A judge looked at Jill Switzer's male client and assumed he was the lawyer. Jill, the person actually representing him, was mistaken for a social worker.

For someone approaching 50 years in the profession, it is one of many experiences that explain her willingness to say what she thinks. When Neal Goldstein asks whether her career gave her the freedom to speak openly, Jill answers: "I speak whether I have freedom or not."

Known for her Old Lady Lawyer column at Above the Law, Jill joins Neal to discuss being underestimated, the stigma attached to a law school name, and the difference between confidence and an ego that prevents a lawyer from asking for help.

She also remembers a newsroom mentor who shared everything he knew, describes the micromanagement that drove her to leave a job, and questions why lawyers risk their professional standing for a moment of satisfaction on social media.

Their conversation turns to the relationships that make difficult work possible, why a complicated question sometimes requires a phone call, and what Jill is still figuring out as she considers her next chapter. It closes with a remembrance of a longtime friend whose determination and generosity left a lasting mark on her life.

Read Jill Switzer's columns at Above the Law.

Follow or subscribe to That One Lawyer Podcast for more conversations with Neal Goldstein about relationships, identity, and the human side of practicing law.

Find Jill Switzer's Old Lady Lawyer columns at Above the Law. https://abovethelaw.com/author/jillswitzer/

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Emma Lilley was told that going in-house early would damage her legal career. But the conventional route already felt like a place where she didn't belong.

Growing up in a working-class family in Stoke-on-Trent, Emma had no family roadmap into law. She originally wanted to study music. When that plan fell through, an available university place led her to a law degree, where she found herself trying to understand things other students seemed to know already.

In this conversation with Neal Goldstein, the solicitor behind In-house Potter and founder of InHOCO shares how discovering in-house legal work changed her relationship with the profession. She talks about the criticism she faced, the people who took a chance on her, and why her upbringing became one of her greatest strengths.

There is also an unexpected encounter with Jimmy Carr in Starbucks before a legal exam, a candid discussion about AI and junior lawyer training, and a closer look at the human skills that help lawyers make a difference inside a business.

Emma explains how her community supported her campaign for regional solicitor admission ceremonies and why making those milestones accessible matters to families. At the end, she remembers the grandfather she wishes could have seen what that campaign achieved.

Along the way, Neal and Emma explore the difference between pursuing a career that earns other people's approval and building one that feels right to you.

Find Emma Lilley on LinkedIn and Instagram at @emmalilleylaw, and explore In-house Potter and InHOCO.

Follow or subscribe to That One Lawyer Podcast for more honest conversations about the people, relationships, and decisions that shape a life in law.

Have you ever felt you had to become someone else to fit in as a lawyer?

In this selected replay from an earlier episode of That One Lawyer Podcast, Neal Goldstein revisits his conversation with corporate lawyer Lani Medina about the pressure to fit a professional mold and the strengths that pressure can cause you to overlook.

Lani, a Puerto Rican attorney raised in the Bronx and the first lawyer in her family, recalls feeling out of place at Columbia. She talks about being an introvert in an extroverted world, learning to value her ability to listen, and making herself visible so younger lawyers can see another version of what a corporate attorney can look like.

Their conversation explores client trust, bringing a human touch to corporate law, and handling difficult people with kindness and professionalism. Lani also shares why she speaks openly about OCD and anxiety, despite uncertainty about how those disclosures will be received.

They close by discussing whether lawyers can embrace artificial intelligence while preserving their authenticity, judgment, and responsibility to clients.

Follow or subscribe to That One Lawyer Podcast for more honest conversations about the human side of being a lawyer.

In Part 2 of Neal Goldstein's conversation with Brian Cuban, the focus turns to the lawyer Brian became while his personal life was unraveling.

Brian speaks candidly about his years practicing personal injury law and why he has described himself as an "ambulance chaser." He and Neal discuss the referral relationships, chiropractors, settlements and ethical questions surrounding that period of his career, without pretending the past was cleaner than it was.

