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

Building a Life Before Building a Legal Career feat. Daniel J. Hennessy

Daniel J. Hennessy took an unconventional path to law school. After years working in ministry, education, nonprofit leadership, and even serving in Rome with the Vatican Museums, Daniel enrolled in law school in his forties. Today, he works as in-house counsel for a national real estate development company, helping cities bring transformative projects to life while maintaining the family-focused life he and his wife envisioned.   Lawyer Side Hustles One of the themes throughout Daniel's story is embracing change. Before law school, he successfully built careers in entirely different fields. Rather than viewing those experiences as detours, he sees them as essential parts of the person and lawyer he became. “Don't be afraid to make the changes that you need to make, even if they seem really big and scary,” Daniel J. Hennessy expresses in Episode 250 of You Are a Lawyer. Daniel encourages law students and lawyers to focus less on the degree itself and more on understanding who they want to become. For him, success was not about following a predetermined path but about aligning his work with his values, relationships, and priorities. His journey serves as a reminder that law can be part of a meaningful life without becoming the entire identity.  This episode is produced by Skip the Boring Stuff [https://www.skiptheboringstuff.com/], a podcast strategy company for business owners and creatives.

Why Relationships Matter in Law feat. Santiago Cueto

Santiago Cueto is an international business attorney, law firm owner, and author based in Miami, Florida. In this episode, Santiago shares how an interest in global affairs led him to law school, why he always envisioned owning a law firm, and how lawyers can build successful careers by combining legal knowledge with communication, leadership, and business development.  Lawyer Side Hustles Beyond practicing law, Santiago has embraced writing, speaking, mentoring, and entrepreneurship. He recently authored Winning Lawsuits in Florida, a book designed to answer the questions clients most frequently ask about litigation and dispute resolution. The project grew out of a client handbook his firm had already developed and became a way to educate a broader audience.  “Writing is a good way to get yourself known,” Santiago Cueto expresses in Episode 249  of You Are a Lawyer. Santiago is also passionate about helping younger attorneys develop confidence, communication skills, and professional judgment. Through mentoring his team and sharing practical business insights, he encourages lawyers to think beyond legal doctrine and focus on the traits that ultimately drive long-term success. His perspective reflects a belief that law school provides the foundation, but growth continues throughout an entire career.   This episode is produced by Skip the Boring Stuff [https://www.skiptheboringstuff.com/], a podcast strategy company for business owners and creatives.

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 Hustles Katherin’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 [https://www.skiptheboringstuff.com/], a podcast strategy company for business owners and creatives.

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 Hustles In 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 [https://www.skiptheboringstuff.com/], a podcast strategy company for business owners and creatives.

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 Hustles Wendy’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 [https://www.skiptheboringstuff.com/], a podcast strategy company for business owners and creatives.