James Isenhour spent 20 years in the Air Force working on avionics, the computer systems that keep aircraft in the air. Along the way he earned a bachelor’s degree and a master’s degree. He figured that combination, plus two decades of military experience, would open doors in IT once he got out.
It did not work out that way, and he told us why on the award-winning Get Into IT Live.
A Career Built on “Later”
James wanted to cross-train into an IT career field during his time in the Air Force, but the opportunity never came through. “I was always told, well, later on down the road you can change roles,” he said. So he kept building his resume the best way he could: two degrees, a certification back in 2000 that came with a promise it would never expire (it did, once the industry rolled out a newer version). The cross-training opportunity? Never arose.
When he left the Air Force in 2021, he landed a role at JAG Aviation to run the avionics department. There was just one problem. “Once I got to JAG Aviation, I realized there is no IT support,” he said. “There is no one really doing this.” So he stepped in and took that on too, applying what he was learning in his coursework to bring the network up to speed.
Two Degrees Were Not Enough
Here is the part that surprised James most: when he interviewed for IT roles, his education and experience did not close the deal. “The questions were always, well you knew that back then, but do you know about the newer things (in IT)? What’s going on today?” he said. He had two legs of what he calls the three-legged stool of hiring: education and experience. He needed the third. “You have the education, you have the on-the-job experience, or you need certifications. I had one of the three.”
That gap brought him to MyComputerCareer. Even though his background qualified him to start in the Cyber Security Engineer advanced program, he asked to step back into the Cyber Security Specialist program first. “I didn’t want to jump in and miss some things,” he said. From there he moved forward into CSE and picked up his CCNA and CySA+ along the way, both certifications employers in the field actively look for.
Structure Made the Difference
James is candid about how hard the program was, even for someone with his background. “I’m not going to sugarcoat it for any future students,” he said. “It’s tough.” He knew he could have studied for these certifications alone. What he could not replicate on his own was accountability. “Did I have someone pushing me along the way to make sure they held me accountable? No, I wouldn’t have had any of that.”
He also credits the Career Services team with translating two decades of military experience into language civilian employers understand, then putting that resume in front of the right people.
Eleven Days at AWS
At the time of the interview, James was 11 days into a new role at Amazon Web Services as an infrastructure delivery manager. His LinkedIn also notes an active security clearance, something he says can move a candidate to the front of the line when a company needs someone who can start fast in a restricted environment.
Even at a company the size of AWS, James is sticking to the advice he gives every new IT professional: master the job in front of you before you chase the next one. “Become an expert,” he said. “Do everything you can in that current position to show that you are going to be a great fit for that next position, because they hired you for a position.”
His Advice for Veterans, and Anyone on the Fence
James thinks veterans often undersell themselves without realizing it. “A lot of military veterans don’t realize how much money and leadership training has been given to them,” he said, pointing out skills like leading a team or solving a problem with limited resources translate directly to civilian IT roles, once you learn how to position them in civilian terms.
And for anyone weighing whether to make the leap into IT training at all, his advice is simple: “If you’re not moving forward, you’re falling behind.” Even after certification, he said, the learning does not stop. It just changes shape.
Want to hear James tell the whole story in his own words? Catch the full episode on YouTube. And if his path sounds like the push you needed, take a look at our advanced IT training programs. Your opportunities at MyComputerCareer and in IT are endless…take the leap!