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From the military to Maine, veterans find second career, community

Photography by Enid Arvelo Photography  

Abby Ammons by Abby Ammons
November 17, 2025
| SPONSORED
Boots2Roots Executive Director Randy Bell stands among tall grass with a charming lighthouse and water in the background.

Boots2Roots Executive Director Randy Bell, a Navy veteran.

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Boots2Roots, a Maine-based organization wants to be your first stop in transition planning from the military. 

If civilian life is in your future — soon or even two years down the line — you don’t have to plan it alone. Boots2Roots matches transitioning service members to hiring Maine employers, yet it goes beyond job placement. The nonprofit, its dedicated staff, and “teammates” of the program also create a community for military families.  

Support for the whole family

Boots2Roots has helped close to 400 service members and their families move to the Pine Tree State and secure work in 14 of the state’s 16 counties. Along with counseling and mentorship, Boots2Roots encourages networking by introducing teammates to business professionals and making connections between incoming and established veteran families. (Thirsty Thursdays are a big hit for monthly social events!)  

Randy Bell is a Navy veteran who learned about the organization while stationed in Japan. Eventually brought on as the Boots2Roots program manager before his promotion to executive director, Bell stressed that its support programs are designed to support the whole family as they relocate to Maine. Boots2Roots helps service members as well as their spouses to procure their ideal jobs.   

“My wife, who also went through the program, was interviewed and offered a job before we even left the country of Japan, because she’s a dental hygienist,” Bell said, “so she was actually hired before I was.”  

Job preparation

From career coaching to resume preparation, Bell explained how transitioning service members are connected to Maine employers to find their dream post-service job in the time frame they want.   

“When the teammate contacts us, how we allocate our resources — our resources being our staff’s time and our efforts — it all orbits around the teammate’s desired start work date,” he said, adding that the staff are all military veterans or spouses. 

“Perhaps most importantly — and our biggest asset — is our ability to leverage our existing and ever-growing network to our teammates, which allows them to… get a warm handoff between us and the employer,” he said. He went on to say that over 55% of teammates have never been in Maine, so they don’t have any existing connections or “an inside track.” 

“There’s no job too big or too small. We’ll help anybody, and a lot of that is about discerning what it is that they think they want to do or need to do, and then being their cheerleader to help them become successful.”  

Boots2Roots community

When Ashley Osborne’s husband decided to leave the Navy after a 16-year career to provide more structure for their children, ages 6 and 8, they set their sights on the northeast. While exploring all of their options, they discovered the Boots2Roots program.    

A couple stands on a gravel path surrounded by trees, tall grass and flowers.
The Osbornes, who recently moved to Maine after learning about the Boots2Roots program.

“It was great to just have this organization that was able to come alongside you and knew the area, had connections, [and] was able to provide suggestions,” she said.   

Osborne said it is “an organization that really had our best interest at heart,” making it “much easier for us to get established up here and get connected.” 

With routine calls to her Boots2Roots contacts for in-town recommendations — such as a veterinarian for their dog — she said, “That honest feedback […and] their connections and their suggestions were just on point.”  

“We made the transition as easy as possible, but it still takes time [to settle in],” she said. “But again, we just had this resource… Any question, they never made us feel like a question was silly or stupid; it just made the transition that much easier.”  

Osborne described the Boots2Roots world as a miniature version of the military community she has known her whole life, first as the daughter of a Coast Guard veteran and then as a military spouse. 

“You know [the] military sisterhood-type thing with the spouses? It was like that insta-connection of someone [who] had that same background, that understanding of … packing up and moving every few years, and that sense of relief that you got where we don’t have to move again unless we want to.” 

Osborne concluded that the passion of the organization “was more nurturing than some of the assimilations” she experienced when PCSing to duty stations.  

If you are a service member or military spouse preparing for the next stage of life after the military, visit Boots2Roots to find out more about program support. Check out the rest of our Veteran Transition Toolkit here.

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Tags: Abby AmmonsAshley OsborneBoots2RootsEnid Arvelo PhotographyMaineRandy Belltransitioning veteran
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Abby Ammons

Abby Ammons

Abby Ammons is a writer, military spouse, and mother to two fiery girls. She is the daughter of an Army pilot and granddaughter of an Air Force veteran, and she believes that intentional change starts with listening to other people’s stories. With her husband currently serving with the 82nd Airborne Division, Abby is often reminded of her grandmother’s words of wisdom: “the military really is an adventure.”

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