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

Ruma Mazumdar is a New Jersey real estate and estate planning attorney who built a successful virtual law firm after leaving Big Law. In this episode, she shares how working as a paralegal shaped her legal career, why she chose entrepreneurship despite growing up around family business, and how redefining success led her to build a practice that supports the life she actually wants.

Lawyer Side Hustles

Launching her own law firm wasn't originally part of Ruma's plan. Growing up with entrepreneur parents, she witnessed the sacrifices that came with running a business and initially wanted the stability of traditional employment. But after several years in private practice and the shift toward remote work during the pandemic, she realized she wanted to build something on her own terms.   

Today, Ruma operates a fully virtual law firm while living outside the state where she practices. She has also embraced human design as a framework for understanding how she works best, allowing her to build a business that prioritizes sustainability over constant growth. Her journey demonstrates that entrepreneurship isn't simply about owning a business. It's about intentionally creating a career that aligns with your values and lifestyle.

This episode is produced by Skip the Boring Stuff, a podcast strategy company for business owners and creatives.

Jay Coleman is a criminal defense attorney, probate attorney, Social Security attorney, and law firm owner based in Arkansas. Returning to You Are a Lawyer six years after his first appearance, Jay reflects on how his career has evolved, the realities of running a law practice, and why finding balance has become just as important as building a successful legal career.  

Lawyer Side Hustles

For Jay, entrepreneurship wasn't always part of the plan. Like many lawyers, he initially imagined working for someone else. Running his own firm gradually taught him that practicing law and operating a business require two very different skill sets.  

Today, Jay spends as much time thinking about leadership, operations, and creating systems as he does practicing law. He's also intentionally working toward something many lawyers struggle to achieve: balance. Rather than measuring success solely by billable hours or case outcomes, he's learning to prioritize his own health, hobbies, and relationships alongside his growing practice. His journey reflects a reality many lawyers experience but don't often discuss openly. 

This episode is produced by Skip the Boring Stuff, a podcast strategy company for business owners and creatives.

Amber Johnson is an attorney whose legal career has evolved from civil rights and compliance work into helping small businesses compete for multimillion-dollar airport contracts. In this episode, Amber shares how her law degree opened unexpected doors, why transportation is full of legal careers beyond aviation law, and how lawyers can use their skills to build stronger organizations and stronger communities. 

Lawyer Side Hustles

Although Amber no longer practices law full time, she intentionally maintains her law licenses while continuing to grow her leadership career. Along the way, she has discovered that the skills lawyers develop are remarkably transferable across industries.  

Amber's professional journey has taken her from diversity, equity, and inclusion work to civil rights compliance, public transportation, and now airport operations. Each transition built upon the last, proving that legal careers don't have to follow a straight line. Instead of limiting herself to one definition of success, she continues finding new ways to combine law, leadership, and community impact. 

This episode is produced by Skip the Boring Stuff, a podcast strategy company for business owners and creatives.

Anjie Vichayanonda is the founder and CEO of Leg Up Legal, a mentorship platform that connects aspiring law students with attorneys before they apply to law school. In this episode, Anjie shares how mentorship changed the course of her own career, why exposure matters before making the investment in law school, and how lawyers can use their knowledge to create opportunities for others.

Lawyer Side Hustles

Leg Up Legal began as an effort to solve a problem Anjie experienced firsthand. She knew how difficult it could be for aspiring lawyers to find mentors, learn about different practice areas, and understand what life as a lawyer actually looks like before committing to law school. Instead of accepting that challenge as inevitable, she built a platform designed to make mentorship more accessible. 

In addition to running Leg Up Legal, Anjie also became a published co-author of Networked, an anthology written alongside 19 other women lawyers during the COVID-19 pandemic. The project captured stories of resilience, career pivots, personal challenges, and professional growth during a historic moment. Both the book and Leg Up Legal reflect Anjie's broader passion for helping people navigate uncertainty through connection, mentorship, and community.  

This episode is produced by Skip the Boring Stuff, a podcast strategy company for business owners and creatives.

Bob Hartmann is a criminal defense attorney, author, and rainmaker who has spent nearly four decades building a successful law practice. In this episode, he shares why bringing in business is one of the most important skills lawyers can develop, how entrepreneurship created the lifestyle he wanted, and why lawyers should stop being afraid to build careers on their own terms.  

Lawyer Side Hustles

Bob’s side hustle eventually became a second professional identity. After years of building his own successful practice, he began teaching other lawyers how to develop business, create referral networks, and build sustainable firms. His upcoming book, Making It Rain: The Art of Building a Successful Law Practice, shares practical lessons for attorneys who want greater control over their careers and financial futures.

Much of Bob’s motivation comes from personal experience. By operating his own practice, he was able to coach his daughter's softball teams, attend her games, travel with her during recruiting visits, and prioritize family without sacrificing professional success. His story demonstrates that entrepreneurship is not only about earning more money. It can also create the flexibility and freedom to build a life aligned with your values.

This episode is produced by Skip the Boring Stuff, a podcast strategy company for business owners and creatives.

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.

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, a podcast strategy company for business owners and creatives.

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. 

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, a podcast strategy company for business owners and creatives.

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. 

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.

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.

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.

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. 

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.