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Seth Rokosky, partner at Duane Morris LLP, didn’t build his career by following a straight line.

From choosing New York over D.C. to make a dual legal career work, to carving out an appellate practice where few opportunities existed, Seth shares how long-term thinking, tradeoffs, and persistence shaped his path.

In this episode, we talk about how he approached career decisions alongside his wife, what it really takes to build a niche practice from the ground up, and how his background in competitive chess influences the way he thinks about strategy, risk, and decision-making.

A practical conversation on planning ahead, adapting when things don’t go as expected, and building a career that actually fits your life.

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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.

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Kenneth Nunnenkamp, partner at Blank Rome LLP, has built a career that certainly didn’t follow a straight line.

Early on, he made a high-risk move leaving big law for an in-house role at a startup, trading stability for equity and opportunity. When it didn’t play out as expected, he had to recalibrate — eventually finding his way back to private practice with a clearer perspective on risk, value, and what actually matters over the long term.

In this conversation, Ken shares how those decisions shaped his career, from his time as a Marine Corps JAG officer to his work today in national security, cross-border matters, and anti–money laundering.

He also reflects on how priorities shift over time, why not every opportunity is worth taking, and how success becomes less about titles and more about doing work that’s genuinely engaging.

A grounded look at career decisions, trade-offs, and building something that lasts.