Ashley Mason Gets Comfortable with the Uncomfortable

It was her favorite game growing up. Ashley Mason ’19 and her three sisters would pretend to each own a shop where they would “buy” things from one another with toy money. “I was probably 5 or 6 years old, and I became obsessed with the game, while my sisters eventually became sick of playing it. I loved the simulation of running a business,” Mason recalls. Given her love of that early game—along with hosting regular lemonade stands and logging babysitting hours—it’s no surprise that Mason’s entrepreneurial spirit continued to flourish into her teen years and beyond. 

Now the owner of Dash of Social, a successful social media and marketing consulting firm, Mason was always determined to chart her own path, and when life taught her a heartbreaking lesson, she realized she didn’t want to wait to get started. 

Blogging and Business 101

In high school, Mason created a fashion and lifestyle blog—a natural fit for someone who enjoyed reading and writing. “I was spending 10 to 15 hours per week on that blog, brainstorming content and publishing it,” she recalls. “So I wanted to make sure that more than just my family was reading it, and I wanted to find a way to earn money from it.” 

To achieve these goals, Mason turned to social media to market her blog, teaching herself how to leverage the tool from a business standpoint at the age of 16. As she honed her skills, she started freelancing with other companies, helping them harness social media for their own business purposes. 

While Mason knew that owning a business would be her career path, there was a gnawing voice in the back of her mind that told her she was doing things out of order and that she was too young to be a business owner. “I felt like society had this predetermined notion of what we’re expected to do with our careers, so I kept telling myself that I had to wait,” she says. 

Meanwhile, Mason was also applying to college. Having heard “great things” about Stonehill’s business program and liking the feel of campus, she applied, was accepted, and received a scholarship. Entering as a marketing major, Mason was eager to learn the theory behind the work she had been doing. “Business 101 is the course that stuck out to me most that fall semester as it was my first educational look into business,” she recalls. “That’s also when I had my first class with Professor [Robert] Carver, who became a mentor to me.”  

A Diagnosis “Out of Nowhere” Leads to a Startup

During winter break of her first year, Mason’s mom was diagnosed with terminal brain cancer. “This sudden diagnosis came out of nowhere for someone who was so healthy. It really made me realize that life is short, and we don’t have as much time as we think to follow our dreams and pursue what we are passionate about.” 

While Mason shifted into a caretaker role, she continued to attend classes, and at the beginning of her sophomore year, she decided to start Dash of Social. “For the next three years, I hustled, to put it lightly. I was a full-time student, caring for my mom, and building a business. My weekdays started at 4 a.m. and went until midnight.” 

Her professional goal—which Mason then achieved—was to be able to pursue Dash of Social full time after she graduated. “One of the things I really admired about Stonehill was that my professors and advisors supported me in my business,” she says. “It was gratifying to know that I had people behind me who believed in what I was doing as much as I believed in it.”

Today, Dash of Social, based out of Mason’s home office in Middleboro, has been in business for more than six years, has six employees and has worked with 250 clients. Mason has been featured in Business Insider, received a “40 Under 40” award by Cape and Plymouth Business, delivered a TED talk, and is frequently invited to speak at events and on podcasts about entrepreneurship and her business strategy. Mason is also a dedicated volunteer, serving as a board member of South Shore Young Professionals, the Middleborough Public Library, and the Brockton Visiting Nurse Association, about which she is particularly passionate because of the VNA's hospice work. 

Comfortable with the Uncomfortable

On Mason’s desk, there is a sign that reads, “Get comfortable with the uncomfortable.” It serves as a mantra of sorts. In business and in life, she tries to step out of her comfort zone—even if it makes her uncomfortable—reminding herself of that early lesson “to do the things we care about now.”

Mason's mom passed away in 2018, during the summer before her senior year at Stonehill. She often thinks of how her mom lived her life and the things she used to say. “She was known for being incredibly optimistic,” recalls Mason. “That was one of the things that people always noted about her. She always had a giant smile on her face.” 

Her mom was also determined not to be a statistic. “The prognosis for her type of cancer was not long, but she lived for another two and half years after her diagnosis," Mason recalls. "She would always say, ‘I’m not a statistic.'"

It’s something that Mason keeps in mind in her own life, as a business owner who started Dash of Social when she felt the time was right. She notes, “I’m not conforming to what’s always been done.”