Sidebar Advisors
Sidebar Advisors Attorney Podcast explores the career moves, risks, and decisions that shape a life in law.
Hosted by Niraj Chhabra, financial planner and founder of Sidebar Advisors, the show features candid conversations with attorneys, legal leaders, and professionals connected to the legal industry.
Guests share how they navigated firm changes, leadership, business growth, career pivots, and the moments that pushed them to bet on themselves.
Each episode offers a practical look at the professional, personal, and financial choices attorneys face as their careers evolve.
Sidebar Advisors
Elie Honig: From Prosecutor to CNN’s Senior Legal Analyst
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Elie Honig — former federal prosecutor and now CNN’s senior legal analyst — has built a career that doesn’t follow the traditional legal path.
After more than a decade prosecuting major federal cases, Elie stepped into private practice and eventually into media, where he’s become a trusted voice translating complex legal issues for a national audience.
In this episode, he shares what that transition actually looked like, including the risks, tradeoffs, and moments of uncertainty along the way. We discuss the differences between life as a prosecutor and in private practice, how credibility is built outside the courtroom, and what it takes to communicate legal ideas in a way people actually understand.
It’s a candid conversation about career optionality, public-facing roles, and what lawyers can do with their skillset beyond the traditional path.