Sydney Siegel grew up in Beverly Hills. Today, as a public defender in Brooklyn, she represents people whose lives often look nothing like hers. She doesn't try to hide that difference.

In this episode of That One Lawyer Podcast, Sydney joins Neal Goldstein to discuss earning clients' trust without pretending to share their experiences. She explains how meeting the people behind criminal complaints changed her assumptions about defense work, and how a conversation with a homeless client challenged her own desire for more.

Sydney also shares the story behind a transportation project she developed during an internship in Los Angeles. After seeing a man struggle to reach court, she pitched Uber on providing ride vouchers for public defender clients. The project grew from a simple observation: people sometimes need practical help before they can meet the demands of a criminal case.

From Division I track at Columbia to Brooklyn Law School, Survivor, and The Challenge, Sydney has pursued a life with several competing ambitions. She talks about what reality television taught her about confidence, how those lessons show up in negotiations with prosecutors, and why she wants her legal work to remain at the center of her professional identity.

The conversation also includes her father's example of enjoying a legal career while being present at home, the importance of courthouse relationships, and her account of workplace antisemitism after October 7.

Follow or subscribe to That One Lawyer Podcast for more candid conversations with Neal Goldstein about law, relationships, identity, and the lives we build along the way.

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Sydney Segal- IG - https://www.instagram.com/queensydney?obrf=MTY5bXVzejB4Zmp6Zw== LI - https://www.linkedin.com/in/sydney-segal-144b66100/

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/

Subscribe to That One Lawyer Podcast for candid conversations about the people behind the profession, the relationships that shape a career, and what it means to build a life while practicing law. https://www.youtube.com/@ThatOneLawyerPod

Hosted by Neal Goldstein. IG: https://www.instagram.com/nealgoldsteinlaw/

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LinkedIn: https://www.linkedin.com/in/nealagoldsteinlaw

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.