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

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...

Arivee Vargas is a first-generation Latina lawyer who went from Big Law litigation to in-house corporate leadership, all before pivoting to become an author, executive coach, and speaker. She shares the raw story of her identity crisis after having her first child and how that led her to develop the framework for her book, Your Time to Rise, focusing on aligning your career with your deepest values. This conversation is es...

Yladrea Drummond went from being “team no care about the law" to becoming a highly successful trial attorney and solo firm owner in Maryland and DC. She openly shares the grit required to get barred after a seven-year journey, how she transitioned her practice from family law to dominating criminal defense, and the non-negotiable value of complete autonomy that running her own firm provides. This conversation is a raw, hon...

Rob Levine is the founder of a multi-state law firm and an advocate for operational efficiency in legal practices. In this episode, he breaks down the vital role of case managers in improving law firm operations, building better client relationships, and increasing profitability. Whether you're a solo attorney or managing a growing team, this conversation will change how you think about delegation and workflow.

LAWYER S...

Debra Whitson is a New York-based attorney, former prosecutor, family law mediator, and author of Divorce Like a Pro. In this conversation, she shares how mediation offers a healthier alternative to courtroom battles—and why divorce doesn’t have to destroy families. With decades of experience, Debra helps clients find clarity, peace, and dignity in even the most difficult transitions.

LAWYER SIDE HUSTLES

Debra’s ...

Elise Holtzman left Big Law to raise her children, without a clear roadmap for what came next. Now she’s a leadership coach and founder of The Lawyer’s Edge, helping lawyers build confidence, develop business skills, and grow professionally. In this episode, Elise shares the mindset shifts that led her from practicing law to coaching those still in the field.

LAWYER SIDE HUSTLES

What began as a curiosity became a...

Lamia Rahman is a Forbes 30 Under 30 honoree, TEDx speaker, and co-founder of SEEKR, a tech startup creating wearable AI devices for the blind. In this inspiring episode, Lamia shares her journey from law school in Hong Kong to the front lines of legal tech, accessibility, and advocacy.

LAWYER SIDE HUSTLES

SEEKR began as a passion project and has since grown into a globally recognized AI startup. The company deve...

Daniel Rosenberg is a former prosecutor and defense attorney turned novelist who’s turning real-life courtroom experience into gripping legal thrillers. In this episode, he shares how his background in acting and law helped him build a successful writing career, why COVID was the creative catalyst he needed, and how his novels teach readers about the legal system, without getting lost in legalese.

LAWYER SIDE HUSTLES

Dan...

Candace Spencer is a legal consultant, mediator, and food justice advocate based in Washington, D.C. With a unique blend of legal insight and a lifelong passion for food, Candace has built a career at the intersection of environmental mediation, sustainable agriculture, and racial equity. In this episode, she shares how she’s using her legal background to support Black farmers, empower dairy-free living, and reshape the fo...