“Hard work pays off, and when passion meets purpose, it’s a winning combination,” says Diana Grinnell, an accomplished Chicago REALTOR® whose journey into real estate is as inspiring as her commitment to her clients.

Diana spent her formative years in the Eastern Shore of Maryland, where her parents, both medical professionals, instilled in her a strong work ethic. 

“My dad was a cardiologist, and my mom was a nurse,” Diana says. “They both worked their way through demanding education programs with grit and determination.” Their example motivated Diana to carve out her own path while maintaining that same high level of discipline and drive.

Diana pursued a bachelor’s degree in business administration with a focus in marketing and communications at Emory University in Georgia. A fortuitous internship at FOX News during college set the stage for a career in advertising sales. After graduating in 2008, she landed a full-time position with FOX News and soon relocated to Chicago—the city she now proudly calls home. 

“The first six months were tough,” Diana reflects. “I didn’t know anyone, and I was definitely out of my comfort zone. It forced me to put myself out there and build a network. The experience certainly helped me later when I launched my real estate career.”

Her advertising career spanned nearly a decade, during which she honed her skills in negotiation and client relations. However, the corporate world left her longing for a more personal and meaningful connection to her work. In 2017, after reflecting on her rewarding experience with purchasing a home in 2015 and on how well her skill set would translate into the role of a REALTOR®, Diana decided to pivot into real estate. 

“I wanted to help people with one of the biggest financial, and often emotional, decisions of their lives,” she explains. “It’s not just about finding a house; it’s about helping people create a home.”

But Diana had no established network or sphere of influence in Chicago to lean on within real estate, so she leaned on her grit-and-determination know-how and built her business from scratch. 

“When I started, I decided to be ‘the Yes Girl,’” she says. “I said yes to everything: I went to every showing, shadowed every listing appointment, attended every photoshoot, and hosted every open house that I could.”

Her hard work paid off as she absorbed invaluable lessons from her mentors, Bari Levine Bruszer and Elena Theodoros Tamillo, and other seasoned professionals, and developed her own unique approach to real estate. One part of her approach? Diana often stages properties herself, using her inventory of furniture to ensure homes are shown in their best light.

“A client once compared me to Martha Stewart. That really resonated with me,” she shares. “I love helping people envision the possibilities, physically and financially, of various cosmetic updates they could easily make to love a potential home.”

This attention to detail, combined with her ability to educate and support clients, has earned Diana a loyal following. She’s passionate about empowering her clients to make informed decisions, whether they’re buying their first home, upgrading for their growing family, or selling to start a new chapter. 

“Real estate isn’t just about finding a dream home,” she says. “It’s about helping people navigate life transitions with confidence and ease.”

Diana’s personal life is a testament to her ability to balance work and family. She and her husband, Matt, have two children: Gavin (6) and Harper (3). As a family, they enjoy exploring Chicago’s vibrant neighborhoods, playing pickleball, and traveling whenever possible. 

“Being a mom gives me an informed perspective whenever I’m helping families find homes,” Diana notes. “I understand what to look for—everything from the proximity to schools and parks, to the number of stairs, to stroller and toy storage possibilities.”

Diana also makes time to give back to the community through Digs with Dignity, a charity that aligns with her passion for transforming houses into homes. Her annual tradition of baking and delivering over 100 pies to clients during Thanksgiving is another way she nurtures connections and expresses her gratitude.

As her life and career evolve, Diana looks forward to understanding the milestones in her clients’ lives all the more, so as to better help them navigate the new phases and real estate needs in their lives.

“Real estate has allowed me to create the life I only dreamed of,” she says. Her advice to aspiring REALTORS®? “Say yes to every opportunity, and surround yourself with smart, supportive people. Be a sponge, and always keep learning.”

For Diana, success is measured by the relationships she builds and the lives she impacts. 

“My clients become my friends, and I want them to feel like they have a ruthless, fearless family member in their corner,” she says. “At the end of the day, I want people to see the hard work [I do] behind-the-scenes and know that they’re in good hands.”