The double lives of real estate agents: Why many Massachusetts brokers have day jobs

Meg Grady, left, works at her day job in financial consulting at a desk outside her son Milo's room. Meg works as both a financial consultant and a real estate agent in East Boston. Andrew Burke-Stevenson

By Megan Johnson

April 7, 2026 | 9:58 AM

5 minutes to read

Meg Grady starts her day before 4:30 am. She immediately responds to emails, reviews tenant applications, then joins calls with India and works a full day as a remote strategic sourcing associate for a financial consulting firm. Come 5 p.m., she starts her second full-time job as a real estate agent, running showings until about 8 p.m on weekdays and doing open houses all weekend. A single mom, she also spends her weekends shuffling her 7-year-old son, Milo, to neighborhood activities like swimming lessons and soccer games. In a tumultuous market, she’s just one of many real estate agents who are pulling double duty with two full-time jobs.

Meg Grady checks her phone for business notifications as son Milo Grady, 7, plays on his iPad while both sit outside a house Meg is preparing for sale. – Andrew Burke-Stevenson

When COVID hit, and mortgage rates dropped to historic lows, everyone wanted to get into real estate. Attracted by flexible schedules and independence, some newer agents found success thanks to market conditions. Flash forward a few years, and things have changed quite a bit. In early 2025, a report by Inman, a digital real estate news source, claimed that 71 percent of real estate agents didn’t close any deals the previous year. Similarly, a 2024 report by the Consumer Federation of America revealed that over 1.5 million agents sold just 5 million to 6 million homes annually, leading to most agents being unable to sustain themselves solely on sales commissions. And in an expensive state to live like Massachusetts, it’s no surprise that you’ll find plenty of agents like Grady working multiple careers.

“I think that real estate is just so up and down that having a job that’s more stabilized takes the pressure off,” said Grady, a realtor with Lantern Real Estate and the founder of EastieLove. “I’m quality versus quantity. I’m blessed enough not to have to worry about, ‘Where’s my next paycheck coming from?’ or ‘What if I don’t get this commission?’”

Milo Grady, swings around the railing on a house his mother, Meg Grady, (background, left) is preparing for sale as she talks to people picking up things from the house. *– Andrew Burke-Stevenson*

Meg Grady walks into a house that she is emptying for sale in East Boston. Grady works as both a financial consultant and a real estate agent. – Andrew Burke-Stevenson

Kate Ziegler Romano, an agent with Arborview Realty, saw unparalleled sales during COVID, closing 42 deals in 2021. At one point, she sometimes stopped posting open house signs.

“It was like, why even bother. There’s a line out the door,” she laughed, referring to managing large groups of people during the pandemic.

However, recent years have been a bit more challenging. Still, she’s grateful after hearing of other agents selling their primary homes because they can’t afford to pay the mortgage. To stabilize her income, she and her husband pull double duty as property managers for buildings they own.

“That income coming in really helps stabilize when you have down years as a real estate agent,” she says.

Of course, having two jobs can lead to chaos. Recently, the couple loaded up their two sons and their ski gear for a drive to New Hampshire, only to get a call that a tenant’s water heater was leaking all over the basement floor. Several days later, another heater blew.

While staying entertained on his iPad as his mom works, Milo Grady sits outside the East Boston house and looks toward his mother, Meg Grady. *– Andrew Burke-Stevenson*

Meg Grady (center) talks to Eastie resident KJ Mills as her son Milo Grady, (far right), looks at yarn. While emptying a house for sale, Meg posted the yarn and other objects on the neighborhood “Buy Nothing” page, where community members give away things locally instead of selling them. *– Andrew Burke-Stevenson*

“When you own several water heaters, and they have a lifespan of six to 10 years, they’re kind of always dying,” said Ziegler Romano.

That’s when having multiple incomes comes in handy.

Kevin Gehl, a real estate adviser with The Collective at Compass, pulls double duty as a play-by-play announcer for men’s and women’s hockey on ESPN and Hockey East on NESN. He started dipping his toes into real estate about seven years ago, but really got into it when COVID hit, and he didn’t broadcast a game for about nine months. His wife, Lara Shuqom, was already a successful realtor, and they were at their busiest. Flash forward to 2026, and he’s still doing both careers. Like the others, Gehl sees that as a positive, even though the couple had to close deals on Thanksgiving and Christmas last year.

“As I’ve ramped up real estate, I’ve found ways to be as productive as possible with broadcasting,” he shared. “Focusing on football, basketball, and hockey during the winter months, I can maximize my time before the busy spring and summer real estate markets.”

Kevin Gehl, Real Estate Advisor with The Collective at Compass, is also an announcer for hockey on ESPN and Hockey East on NESN. Photo: Lara Kimmerer Kate Ziegler Romano is a real estate agent with Arborview Realty as well as a property manager. Photo: Kayla Teves/Monarch Collaborative Tonia Scalise of William Pitt Sotheby’s Realty in Lenox. Photo: Browtine Photography

Tonia Scalise of William Pitt Sotheby’s Realty in Lenox has always been a multitasker. She even once negotiated an offer in the labor and delivery room before giving birth. When the market crashed several years later and she was going through a divorce, she found herself working five jobs to make ends meet and pay for her daughter’s ballet lessons. In addition to running her own real estate business, she owned the Berkshire Wellness Center and used it as a location for mediation, life, and divorce coaching. She also provided overnight elder care services and did catering on nights when her daughter was with her dad. Almost 30 years later, Scalise has found tremendous success as an agent, but still works two jobs, running her own real estate staging company on the side.

“I have a lake theme to go. I have a farm-to-table theme for the farmhouse,” said Scalise of her staging designs. She said she works up to 60 hours a week. “I loved it so much, and I still do, just like the first day I started.”

Looking back, Ziegler Romao feels that years like 2000 and 2001 gave a lot of people a false sense of stability, because they viewed it as “real estate was just easy, and things would always be the same.” But as many realtors have discovered, riding the ups and downs of the market requires unwavering dedication.

“You could just get into this business and sell everything, as long as you could get some listings and get some clients, then you’d be fine,” Ziegler Romano recalled. “And it’s not that simple.”