James “Jim” Deeley isn’t one to follow a straight or predictable path. A legal professional, he’s also an avid game master with a career full of unexpected turns and plot twists. It all makes for a great story, much like the tabletop gaming adventures he loves.
A Virginia Peninsula Community College alum, Deeley added a new chapter to his story this summer when he became a paralegal at The Zaremba Center for Estate Planning & Elder Law in Williamsburg. The opportunity meant a lot because it was his first time “being headhunted” for a job. He remembers taking the recruiter’s phone call while preparing for a trip to Indianapolis for Gen Con. It’s the largest tabletop gaming convention in North America and Deeley’s biggest event of the year.
“I got the call in mid- or late-July. That was very different than applying for a job. The person who called me, the gentleman’s name was Mr. Vetter. I can’t imagine a better name for someone who does what he does for a living,” he recalled, with a grin.
Deeley said he listed VPCC Professor Amy Anderson among his references, and she took Vetter’s phone call as she was boarding a flight. He wasn’t surprised by the gesture, noting Anderson, who is head of Legal Studies at the College, is a true advocate for her students.
“She was getting on a plane to leave the country, and she was willing to take a call, take an interview question from someone to give me a leg up toward the job. That’s … that’s dedication,” he said.
Anderson said she was delighted to give the reference and was inspired by Deeley’s response.
“I’ve had a lot of students over the years take the time to express gratitude for their experiences while in the Legal Studies program, and that’s always humbling and much appreciated,” said Anderson.
“Only Jim has handwritten me a letter, though, which still echoes with its last line exhorting me to remember that my work ‘changes lives,’ and how that encouraged me to keep on with my job at the College during a pretty dark and difficult time,” she stated, adding it’s rewarding to see his continued growth as a legal professional, working to positively impact others.
He accepted the job in August and has since been the firm’s “primary production person.” Once the attorney meets with clients to create an estate plan, Deeley explained, he takes on nearly the entire workflow although reviewing is “mostly done by the attorneys.” He prepares the engagement letters and invoices, creates the estate plan documents, and produces the final estate planning book before the clients sign all their documents.
“In turn, people walk out with their estate planning in order. One of the things I like about my profession is that it’s a proactive part of the law. We do things before they’re necessary,” he said.
“We set up things to make sure that it moves smoothly through the process of distributing your life’s work to your heirs … We give people peace of mind, and that is an incalculably good experience at the end of the day,” added Deeley, pointing out he was previously a legal assistant with John W. Lee P.C. Law Offices and had a receptionist/paralegal-in-training stint at another firm before that.
The legal field wasn’t Deeley’s first choice. He majored in political science at Christopher Newport University (CNU) and minored in theater. He earned a bachelor’s degree and originally considered a career in diplomacy.
“Younger me thought I was going to go to the State Department, be a diplomat and save the world one peace treaty at a time. That future did not pan out,” said Deeley, now age 44. “So, I ended up stuck in my recession survival job from the 2008 recession for over 10 years.”
His pizza delivery job involved long hours – sometimes 80 hours a week – for little pay. He was even robbed once while working. Conditions convinced Deeley something had to change. Reflecting on an experience from CNU helped him get on track for a fresh start.
“I was taking a class in constitutional law from Professor William Thro, who was the State Solicitor General (for Virginia at the time), and I was one of only two people to get an A on his final exam,” he recalled. “He wrote on my exam, ‘If you haven’t considered law school, you should.’”
Deeley liked the idea, but instead of going straight into law school, he assessed his options. He considered affordability, the amount of time he wanted to invest, and he enrolled in VPCC’s Associate of Science in Paralegal Studies program.
“I’ve already got my bachelor’s. I’ve already done most of my early coursework … I thought to myself, ‘if I construct it just so I could get in and out in a year.’ It mostly worked out that way,” he said.
Deeley completed his VPCC studies in 2019, graduating with honors, and got his first paralegal position in 2020. Getting hired in the field so soon after graduating made him really appreciate a project Anderson had assigned.
“As a student, you’re like, ‘Why am I doing this?’ And then, as a professional, you realize it’s networking. She has you go out into the community and interview either a lawyer who hires paralegals or someone who is a paralegal,” he explained. “Not only do you get the real-world perspective of the job, but you meet people who might be looking to hire people to do the job, and you’re building your professional network. It’s a brilliant assignment.
“I sincerely hope students are continuing to do the interview project. And if they want to interview me now, I’m happy to sit on the other side of the table,” he added with enthusiasm.
Anderson, almost like a proud mom, could not be happier for Deeley.
