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

Why Lawyers Need to Be Accountable feat. Anne Marie Engel

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 work as an accountability architect and fractional general counsel brings all of her experience together into one model. She works with businesses to audit their legal structures, build systems, and create processes that reduce risk while supporting growth. Instead of acting as a traditional outside lawyer, she steps in as a partner who helps leaders understand what their legal function should actually be doing. “I can come in and we’re going to map out your legal issues and we’re going to set the legal operations up in your business,” Anne Marie Engel expresses in Episode 242 of You Are a Lawyer. Her work focuses on structure, clarity, and accountability. She helps companies move away from reactive legal strategies and toward intentional systems that support their goals. It is less about solving isolated problems and more about building a foundation that prevents them. This episode is produced by Skip the Boring Stuff [https://www.skiptheboringstuff.com/], a podcast strategy company for business owners and creatives.

What It Takes to Run a Law Firm feat. Sean Olson

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

The Mindset You Need to Pass the Bar feat. Caroline Vickers (December 2021)

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

Leaving Law From a Place of Happiness feat. Aman Costigan

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

Finding the Creative Side of Law feat. Victoria Inoyo

Victoria Inoyo is the Director of Advising at Juris Education [http://juriseducation.com], 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 [https://www.skiptheboringstuff.com/], a podcast strategy company for business owners and creatives.