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
Benjamin Softness of King & Spalding: Career Risk, Optionality, and Leaving a Dream Job
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For many attorneys, landing an in-house role at a company like Google feels like the destination. Benjamin Softness made the unusual decision to leave.
In this episode of the SideBar Advisors podcast, Benjamin, now a partner at King & Spalding, reflects on his path from private practice to Google and back again.
We discuss how in-house experience changes the way lawyers think, the tradeoffs between stability and long-term upside, and why career decisions become more complicated as family, ambition, and professional goals evolve.
We also talk about AI governance, regulatory risk, dual-lawyer households, and what Benjamin calls the "cranking years" — a period when many professionals are simultaneously building careers, raising families, and investing heavily in their future.