Benjamin Softness: Career Risk, Optionality, and Leaving a Dream Job
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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.