On The Brink With Andi Simon

On this episode of On the Brink with Andi Simon, I had the immense pleasure of speaking with Jessica Fairchild—an extraordinary lawyer, entrepreneur, and advocate for a new kind of workplace culture. Jessica's story is one of continual reinvention, courageous pivots, and an unwavering commitment to values-driven leadership. Jessica is the co-founder and partner at Fairchild and Bair, a Chicago-based law firm built on flexibility, trust, and purpose. As you’ll hear in our conversation, her 25-year legal career has not followed a traditional path. And that’s exactly what makes her story so compelling. From Accounting Major to M&A Trailblazer Jessica didn’t grow up dreaming of being a lawyer. In fact, she studied accounting in college and only considered law school after enjoying a business law class. With no attorneys in her immediate family, this leap was both unexpected and bold. But as she puts it, “I followed my gut.” After cutting her teeth in a large Chicago law firm, she took a big risk—leaving to be