Spring house hunting
Meg Grady (left) works at her day job in financial consulting at a desk outside her son Milos’ room. Meg works as both a financial advisor and real estate agent in East Boston. Andrew Burke Stevenson
Meg Grady starts her day before 4:30 a.m. She responds immediately to emails, reviews tenant applications, then attends interviews with India and works a full day as a remote strategic sourcing representative for a financial advisory firm. She starts her second full-time job as a real estate agent at 5 p.m., conducting showings until about 8 p.m. on weekdays and hosting open houses throughout the weekend. As a single mother, she also spends her weekends accompanying her seven-year-old son Milo to neighborhood activities such as swimming lessons and soccer games. In a turbulent market, she’s just one of many real estate agents doing double duty with two full-time jobs.
Meg Grady checks her phone for work notifications while son Milo Grady, 7, plays on his iPad as they both sit in front of a house Meg is preparing to sell. –Andrew Burke-Stevenson
When Corona hit and mortgage rates fell to historic lows, everyone wanted to get into real estate. Some newer agents were attracted to flexible schedules and independence and found success thanks to market conditions. Flash forward a few years and things have changed quite a bit. In early 2025, a report from Inman, a digital real estate news source, said 71 percent of real estate agents had not closed any deals in the previous year. Similarly, a 2024 report from the Consumer Federation of America found that over 1.5 million agents sold only 5 to 6 million homes annually, leaving most agents unable to support themselves on sales commissions alone. And in an expensive state like Massachusetts, it’s no surprise that there are many agents like Grady who pursue multiple careers.
“I think real estate just goes up and down so having a more stable job takes the pressure off,” said Grady, a real estate agent at Lantern Real Estate and founder of EastieLove. “I focus on quality over quantity. I’m so blessed that I don’t have to worry about, ‘Where’s my next paycheck coming from?'” or ‘What if I don’t get that commission?'”
Milo Grady swings around the railing of a house that his mother, Meg Grady (in the background, left) is preparing for sale as she talks to people removing things from the house. –Andrew Burke-Stevenson
Meg Grady enters a house in East Boston that she is putting up for sale. Grady works as both a financial advisor and a real estate agent. –Andrew Burke-Stevenson
Kate Ziegler Romano, an agent with Arborview Realty, saw unprecedented sales during the COVID-19 pandemic, closing 42 deals in 2021. Eventually, she sometimes stopped posting open house signs.
“It was like, should you even bother? There’s a line out the door,” she laughed, referring to managing large groups of people during the pandemic.
However, the last few years have been a little more challenging. Still, she’s grateful after hearing from other agents who have sold their primary homes because they can’t afford to pay the mortgage. To stabilize their income, she and her husband take on dual roles as property managers for the buildings they own.
“That income really helps stabilize after you’ve worked as a real estate agent for years,” she says.
Of course, working two jobs can lead to chaos. Recently, the couple invited their two sons and their ski equipment for a trip to New Hampshire, only to receive a call that a tenant’s water heater was leaking all over the basement. A few days later another heater broke.
As Milo Grady chats on his iPad while his mother works, he sits outside the house in East Boston and looks at his mother, Meg Grady. –Andrew Burke-Stevenson
Meg Grady (center) talks with Eastie resident KJ Mills while her son Milo Grady (far right) looks at yarn. While emptying a home for sale, Meg posted yarn and other items on the neighborhood’s “Buy Nothing” page, where local community members give away items instead of selling them. –Andrew Burke-Stevenson
“If you have multiple water heaters and they have a lifespan of six to 10 years, they’re always going to break somehow,” Ziegler Romano said.
Then it comes in handy to have multiple incomes.
Kevin Gehl, real estate consultant with The Collective at Compass, will pull double duty as play-by-play announcer for men’s and women’s hockey on ESPN and Hockey East on NESN. He started dabbling in real estate about seven years ago, but didn’t really get excited until COVID hit, and he didn’t broadcast a game for about nine months. His wife, Lara Shuqom, was already a successful real estate agent and they were at their best. If we look to 2026, he is still pursuing both careers. Gehl, like the others, sees this as a positive, even though the couple had to sign contracts at Thanksgiving and Christmas last year.
“As I’ve expanded my real estate, I’ve found ways to be as productive as possible with broadcasting,” he shared. “Focusing on soccer, basketball and hockey during the winter months allows me to make the most of my time before the busy real estate markets in the spring and summer.”
Kevin Gehl, real estate consultant at 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 and a property manager. Photo: Kayla Teves/Monarch Collaborative 
Tonia Scalise of William Pitt Sotheby’s Realty in Lenox. Photo: Brownine photography
Tonia Scalise of William Pitt Sotheby’s Realty in Lenox has always been a multitasker. She once even negotiated an offer in the labor and delivery room before the birth. When the market crashed a few years later and she got divorced, she had to work five jobs to make ends meet and pay for her daughter’s ballet classes. In addition to running her own real estate business, she also owned the Berkshire Wellness Center and used it as a place for mediation, life and divorce coaching. She also provided overnight elder care services and handled catering on the evenings her daughter was with her father. Almost 30 years later, Scalise has found great success as a real estate agent, but still works two jobs and runs her own real estate brokerage business on the side.
“I have a lake theme next. I have a farm-to-table theme for the farmhouse,” Scalise said 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 believes that years like 2000 and 2001 gave many people a false sense of stability because they saw it as if “real estate was just easy and things would always stay the same.” But as many real estate agents have discovered, weathering the ups and downs of the market requires unwavering commitment.
“You could just get into this business and sell anything, as long as you could get a few offers and get a few customers, then you’d be fine,” Ziegler Romano recalls. “And it’s not that simple.”
Meg Grady and son Milo walk home after giving away items from a house Meg is putting up for sale in East Boston. –Andrew Burke-Stevenson
Megan Johnson
Megan Johnson is a Boston-based writer and reporter whose work appears in People, Architectural Digest, and The Boston Globe, among others.
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