebrand began researching and looking for resources to get his dream started. He contacted an active-duty recruiter, but that avenue didn’t yield the results Hildebrand wanted.

So, he started looking within the Air Force Reserve. That hunt led him to the commander of the 47th Fighter Squadron, an A-10 Thunderbolt unit stationed at Barksdale at the time.

Hildebrand explained what he wanted to do. The commander listened carefully, then shook his head no. The 47th FS was a pilot training unit, the commander explained. Hildebrand would need prior experience flying the jet before he could be part of the unit.

But the commander’s answer didn’t deter the NCO, it just made him start asking questions.

“Well, where can I go to get hired as an A-10 pilot?” Hildebrand asked.

Surprised by Hildebrand’s persistence, the commander suggested he try reaching out to the 926th Fighter Squadron, another Reserve A-10 unit in New Orleans at the time.

Hildebrand called the commander there, who was also taken aback by the brazen request. Neither was quite sure what to do with a medical technician who showed up asking to be a pilot in their unit.

Just as before, the 926th commander explained he couldn’t help Hildebrand. And like before, Hildebrand peppered him with questions about who could.

As the cycle repeated itself, with each denial being met by Hildebrand with more questions about where to go and what to do next, each commander suggesting another unit to try.

“It isn’t that I can’t take ‘no’ for an answer, it’s that I’m always just looking to see if there is a ‘yes’ behind it,” said Hildebrand of his search for answers.  "I’ll keep trying until it happens and if it doesn’t work out, I’ll try something else.”

Hildebrand changed tactics, moving from fighters to bombers. He went to the 93rd Bomb Squadron, who listened to his story and decided to give him a chance at becoming a B-52 Stratofortress pilot. Persistence had finally paid off.

“I don’t think they knew what they were getting into,” said Hildebrand with a laugh. “I didn’t even know what I was getting into!”

The Texan took his “yes” and ran with it. He’d overcome all the objections, now he’d have to overcome the next obstacle: inexperience.


Not giving up until he tried


Hildebrand admitted to being completely lost when he entered the aviation world. On his very first flight in a Cessna, a bird hit the windshield of the plane. Wide-eyed, Hildebrand turned to his instructor.

“Is this going to happen a lot?” he asked. The instructor just shook his head and laughed.

During pilot training, Hildebrand found himself surrounded by classmates who had backgrounds in aviation and the military. Determined not to be left behind, Hildebrand doubled down on his efforts, completing a year of training in the T-37 Tweet and T-38 Talon.

He described learning to fly the jet as “the best year and toughest year of my life.” Hildebrand, fought to learn the ins and outs of flying and master the tiny trainer. But he loved the challenge and ultimately made it through his first year of pilot training.

All the flying struggles seemed to disappear when Hildebrand finally got to the B-52 Formal Training Unit. He immediately took to the big bomber, feeling right at home in its cockpit.

“I always felt comfortable in the B-52, although some of my instructors might tell you something different,” he said. 

Hildebrand’s struggles in the cockpit were over, but he still faced challenges as he moved up in rank and took on greater responsibility and leadership. He is quick to say he’s been surrounded by great friends and mentors who helped him every step of the way.

If history is any indicator, he’ll use past experiences to guide and mentor others, always looking for ways to help them reach their potential, the lines from Eddie Guest’s poem ringing in his mind. #ReserveResilient

(Daigle is assigned to the 307th Bomb Wing public affairs office.)

Social Media

Facebook Twitter
The August 2021 issue of Citizen Airman Magazine is online now! #ReserveReady #ReserveResilient #ReserveReformhttps://t.co/UxoX3OrEMk
Embrace Change ... or Be Left Behind (Commentary by AFRC Command Chief CMSgt. Timothy White Jr.) #ReserveReadyhttps://t.co/uUl1IukKI5
Change ... (Commentary by Lt. Gen. Richard Scobee) #ReserveReady #ReserveResilient #ReserveReformhttps://t.co/RrYDJxuelk
Reserve Advisors bridge gap between commands (Story by @HQRIO) #ReserveReady https://t.co/8O7L0OapaQ
Reforming the Fighter World: Reserve Airman makes history with innovative F-35 project #ReserveReady #ReserveReformhttps://t.co/a35MeqewOj
Making Mech-Techs: Duke Field maintainers implement innovative training program (Story by the @919sowDuke)… https://t.co/Xc7GRBGFCa
Expanding Capabilities: 414th Fighter Group leads flying ops for the first time #ReserveReadyhttps://t.co/g6lm9pljhK
Ready to Help: Texas Reservists deliver critical medical supplies to India (Story by the @433AW) #ReserveReadyhttps://t.co/v7OasTJh1C
An Arctic Ministry: IMA chaplain serves at northernmost military installation #ReserveReady #ReserveResilienthttps://t.co/A1OObnZf2b
Up Close and Personal: Recruiters gather to learn all about @22ARW, the #KC46 and the Wichita area #ReserveReadyhttps://t.co/951sl92OaA
Gratitude at Gunpoint: Flight surgeon uses resiliency skillset to beat adversity (Story by the @307BombWing)… https://t.co/l1rz3WPIAl
Breaking Barriers: Charleston defenders achieve pair of firsts (Story by the @315AW) #ReserveReadyhttps://t.co/7Xa39K7tmp
Where do you find resilience? For Col. Isaac Davidson, its's a combination of faith and family #ReserveResilienthttps://t.co/RwBUXh3auF
Nexus Dawn: Exercise provides Reservists vital training and readiness tests in spite of pandemic (Story by the… https://t.co/KDLEbmCjS0
Readiness, Resilience, Reform: Reviewing the command's progress on its three strategic priorities showcases innovat… https://t.co/sTlMz2RN4x
The June 2021 issue of Citizen Airman Magazine is online now! #ReserveReady #ReserveResilient #ReserveReformhttps://t.co/r8oawbcUc1
Shoot for the Stars: Resilient and motivated leader encourages goal setting in 2021 (Story by the @302AirliftWing)… https://t.co/6RmvtnMqCp
Learning by Doing: Reserve recruiters participate in joint air operations #ReserveReady #ReserveRecruitshttps://t.co/LCsBHZEnXf