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

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...

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...

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 l...

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...

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 pr...

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 f...

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...

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 entrepren...

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 c...

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 h...

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...

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...

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...

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 Hustles Today, Aman introduces herself as a life strategi...

Victoria Inoyo is the Director of Advising at Juris Education , an edtech platform advising students toward careers in law, and a lawyer working in business affairs and creative marketing at Apple. In this episode, Victoria shares how she navigated law school as a first generation American, why she chose the creative side of the legal industry, and how she now helps aspiring lawyers “take the elev...

Kyla Denanyoh shares six key aspects of being a podcast host, emphasizing the power and control that comes with managing a show, the importance of streamlining processes, the freedom to choose guests, the potential for monetization, and the transformative impact podcasting can have on one's life and career. The discussion highlights the tools (Honeybook) and strategies that can make podcasting eas...

Kyle Sherman is a trial specialist, civil plaintiff’s attorney, and founder of Trial Structure. In this episode, Kyle shares why law school was the hardest season of his life, how Jerry Spence Trial College reshaped his confidence, and why he believes jury work is about persuasion, not convincing. What Can You Do with a Law Degree Kyle’s career demonstrates that legal education is less about memor...

In this episode, Kyla Denanyoh shares her journey from law firm volunteer to law school graduate and beyond. Kyla is interviewed by a fellow Southern University Law Center (SULC) alum, Vernon W. Thomas and she discusses her experiences at SULC, the challenges of the bar exam, and her unexpected career path that led her to work in a call center before finding her footing in the legal profession. Ky...

Lawrence Blackmon is a trial attorney, Mississippi House Representative, and the CEO of Legal Ease , a consumer facing legal tech company using artificial intelligence to help people handle certain non complex legal matters without hiring an attorney. In this episode, Lawrence shares how mock trial shaped his confidence, how he stepped into public service, and why he believes lawyers can use their...

Francesca Chang is a lawyer, former travel blogger, and entrepreneur who sued the U.S. Department of Education to discharge nearly $260,000 in student loan debt. In this episode, Francesca shares what it was like to declare bankruptcy, represent herself pro se, and fight for relief in a system with a historic 0.1 percent success rate. Lawyer Side Hustles Before pursuing bankruptcy relief, Francesc...

SeNita McRae is a legal operations professional with a background in broadcast journalism, public administration, and law. In this episode, SeNita shares how she built a thriving career in eDiscovery and legal operations, why passing the bar was not required for her success, and how every degree she earned eventually fit together. What Can You Do with a Law Degree After law school, SeNita’s career...

John Lopez is the Legal Director of the Youth Sentencing and Reentry Project , where he supports children charged as adults across Pennsylvania. In this episode, John shares how combining law and social work allowed him to practice in alignment with his values, and why treating people as people is central to meaningful legal advocacy. Lawyer Side Hustles Outside of his legal role, John co-founded...

Casey Berman is the founder of Leave Law Behind and a former in-house lawyer who helps attorneys transition into careers that better align with their skills, values, and lives. In this episode, Casey shares how he left traditional legal practice, built a remote business from Hawaii, and helps lawyers rethink identity, risk, and what fulfillment can look like after law. Lawyer Side Hustles Casey be...

Bianca Van Heydoorn is the Executive Director of the Youth Sentencing and Reentry Project in Philadelphia. In this episode, Bianca shares how criminal sociology, reentry work, and lived experience shaped her leadership, and why meaningful justice work starts with proximity, dignity, and seeing young people as children first. Lawyer Side Hustles and Parallel Work While Bianca is not a lawyer, her w...

Michelle Words is a business law professor and licensed attorney who has spent the last seven years living and teaching abroad in the Middle East. In this episode, Michelle shares how her law degree became a tool for freedom, travel, and reinvention, and why choosing the life you actually want matters more than following a traditional legal script. Lawyer Side Hustles Michelle’s life abroad grew o...