Sidebar Advisors
A podcast exploring the careers, choices and strategies shaping today’s legal landscape.
Hosted by Niraj Chhabra, each episode explores the intersection of law, career growth, and financial decision-making. Through conversations on leadership, professional development and business building, we unpack the moments that define success.
For those thinking about what’s next or looking to grow and feel more fulfilled in their current role, these conversations offer a thoughtful look at building a meaningful and successful career in and around the legal world.
Sidebar Advisors
Benjamin Softness: 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.