HARTLAND — When Sheilla Files was working as a paralegal for a law firm in the 1970s, she told a partner there that she wanted to become a lawyer. He didn’t take her seriously.
“She was told in his opinion that women didn’t belong as lawyers or as judges, that her best bet was to know her place and to stay behind a desk ... out of site and out of mind,” recalled Files’ daughter, Chris Files. “That didn’t sit well with her.”
It also didn’t sit well with Files’ husband, David Files, who encouraged her to pursue a law degree. Files, who died at 74 on Sept. 26, 2021, after a long battle with cancer, did just that. David, who rearranged his work schedule during the years Files was working full-time and going to school part-time so that he could care for the couple’s three daughters, had died suddenly just two months earlier on July 14. They were married for 54 years.
“She was always, speaking to her personality, more worried about him and how he would survive if she were not there than worry about her own self,” Chris Files said. “The love that they had for one another is unparalleled. They always did for each other, but she certainly, more so, would look out for him.”
The couple were introduced after David met one of Sheilla’s brothers while hunting in Brownsville, Chris Files said. Initially, Sheilla wasn’t so sure about him, but David quickly won her over. After their deaths, their daughters came across a diary that David had given Sheilla in the lead-up to their marriage on June 11, 1966.
His inscription read, “I couldn’t find a diary for 100 years. That’s what I wanted to get you because that’s what I want to spend with you,” recounted Deb Sleeper, of Hartland, the couple’s middle daughter. “Her entries every single day were just ‘I love him so much I can’t wait until we get married.’”
“It was so awesome to be able to have that information because it’s this side of Mom and Dad that, (while) … you could tell that they meant the world to each other, there wasn’t that outward display of emotions.”
Instead, it was expressed more through their actions and the support they had for each other’s pursuits. Growing up, Sheilla had wanted to be a police officer, but was told that women weren’t allowed to take such jobs. Then, she turned her attention to law and became a paralegal. Her drive toward the law stemmed from a childhood in which she moved around a lot. Due to her father’s job working on Vermont’s interstate highway system, she attended 26 different schools before graduating from Windsor High School. Through it all, she maintained an A-plus average, Chris Files, the couple’s youngest daughter, said. She saw education as stability and a way to a better life circumstance.
“The law and the idea of fairness and justice regardless of race or creed or monetary background, that was why it appealed to my mom so much,” Chris Files, of Hartland, said. “My mother knew from a very young age that nothing was going to be given to her. If she wanted anything, she was going to have to earn it.”
After that comment from a law partner, Sheilla Files started taking classes at Community College of Vermont — without the law firm’s knowledge or support — and earned an associate’s degree, Chris Files said. Then, with David’s steadfast support, she set her sights on the next steps.
“I think for her it would have been enough for her to be working full time and raising children and being married,” Chris Files said. “She would have had other goals still, but he was the one who really said ‘you can do so much more than that’ and he supported her while she did that.”
Next was a bachelor’s degree from Boston University, which involved working every day from 7 a.m. to 4 p.m. before traveling up to four days a week to Boston to attend night classes. She’d come home around 2 or 3 a.m. and the next day would repeat the cycle.
During those few years, David Files helped their daughters with homework. He prepared meals and brought them along to the family’s rental properties. In addition to the rental properties, he was a real estate agent, insurance salesman and Navy veteran.
“We became skilled in all things carpentry as kids,” Sleeper said. “At the time we didn’t really feel as though Mom was ever around.” That being said, “when she was home she was Mom a thousand percent. She was cooking, she was arranging the house a million times due to my dad’s dismay.”
Next up was Vermont Law School, which brought her closer to home. Sheilla earned a law degree in 1984. She didn’t pass the bar exam the first two times she took it, which frustrated her.
“My father again stepped up and would not let her give up,” Chris Files said. “He said ‘you’ve come this far, don’t let them get the best of you, you’ve got to do this.’ ”
The third time ended up being the charm. Eventually, she ended up working at a probate law firm in Springfield, Vt., where she became partner. There, she met Patti Page who was employed as a secretary at the firm. The first two attributes that come to mind about Sheilla, Page said, were her humility and her kindness. A month after working at the firm, Page’s father became quite ill and later died.
“Not only was I learning a job, a new job, a new area of work, but I was dealing with my father’s illness and ultimately his death and Sheilla was definitely my guiding angel, my guardian angel that day,” Page said. It was as simple as how Files would ask how Page was doing after she returned from the hospital. “Her kindness is what I think I remember the most about Sheilla. Her quiet kindness.”
It was also on display in how she treated everyone she encountered.
