Starting over: 3 agents who left it all behind and never looked back

Real estate has a reputation for attracting people from all walks of life but making the jump is rarely as simple as it sounds. Three agents from across Canada share how they left behind very different careers, navigated the uncertainty of starting over and found their footing in an industry that demands everything you’ve got.

From the classroom to the closing table

Matt Biggley, a salesperson with Remax Capital Diamond in Windsor-Essex, Ont., spent 17 years as a teacher. As a guidance counsellor — a role he describes as the envy of most in the profession — he was on a clear path to becoming a principal. On the side, he and a few teacher friends bought rental properties, and his wife was building momentum in renovations.

In 2020, Biggley made a New Year’s resolution to get his real estate licence and planned to take a six-month leave from teaching in 2021 to test the waters. He got his licence in August 2020, then returned to the classroom a few weeks later.

“Being at school all day and then being out doing real estate at night was incredibly taxing — physically, mentally, on my family,” he said. “To do any kind of real estate at scale, you have to only do real estate.”

He took a semester off teaching in June 2021. That same month, his brother died by suicide, leaving behind a note saying he had wanted to be a real estate agent. Biggley took it as a sign he was heading in the right direction. Once he committed to real estate full time, he found the work had a lot of integrity to it and gave him a sense of purpose similar to teaching — along with far greater financial rewards. The decision was made.

What drew Biggley to real estate was its meritocracy. Unlike teaching, the harder you work, the more you’re rewarded. A self-described lifelong learner, he embraced the no-limits nature of the industry.

“The best Realtors are learners and growers,” he said. “The money will definitely come because there is such a financial opportunity if you do a great job.”

For anyone considering the switch, Biggley recommends getting adjacent to the industry first — picking up rental or investment properties before going all in. And he cautions that trading the stability of a salaried career for the ups and downs of real estate is a real adjustment. Expect the unexpected.

From the stage to the sold sign

Sean Miller’s path to real estate looked nothing like Biggley’s. Before joining Property.ca in Toronto, he was a well-known DJ and music producer, playing festivals around the world and high-end nightclubs in the city. The lifestyle, however, wasn’t compatible with the family life he wanted — and the money wasn’t reliable enough to sustain it.

Miller first got wind of real estate through contacts in his network, including a music producer who was getting into the business and offered to bring Miller on board. That arrangement fell through, but a chance encounter with the manager of a restaurant led him to Property.ca, a startup at the time. He reached out to the owner and was hired on the spot. That was 12 years ago. Miller is now one of the company’s top agents, having watched the team grow from 12 to more than 450 agents.

Like Biggley, Miller juggled both careers for four to five years before fully committing to real estate. The death of his best friend prompted him to take stock of his priorities — and real estate won out.

“The music wasn’t really sustaining our lifestyle, so I had to think of something else to do,” he said. “It was more to bring in some extra income on the side. I didn’t necessarily think I was going to love it as much as I did until I started getting successful with it.”

His previous career wasn’t wasted, either. The music industry taught him perseverance and how to market himself creatively — skills that translated directly into real estate. Miller started with leases, then gradually worked his way up to buyers. Success, he says, came down to work ethic.

His advice to those looking to make the switch: don’t expect to get rich fast, go all in rather than treating it as a side hustle and find a team you can learn from.

“You have to throw yourself out there and fail many times before you become successful,” he said. “You’ve got to have a lot of confidence.”

From hard hats to house keys

Ryan Elliott was working a steady 8 a.m. to 4 p.m. job as a health and safety professional in St. John’s, N.L., when boredom started to creep in. He picked up a flip project, called his agent to sell it — and when that agent turned out to be unavailable, he thought: why not sell it himself?

That moment set things in motion. Elliott started helping friends with their own purchases, then stepped away from real estate for a period — and quickly realized he missed it. He went part time, and two years later, made it his full-time career with Royal LePage.

What sealed it was how dynamic the work felt compared to his previous life. Every day was different. There was no ceiling on how much effort he could put in, and the rewards reflected that.

“I’m very much a go, go, go person,” said Elliott. “I had nothing else to do (in the evening), nothing else to look forward to.”

His start was slow — his first sale came three to four months in — and he relied heavily on friends and family to get his business off the ground. That experience shaped how he approaches those relationships now.

“A friend or family member still needs to be treated like a client,” he said. “You still have the job to do and you need to be professional.”

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