On a quiet evening not long ago, Joan Clay sat with a young participant from her Baby B.O.S.S.™ program. The teenager, nervous about her first job interview, admitted she had never even seen a proper résumé. By the end of the workshop, she walked out smiling with one in hand, armed with practice from a mock interview and the confidence to step into her future. For Joan, moments like this are everything.
“I realized that this next generation is different,” Clay says. “When I was growing up, you went to college and had a career. You didn’t change jobs that often. Our youth are not on the same track. They want to have their own businesses. We have to honor that by providing them with the tools they need to succeed, no matter how they choose to go forward in their lives.”
Clay didn’t set out with a roadmap to community leadership. As a child, she once thought of nursing, but her passion shifted in high school when she discovered a love of writing. “I discovered a love of journalism and majored in Communications with an emphasis in journalism and public relations,” she recalls. That training sharpened her voice and her ability to tell stories—skills that now echo in the way she connects with communities and inspires the next generation.
Her eventual path into law added another dimension: advocacy. Through The Village Legal and Community Project (TVLCP), she began offering pro-bono legal services, helping people navigate contracts, disputes, and the fine print that too often trips up small business owners. But something gnawed at her.
“Families and communities thrive when there is economic stability,” she explains. “I asked how we could help entrepreneurs and our youth in a proactive manner, versus a reactive one. Knowledge is power.”
That question became the foundation of the B.O.S.S.™ Program, a hands-on initiative to give entrepreneurs the skills and tools they need to succeed. Participants learn how to form the right business entity, create a strong plan, and avoid common pitfalls. “During the COVID-19 pandemic, many people were unable to obtain the PPP loans they needed to keep their businesses afloat because they lacked the necessary paperwork. Our B.O.S.S. cohort lays it all out there for entrepreneurs,” Clay says.
One graduate came in with a weekend baking hobby and left ready to run a full-time catering company. Another realized he was turning down customers because his 9-to-5 kept him tied up. After completing the program, he made the leap into business ownership—and hasn’t looked back. These aren’t isolated wins; they’re part of a ripple effect Clay is proud to witness.
While adult entrepreneurs benefit from the B.O.S.S.™ Program, Clay also invests heavily in young people. Baby B.O.S.S.™ and Resume Bootcamp help teens build skills rarely taught in school. From drafting a résumé to practicing interview etiquette, these programs empower youth to enter the workforce or even pursue their own businesses with confidence.
“I may have had someone to help me prepare for my first job, but not everyone does,” Clay says. “We don’t judge, we don’t criticize, we empower.”
For her, the work is deeply personal. She sees the potential in every student and believes their dreams deserve structure and support. In an era where many young people imagine futures that look different from their parents’ or grandparents’, Clay sees possibility, not limitation.
The heart of TVLCP’s programs is connection. Participants don’t just attend classes; they become part of a network of mentors, subject matter experts, and peers who understand the challenges of building something from the ground up. “We don’t just disappear once the cohorts are over,” Clay notes. “Participants are welcome to reach out to me with questions, feedback, or concerns.”
Through partnerships with tax professionals, business plan writers, and bookkeepers, participants leave with more than knowledge—they leave with access. That access is often the difference between an idea that fizzles and a business that thrives.
This fall, TVLCP will shine a spotlight on this work. On September 25, 2025, The Village Legal and Community Project will host its Annual Fundraising Gala at The Secret Garden in Chicago. The evening promises elegance and impact, with a VIP wine tasting, silent auction, and an awards ceremony recognizing community changemakers.
But beneath the sparkle is a mission. Funds raised will expand programs like B.O.S.S.™, Baby B.O.S.S.™, and Resume Bootcamp to reach more neighborhoods across Chicago and beyond. “I want to expand all three programs,” Clay says. “I would love to have multiple B.O.S.S. cohorts running simultaneously in different parts of the city. Our communities are underserved and under-resourced—but with the right tools, we can change that.”
Joan Clay doesn’t just see the problems—she builds solutions. From entrepreneurs who finally feel confident enough to register their LLCs, to teens walking taller after their first mock interview, her work has measurable impact. And on that September evening at The Secret Garden, the city will gather to honor, support, and sustain the vision she has set in motion.
✨ Save the Date: September 25, 2025, 6–11 PM at The Secret Garden, 3302 S. Morgan St., Chicago IL.
Join The Village Legal and Community Project for an evening of celebration, empowerment, and investment in Chicago’s future.