On a summer day in July, a group of high school girls from Chicago’s South and West sides gathers in a conference room at Croke Fairchild Durate & Beres. For many, it’s their first trip to River North — and their first time stepping inside one of the city’s prestigious corporate offices.
They’ve come for the Girls in the Game Leader-to-Leader Interview Program, which pairs teen girls with professionals across Chicago to learn about career paths, build confidence, and practice leadership in a professional setting.
On this afternoon, they sit around a conference table with Croke Fairchild Durate & Beres co-founder and attorney Jessica Fairchild, along with five other women from the firm, including Accounting and Finance Specialist Jessica Sutton and Marketing Director Kalen Daniels. The teens take turns introducing themselves and asking prepared questions about each woman’s career path. At first, some fidget with papers or avoid eye contact. But as the conversation flows, voices grow steadier, questions more confident.
Afterward, Fairchild and her team lead the girls upstairs to the 34th floor, where the view of Lake Michigan and the skyline draws gasps and phone cameras. Many say they’ve never seen their city from this high up. Over a taco lunch back in the conference room, the conversations turn more candid, touching on challenges, ambitions, and life beyond high school.
Building Confidence and Leadership
The Leader-to-Leader Interview gives young women a rare chance to see career paths they might never have imagined. For many, it’s a first opportunity to meet professionals and hear firsthand about jobs they hadn’t considered. Without that kind of exposure, it can be difficult to picture futures beyond the possibilities they’ve seen in their own communities.
“So much [of this leadership program] is if you see it, you can be it,” says Dawn Kobel, Director of Development and Communications of Girls in the Game. “These girls may not know anything about a career in law outside of being a lawyer. It’s interesting for them to come to these events and learn that there are finance people and marketing people — that you can still work in the legal world and not be an attorney. It’s opening doors to explore careers they didn’t know existed.”
Before the event, the girls research their panelists and prepare thoughtful questions about their jobs, practicing communication, time management, strategic thinking, and problem-solving. The event itself becomes a live exercise in networking and curiosity.
“One of the most valuable things you can pick up along the way is having the confidence to talk about yourself and learn to ask questions about somebody else,” says Kobel. “I think those kinds of takeaways, while they may not be the most obvious, are some of the most valuable for the girls.”
More Than Leadership
While the Leader-to-Leader program is an important aspect of their curriculum, it’s a small part of what the organization does for girls of all ages in Chicago. At its core, Girls in the Game focuses on sports-based youth development (SBYD), using sports as a tool to develop positive outcomes in the lives of girls throughout Chicago.
Programs include after-school sports such as basketball, soccer, lacrosse, tennis, and yoga. They also have one-time programs, such as their Game Days, which are one- to three-hour events where girls rotate through stations focused on health, leadership, and sports. Summer camps engage girls in physical activity alongside leadership-building exercises.
While sports are the center of many programs, the goal is not to develop all-star athletes, but to help girls of all ages practice social-emotional skills, connect with role models, learn more about future career paths, and have positive influences that can help them navigate their middle and high school years.
Inspiring Business Leaders
The day leaves a mark on the professionals, too.
“An opportunity to talk to high school girls about anything is a valuable opportunity for me,” says Associate Attorney Schera Sampson. As a retired professional basketball player turned attorney, Sampson says she resonates with Girls in the Game, especially when it comes to showing girls that it’s okay when things don’t pan out as expected.
“Nothing in life is permanent,” says Sampson. “If the risks you take result in something that doesn’t pan out right now, that’s part of your story. It might not be part of your story now. It might be part of your story when you’re 34 or 38 or 42, but it all is going toward that story.”
Associate Attorney Camila Di Mauri underscores the impact of giving girls the chance to see women thriving in a range of professional careers.
“You can’t be it if you can’t see it,” she says, echoing the program’s guiding purpose. “Seeing other women as lawyers or accountants gives them something to picture for themselves.”
Fairchild adds that the event also strengthened her own team’s bonds. “I really think our team is getting as much out of it as the girls,” she says. “Sharing their stories and making a difference in younger girls’ lives — that stays with you.”
How to Help
Girls in the Game helps girls discover strength and build confidence through sports and leadership programs. Donations help the organization fund its year-round and summer programs.
You can also get involved by purchasing items from the Amazon wish list or donating gently used items. You can also volunteer to host a Leader-to-Leader event or attend one of their annual fundraisers.
Jessica Braun Gervais is a Chicago-based freelance writer specializing in health, wellness, and fitness. She earned a B.A. in Journalism from Columbia College and has written content for various health and wellness institutions. Jessica Braun’s passion for wellness comes from her life as an elite athlete competing in Muay Thai kickboxing competitions across the country. When she’s not writing or training, Jessica Braun enjoys reading thrillers, discovering new coffee shops, and cuddling with her rescue dogs, Brady and Gianna.
