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

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 mult...

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...

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 calle...

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...

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 paralle...

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 reflec...

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 brandi...

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...

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 h...

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, ...

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 ...

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 l...

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 b...

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 ...

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 ...

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

Acco...

Stephen Weisberg is a Detroit-based tax attorney who helps individuals and business owners resolve IRS controversies and tax-debt issues. In this episode, he shares how the 2008 recession launched him from corporate bankruptcy work into tax law, why most people wait too long to seek help, and what every lawyer (and taxpayer) should know before they get that letter from the IRS.

What You Can Do With a Law Degree

S...

Sergio Gregorio is a lawyer, podcast host, and creative who’s redefining what it means to have a legal career. In this conversation, he shares how growing up in Brooklyn, studying journalism, and working in federal service shaped his storytelling instincts, and why today’s lawyers must balance visibility, authenticity, and creativity in the digital world.

LAWYER SIDE HUSTLES

Sergio’s podcast, Frolic & Detour,...

Laura Terrell is an executive coach, general counsel, and former special assistant to the president who has built a career across government, private practice, and nonprofit leadership. In this episode, she shares how coaching helps lawyers advocate for themselves, embrace career pivots, and find clarity in uncertain times.

LAWYER SIDE HUSTLES

Alongside her legal work, Laura built a thriving executive coaching pr...