“I grew up around real estate 24/7,” says Jessica Garry, broker at Garry Real Estate, the firm named after her REALTORⓇ parents. “I remember having to sit in the car during showings, going to attorneys' offices for closings, and playing with my parents’ branded paper and pens and balloons, and seeing their faces on the shopping carts at Jewel Osco.”

Even while growing up in close proximity to the family business, after high school, Jessica decided to forge her own path. Over the next six years, Jessica not only earned three associate’s degrees and a bachelor’s degree in business management with honors from Benedictine University, but she also experimented with running her own businesses, testing the waters of future career options, all while holding multiple jobs that included bartending, doing retail at Woodfield Mall, and working as a Starbucks barista.

But that kind of hustle was nothing new for Jessica. “I’ve been working since I was fifteen years old; I had my parents sign off on a work permit for me,” she explains. “In college, I was motivated by my entrepreneurship course professor when he offered one hundred points extra credit to any student who could sell more online than he did. I started selling used clothes, accessories, and anything I could get my hands on. I ended up achieving ‘Posh Ambassador’ status on Poshmark with over 100k followers.” Jessica continued her entrepreneurial streak as a freelance makeup artist and an Etsy store proprietor. 

It was when the COVID pandemic closed down many hospitality establishments and left her out of work that she finally gave real estate serious consideration. 

“I graduated college just to go back to school to get my real estate license. I guess you could say I'm a real scholar,” Jessica jokes. “I had nothing to lose. I was freshly unemployed for the first time since age fifteen, and it seemed like that misfortune was the perfect opportunity as it led me to where I was meant to be.”

“I loved the idea of the freedom the job [of a REALTOR®] provides,” she adds. “My parents never missed holidays or birthday parties, and they weren’t micromanaged by bosses, which I’d experienced and hated. I knew real estate had to come with some drawbacks and risks, but I knew I would love the work-life balance.”

From the beginning of her REALTOR® career, Jessica had to retrain her brain so as to not limit herself or sell short her own abilities, no matter her young age and perceived inexperience.

“I thought that since I was taught under [the mentorship of] my father—who has been in real estate thirty-nine years—that I needed to have all the experience and knowledge he had,” explains Jessica. “I thought people would look at someone like him, then at someone like me, and choose him. But that was just a limiting belief I had as a young woman starting out in an incredibly hard industry. I overcame that by proving myself wrong and working hard to gain my own clients and sales.”

Now approaching her fifth year as a REALTORⓇ, Jessica has gained more confidence in herself as she continues to develop her own approach with clients and build her own personal brand: Change Your Address with Jess. She’s also completely rebranded the family firm by leveraging her expertise in marketing, social media, and technology to help modernize the agency. Ever-resourceful, Jessica has taught herself photography, web design, and other marketing tactics to grow the business, both for her own benefit and Garry Real Estate.

“The most rewarding parts of my business have been helping my clients achieve their goals and proving to myself that I can do this,” says Jessica. “I know I have come a long way in this industry, and I am proud of myself for that. The feeling of seeing how happy my clients are after I’ve helped them—whether they are first-time home buyers or a seller that is moving out of state—never gets old.”

Though Jessica may not have initially embraced real estate as a serious career option, she now sees it as the perfect fit for the life she dreams of. She’s also happy her career path has come full circle with a beautiful blend of entrepreneurship and marketing.

“Real estate fits into my dreams and goals. I plan on real estate being my lifelong career, just like it has been for both my parents,” she says. “It is my dream to run my own successful business while being an excellent role model to those around me as well as new agents starting out in the industry. I also want to be able to travel and be there for holidays with my family. Real estate gives me the opportunity to do all of that.”