Debra Whitson is a New York-based attorney, former prosecutor, family law mediator, and author of Divorce Like a Pro. In this conversation, she shares how mediation offers a healthier alternative to courtroom battles—and why divorce doesn’t have to destroy families. With decades of experience, Debra helps clients find clarity, peace, and dignity in even the most difficult transitions.
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Debra Whitson is a practicing attorney with nearly 30 years of experience in New York State. Before founding her virtual mediation practice, she worked as a real estate agent and marketing professional for IBM, then spent a decade as a criminal prosecutor, focusing on special victims cases. Today, she runs a private law firm and a virtual mediation company that specializes in prenuptial agreements, divorce, and family conflict resolution.
"In law, we're storytellers, first of all. I tell my clients that I'm there to tell their story to the court in the most compelling way and persuasive way possible," shares Debra Whitson on You Are A Lawyer.
Her experience spans corporate sales, courtroom advocacy, and now, collaborative mediation. With a strong commitment to helping families navigate difficult situations with dignity, Debra offers clients not just legal guidance, but emotional support, practical tools, and options beyond litigation.
Debra’s path to law school began at age 14, when a close family friend was murdered, and she nearly saw their killer walk free on a legal technicality. That early exposure to the justice system inspired her to become a prosecutor and fix what felt broken.
"At that point, I thought… there’s something wrong with the legal system, and it’s broken if that could happen," reflects Debra Whitson on Episode 75 of You Are a Lawyer.
She studied Human Development and Family Studies at Cornell, blending her interests in psychology and justice. That foundation continues to influence her work today, particularly her empathy-driven approach to law and mediation.
Debra’s career is proof that a JD can unlock many doors. After years as a government prosecutor, she moved into family law and now uses her skills as a mediator, coach, and author. The law, she says, offers broad opportunities to make an impact.
"There’s so many things you can do... no matter what your talents or interests are, you can find something to put your legal knowledge and degree to work," explains Debra Whitson, on this episode of You Are a Lawyer.
From courtroom advocacy to conflict resolution to writing books that reach the masses, Debra has built a multifaceted career grounded in legal expertise, but shaped by human connection.
Debra’s side hustle became a calling: she wrote Divorce Like a Pro to provide an accessible, empowering guide for anyone going through separation or family breakdown. The book distills her real-world experience into practical advice and it’s a resource she wishes more people had earlier.
“I wrote the book because I found myself saying the same things over and over again to clients… there are better ways.,” shares Debra Whitson in Episode 75 of You Are a Lawyer.
When she’s not running her practice or writing, Debra is a global advocate for women’s rights through Zonta International. Her passion for service, travel, and equity informs her entire professional ethos, from her client relationships to her vision of justice.
Debra is licensed to practice law in the state of New York.
This episode is produced by Skip The Boring Stuff, a podcast strategy company for business owners and creatives.
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