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

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, a podcast strategy company for business owners and creatives.

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 Degree Caroline’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.

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 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.

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 elevator” instead of the stairs through the admissions process. Lawyer Side Hustles In addition to her work in business affairs, Victoria serves as the Director of Advising at Juris Education, an edtech platform advising students toward careers in law. The platform supports applicants nationwide and internationally through every stage of the admissions process. “This is what I wish I had,” Victoria Inoyo expresses in Episode 238 of You Are a Lawyer.She sees mentorship as a way to close information gaps and reduce unnecessary stress. By helping students identify their goals early and understand the full spectrum of legal career options, she is building access and confidence for the next generation of lawyers. This episode is produced by Skip the Boring Stuff, a podcast strategy company for business owners and creatives.

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 easier and more effective, ultimately encouraging others to embrace the medium. Celebrate six years of podcasting with Kyla Denanyoh! This episode is produced by Skip the Boring Stuff, a podcast strategy company for business owners and creatives.

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 memorizing doctrine and more about learning how to relate to people. He explains that jury trial work is not primarily about statutes or case law. It is about understanding human behavior, credibility, and persuasion. “Jury trial work is not law. Jury trial work is relating to people," explains Kyle Sherman, on this episode of You Are a Lawyer.Through his own growth, especially after attending Jerry Spence Trial College, Kyle reframed trial advocacy as structured storytelling. Legal training gave him analytical tools, but his success in the courtroom comes from listening, adapting, and presenting cases in a way jurors can understand and internalize. This episode is produced by Skip the Boring Stuff, a podcast strategy company for business owners and creatives.

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. Kyla also delves into her motivation for starting the podcast, the importance of mindset in content creation, and the value of sharing diverse stories within the legal community. Kyla Denanyoh explores themes of risk-taking, entrepreneurship, and personal growth. Kyla shares her journey from law school to podcasting, emphasizing the importance of embracing risks and creating opportunities. They discuss the evolution of her podcast, the challenges of monetizing content, and the significance of self-care and leisure in a busy life. The conversation culminates in reflections on the value of a law degree and the importance of taking risks in both personal and professional realms. This episode is produced by Skip the Boring Stuff, a podcast strategy company for business owners and creatives.

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 training far beyond traditional practice. Lawyer Side Hustles Lawrence co-founded Legal Ease in 2023 with the goal of making legal easier and more accessible for consumers. Legal Ease is built to help people handle what he calls non complex legal matters without going through the full traditional attorney process, especially when the work is largely checklist driven and expensive simply because it requires a lawyer’s time to ask questions and process information. “I like getting up every day and working towards building something,” Lawrence Blackmon expresses in Episode 234 of You Are a Lawyer. He describes Legal Ease as consumer facing legal technology powered by artificial intelligence, designed for matters like expungements, no fault divorce, and certain personal injury situations. The platform is meant to guide users through the same questions a lawyer would ask and help them move through the process without paying what he calls exorbitant fees. He even names the AI component of the platform. This episode is produced by Skip the Boring Stuff, a podcast strategy company for business owners and creatives.

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, Francesca built multiple careers outside traditional practice. From legal marketing to entrepreneurship to travel blogging in Taiwan, she consistently followed alignment over expectation. “Don’t let the debt keep you strapped to something you don’t want to do,” Francesca Chang expresses in Episode 233 of You Are a Lawyer.Her journey reflects the broader YAAL theme that a law degree is a tool, not a cage. Whether building businesses abroad or litigating pro se against the Department of Education, Francesca’s path demonstrates that lawyers can redefine success on their own terms. This episode is produced by Skip the Boring Stuff, a podcast strategy company for business owners and creatives.

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 took an unexpected turn into eDiscovery and legal operations. Starting as a project attorney in document review, she gradually moved into litigation support, preservation coordination, and eventually legal operations roles embedded within large corporate environments. “This is an industry that I would stay in," explains SeNita McRae, on this episode of You Are a Lawyer.Her legal training allowed her to translate complex technical concepts for attorneys while also working directly with vendors and internal teams. SeNita’s experience shows how a JD can be a powerful credential even without bar licensure, particularly in operational, technology driven legal roles. This episode is produced by Skip the Boring Stuff, a podcast strategy company for business owners and creatives.

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 a nonprofit called Toolshed Boxing with his sister, providing trauma-informed boxing and yoga programs for kids in the Lehigh Valley. While the programs involve physical movement, the real focus is connection, mindfulness, and helping young people feel safe in their bodies. “The real transformative thing is the relationship,” John Lopez expresses in Episode 231 of You Are a Lawyer.Through both his legal and community work, John demonstrates that advocacy can take many forms. Whether in courtrooms, classrooms, or parks, his work centers on presence, care, and helping people reconnect with themselves. This episode is produced by Skip the Boring Stuff, a podcast strategy company for business owners and creatives.

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 began Leave Law Behind in 2008 by writing online about his own experience leaving law. What started as a personal, cathartic project eventually gained traction as lawyers around the world resonated with his story and reached out for support. “People started reaching out and saying, can you help me and I will pay you for your time,” Casey Berman expresses in Episode 230 of You Are a Lawyer.Today, Leave Law Behind is a robust platform offering resources, coaching, and guidance to lawyers exploring new paths. Casey’s work reflects how side projects, creativity, and experimentation can grow into meaningful careers, especially when lawyers allow themselves to try something new without attaching to a specific outcome. This episode is produced by Skip the Boring Stuff, a podcast strategy company for business owners and creatives.

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 work runs parallel to legal advocacy. She leads an organization committed to holistic legal support, positive youth development, and adolescent brain science, while also building sustainable infrastructure so the work can continue long term. “We should not be living to work but work should be an adjunct to our life,” Bianca Van Heydoorn expresses in Episode 229 of You Are a Lawyer.Bianca is also deeply intentional about leadership succession. She is actively working to prepare YSRP for a future executive director with lived experience of incarceration, reflecting her commitment to stewardship, shared power, and building institutions that last beyond any one leader. This episode is produced by Skip the Boring Stuff, a podcast strategy company for business owners and creatives.

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 out of a moment of reflection and loss. After being laid off from her corporate role and losing a close friend from law school unexpectedly, she reevaluated what she wanted from life. Travel, time, and freedom rose to the top, leading her to pursue teaching opportunities overseas. “Life is too short and you need to do what it is that you enjoy,” shares Michelle Words in Episode 35 of You Are a Lawyer.In addition to teaching, Michelle hosts the Flipping the Script podcast, where she helps women navigate change and embrace new chapters. Through podcasting, mentorship, and future plans to support women of color living abroad, her work continues to center empowerment, self authorship, and the courage to rewrite your own story. This episode is produced by Skip the Boring Stuff, a podcast strategy company for business owners and creatives.

David Sclar is a technology lawyer and the author of Workplace Strategies for Technology Lawyers. In this episode, David explains why soft skills are essential for modern legal careers, how he found his place in law after early uncertainty, and what lawyers can do to build careers that align with how they actually work. Lawyer Side Hustles David’s book grew out of real-world experience rather than personal branding. While working at a startup, he began documenting lessons learned from chaos, growth, and leadership. Over time, those notes became a concise resource designed to help lawyers work better with clients and colleagues. “I wanted to make this book as efficient as possible in giving people practical, useful information,” David Sclar expresses in Episode 227 of You Are a Lawyer.In addition to writing, David spends time mentoring and advising early-career lawyers. His work outside traditional legal practice focuses on helping others navigate uncertainty, find mentorship, and build careers that feel sustainable rather than performative. This episode is produced by Skip the Boring Stuff, a podcast strategy company for business owners and creatives.