When Being a Lawyer No Longer Fits feat. Casey Berman
- Kyla Denanyoh
- 6 hours ago
- 3 min read
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.
About This Episode
Background
Casey Berman was born and raised in San Francisco and came of age professionally during the dot-com boom of the 1990s. After law school, he worked as in-house counsel at a technology company, where he handled software licensing and enjoyed many aspects of the role, including the people and the culture.
“The world needs lawyers. We need good lawyers who care about the clients. It just was not a fit for me," shares Casey Berman on You Are A Lawyer.
Over time, Casey realized that traditional legal work did not align with his strengths or interests. He wanted work that felt more proactive, creative, and expansive. Rather than forcing himself to stay in a role that did not fit, he began to explore what life and work could look like beyond law, even when that choice felt uncertain and unconventional.
Why Law School
Casey’s decision to attend law school was shaped by expectations and circumstance rather than a deep personal calling. Like many lawyers, he entered the profession without fully understanding what day-to-day legal work would actually involve, or how closely it would align with who he was.
“Many of us went to law school for good reasons, and many of us did not. I was one of those who just kind of went to make my parents happy," explains Casey Berman on Episode 230 of You Are a Lawyer.
After practicing, Casey recognized that the issue was not competence or effort, but alignment. He saw that changing practice areas or environments might work for some lawyers, but for others, including himself, the work itself was the mismatch. That realization became foundational to how he now supports lawyers navigating similar questions.
What Can You Do with a Law Degree
Leaving legal practice did not mean abandoning legal skills. Casey emphasizes that lawyers carry portable, transferable strengths into every role they take on, including writing, strategic thinking, risk mitigation, and being the adult in the room.
“You are really not leaving the law," shares Casey Berman on Episode 230 of You Are a Lawyer.
Through Leave Law Behind, Casey helps lawyers see how their skills translate into roles across operations, compliance, recruiting, sales, consulting, and entrepreneurship. His work reframes the law degree not as a constraint, but as a powerful foundation that remains valuable in many different containers.
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.
About Casey Berman
Casey is licensed to practice in the State of California.