A Real Estate Career Shaped by Change, Community, and Mentorship

By Jill Miles

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Real estate is rarely a straight line. Mine certainly hasn’t been.

I entered the business in 2002 in Naples, Florida, as part of a family partnership with my husband and in-laws. Like many who entered the industry in the early 2000s, we experienced tremendous success early on. The market was strong, demand was high, and growth seemed almost inevitable. At the time, it felt like momentum would always carry us forward.

Then 2008 happened; the mortgage crisis started in 2006 and culminated in 2008.

 

The market crash changed everything. It tested not only the business, but our resilience and perspective. My husband stayed the course, keeping the real estate company operating through some of the most uncertain years the industry has ever seen. I stepped into a different role, taking a position as Membership Director for a private country club. It wasn’t a step away from real estate so much as a necessary pivot — one that taught me valuable lessons about leadership, communication, and relationship-building in a different area of sales.

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A few years later, my role at the club evolved into a hybrid position as Communications Director, allowing me to bring marketing and messaging skills together with my continued involvement in our real estate business. I was once again wearing multiple hats, something that would become a recurring theme in my career.

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In 2014, life shifted again when our son headed to Indiana University. We relocated to Central Indiana, and my husband began a new chapter as Director of Mortgage Operations for a community bank — a role that would eventually lead him to become Chief Retail Banking Officer. I continued traveling back and forth to Florida for several years, balancing my communications role, family responsibilities, and our real estate operations.

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During that time, I became deeply involved in the Peru, Indiana community. I was a founding Vice President of ReDiscover Downtown Peru, a Main Street organization focused on revitalizing the heart of our town. It was through that work that I noticed a run-down, vacant building downtown — one that sat unused, quietly waiting for its next chapter.

After watching it remain vacant for more than a year, I decided to take a leap. In the summer of 2016, I purchased the building and undertook a full renovation. The first floor was transformed into office space, the second floor into residential living. That building became more than a renovation project — it became the foundation for something entirely new.

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That same year, I opened our Indiana real estate brokerage — this time on my own.

Starting an independent brokerage from scratch was both exhilarating and humbling. In our earlier family business, I had been firmly behind the scenes, managing marketing, contracts, and operations while my husband was the face of the company. Now, I was responsible for everything. Leadership, compliance, recruitment, coaching, vision — there was no one else to lean on.

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The early years, especially 2016 and 2017, were a shock to the system. I had to elevate my skills, expand my knowledge, and become comfortable making decisions without a safety net.

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Not long after opening, the F.C. Tucker Company learned about our brokerage, and we entered into a franchise partnership that lasted six years. Those years were marked by strong growth. We attracted several highly productive agents, and our brokerage quickly rose to the top — ranking number one in our county for many years and consistently placing within the top five among our local Board of Realtors.

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While I continued to list and sell properties myself, my primary focus was — and still is — mentoring, coaching, and supporting the agents in our office. Watching agents gain confidence, grow their businesses, and find their footing has always been the most rewarding part of this career for me.

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When our franchise agreement ended, I made the decision to return to our original independent brokerage name from our Naples days. The rebrand was extensive: new colors, new fonts, new signage, a new website — a complete refresh. It was a significant undertaking, but one that allowed us to realign our brand with who we truly are.

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The past four years under our “old-new” banner have been a period of reflection and refinement. Some of our top-producing agents have gone on to start their own brokerages — a reality of leadership that I’ve come to embrace rather than resist. I’m proud to say that those relationships remain strong, and each of them has expressed appreciation for the support and mentorship they received along the way.

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Looking back, I see how much I had to learn — and how much I continue to learn. Running a business on your own is not for the faint of heart. Real estate is risky. There are no guarantees, and there are many days when the work happens long before the paycheck does — if it comes at all.

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Yet, despite the challenges, I find my passion consistently returns to one place: helping others. Listening to their concerns. Talking through problems. Offering perspective. Sometimes simply being a steady presence. Over the years, I’ve joked that I’ve become a second mom to many of my agents — and there’s more truth in that than humor.

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Now, as I step into a new season of life as a grandmother, my focus is shifting once again. I remain active on several local boards and deeply value community service. I don’t know exactly what the next few years will look like — but I do know that change is coming, and I welcome it.

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If real estate has taught me anything, it’s that adaptability is essential, relationships matter, and leadership is less about titles and more about showing up when it counts.

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This career has stretched me, humbled me, and challenged me — and it has given me the opportunity to build not just businesses, but people and communities. And that, more than any ranking or recognition, is what I’m most proud of.