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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.

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What actually separates durable law firms from those that won’t make it through the next decade?

In this week's episode, Niraj Chhabra, CFP, MBA, CLTC, CRPC sits down with Bruce MacEwen, founder of Adam Smith, Esq., LLC, to unpack how law firm economics and structures are being reshaped in real time.

They discuss why the traditional business model is breaking down, how the industry is shifting toward a smaller group of elite firms, and what makes those firms fundamentally different.

A major theme throughout the conversation is AI — not as a distant threat, but as something that could quickly challenge the billable hour and reduce the need for large associate classes.

Bruce also shares:

• why many firms aren’t prepared for what’s coming
• how career paths for lawyers could change dramatically
• what happens when firms are forced to shrink
• and why the most valuable skill going forward may not be legal expertise

It’s a candid, forward-looking conversation for anyone thinking about the future of the legal industry.

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Negotiation, compensation, and advancement shape a lawyer’s career — but most attorneys are left to navigate those decisions without much transparency.

In this episode of the Sidebar Advisors Podcast, Niraj Chhabra sits down with Jill Cruz, executive coach, career strategist, and founder of JLC Consulting.

Before launching her practice, Jill spent years in senior HR and talent leadership roles inside law firms, advising on hiring, promotion, and compensation decisions. Today, she helps attorneys better understand their value, navigate career inflection points, and advocate for themselves more effectively.

They discuss what Jill learned from seeing these systems from the inside, why so many attorneys underestimate their leverage, how negotiation really starts long before an offer is made, and why mindset plays such a big role in whether people step into bigger opportunities.

They also talk about the structural and cultural barriers that continue to affect women and attorneys of color, and how Jill’s research has shaped the way she coaches today.

To learn more or connect with Jill:

Website: www.jlc.consulting
Email: jcruz@jlc.consulting

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Michelle Calcote King, Principal & President of Reputation Ink, joins the podcast to break down how professional services firms — especially law firms — can turn their expertise into real visibility, credibility, and growth.

At Reputation Ink, Michelle works with law and other B2B firms to help them become known authorities, earn meaningful media coverage, and build reputations that drive business development.

In this episode, we talk about why marketing should look different depending on firm size, how owned, earned, and paid media actually work together, and what clients are paying attention to today.

We also get into what separates firms that consistently generate opportunities from those that struggle to stand out — and how to build a strategy that creates long-term visibility, not just short-term activity.

If you’re thinking about how your firm shows up in the market, or why it’s not translating into growth, this is a practical conversation worth listening to.

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Trini Ross spent over 30 years in federal service, ultimately serving as the United States Attorney for the Western District of New York — overseeing major cases involving violent crime, civil rights, and public corruption.

In this conversation, she shares what that level of responsibility actually looks like day to day — from leading through high-profile, emotionally charged cases to managing a team under constant pressure and scrutiny.

We talk about how she built her career in public service, the mindset required to make difficult decisions, and the moments that forced her to step back and reassess.

She also reflects on leaving government, transitioning into private practice, and why she chose to build something new rather than follow a traditional path.

This is a candid look at leadership, responsibility, and what it means to do the job well when the stakes are real.

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In this episode of the Sidebar Advisors Podcast, Niraj Chhabra sits down with Kathryn Hatfield and Stefani Schwartz, the founding partners of Hatfield Schwartz, a women-owned labor and employment law firm that has grown steadily since launching during the uncertainty of COVID.

The two first met while practicing at a 60-lawyer firm and quickly realized they shared a similar vision for how a practice could operate — one grounded in partnership, autonomy, and strong client relationships.

They talk through what was happening in their lives when they made the decision to leave, how they prepared financially and personally for the transition, and how they’ve navigated the dynamics of building and scaling a firm together.

Along the way, Kathryn and Stefani discuss:

• How they prepared for the financial realities of launching a firm
• Why complementary strengths made their partnership work
• What they’ve learned about hiring and mentoring younger attorneys
• How they think about culture as their team continues to grow

Their story offers a candid look at what it actually takes to step away from stability and build a practice with intention.