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

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.

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 HustlesIn 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 DegreeKyle’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 HustlesLawrence 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 HustlesBefore 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 DegreeAfter 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 HustlesOutside 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 HustlesCasey 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 WorkWhile 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 HustlesMichelle’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 HustlesDavid’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.

Mary Ellen O’Connor is a New York law firm owner who practices workers’ compensation and Social Security disability law. In this episode, Mary Ellen shares how she moved from teaching to law, built a firm rooted in advocacy and empathy, and created a legal career that supports both families and real impact.Lawyer Side HustlesIn addition to running her firm, Mary Ellen has intentionally built a workplace culture that reflects her values. She leads a team of attorneys and staff with flexibility, empathy, and realism, offering split shifts, family-friendly policies, and an environment where people are treated as humans first.“We should not be living to work, but work should be an adjunct to our life,” Mary Ellen O'Connor expresses in Episode 226 of You Are a Lawyer.Rather than a traditional side hustle, Mary Ellen’s parallel work shows up in leadership and mentorship. She models what it looks like to build a legal business that prioritizes sustainability, inclusion, and respect, proving that success in law doesn’t have to come at the expense of family, health, or humanity.This episode is produced by Skip the Boring Stuff, a podcast strategy company for business owners and creatives.

Akshay Verma is the Chief Operating Officer at SpotDraft and a former environmental lawyer whose career spans law firms, legal operations, and executive leadership in tech. In this episode, Akshay shares what it felt like to leave firm life, take a financial risk for his family, and build a career that better aligned with how he wanted to live and work.Lawyer Side HustlesAlongside his executive career, Akshay has become deeply involved in teaching and mentorship. He teaches at Santa Clara Law University and regularly speaks to law students and early-career lawyers about the evolving nature of the legal profession. These roles allow him to reflect on how dramatically the landscape has changed since he graduated and to help students see opportunities that didn’t exist when he was in their position.“The world is literally your oyster right now,” Akshay Verma expresses in Episode 225 of You Are a Lawyer.While Akshay doesn’t frame this work as a traditional side hustle, it reflects a meaningful extension of his professional identity. Through teaching and public speaking, he contributes to reshaping how lawyers think about success, fulfillment, and career flexibility. His work outside his day job reinforces the idea that a legal career can be expansive, iterative, and deeply personal, not just confined to a single title or track.This episode is produced by Skip the Boring Stuff, a podcast strategy company for business owners and creatives.

Lora Cheadle is a former insurance defense attorney who traded burnout for a career built on wellness, boundaries, and helping high achievers navigate betrayal in both personal and professional life. In this episode, she explains why many lawyers mislabel their exhaustion as burnout when it is actually the rupture of unmet expectations, unmanaged stress, and years of self-neglect. Lora shares how fitness, neuroplasticity, and coaching transformed her life and fuel the work she does today.Lawyer Side HustlesLong before she transitioned out of traditional practice, Lora taught step aerobics as a creative outlet and source of joy. That passion evolved into a broader commitment to wellness, somatic health, and stress reduction. As she explored posture, breathing, and body-based healing, she recognised how deeply physical habits affect emotional and cognitive performance. This curiosity led her to study nutrition and later become a clinical hypnotherapist so she could support the neuroplasticity work her clients needed.“Fitness was my respite. People need to somatically process stress. Good posture makes a difference in the way we can breathe and in our brain functioning,” Lora Cheadle expresses in Episode 224 of You Are a Lawyer.She eventually built Life Choreography Coaching and Advocacy, a business inspired by the idea that life, like dance, requires both choreography and improvisation. Lora also wrote It’s Not Burnout, It’s Betrayal, a book explaining how professionals can use her Fuel Up framework to identify ruptured expectations, process emotional overwhelm, and rebuild their sense of identity after chronic stress.This episode is produced by Skip the Boring Stuff, a podcast strategy company for business owners and creatives.

