How a Retired Colonel Makes Helping Vets Transition His Mission

Representatives from USAA tour U.S. Army Futures Command and the Army Applications Laboratory (AAL) during a visit to Futures Command headquarters in Austin, Texas.
Representatives from USAA tour U.S. Army Futures Command and the Army Applications Laboratory (AAL) during a visit to Futures Command headquarters in Austin, Texas, Aug. 1, 2019. (John G. Martinez/U.S. Army photo)

Retired Col. John DiPiero, affectionately known to his former USAA colleagues as "Dipper," joined the Air Force because he wanted to fly airplanes. "Actually, it's one word," he says. "'Fly.' My father was a career military guy, and I grew up around it. I always had a penchant for aviation. That was the primary motivation for my joining the Air Force. I wanted to be a pilot."

He was one of the fortunate few whose dream of flying for the United States Air Force came true. But DiPiero soon learned that military service encompasses a great deal more than flying.

"After serving for 29 years ... you grow into other aspects of who you are," he says. "And as you mature, you realize that maybe you have more to give than just being an aviator."

In 2000, DiPiero started planning his retirement and preparing for his post-military career. Throughout his career, he had served not only as a pilot but also as a senior leader, managing people and programs. He knew these skills were valuable, but navigating through the world of hiring managers, interviews and resumes seemed a bit daunting. At the time, there were not many transition programs available for airmen leaving the service.

"My biggest challenge was that I didn't know what I wanted to do. I didn't want to be an airline guy. I wanted something different. I wanted to do something different that challenged me in a different way," he says.

Through a series of fortunate events, DiPiero became the commandant of cadets at a well-known military academy in Front Royal, Virginia. After serving there for two years, he moved on to USAA in San Antonio, where he served its members for 16 years before retiring in 2019.

When his fellow veterans learned that DiPiero landed a job at USAA, they began peppering him with questions about how he did it, and what tips he could offer them. True to his character, DiPiero was happy to offer support as well as honest advice gained through his own experience. He became the "go-to" guy for veterans facing civilian career challenges.

Through his own transition experience, DiPiero realized that the most powerful tool in the transition arsenal is the ability to network. "People -- the connections you have with people are so critically important in this process," he says.

DiPiero says he often reminds vets that it takes time to become a leader in the civilian sector. The proving grounds are different, and you must build a civilian track record if you want to move up the corporate ladder. He advises veterans that a perfect job, one where you fulfill a dream role for the rest of your life, probably doesn't exist.

"You had a number of different roles in the military. ... Guess what's gonna happen on the outside? The same thing," DiPiero said. "So start early, know yourself, figure out what's motivating you, and then move in that direction."

DiPiero suggests that veterans who miss the camaraderie and sense of purpose integral to military service may not find the same fulfillment in a civilian career but can find it in giving back to their communities.

"If you're the type of person that somebody's asking to help, you should be proud of that," he said. "They think of you in a certain way. You're the type of person that's got the skills and the ability to be purposeful in helping other people. It's a great way to feel needed. It gives you purpose in your life. Volunteering opportunities come for different reasons at different times. For me, I volunteer to give back, help people and stay busy."

When asked why volunteering is important to him, DiPiero said: "I was raised in a family that taught me to care about people. That set the groundwork for me."

He started volunteering early in his career, working with the junior officer counsel, assisting with school projects and coaching sports programs. He advises others to volunteer based on where they are in their lives and what's available at the time.

Even in retirement, DiPiero has continued to work with numerous organizations, most of which focus on veteran transition and employment. While at USAA, he helped his colleagues see how they could make an impact in veterans' lives through organizations such as these.

"By volunteering ... you help to expand the opportunity to learn not only for yourself but for other individuals," DiPiero said. "When I'm volunteering, and I'm trying to help somebody, I listen. I listen hard, and I ask a lot of questions before I start telling them what I think, because I need to know where they are coming from. I need to learn what's important to them.

"Volunteering your time and talents is the best way to continue serving your nation, community and other vets/spouses. You have more to give, and you are needed. Countless opportunities exist in so many areas. Find those that resonate with you personally, and you'll make a difference. It feels good, too."

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