By Gabrielle Chisolm, Communications Intern, a junior majoring in English at the University of Maryland

Michael O’Brien grew up in Western Massachusetts and has never strayed far from home. “Pittsfield (MA) has always been home base for me,” he says. “It has the pace of a small town while offering city-like advantages.”

While studying communications as an undergraduate at the Massachusetts College of Liberal Arts in nearby North Adams (MA), Michael experienced a double take on his career aspirations. He realized that personal goals–like starting a family–required a profession that offered flexibility and stability. “I pursued communications because of my passion for journalism, but I wanted a career that better aligned with the life I was building,” he shares.

Michael did an about face and focused his professional goals on finance. The transition was far from easy. “In most careers, strong communication and emotional intelligence are crucial, but in terms of technical knowledge, it was not a smooth transition. I had to develop a whole new skill set,” he admits.

Networking over golf strokes at his local country club opened the door for a job offer. “A club member offered me a position at his insurance brokerage,” Michael recalls. “I latched on to the opportunity, understanding there was significant preparation required. I had to take a lot of finance courses and obtain proper licensing.”

After two years as an insurance agent, Michael sought a more client-centered role, which led to a new job as a Financial Advisor at Berkshire Money Management (BMM). “Being a relationship lead for clients has been incredibly meaningful,” he says. “I’ve helped families navigate major life challenges. I really enjoy being able to help people build the lives that they desire and reach their financial goals.”

The recommendation of BMM colleague Lauren Beckett, an active DLE member, steered Michael to his first DLE event last December. He quickly got immersed–and has served as a co-planner and facilitator for the popular in-person DLE Meetup program. 

Michael credits the DLE with helping him continue to step outside of his comfort zone. “I’m at a point where I’m intentionally placing myself in unfamiliar situations–and it’s been really rewarding,” he reflects. “Linda (Dulye) is super encouraging and isn’t afraid to give you a nudge, which led me to take on the responsibilities of organizing and leading (with DLE members Mystie Ford and Cam Hadley) the April Meetup on staying accountable.”

Michael offers a word of advice for others who are second-guessing their career paths. “It can be hard to suddenly realize that you no longer want to pursue it–but remember that there’s real value in self-discovery.”

Incidentally, Michael is pursuing his personal goal of starting a family, with an October  2025 wedding to fiancée Arianna Evans.