Real estate attracts people from many different backgrounds, but transitioning into the industry is rarely simple. Three Canadian agents share how they left established careers, navigated uncertainty, and built successful practices in a field that demands commitment, persistence, and adaptability.
From the classroom to the closing table
Matt Biggley, a salesperson with RE/MAX Capital Diamond in Windsor-Essex, Ontario, taught for 17 years. As a guidance counsellor, he was on a steady path toward school leadership. Outside work, he and friends invested in rental properties while his wife focused on renovations—sparking his interest in real estate.
In 2020 he resolved to get his real estate licence. He earned it in August and briefly continued teaching, but balancing full-time school duties with evening real estate work proved exhausting for him and his family. In June 2021 he took a semester off and ultimately committed to real estate full time.
The transition was personal as well as professional. After his brother passed away, leaving a note expressing a wish to work in real estate, Biggley felt affirmed in his decision. He found that the industry offered a sense of purpose similar to teaching but with greater financial upside.
What appealed to him most was the meritocratic nature of the business: effort directly influences results. A lifelong learner, Biggley embraced the idea that growth is continuous and payoffs follow consistent work and skill development.
His advice for prospective switchers is practical: get adjacent experience first—buy rental or investment properties to learn the ropes—and be prepared for the income variability that replaces a salaried position. Expect ups and downs and plan accordingly.
From the stage to the sold sign
Sean Miller’s route into real estate was very different. A former DJ and music producer active on festival stages and in high-end clubs, Miller found that the lifestyle clashed with his desire for family stability and reliable income.
Introduced to real estate through industry contacts, he initially explored an opportunity with a music producer turned agent that didn’t pan out. A chance meeting with a restaurant manager connected him to Property.ca, then a small startup. He reached out and was hired—12 years later he’s one of the company’s top agents and has seen the team grow from a dozen to more than 450 agents.
Miller balanced music and real estate for several years before choosing the latter after a close friend’s death made him reevaluate priorities. The skills he developed in music—self-promotion, creative marketing, resilience—translated well to property sales. He began with leasing and gradually moved into buyer representation, crediting persistence and strong work ethic for his success.
His guidance for others: don’t expect overnight riches; commit fully rather than treating real estate as a casual side project; and join a team where you can learn from experienced colleagues. Early failures are part of the learning curve and confidence grows with practice.
From hard hats to house keys
Ryan Elliott moved from a steady health-and-safety role in St. John’s, Newfoundland and Labrador into real estate after tackling a renovation flip. When his agent wasn’t available to sell it, he decided to list the property himself. Helping friends with purchases followed, and although he briefly stepped away, he soon returned part time and then went full time with Royal LePage.
Elliott was drawn to the variety and pace of real estate. Each day brought different challenges and opportunities, and he appreciated that effort directly influenced results. His early months were slow—his first sale arrived three to four months after he began—and he relied heavily on friends and family to build momentum.
That early reliance shaped his client approach: even when working with friends or family, professionalism matters. Treat every contact as a client, fulfill your responsibilities, and maintain clear boundaries to protect relationships and your reputation.
Across these stories, common themes emerge: a willingness to learn, the discipline to treat the transition seriously, and the humility to start small while building skills and networks. Real estate rewards persistence, creative marketing, and relationship-building, but it also requires accepting income variability and embracing continuous professional development. For those ready to commit, the industry can offer purpose, autonomy, and meaningful financial opportunity.