Their conversation also explores addiction and mental health in the legal profession, the role of lawyers assistance programs, and the complicated reality of lawyers who may continue functioning professionally while struggling privately.

Brian also discusses his transition into writing and his novel The Ambulance Chaser, which draws from a professional world he experienced firsthand.

The conversation ultimately returns to connection, recovery and what it means to show up for another lawyer who may be struggling. Brian closes with a deeply personal story about a lawyer he knew and what he wishes he could say to him today.

Follow or subscribe to That One Lawyer Podcast for conversations about the people, relationships and experiences behind the practice of law.

Brian Cuban - https://briancuban.com/

Brian Cuban - LI - https://www.linkedin.com/in/briancuban/

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Brian Cuban's story did not begin with recovery, writing, or being Mark Cuban's brother. It began with a kid in Pittsburgh struggling with shame, bullying, body image, and an overwhelming desire to belong.

In Part One of this two-part conversation, Brian talks about the childhood experiences that shaped his identity, the loneliness he carried to Penn State, the eating disorder and drinking that followed him into law school, and why he became a lawyer even though he never really wanted to practice law.

Brian also recounts one of the darkest moments of his addiction and the role his brothers, Jeff and Mark, played when his life was in danger.

This is a conversation about the things people carry with them long before anyone else can see the consequences, and about the family connections that can matter when everything else begins to disappear.

Follow or subscribe to That One Lawyer Podcast so you don't miss Part Two of Neal Goldstein's conversation with Brian Cuban.

When does the relationship with a client end?

For many lawyers, the practical answer is when the case ends. Neal Goldstein sees it differently.

In this episode, Neal talks about treating clients as more than transactions and why some of the most important relationships in a legal career continue long after the immediate legal work is finished.

He discusses calling clients before they call you, staying connected without an agenda, listening instead of self-promoting, building genuine relationships with referring attorneys, and learning how to have conversations with people from every walk of life.

Neal also looks back at his early days practicing law, when conversations with taxi drivers and other people he encountered in everyday life unexpectedly became sources of relationships and referrals.

The episode closes with a deeply personal example. More than a year after resolving a client's case, Neal learned that her husband had died. He called her and took her to lunch. There was no case to discuss and no business objective. There was simply a person he'd developed a relationship with who was going through a difficult time.

This conversation was originally recorded several years ago for a different project, but the central idea remains remarkably relevant: being a lawyer is about more than what happens while a file is open.

Follow or subscribe to That One Lawyer Podcast for more conversations about the relationships, decisions, experiences, and human side of building a life in the law.

Bert Neuborne entered Cornell at 16 expecting to become a doctor. Organic chemistry helped change those plans. A few years later, after Harvard Law School and three years on Wall Street, he took a one-year leave to work at the Civil Liberties Union.

On his second day, Muhammad Ali walked through the door looking for legal help in his fight against the draft.

Neuborne knew he had found his work.

In Part 1 of his conversation with Neal Goldstein, Neuborne looks back at practicing civil liberties law during the extraordinary legal and cultural changes of the 1960s and 1970s. He discusses knowing civil rights worker Michael Schwerner, working alongside figures including Ruth Bader Ginsburg, and the period when constitutional lawyers could sometimes watch arguments that began around a lunch table become real changes in the law.

He also tells the remarkable story of representing B-52 pilots and bombardiers who refused to continue bombing Cambodia without understanding why they were being ordered to do it. The case ultimately sent Neuborne across the country in search of Justice William O. Douglas and produced a temporary injunction stopping the bombing.

Neuborne also explains the constitutional philosophy behind Madison's Music and why he believes the First Amendment makes more sense when its protections are read as parts of one coherent democratic story.

It is a conversation about risk, constitutional power, finding meaningful work, and what one lawyer learned from spending decades testing the boundaries of American civil liberties.

Follow or subscribe to That One Lawyer Podcast for Part 2 of Neal Goldstein's conversation with Bert Neuborne.