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

Daniel J. Hennessy took an unconventional path to law school. After years working in ministry, education, nonprofit leadership, and even serving in Rome with the Vatican Museums, Daniel enrolled in law school in his forties. Today, he works as in-house counsel for a national real estate development company, helping cities bring transformative projects to life while maintaining the family-focused life he and his wife envisioned. Lawyer Side HustlesOne of the themes throughout Daniel's story is embracing change. Before law school, he successfully built careers in entirely different fields. Rather than viewing those experiences as detours, he sees them as essential parts of the person and lawyer he became.“Don't be afraid to make the changes that you need to make, even if they seem really big and scary,” Daniel J. Hennessy expresses in Episode 250 of You Are a Lawyer.Daniel encourages law students and lawyers to focus less on the degree itself and more on understanding who they want to become. For him, success was not about following a predetermined path but about aligning his work with his values, relationships, and priorities. His journey serves as a reminder that law can be part of a meaningful life without becoming the entire identity. This episode is produced by Skip the Boring Stuff, a podcast strategy company for business owners and creatives.

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 DegreeAfter law school, SeNita’s career took an unexpected turn into eDiscovery and legal operations. Starting as a project attorney in document review, she gradually moved into litigation support, preservation coordination, and eventually legal operations roles embedded within large corporate environments.“This is an industry that I would stay in," explains SeNita McRae, on this episode of You Are a Lawyer.Her legal training allowed her to translate complex technical concepts for attorneys while also working directly with vendors and internal teams. SeNita’s experience shows how a JD can be a powerful credential even without bar licensure, particularly in operational, technology driven legal roles.This episode is produced by Skip the Boring Stuff, a podcast strategy company for business owners and creatives.

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 HustlesCasey 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, a podcast strategy company for business owners and creatives.

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 HustlesMichelle’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, 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 HustlesIn 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, a podcast strategy company for business owners and creatives.