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

Hosted by Kyla Denanyoh

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257

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Jun 2026

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About the show

Are you an ambitious lawyer who feels limited in life? A law student who daydreams about impacting the world? Did you struggle with the bar exam? Are you bored working as a lawyer? You Are A Lawyer is an interview-based podcast that promotes lawyers with fearless career changes, ambitious side hustles, and extraordinary lives. On this top-rated podcast, Kyla talks to law school graduates, attorneys, and lawyers about the risks they've taken, the joys (and challenges) of law school, and their transitions out of legal careers. You Are A Lawyer will motivate you to start that business, unpack some drama from law school, consider a nontraditional career, and push you to embrace the hobby you’ve been hiding. There are so many ways to use your law degree. Whether you’re working as an artist, tech investor, coach, or blogger, if you’ve graduated from law school, YOU ARE A LAWYER, and your law degree is valuable. Find more episodes and resources at www.youarealawyer.com. Contact Kyla with any questions: hello@youarealawyer.com.

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60 recent

June 11, 2026Episode 24837 min

Criminal Justice Through a Creative Lens feat. Katherin Hervey (October 2021)

Katherin Hervey is an award-winning filmmaker, artist, former public defender, and co-founder of On the Border Films. In this episode, Katherin shares how her legal background shaped The Prison Within, why storytelling became her form of advocacy, and how creativity helped her continue the work of justice outside traditional practice. Lawyer Side HustlesKatherin’s creative work is not a side project anymore. It is her life’s work. As a filmmaker, director, producer, and artist, she uses storytelling to examine the hidden corners of the American landscape and the human experiences often ignored by traditional systems. The Prison Within premiered at the Santa Barbara International Film Festival, won Best Social Justice Documentary, and has since become part of legal education, prison curricula, and broader conversations about criminal justice reform. “For The Prison Within, it was my baby, it came from my heart,” shares Katherin Hervey in Episode 34 of You Are a Lawyer.Her filmmaking continues the advocacy she began as a public defender, but in a different form. Rather than arguing cases one at a time, Katherin creates work that invites audiences to question punishment, trauma, accountability, and humanity. Her path reflects a core YAAL truth: legal training can become a creative tool when lawyers allow themselves to follow the work that feels most honest. This episode is produced by Skip the Boring Stuff, a podcast strategy company for business owners and creatives.

June 4, 2026Episode 24724 min

Building a Law Career on Purpose feat. Jennifer Gardner

Jennifer Gardner is a trial attorney, administrative judge, speaker, and law firm owner based in Los Angeles. In this episode, Jennifer shares how she built a career rooted in leadership and service, why lawyers need stronger communication and influence skills, and how legal professionals can use their creativity far beyond traditional practice.Lawyer Side HustlesIn addition to running her law firm and serving as an administrative judge, Jennifer has expanded into leadership education and public speaking. She now teaches professionals and lawyers how to improve their influence, communication, persuasion, and visibility skills while helping highly sensitive communicators become stronger leaders.“These are the irreplaceable human skills that I think are going to become more valuable as we use AI more and more,” Jennifer Gardner expresses in Episode 247 of You Are a Lawyer.Jennifer also created a free guide called How to Save Money on Legal Fees Before Hiring a Lawyer to help people navigate legal problems more efficiently and communicate more effectively with their attorneys. Her broader work reflects a consistent theme throughout her career: empowering people through education, preparation, and thoughtful leadership. This episode is produced by Skip the Boring Stuff, a podcast strategy company for business owners and creatives.

May 28, 2026Episode 24629 min

Building a Career That Fits Your Life feat. Wendy S. Meadows

Wendy S. Meadows is a family law attorney, mediator, coach, adjunct professor, and author of Sparkle & Grit. In this episode, Wendy shares how burnout pushed her to rethink her career, why coaching became a natural extension of her legal work, and how lawyers can build lives that actually fit who they are becoming. Lawyer Side HustlesWendy’s coaching business grew out of her own burnout and reinvention. What started with fitness coaching and personal development eventually evolved into helping lawyers navigate career pivots, entrepreneurship, confidence, and work-life balance. She now coaches attorneys across the country while still maintaining the parts of legal practice she genuinely enjoys, including mediation and collaborative family law. “What I've been able to cobble together is take all my favorite parts of my job and just amplify them,” Wendy S. Meadows expresses in Episode 246 of You Are a Lawyer.Her book, Sparkle & Grit, became another extension of that work. Wendy wrote the book as a guide for the version of herself who felt stuck years earlier, hoping other women would feel less alone while figuring out what comes next. Her career today blends law, coaching, writing, entrepreneurship, and education into something that feels intentionally designed rather than inherited. This episode is produced by Skip the Boring Stuff, a podcast strategy company for business owners and creatives.

May 21, 2026Episode 24526 min

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 HustlesKristyan’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, a podcast strategy company for business owners and creatives.

May 14, 2026Episode 24434 min

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 HustlesBeyond 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, a podcast strategy company for business owners and creatives.

May 7, 2026Episode 24327 min

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 HustlesElaine’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, a podcast strategy company for business owners and creatives.

April 30, 2026Episode 24226 min

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 HustlesAnne 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, a podcast strategy company for business owners and creatives.

April 23, 2026Episode 24118 min

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 HustlesWhat 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, a podcast strategy company for business owners and creatives.

April 16, 2026Episode 24026 min

The Mindset You Need to Pass the Bar feat. Caroline Vickers (December 2021)

Caroline Vickers is an attorney, entrepreneur, and founder of Bar Prep Champs, where she coaches first time and repeat bar takers to pass the exam with strategy and confidence. In this episode, Caroline shares how her own law school experience shaped her career, why mindset is the missing piece in bar prep, and how she built a business helping lawyers overcome shame and finally pass.What Can You Do with a Law DegreeCaroline’s legal career included clerking for multiple judges, working in private practice, nonprofit work, and federal government service. She had the credentials. She had the licenses in Maryland and DC. She had the traditional path. But as she began helping friends study for the bar while working as a law clerk, something clicked. She saw a pattern in repeat takers that was not about intellect.“I realized that there's a mindset piece that's missing from the bar exam experience and nobody's really talking about it," explains Caroline Vickers, on this episode of You Are a Lawyer.Her law degree gave her credibility, but more importantly, it gave her perspective. She understood how law students think, how lawyers internalize failure, and how ego and shame can derail performance. Instead of staying inside the courtroom, she chose to build something that addresses the emotional and strategic gaps law school leaves behind. Her JD did not limit her to practice. It equipped her to coach at scale.This episode is produced by Skip the Boring Stuff, a podcast strategy company for business owners and creatives.

April 9, 2026Episode 23930 min

Leaving Law From a Place of Happiness feat. Aman Costigan

Aman Costigan is a former law firm partner, life strategist, yoga teacher, podcaster, and financial independence advocate. In this episode, Aman shares why she left the law from a place of happiness and completion, how she and her husband planned their exits strategically, and why financial literacy is the key to career freedom.Lawyer Side HustlesToday, Aman introduces herself as a life strategist, vision board workshop leader, podcaster, and tarot reader. She works one on one with high achieving women to turn ideas into execution through planning, accountability, and strategic prioritization.“I follow through and I do it,” Aman Costigan expresses in Episode 239 of You Are a Lawyer.She also runs The Sisterhood, a yearly program where women turn vision boards into lived reality. For Aman, strategy and intuition coexist. Planning and manifestation coexist. Law was one skillset. Execution is another. And she continues to build, speak, teach, and create on her own terms.This episode is produced by Skip the Boring Stuff, a podcast strategy company for business owners and creatives.