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

When Being a Lawyer No Longer Fits

Casey Berman is the founder of Leave Law Behind [https://go.leavelawbehind.com/home] 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 in 2008 by writing online about his own experience leaving law. What started as a personal, cathartic project eventually gained traction as lawyers around the world resonated with his story and reached out for support. “People started reaching out and saying, can you help me and I will pay you for your time,” Casey Berman expresses in Episode 230 of You Are a Lawyer. Today, Leave Law Behind is a robust platform offering resources, coaching, and guidance to lawyers exploring new paths. Casey’s work reflects how side projects, creativity, and experimentation can grow into meaningful careers, especially when lawyers allow themselves to try something new without attaching to a specific outcome. This episode is produced by Skip the Boring Stuff [https://www.skiptheboringstuff.com/], a podcast strategy company for business owners and creatives.

What Justice Looks Like When You Start With People

Bianca Van Heydoorn is the Executive Director of the Youth Sentencing and Reentry Project [https://www.ysrp.org/] 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 parallel to legal advocacy. She leads an organization committed to holistic legal support, positive youth development, and adolescent brain science, while also building sustainable infrastructure so the work can continue long term. “We should not be living to work but work should be an adjunct to our life,” Bianca Van Heydoorn expresses in Episode 229 of You Are a Lawyer. Bianca is also deeply intentional about leadership succession. She is actively working to prepare YSRP for a future executive director with lived experience of incarceration, reflecting her commitment to stewardship, shared power, and building institutions that last beyond any one leader. This episode is produced by Skip the Boring Stuff [https://www.skiptheboringstuff.com/], a podcast strategy company for business owners and creatives.

A Law Degree That Travels With You (October 2021)

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 reflection and loss. After being laid off from her corporate role and losing a close friend from law school unexpectedly, she reevaluated what she wanted from life. Travel, time, and freedom rose to the top, leading her to pursue teaching opportunities overseas. “Life is too short and you need to do what it is that you enjoy,” shares Michelle Words in Episode 35 of You Are a Lawyer. In addition to teaching, Michelle hosts the Flipping the Script podcast, where she helps women navigate change and embrace new chapters. Through podcasting, mentorship, and future plans to support women of color living abroad, her work continues to center empowerment, self authorship, and the courage to rewrite your own story. This episode is produced by Skip the Boring Stuff [https://www.skiptheboringstuff.com/], a podcast strategy company for business owners and creatives.

Soft Skills Every Lawyer Needs

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. “I wanted to make this book as efficient as possible in giving people practical, useful information,” David Sclar expresses in Episode 227 of You Are a Lawyer. 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 [https://www.skiptheboringstuff.com/], a podcast strategy company for business owners and creatives.

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.