“She respected individuals no matter what we were doing in the office,” Page said, adding that she always had something kind to say to everyone. “It wasn’t a lot of words, but she would look up at you when she said thank you. You knew it was sincere.”
As a lawyer, Files’ strength was in research and she didn’t particularly like going in front of the courtroom.
“She just didn’t like being in the limelight,” Page said. “She would much prefer to do the work behind the scenes.”
Files had a reputation for going above and beyond with her clients, sometimes going outside the realm of what people think lawyers do. Barbara Carlson became friends with Files in 1990 after she handled a real estate transaction for her. After closing on a home in Weathersfield, Carlson was wondering where she could get a mattress that day. Files said her husband had a shop with mattresses and they’d take care of it.
“Sheilla and Dave delivered it to me that night,” Carlson said. “How many attorneys would do that for a client? It just blew me away.”
In the mid-1990s, Files opened her own practice in Hartland and while Files was good at her job, she didn’t always enjoy the work.
“Even though she did not care for family law, she was great at it because she listened and she was very intuitive at reading between the lines. If someone didn’t necessarily say something, she could ferret out the truth,” Chris Files said. “She always would say that no one won in family law. It just wasn’t the idea that she had had of things being fair and the law being used to created a justice for all.”
During that time, the couple also supported people in the community who were struggling. David Files owned a store in Windsor where he sold antiques, furniture and collectibles. Sometimes, people would come in and try to sell him items so they could get money for living expenses.
“He would get to know these individuals and many of them would actually ultimately come to live with us,” Chris Files said. “They actually became the equivalent of foster parents to adults who were from backgrounds that where maybe the parents were alcoholics or on drugs and just didn’t care about the kids.”
The Files became mentors to them. David Files taught them carpentry and gave them jobs working on the rental properties.
“They did it quietly, they did it without fanfare,” Chris Files said. “In addition to raising their own children, they really raised a whole other community of people as well.”
Sometimes it wasn’t easy for their children, Sleeper said. Like with their mother’s education, they’d have to share her attention with others. But they also learned from their parents what it meant to truly help other people and put the concept of charity into action.
“At the time all I remember feeling was ‘this isn’t fair, they’re not your kids, we are,’ but now it just makes me wish that I could be half the person that they were and do it myself,” Sleeper said.
Files retired from law in the early 2000s, around the time Chris Files opened a bridal and prom shop business in Hartland. For a time, the law office and shop shared a building. The two were partners, and once Sheilla Files fully retired from law, she worked in the shop where she delighted in helping people find garments for their wedding.
Around 10 years ago, she was diagnosed with stage 4 cancer. It was tough for the family, especially David, but she took it in stride. She thought nothing of driving down to the Florida home where she and David wintered. At one point, her aunt, Katrina Durand, and a friend accompanied Sheilla and her sister Midge on one of those trips. Even though she was undergoing treatment at the time, she didn’t let it faze her.
“She was so upbeat. You’d talk to her on the phone and you would never know there was anything wrong with her. Never,” Durand said.
Files frequently kept up with her friends by phone, always checking in to see how they were doing and not speaking much about her own challenges.
“You’d talk to her and she would cheer you up. Her attitude was ‘Hey it is what it is, I can’t do anything about it.’ She was just laughing and cheerful,” Carlson said. “You felt wonderful after talking to her which is something I think is a trait we all wish we had, but it’s unusual.”
That was on display during the couple’s 50th anniversary celebration in 2017. Even though they were both battling health challenges, those who attended couldn’t tell. As a couple, David Files was always the more outgoing one. Strangers became friends over the course of a single conversation. Sheilla, meanwhile, was content to sit back and observe. It’s what made her such a good mother, friend and lawyer.
“She was just observing people and kind of getting to know them based on their actions and what they said before she would volunteer to speak,” Chris Files said.
At the time of their deaths, David Files was working on fixing up an old coaching inn on Lake Seymour in Morgan, Vt., where the family once had a camp. David, despite the obvious pain he was in from arthritis, was determined to make the old inn wheelchair-accessible for Sheilla to enjoy.
“They found this one and it became Mom’s dream property and all he wanted to do was restore it for her so she could go up there,” Sleeper said. “It meant so much to him to make it so she could go up there. Unfortunately, she didn’t make it up there but that’s what he was working for.”
Their devotion to each other and their family made it possible for Sheilla to see through her professional dream, which became David Files’ dream as well.
“To have a job, go to school and have a family. That’s not an easy road for a woman,” Page said. “I think very few would succeed the way Sheilla Files succeeded. That took her husband, her daughters, her whole family for her to do that and she’d be the first one to say that, I’m sure.”
Liz Sauchelli can be reached at esauchelli@vnews.com or 603-727-3221.