Bill Benson, a retired U.S. Army colonel and executive director of Boots2Roots, in the nonprofit’s office. Boots2Roots help veterans transition back to civilian life and find jobs. Brianna Soukup/Staff Photographer

Bill Benson always felt called to military service, but he never planned to make a career of it.

In fact, the retired colonel tried to leave the Army 10 years into what would ultimately be 24 years of service.

He was told he owed a little more time. A few years later, after 9/11, he needed no further convincing.

For the next decade, Benson said, he was either preparing to deploy, deployed or recovering from deployment. In total, he spent 42 months serving in Iraq and Afghanistan.

“Those were really difficult times but they were also very purposeful. I felt like I was contributing” he said. “I wasn’t necessarily in favor of the invasion of Iraq, but I committed to the Army. I believe in service to our country, and I felt like I could do the job and I felt like I could influence others to do that job well.”

Now, he’s serving in another way: helping active-duty military members prepare to enter the civilian workforce.


Benson, 54, of Gorham, is the executive director of Boots2Roots, a Portland-based nonprofit that starts working with service members up to a year before they begin the transition from active duty and tries to help them find meaningful work within two months of arriving in Maine. Boots2Roots does not charge for its services. The goal is for the veterans to remain for at least one year in their first post-military jobs.

The organization is currently stepping up its recruitment effort to try to do its part to alleviate the state’s ongoing labor crisis. Boots2Roots has found jobs for more than 125 veterans since it began its work in 2016.

By the time Benson left the Army in 2014, he had spent more years in the military than out of it. And since he enlisted straight from college, he was starting from scratch. He had no career to restart.

He knew he had the skills to do just about anything, but he didn’t know how those skills would apply in the civilian world.

“I didn’t know how I was going to fit into another organization,” Benson said. “That concerned me.”

Though he didn’t have any experience as a business owner, he and his wife purchased a small business manufacturing wood products for home building, which they ran for five years before selling it in 2019.


“If I was a business owner, I would have a little more control over my day-to-day and how I fit into the culture,” he said. “Even though it was a risk, it was at least subconsciously a way for me to have more control over my transition.”

He sees a lot of his own initial worry in the veterans he now works with.

“Understanding that they’re valued and that they can be a contributor to a business or a community is really important,” he said. “That’s the most common thing people are struggling with, even if they can’t articulate it. They don’t know how they’re going to fit in.”

In his first few years in the military, soldiers were discouraged from wearing their uniforms when traveling, Benson said. But public perception of the military became significantly more positive after 9/11.

“It wasn’t unusual for you to walk through the airport and if you had your uniform on, people would stop and clap,” he said. “It made you feel like you were part of something larger and had the support of those around you.”

Benson is aware of how vastly his experience differed from the Vietnam veterans who came before him.

“They were not welcomed home and they spent most of their lives not talking about it,” he said.

He’s concerned with waning participation in the military, which he said contributes to the way it functions as a self-contained unit. It often operates as its own little world, separate from the rest of society.

“I don’t want to downplay the risks. Certainly, there are negatives that can be associated with military service,” he said. “(But) it is a way to serve. If a society can’t find volunteers to join its armed forces, then we’ve got bigger issues than just the strength of the military.”

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