Laurie Pascoe practiced law in Ottawa, Ontario for more than forty years while writing over fifty articles, teaching continuing legal education, and serving thousands of clients. In this episode, Laurie explains why lawyers must evolve, how client service impacts malpractice claims, and why thinking like a client can make your legal practice more effective and more enjoyable.Lawyer Side HustlesWriting has been Laurie’s creative and intellectual outlet. He has written articles for lawyers and articles for clients, using writing as a way to educate, clarify legal issues, and reduce client overwhelm. Long before law firm websites were common, he built one of the first in Ottawa and filled it with free educational content. He also became one of the earliest lawyers in the region to advertise legally after restrictions were lifted.“I had so many articles that when the internet came along, I had a million things to throw on my website right away,” shares Laurie Pascoe in Episode 79 of You Are a Lawyer.His most significant project became his book, Innovative Legal Service Applications: A Guide to Improved Client Services, published by the ABA. For Laurie, these writing projects were not hobbies. They were a way to teach lawyers, improve client outcomes, and share practical tools to help the profession evolve. His side work helped shape how many lawyers think about systems, client service, and ethics.This episode is produced by Skip the Boring Stuff, a podcast strategy company for business owners and creatives.

Stephen Candelmo is a corporate lawyer turned tech founder who has spent nearly thirty years advising emerging companies and building his own ventures. In this episode, he explains how a recession, a machine learning experiment, and a desire for fairness inspired him to create Paralex, a legal platform that delivers fixed-fee, AI-powered legal services for small businesses and startups. He also shares why he believes the legal profession is on the edge of a major transformation.Lawyer Side HustlesStephen’s entrepreneurial path began long before Paralex. While still practicing corporate law, he launched a machine learning startup focused on sentiment analytics. The company served well-known customers and gave him a deeper understanding of product design, customer behavior, and the commercial side of technology. Years later, when large language models became available, he immediately began prototyping legal use cases instead of simply experimenting for fun.“Once you start innovating, you are always on the lookout for the next thing. It becomes a shift in mindset,” Stephen Candelmo expresses in Episode 222 of You Are a Lawyer.Paralex is the culmination of decades of corporate experience, business curiosity, and belief in legal accessibility. His side ventures were never hobbies. They were stepping stones that helped him create a platform where AI handles routine legal tasks while lawyers provide oversight, judgment, and accountability. For Stephen, entrepreneurship is not separate from being a lawyer. It is an extension of what lawyers can do when they combine their training with creativity.This episode is produced by Skip the Boring Stuff, a podcast strategy company for business owners and creatives.

Daria Levina is a lawyer, academic, and business owner whose path spans Russia, the United States, Italy, and now Berlin. With two law degrees, a PhD in law, and a thriving admissions-advising business, Daria brings a global perspective to legal education and career design. In this episode, she shares what makes a PhD different from a JD, how stand-up comedy transformed her thinking, and why she believes education should be accessible to everyone.Lawyer Side HustlesOne of the most distinctive parts of Daria’s career is her entrepreneurial project, Harvard State of Mind, an admissions-advising business she built from years of helping friends apply to graduate and professional programs. What began as casual essay review turned into a robust library of courses, guides, and one-on-one services. Motivated by her own experience with education as a tool for social mobility, Daria is committed to making elite institutions feel accessible rather than exclusive.“Education has been not just a means of social mobility but pretty much the only means of upward mobility that was available… and I wanted to make that accessible,” Daria Levina expresses in Episode 221 of You Are a Lawyer.In addition to running her business, Daria performs stand-up comedy in Berlin. It has been a creative outlet that she describes as both therapeutic and unexpectedly practical. Comedy helps her process difficult experiences, develop new perspectives, and appreciate the collaborative nature of creative work. It’s proof that lawyers can be analytical and artistic at the same time.This episode is produced by Skip the Boring Stuff, a podcast strategy company for business owners and creatives.

Edward Cohn is a criminal defense attorney who has spent 23 years running his own solo practice across three states. In this episode, he shares why opening his own firm right out of law school gave him the freedom he always wanted, how a background in music shaped his confidence and creativity, and why some lawyers thrive when they build their practice on their own terms.Lawyer Side HustlesWhile Edward doesn’t have a traditional ‘side hustle’, his entire career reflects an entrepreneurial mindset that many lawyers overlook. Instead of building a firm with multiple attorneys, he intentionally crafted a lean practice powered by autonomy, flexibility, and meaningful work. He writes his own pleadings, manages client communication, and supplements his bandwidth by hiring students or contractors when needed.“You’ve got to be a hustler. You’ve got to have that drive in you… For me, I always had that,” Edward Cohn expresses in Episode 220 of You Are a Lawyer.Running a solo practice is his entrepreneurial venture, one that lets him control his schedule, spend time with his homeschooled daughter, and avoid the burnout that many lawyers face. His story shows that autonomy itself can be a form of creativity, and that building a practice intentionally can function as the ultimate professional side project: one that supports your life instead of consuming it.This episode is produced by Skip the Boring Stuff, a podcast strategy company for business owners and creatives.