Lessons Learned Across Generations in Real Estate

2026 will be a year of perspective and momentum, and while the past few years have continued to test the real estate industry in ways few could have predicted, I look back with real pride and gratitude. Busby Group remains a team of strong, savvy, and deeply knowledgeable professionals who genuinely support one another, more importantly, work tirelessly to help our clients achieve their dreams of homeownership at every price point. Sometimes it truly does take a village.

As a Baby Boomer, I believe that looking ahead still requires vigilance and adaptability. Interest rates have normalized compared to the historic lows of the early 2020s, inventory continues to ebb and flow by neighborhood, and economic and political shifts, both locally and nationally, always warrant close attention. One thing that has not changed: real estate remains a long-term, relationship-driven business.

Much of our team is made up of Millennials, and that continues to be a tremendous advantage. Millennials are now firmly established as the largest segment of homebuyers, and they are increasingly joined by Gen Z entering the market for the first time. At the same time, the largest intergenerational transfer of wealth in history is well underway, with trillions of dollars expected to pass from Boomers to their children and grandchildren over the coming decades. Real estate remains one of the primary places families are choosing to build, protect, and grow that wealth. Whether you’re a Boomer, Gen X, Millennial, or Gen Z, there are constants in real estate that continue to hold true.

I still remember reading that Andrew Carnegie once said that the majority of millionaires built their wealth through real estate. I bought my first condo at age 25 in New York City, back when “Yuppie” was a common label. Like many young buyers, I sold it to move up to the next stage of life, and eventually to Chicago, a city I had never even visited before relocating. Mortgage rates at the time were in the double digits, and neighborhoods like Lincoln Park looked very different than they do today.

With no internet, no online listings, and no digital tools, we relied entirely on a seasoned Realtor recommended by my mother-in-law. It turned out to be some of the best advice I’ve ever received. She didn’t just help us find a home, she helped us find a neighborhood, a lifestyle, and a sense of belonging. That relationship extended far beyond a single transaction, and it shaped how I understand real estate to this day.

Years later, I know what I didn’t know then: what makes a good investment in Chicago, what tends to hold value, and what doesn’t. I also learned something just as important - the way a client feels after the transaction matters enormously. That philosophy is exactly why referral business continues to be the backbone of Busby Group.

I learn as much from the younger members of our team as they learn from me, and not just about real estate. My children are now well into adulthood, so I understand the mindset of today’s Millennial and Gen Z buyers. They come prepared, ask thoughtful questions, and are optimistic about building their future. In return, they keep me current on everything from new restaurants to wellness trends and technology. From my team, I’m constantly learning new strategies, new tools, and new ways to simplify and elevate the client experience.

The market will always evolve, but one thing never changes: real estate is about the experience. That experience begins with the very first conversation and continues well beyond the closing table. Making every step thoughtful, efficient, and genuinely enjoyable is what creates lifelong clients and lasting relationships.

We firmly believe that the experience Busby Group provides can never be replaced by an algorithm or a discounted service alone. Representation matters. I once worked for a destination club owned by a real estate development company, where every decision revolved around the client experience. Focusing on that experience didn’t just benefit the client - it made the work itself deeply rewarding. That lesson has stayed with me.

Having team members of different ages, backgrounds, and perspectives allows Busby Group to deliver well-rounded advice, nuanced market insight, and exceptional service, while having a lot of fun along the way. That’s how we continue to rank among the top 1% of Chicago real estate brokers. We love matching buyers with homes in every Chicago neighborhood. In many ways, we truly are matchmakers.

One of the most satisfying moments in this business is still saying, “We have a deal.” It marks the beginning of a new chapter. There may be nerves, excitement, and even a few bittersweet emotions along the way, but navigating those moments with knowledge, integrity, and discretion is exactly why having the right broker matters.

Here’s to moving forward in 2026 - using everything we’ve learned from the past to guide us confidently into the future.

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