You Are A Lawyer: Take Risks and Change Careers in Law

Lawyers Deserve Freedom Too feat. Kristyan Gilmore

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.  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.  This episode is produced by Skip the Boring Stuff [https://www.skiptheboringstuff.com/], a podcast strategy company for business owners and creatives.

When Your Legal Career Doesn’t Go as Planned feat. Patrick Jester

Patrick Jester is a metrology consultant, law school graduate, and JD Advantage professional who built a meaningful career outside traditional legal practice after facing repeated bar exam setbacks. In this episode, he shares how he navigated disappointment, trusted the process, and created a path that aligned with his skills, faith, and long-term vision.   Lawyer Side Hustles Beyond his primary career, Patrick has remained committed to causes that originally drew him to law school, including advocacy work related to foster care. While his professional path shifted, his underlying motivations, helping people and contributing to meaningful systems, did not disappear. Instead, they evolved alongside his career. “I still participate with advocacy groups for foster parents and foster children and adoptive children as much as I can,” Patrick Jester expresses in Episode 244 of You Are a Lawyer. Patrick also speaks openly about the emotional and mental journey that came with redefining his career. Through mentorship, leadership roles in professional organizations, and sharing his story, he contributes to a broader conversation about resilience and non-linear success. His work outside traditional practice reflects a deeper truth: fulfillment often comes not from following a prescribed path, but from staying aligned with your values even when the path changes.  This episode is produced by Skip the Boring Stuff [https://www.skiptheboringstuff.com/], a podcast strategy company for business owners and creatives.

The Power of Travel for Lawyers feat. Elaine Lee

Elaine Lee is a lawyer, travel journalist, and author of Go Girl: The Black Woman’s Book of Travel and Adventure. In this episode, Elaine shares how she built a legal career rooted in civil rights work, how a trip to Paris changed the trajectory of her life, and how she designed a lifestyle that allows her to travel the world while still using her law degree.  Lawyer Side Hustles Elaine’s “side hustle” became her calling. After traveling the world, she pursued travel writing at a time when there were few, if any, examples of Black women doing that work. When traditional publishing avenues did not open, she created her own opportunity by developing an anthology featuring well-known Black women writers.  “I have figured out a way to combine my life as an attorney and my soul’s work as a travel journalist,” Elaine Lee expresses in Episode 243 of You Are a Lawyer. Her work now centers on storytelling, global citizenship, and empowering women to see the world. Through her books, including Go Girl, she encourages others to travel, explore, and expand their sense of what is possible. Law remains part of her life, but it supports a broader purpose rooted in joy and connection.  This episode is produced by Skip the Boring Stuff [https://www.skiptheboringstuff.com/], a podcast strategy company for business owners and creatives.

Why Lawyers Need to Be Accountable feat. Anne Marie Engel

Anne Marie Engel is a lawyer, fractional general counsel, and self-described accountability architect. In this episode, Anne Marie shares how her 30-year legal career led her to rethink the role of lawyers in business, why accountability and fiduciary duty are being lost in the profession, and how she now helps companies prevent problems before they start. Lawyer Side Hustles Anne Marie’s current work as an accountability architect and fractional general counsel brings all of her experience together into one model. She works with businesses to audit their legal structures, build systems, and create processes that reduce risk while supporting growth. Instead of acting as a traditional outside lawyer, she steps in as a partner who helps leaders understand what their legal function should actually be doing. “I can come in and we’re going to map out your legal issues and we’re going to set the legal operations up in your business,” Anne Marie Engel expresses in Episode 242 of You Are a Lawyer. Her work focuses on structure, clarity, and accountability. She helps companies move away from reactive legal strategies and toward intentional systems that support their goals. It is less about solving isolated problems and more about building a foundation that prevents them. This episode is produced by Skip the Boring Stuff [https://www.skiptheboringstuff.com/], a podcast strategy company for business owners and creatives.

What It Takes to Run a Law Firm feat. Sean Olson

Sean Olson is a trial lawyer and founder of Olson Law Firm in Colorado. In this episode, Sean shares how he transitioned from journalism into law, built a personal injury firm from a solo practice into a growing team, and why he still makes time for the courtroom even as a CEO. Lawyer Side Hustles What started as a solo practice eventually became Olson Law Firm, a growing personal injury firm with multiple attorneys and a full support staff. Sean built the firm by continuously learning, investing in himself, and developing skills beyond traditional legal work, including marketing, business operations, and leadership. “I didn’t understand what was possible,” Sean Olson expresses in Episode 241 of You Are a Lawyer. That growth required humility and adaptability. Sean spent years attending conferences, reading, and refining his approach to both law and business. His work today reflects that evolution. He is not just practicing law. He is building systems, leading people, and creating opportunities for others within his firm. This episode is produced by Skip the Boring Stuff [https://www.skiptheboringstuff.com/], a podcast strategy company for business owners and creatives.