When Diane Jackson was 16, her father left his executive job at Boston’s Logan International Airport and moved the family from Massachusetts to Maine to run The Outpost grocery store on Thompson Lake in Otisfield.

“He was going to chuck that world and come to a place he’d always loved,” Jackson said.

It was the 1970s, and she and her three younger brothers were quickly pressed into work at the business.

“We put in the long hours, but it was wonderful,” she said. “(I) was an extremely shy young girl, kind of being thrown into that situation where you really wanted to be outgoing and friendly, because that’s how your business survived and thrived, making those relationships.”

In the years since, Jackson has run a tavern, raised sheep, cut wood, made furniture, and, for one 10-year stretch, served as the eyes and ears of Maine’s senior U.S. senator.

Hers is an eclectic, ambitious resume with an underlying theme: helping others survive and thrive.


At the end of the month, the Androscoggin County Chamber of Commerce will honor that work by presenting her with its small business advocacy award.

Jackson is one of several account executives in the Maine Department of Economic and Community Development who specialize in growing business. It has her connecting people with resources, and people with people.

“I think it had a lot to do with (my experience at the Outpost) that you’re always trying to help,” Jackson said. “I think that’s where that basis of wanting to connect people to their needs (began.)”

As a teen, she said, she was excited to move to Maine and see beautiful Thompson Lake.

“We didn’t have family in Maine, so a lot of our friends and neighbors that we met were like family,” she said. “There was plenty to do to keep us busy. There was no time to get in trouble. It was great.”

Jackson and her husband, Caldwell “Caldie” Jackson, started running their first business together just three weeks after getting married, when she was 21. He and his brothers had built Twin Bridges Tavern in Harrison, a pub and event space.


“I like to say we brought disco to the area,” she said.

Over the years they raised sheep, beef, red deer and elk on their Breezy Hill Farm in Oxford. She pitched in with his logging business, delivering and splitting firewood “with our children in tow.” They also had a line of reproduction country furniture for many years selling in catalogs such as L.L. Bean.

Jackson was working as an executive assistant for Rick Bennett in the Maine State Senate when she heard about the job opening in U.S. Sen. Olympia Snowe’s office for a regional representative covering Western Maine.

“Probably one of the best decisions I made (was applying for that,)” she said. “I feel very honored to have served someone of the senator’s caliber. While it was a big responsibility, it was just a wonderful feeling to know that when you picked up the phone and someone was very frustrated, you could help them, (and) kind of put their fears to rest.”

She’s juggled many roles at once, and now is no different. Jackson and her husband have three daughters, but they still raise Katahdin sheep and laying hens, and they grow potatoes.

In her current job with DECD, Jackson covers Androscoggin, Franklin and Oxford counties. She works a lot with the Lewiston CareerCenter and frequently fields questions like where to go for help with a business plan, where to turn for licensing issues, how to expand a business or how to sell to an export market.


“I think it’s important to be in a community that’s supportive of growth,” Jackson said. “To have that positive attitude, it makes you want to work harder for them.”

[email protected]

On Jan. 28, the Androscoggin County Chamber of Commerce will host its annual meeting and awards dinner at the Ramada Conference Center in Lewiston, where it will also be announcing some big changes.

Being recognized that night:

Ray Geiger Award — Chamber Champion: Chip Morrison

Theresa Sampson Award — Women’s Business Leadership: Sandy Marquis


Ken Additon Award — Small Business Advocacy: Diane Jackson

Community Service Award: Mark Cayer

Business Leadership Award: Oxford Casino

President’s Award: Peggy Rotundo

Outstanding Member Award: Francis Gagnon

For event tickets and more information, visit androscoggincounty.com.

Only subscribers are eligible to post comments. Please subscribe or login first for digital access. Here’s why.

Use the form below to reset your password. When you've submitted your account email, we will send an email with a reset code.