Lawyers Deserve Freedom Too feat. Kristyan Gilmore

May 20
3 min read

Kristyan Gilmore is an attorney, professor, consultant, and founder of To Be Free, a business advisory company focused on helping entrepreneurs align their work with their values. In this episode, Kristyan shares how the 2008 financial crisis reshaped her legal career, why she believes lawyers should “find their voice,” and how she built a life centered on freedom, teaching, and creative entrepreneurship.

About This Episode

Background

Kristyan Gilmore graduated from Howard Law School during the 2008 housing crisis, a moment that disrupted the career plans of many new lawyers. After having a New York offer rescinded, she returned to Houston, passed the bar, and began working for a defense contractor during a turbulent period tied to the Iraq and Afghanistan wars. The experience was intense and ultimately pushed her to question whether traditional corporate practice aligned with the life she actually wanted.

“That’s what led me to discover my vocation and to try to work my way out of law practice because it was such a crazy experience," shares Kristyan Gilmore on You Are A Lawyer.

At the same time, teaching had quietly been following her for years. She started teaching while studying for the bar exam, initially as a practical way to earn income without taking out additional loans. What began as side work eventually became the thread that connected everything else. Over time, she realized teaching was not simply something she could do. It was the thing she was built to do.

Why Law School

Kristyan’s decision to attend law school came from both cultural expectations and personal ambition. Like many high-achieving students, she grew up hearing that success meant becoming a doctor, lawyer, or engineer. Law felt like the best fit for someone who loved language, storytelling, and communication.

“I still sometimes struggle with it," explains Kristyan Gilmore on Episode 245 of You Are a Lawyer.

What makes her story compelling is that she eventually allowed herself to question whether the traditional legal identity actually fit who she was becoming. Over time, she recognized that she had spent years suppressing the more creative and philosophical parts of herself. Instead of abandoning her law degree, however, she reframed it as a tool she could use to build a more aligned life.

What Can You Do with a Law Degree

Kristyan believes lawyers should stop seeing the JD as a cage and start seeing it as leverage. For her, the law degree created portability, flexibility, and credibility. It allowed her to teach, consult, travel, advise entrepreneurs, and create multiple income streams while still maintaining a legal practice on her own terms.

“I have gotten to the place where I’m doing, I think, exactly what I want to do," shares Kristyan Gilmore on Episode 245 of You Are a Lawyer.

Her framework for this process is called VOICE: vocation, occupation, inspiration, choosing your environment, and execution. The law may begin as the occupation that pays the bills, but she believes lawyers should continue building toward the vocation that gives them purpose. Instead of becoming trapped inside one definition of success, attorneys can use their training to create lives built around autonomy and impact.

Lawyer Side Hustles

Kristyan’s consulting business, To Be Free, helps entrepreneurs streamline operations, clarify their mission and values, and create businesses that support both impact and freedom. She works primarily with creatives, nonprofit leaders, and mission-driven founders who want to spend less time buried in backend operations and more time focused on the work they actually care about.

“The goal is to always monetize the vocation,” Kristyan Gilmore expresses in Episode 245 of You Are a Lawyer.

Her work is deeply personal. Inspired by watching her entrepreneurial parents struggle financially despite being creative and community-driven, Kristyan built a business focused on helping people avoid burnout while still making meaningful contributions. Through automation, systems, and strategic advising, she helps clients create businesses that align with who they really are instead of simply surviving inside systems that exhaust them.