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

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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.