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

When Advocacy Becomes the Career

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

Choosing a Different Kind of Legal Career

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

Healing Lawyer Burnout Through Boundaries and Self-Advocacy

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 Hustles Long 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 [https://www.facebook.com/LifeChoreographer/], 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 [https://workplace-burnout.com/its-not-burnout-its-betrayal-5-tools-to-fuel-up-thrive/], 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 [https://www.skiptheboringstuff.com/], a podcast strategy company for business owners and creatives.

Think Like a Client: Lessons from 40 Years in Law (March 2023)

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 Hustles Writing 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 [https://www.americanbar.org/products/inv/book/422091699/?utm_source=YAAL&utm_medium=newsletter&utm_campaign=2023+discount], 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 [https://www.skiptheboringstuff.com/], a podcast strategy company for business owners and creatives.

Why the Hourly Billing Model Is Broken

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 [https://paralex.ai/], 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 Hustles Stephen’s entrepreneurial path began long before Paralex [https://paralex.ai/]. 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 [https://paralex.ai/] 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 [https://www.skiptheboringstuff.com/], a podcast strategy company for business owners and creatives.