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

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.

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 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.

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 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.

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 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.

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 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.

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 Hustles

Stephen'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.

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 Hustles

One 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.

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 Hustles

While 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.

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.

Anne Hamer is a top-rated family lawyer based in Nashville, Tennessee, whose path to success was anything but traditional. After years in corporate and plaintiff work, and even a decade as a stay-at-home mom, Anne returned to the courtroom with a new sense of purpose. In this episode, she shares how to change your legal career at any age, how her own divorce reshaped her understanding of family law, and why it's never too late to find work you love.

Anne Hamer's Background

Born and raised in Memphis, Anne Hamer has spent much of her life in Tennessee, with a detour to New York for law school at NYU. She laughs now about being the Southern student with the unmistakable accent that made her memorable in class but also taught her to adapt and connect with people from every background. After graduation, she weighed a fast-paced life in Manhattan against a more balanced one back home and chose Tennessee.

Anne's career began in corporate law at a large Nashville firm, where she handled IPOs and mergers but found herself uninspired by the work. After trying litigation, plaintiff work, and even stepping away from practice for 10 years to raise her children, she returned to law with a renewed sense of purpose. Today, she's one of Tennessee's most respected family lawyers, recognised by Super Lawyers for her compassionate yet strategic approach to high-conflict and high-asset divorce cases.

This episode is produced by Skip the Boring Stuff, a podcast strategy company for business owners and creatives.

Chelsea Jones is the founder of Chelsea Anne Media, a social media marketing agency that helps lawyers build personal brands that feel genuine, not forced. In this episode, she shares how one Upwork client turned into a thriving niche, why Instagram remains the most powerful platform for lawyers, and how authenticity can turn online visibility into real relationships.

How Lawyers Can Build a Brand That Works

According to Chelsea, building a personal brand starts with simplicity. Many lawyers assume branding requires elaborate campaigns, but she insists it begins with clarity; knowing who you are, what you stand for, and how you want to be known. From there, structure and consistency do the heavy lifting.

She advises lawyers to define four or five "content pillars" – the key themes or topics that represent their work and personality. Whether it's educational posts, personal stories, or motivational insights, these pillars help create focus and flow. For Chelsea, social media success isn't about perfection or virality. It's about visibility that feels aligned, authentic, and sustainable.

This episode is produced by Skip the Boring Stuff, a podcast strategy company for business owners and creatives.