Jessica Fairchild: On Authenticity in the Legal Business

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 become general counsel for Chicago’s Olympic bid. That three-year detour turned out to be a pivotal moment in her journey. The experience showed her how law could intersect with leadership, creativity, and impact. It also sparked her entrepreneurial spirit. Building a Firm with Flexibility at Its Core Jessica founded her own firm in 2010, without a business plan but with a clear sense of purpose: to build a law practice where she—and others—could bring their authentic selves to work. In 2019, that mission expanded with the merger that formed Fairchild and Bair, alongside like-minded partners. Today, the firm boasts nearly 100 lawyers and a business model that reflects the realities and values of a new generation. What sets Jessica’s approach apart? It’s the deliberate culture of flexibility and inclusion. Whether accommodating a lawyer working remotely from Madrid or welcoming professionals who’ve stepped away from the workforce, the firm embraces nonlinear career paths. “We meet people where they are,” Jessica explains. That philosophy has helped them attract top talent from firms where rigid structures no longer fit. If you would like to watch our interview, it is on YouTube: Law as Business, Practice, and Purpose Jessica is as much a business leader as she is a legal expert. She emphasizes that today’s law firms must be more than traditional billable-hour machines. They must be responsive to change, open to new technologies (including AI), and built around human-centered leadership. Her firm is exploring how AI can make legal work more efficient—not to replace lawyers, but to empower them. And in a profession where many still define themselves by their titles or roles, Jessica is carving out space for lawyers to live full, multidimensional lives. As she wisely notes, “You’ve got to find a place where you can be your authentic self.” Key Takeaways Jessica offers two powerful insights for all professionals—not just lawyers: Find a place where you can be your authentic self. If your current environment doesn’t support who you are, there are others that will. Think of your career as a journey, not a destination. Jessica’s path has included pivots, risks, and new beginnings. That’s what made it rich and meaningful. Why This Matters Now This episode couldn’t come at a better time. With workplaces in flux, AI reshaping industries, and the next generation demanding purpose and flexibility, Jessica’s story provides a blueprint for a new kind of leadership—one that balances innovation with humanity. Tune In & Take Action Enjoyed this episode? Subscribe, share with a colleague, and send us your thoughts atinfo@andisimon.com. Want more stories like this? Check out my books On the Brink, Rethink, and Women Mean Business on Amazon.