“He’s one of those students I think of when we talk about ‘student success,’” she said. “I still recall his first day of the Intro to Law class when all of the students were introducing themselves. Jim announced that he was ‘here to end his 10-year pizza delivery career!’”
“He wanted to throw himself into law, and he did wholeheartedly. From the beginning, he showed himself to be a gifted researcher and writer,” she added, recalling when Deeley told her and Professor Dave Coffey (who was teaching Criminal Law) he would write a paper on a novel topic to impress them, and he did overwhelmingly.
Next on Deeley’s list of goals is sitting for the National Association of Legal Assistants’ Certified Paralegal exam in 2026. He currently serves on the board of advisers for VPCC’s Paralegal Program, is a member of the Virginia Peninsula Paralegal Association and has a notary public credential.
While job responsibilities fill his days, his nights belong to other worlds via the tabletop role-playing game (TTRPG) industry. He runs four games a week from his home via Zoom as a professional game master. Each night features a different game, including samurai epics, Bronze Age myth, Arthurian legend and more.
“There’s a whole world out there. Whatever flavor of fantastical experience you want, it can be found,” he said.
He’s enjoyed this realm since the late 1990s. One of his favorite shops, Jersey’s Cards & Comics in Yorktown, is where his interest in the game master role started. To him, it’s equal parts theater, improvisation and storytelling.
“To give an idea of what it’s like to be the game master, I liken it to being the showrunner of a weekly episodic TV series,” he said. “I control all the extras, set design, the special effects and everything like that.”
“However, the main characters have it in their contracts that they don’t have to follow the script. They show up and adlib the entire thing, and I have to respond to them,” he added, pointing out it’s basically four hours of live improvisational theater, and he has an unlimited budget for extras, guest stars, set design, special effects and more.
He’s also a published writer on the TTRPG scene with work appearing in six books to date. Among them is “Techno-Organic Secrets” forthe Transformers RPG, which he calls a surreal dream come true. He said most works in the role-playing universe are collaborative efforts with multiple authors working on different sections. During editing, sections are pulled together into a cohesive whole, giving the feel that it was all written by the same person.
“My 6-year-old self is beyond thrilled that my name is in a Transformer’s book,” said Deeley, adding he’s writing a part for Star Trek next. “In 1999, I was sitting (in Jersey’s) playing Magic and running Vampire the Masquerade. Now in 2025, I’m walking into the store and pulling this book off the shelf with my name in it.”
His special interests don’t end there. Deeley speaks at conventions, including NekoCon, MarsCon, RavenCon and BurgQuest, lecturing on topics ranging from beginner game mastering to deep dives into specific TTRPG systems.
“I’ve been speaking at local conventions for over a decade now. As a presenter, I am basically lecturing for an hour on a given topic. Some of the things I have spoken on recently are how to write a dystopian future setting, what makes a great villain, and Sci-Fi Futurism in TTRPGs, for example,” he said.
Deeley’s appearing at MarsCon in Virginia Beach in January, lecturing on TTRPG content creation and doing a two-hour seminar on the Art of Game Mastery.
He admits his theater background is central to his TTRPG activities, and his legal training helps him stay organized. Anderson can attest to his penchant for showmanship. She recalls he often brought his theatrical flair to VPCC and is easily one of the best-dressed students she’s taught.
“Whether attending class in full pirate attire or kilt with Super Man shirt … a three-piece suit, or even showing up to thank me for a reference … dressed as Santa Claus and bearing cookies he’d made from his mother’s secret recipe, Jim always makes an impression,” she said, adding whether through his outfits or his tall build, full beard and booming voice, he’s unforgettable.
For Deeley, who moved frequently as a military dependent, Hampton Roads is home since it’s where he’s lived the longest. He said stability is what he looks forward to most on the road ahead. He thinks he’s found it not only in making Newport News his permanent home but also in his new job.
The new position is a refreshing change of pace from the shift work of his pizza delivery days. Besides the salary, said Deeley, the biggest benefit is the law firm’s four-day work week.
“While I work nine to five, Monday through Thursday, (Friday) is my day off. It’s an extraordinary benefit,” he exclaimed. “It’s great having a boss who realizes it’s better for us to have a full three days to recharge because our work is emotionally intense. People are contemplating the end of their lives in our office. It’s heavy. It’s heavy work.”
He hopes to return to immigration law someday, having been exposed to that specialization early in his career as a paralegal in training. For now, he’s satisfied building his expertise, expanding his writing portfolio, and guiding players through worlds of adventure.
In all his accomplishments, Deeley credits VPCC, his professors, his study partners (Chelsea Skinner and Violet Verlardi), and most especially his wife, Kristi.
“She made sure I didn’t quit, even when it was tempting to quit,” he concluded.