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Warrior Perseveres Despite Challenging Transition to Civilian Employment

Rob McGregor

When Rob McGregor retired from the Navy in 2014, he anticipated a smooth landing in civilian life. The former helicopter pilot left the military as a lieutenant commander after 27 years of service, including deployments during the Gulf War and Operation Iraqi Freedom.

But his transition proved to be anything but smooth. In fact, it was turbulent. Rob struggled to get job leads, let alone land a job, for a few years. Then when he did, he struggled to find the right fit. The challenges of the transition brought on severe anxiety and depression.

“It was really tough for me to understand why I wasn’t getting my foot in the door,” he said.

Rob was far from alone in these challenges. About 200,000 service members each year transition to civilian life, which is very different from the uniforms, hierarchy, protocols, and language that characterize the military. This makes the transition difficult for some warriors and means finding the right fit with a civilian employer can be challenging.

But like so many veterans, Rob ultimately persevered and found a meaningful job that’s right for him. For National Hire a Veteran Day on July 25, Wounded Warrior Project® (WWP) is shining a light on Rob’s employment journey and what he learned from the process — to help warriors and employers better navigate the military-to-civilian transition.   

From Flying Blind to Flying High
Shortly after his retirement, Rob submitted a pile of resumes to several companies. With a decorated military history and a college degree, he expected a positive response. But instead, few employers even noticed.

So, he decided to pursue a different path: graduate school. Within two years, he graduated with two master’s degrees, including an MBA. At this point, his confidence was sky-high.

He started submitting resumes once more. But again, he didn’t get any bites. His frustration intensified, and so did his anxiety and depression.

That’s when Rob found WWP’s career counseling program, Warriors to Work®, which helps wounded warriors and their families find their next careers to help their transitions to civilian life. In 2020, Warriors to Work helped place nearly 2,000 wounded veterans and family members in new careers, with combined first-year salaries totaling nearly $94 million.

Rob ultimately connected with WWP career counselor Ty Dixon, who helped the retired Navy officer rework his resume, pursue job leads, and network with employers.

“Ty has always been there,” Rob said. “She has always been supportive and has always been someone I can turn to.”

After initially working with the Warriors to Work program, Rob ultimately landed his first civilian job in a director-level position in 2017. He thought it would be a great fit, but it wasn’t, which further exacerbated his anxiety and depression. Around the same time, Rob was diagnosed with prostate cancer.

“There were a lot of challenges for me as I was going through my transition,” Rob said. “But the support from Wounded Warrior Project was definitely something I could count on.”

That first civilian job, or first few jobs, can be challenging for some veterans. Of warriors who recently began the Warriors to Work program, 41% had four or more jobs within three years of transitioning from the military.

To help Rob navigate these challenges and overcome his invisible wounds, Ty connected Rob with the nonprofit’s telephonic emotional support program, WWP Talk. Simultaneously, he still struggled to find the right job fit and continued to work with WWP’s career counseling program.

“Having that support from Warriors to Work where Ty helped me talk through the things that were going on and understand what I needed personally to feel fulfilled in a role helped me overcome a lot of the challenges I was facing,” Rob said.

And overcome he did. In 2020, Rob accepted the position of chief programs officer at Pine Castle, a Florida-based nonprofit that serves adults with developmental differences. After nearly 30 years of service in the military, Rob found a job in the civilian world where he not only felt comfortable but was once again helping people.

“Service has always been near and dear to me,” Rob said. “That’s why I gravitated to the nonprofit side to where I could continue to help serve individuals. That is what drives me.”

A Journey Others Can Learn From
Rob recently celebrated one year in his new role and is now inspired to help other veterans transition to civilian employment. He recommends fellow warriors do the following:

  • Prepare for your transition and start your job search early. “I retired and assumed that coming back would happen like that,” he said. “It took a while for me to find myself.”
  • Network. Rob retired to Jacksonville, Florida, and had very few relationships there at first. That made his transition more difficult.
  • Stay positive. “There have been many times where I felt like it’s never going to work out, I’m never going to find the right fit for me,” he said. “I just had to keep plugging along.”

Now that Rob is in a hiring position, he also has some advice for employers.

“Companies should try to see the intangibles that a veteran can bring to their organization,” he said.

According to Rob, some of those intangibles include:

  • A relentless work ethic and drive to accomplish the mission at hand.
  • The ability to adjust to different situations and fill gaps when needed.
  • Soft skills that come from working with a variety of people.
  • The desire to serve and make a difference.

Most importantly, Rob recommends both veterans and employers seek support from organizations like WWP to help make that military-to-civilian transition smoother.

“There are a lot of programs that can provide that assistance we veterans truly, truly need,” Rob said. “When you feel like you have nowhere else to turn, try to find somewhere to get help because it will get better.”

WWP is committed to empowering warriors to be successful in the civilian workforce while connecting employers to qualified candidates, supporting their onboarding, and developing a long-lasting relationship through the life cycle of employment. Learn more about Warriors to Work.

Contact:  Jon Blauvelt — Public Relations,, 904.426.9756

About Wounded Warrior Project
Since 2003, Wounded Warrior Project® (WWP) has been meeting the growing needs of warriors, their families, and caregivers — helping them achieve their highest ambition. Learn more.

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