Annie Challenger’s career in real estate is marked by a lifelong passion for homes, personal growth, helping others, and a firm belief that she can accomplish anything. Prior to entering real estate in 2015, she had already had a successful career in sales; raised a large, blended family of seven; and built a dog training company (Your Dog’s Guru, Inc.) into a successful company with her second husband. 

All these endeavors, including real estate, point to Annie’s connection to the North Shore and her upbringing. Born and raised in Winnetka, Annie says she was most influenced by her parents’ values—her mother's kindness, compassion, and honesty; and her father's entrepreneurial spirit—that challenged Annie to be the best version of herself.

It was her childhood fascination with the homes in the North Shore and her inherent passion for architecture, decor, and the unique character of each house that led her to her calling in real estate. Her travels outside of Chicago and her corporate career in sales bolstered her confidence and love of people.

While obtaining her degree in psychology at the University of Arizona, Annie was fortunate to participate in their Semesters at Sea program twice. Traveling the world while studying world cultures was one of the most influential experiences of her life. “Learning about other cultures and realizing how small our world really is was monumental to me,” Annie emphasizes. “To this day, I am still friends with people from all over the world.”

Annie embarked on her sales career as a young woman in the late 1980s, working for a consulting company in Chicago. Becoming the number one sales agent within a male-dominated industry was one of her greatest professional achievements and set the stage for her future successes. “My sales career helped me to know I could be a success in any forum as long as I gave my all,” Annie expresses.  

In the end, it was Annie’s love for meeting and helping people, developing strong positive relationships, and architecture and homes combined with her knowledge and love of the North Shore that led her to become a REALTOR® in 2015. Her background has allowed her to take the stress away from homeowners, making the buying and selling process more enjoyable and fulfilling for everyone involved.

Today, Annie's passion lies in helping her clients navigate the complexities of real estate transactions, ensuring they find success, whether in selling or buying a home. "Getting my clients over the finish line, knowing that I have been able to close the best deal possible, and hearing from my clients that they are happy and could not have done it without me is what I find most rewarding,” she says. 

Looking to the future, Annie sees real estate as an ever-evolving path of growth and learning. Every transaction brings new challenges and opportunities for development, keeping her engaged and motivated to enhance her skills. For Annie, success is measured by the satisfaction and happiness of her clients, making their dreams of selling or purchasing their perfect home a reality.

“I want to learn, grow, and improve until I am no longer,” she says. 

Outside of her professional life, Annie is deeply family-oriented. She and her husband, Michael Jayko, enjoy cooking and baking, traveling, and going to concerts and theatre productions. Julia Child is one of Annie’s personal heroes, and Paul McCartney at Wrigley Field was one of the most memorable concerts she’s ever been to.

Relaxation for Annie comes with spending quality time with her family, friends, and four dogs. She also has a deep fascination with raptors, especially owls, and would love to become a falconer someday. 

Annie also has a deep passion for giving back, as is evident in her support for various charities and community initiatives, including Laugh Your Face Off; Camp Out for Kids; the ALS Association; New Trier—Therapy Dogs, a personal volunteer effort she and Michael did together; the Winnetka Community House; and the Chicago Botanic Garden. “We are better when we work together and lift each other up,” Annie asserts.

For aspiring real estate professionals, Annie's advice is clear: always prioritize the client's needs, conduct thorough research, and strive for excellence in every transaction, respecting and honoring the trust being instilled in you. 

As Annie continues to chart her course in the real estate world, her legacy serves as an inspiration to all who dare to dream big, love deeply, and live fully. Her journey is far from over, but its impact is already immeasurable, promising even greater achievements on the horizon.