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Air Force veteran Sheila O’Connor spent almost two decades in uniform — and nearly a decade after leaving the service without receiving a dollar of the VA disability benefits she’d earned.
After her first five claims were denied, she found VA Claims Insider, put the right strategy in place, and went from 0% to 90% in just 17 months.
The Airman
Sheila O’Connor grew up in a small town in Kansas, where opportunities were limited. After high school, her uncle — a veteran she deeply admired — learned she was considering joining the military and encouraged her to join the Air Force.
She signed a four-year commitment and reported to Randolph Air Force Base in 1990. Working in admin, she was everywhere — the cop shop, the chow hall, the flight line. After separating in 1994, she took about ten years off from military life and finished her bachelor’s degree on the GI Bill along the way. Something, though, was missing.
“I missed that camaraderie of the military.”
That feeling led her back to the Air Force — this time as a traditional reservist from 2004 to 2017, drilling monthly, completing annual tours, and rotating between duty stations at Fort Worth and Whiteman Air Force Base before retiring out of Lackland. Through all of it, a VA disability claim never crossed her mind.
“I thought it was only for other people.”
While living in San Antonio, one of the most veteran-dense cities in the country, Sheila started hearing more conversations about VA benefits after she got out. But even then, she held back.
“I thought it was for the Vietnam vets or the older folks. Somebody else deserves it more. I didn’t want to take from those people.”
It wasn’t that she felt she hadn’t earned it. She just didn’t think it was available to her. She wasn’t limping. She wasn’t in a wheelchair. She could still hold a job.
So she waited. And waited.
Over time, she started to realize that VA disability benefits aren’t something you take away from other veterans. They’re benefits earned through military service.
The First Attempt
In 2023, she finally decided to try. She reached out to two VSOs for help first. Neither ever responded.
So, she filed on her own, submitting five claims all at once. But every claim was denied.
“I basically only had the diagnosis. I didn’t have any of my other backups — the medical evidence, nexus letters, DBQs. I didn’t even know what those were.”
Discouraged, she did what a lot of veterans do.
“I just threw it in a drawer.”
But it stayed in the back of her mind. A year and a half later, she stumbled across VA Claims Insider founder Brian Reese’s videos online. The more she learned, the more she realized how complex the system was — and how much she’d been leaving on the table. She decided she wanted real help, and she was willing to pay for it.
“I didn’t know if I needed the help, but I wanted that help.”
Getting to Work
In mid-to-late 2024, Sheila joined VA Claims Insider and started working with a coach. This time, she understood what the VA needed and how to prove it. The difference was immediate.
Within three months, her first claim was approved at 10%. Three months later, a second claim came in at 30%, bringing her combined VA rating to 40%.
Then she hesitated.
She’d heard the stories. Filing more claims could open up your whole file, and the VA could come back and reduce what you already had. She asked her Veteran Coach directly: at what point do you stop?
“He told me, ‘It’s only over when you say it’s over.’ The facts are the facts, and the evidence is the evidence.”
That was all she needed to hear. She filed a Higher-Level Review on that 30%, won it, and that claim jumped to 50%, pushing her combined total to 60%. She kept going from there. She filed four claims. All four were approved. Two required Higher-Level Reviews. Both won.
“I’m 90% now. And it was all within 17 months.”
For Sheila, that number still feels surreal, especially for a veteran who never deployed and carried the quiet guilt that comes with that.
“You don’t always have to have been in a combat zone or taken shrapnel. I still wore the uniform. I still did the duties. And here I am at 90%, which I never ever in a million years would have thought was possible.”
Her Message to Fellow Veterans
Sheila learned a lesson early in her military career from a supervisor — something about performance ratings that she’s carried with her ever since, and that applies just as much to this.
“Nobody’s going to look out for you better than yourself. You have to be your own advocate. The VA is not going to come knocking on your door and say, ‘Here’s a bucket of money.’ You have to seek out your own benefits. Do it early. You have nothing to lose.”
She’s already recommended VA Claims Insider to veteran friends and relatives. And she’s clear about what made the difference.
“It’s kind of like going into the store. You’re not going to take out a brisket and not pay for it. It’s a small price to pay. I know I couldn’t have done it without you guys. Everything worked for me. I would do it all over again.”
Your Story Isn’t Over
Sheila served for nearly two decades, never deployed, and almost didn’t file at all. She got denied the first time and nearly gave up for good. But with the right guidance, she went from 0% to 90% in just 17 months. Her story proves claim denials don’t mean it’s over — and you don’t have to see combat to deserve the benefits you earned through service.
YOU SERVED. YOU DESERVE.
If you’re a veteran who’s been denied, feels like the system is too complex, or thinks you don’t qualify — VA Claims Insider exists for exactly that reason. The only question is whether you’re ready to find out what your VA disability rating should really be.
About the Author
Eric Webb
Eric has written and worked in the field of Veterans Disability since 2020 and enjoys writing educational content for the veteran population. His prior work has been published in the Official Journal of the American College of Sports Medicine (ACSM). He holds a Degree in Health and Exercise Science.
