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AI is making certain legal tasks faster, but who's actually benefiting from the efficiency? Steven Lerner, senior reporter at Law360, joins Niraj to examine the growing divide between law firms and their clients over AI, what it means for the billable hour, and how technology could reshape law firm profitability, competition, and the development of future attorneys.

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How do you know if you're in the wrong legal career or simply going through a difficult stretch? 

Elena Deutsch, founder of Women Interested in Leaving Law, joins Niraj to discuss why attorneys feel trapped by money, prestige, and professional identity, how to recognize when something needs to change, and why finding a more fulfilling career doesn't always mean leaving the practice of law.

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Sonia Lakhany never really wanted the traditional attorney lifestyle. Eventually, she stopped trying to make herself fit into it.

After four jobs in her first four years of practice, Sonia left firm life and began building a trademark practice around something she valued from the beginning: autonomy.

Today, she has built not only a successful trademark practice but Formal Education, where she teaches other attorneys how to develop trademark practices of their own.

Sonia joins Niraj Chhabra to discuss how she built a career that allows her to work from virtually anywhere, why she deliberately chose not to keep scaling her law firm simply because she could, personal branding, networking, and how teaching other attorneys unexpectedly became a second business.

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BigLaw is making more money than ever, but the traditional career path inside it is becoming much less predictable.

Joe Patrice, senior editor at Above the Law and co-host of Thinking Like a Lawyer, joins Niraj Chhabra to take a broader look at how the legal profession is changing and what those shifts could mean for attorneys building their careers today.

They discuss the rise of non-equity partnership, an increasingly aggressive lateral market, changing relationships between firms and clients, and why developing a portable book of business has become more complicated. Joe also shares his perspective on AI, including why its biggest long-term impact may not simply be replacing work, but changing how the profession trains its next generation of lawyers.

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What if rainmaking isn’t something attorneys are born knowing how to do? 

Elise Holtzman, founder and CEO of The Lawyer’s Edge, joins Niraj to discuss why business development is a learnable skill, how introverts can build business without changing who they are, and why law firms should teach attorneys about leadership, client development and firm economics much earlier in their careers.

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Being a good attorney matters. But when prospective clients are comparing lawyers with similar credentials, experience, and services, what actually makes one stand out?

Dennis DM Meador, founder of The Legal Podcast Network, joins Niraj Chhabra to discuss how the way people evaluate and choose attorneys has changed and why building trust before the first conversation has become increasingly important.

They discuss why attorneys should think beyond individual marketing tactics and build a more consistent ecosystem, how personality and authenticity can differentiate attorneys in a crowded market, and why Dennis believes “your competitive advantage is your humanity.”

Dennis also shares his perspective on social media, podcasting, creating content that actually sounds like you, and why consistency matters more than chasing the next marketing idea.

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What happens when the definition of a successful career starts to change? 

Tara Raghavan joins Niraj to talk about taking greater control of her career, learning business development, navigating change when it doesn’t come naturally, and how experiences outside of work reshaped what success means to her. 

A fitting conversation about growth, perspective, and what comes next for the 100th episode of the Sidebar Advisors Podcast. 

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What does it take to make good decisions when the stakes are high? Sarah Coyne, Partner at Ropes & Gray and former federal prosecutor, joins Niraj to discuss the judgment she developed handling complex investigations and high-profile cases, what changed when she moved to private practice, and why her definition of a successful legal career looks very different today. 

The conversation also gets personal, including motherhood, financial security, her experience with breast cancer, and how her definition of success has evolved from pursuing the next achievement to building a career that leaves room for the other parts of life that matter. 

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Thomas Chou’s career has rarely followed a predictable path.

Now Managing Partner of Morrison Foerster’s Los Angeles office, Thomas spent nearly two decades practicing in Shanghai and Hong Kong, building a corporate practice across the U.S. and Asia before eventually returning to Los Angeles.

In this episode, Thomas joins Niraj Chhabra to talk about the opportunities and unexpected circumstances that shaped that journey, from being trusted to run a major Yahoo transaction as a senior associate to moving overseas, building relationships during the dot-com crash, and taking on leadership roles he never originally planned to pursue.

They also discuss why some of Thomas’s earliest relationships still generate business 25 years later, what practicing in China taught him about client relationships, how attorneys can develop business before they’re expected to have a book, and why becoming a senior lawyer sometimes means knowing which clients and opportunities to walk away from.

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Nema Milaninia’s legal career has taken him from BigLaw to The Hague, inside one of the world’s largest technology companies, and ultimately back to private practice.

Now a partner at Freshfields, Nema advises companies and senior executives navigating complex investigations, regulatory matters, and high-stakes legal and reputational risk. Earlier in his career, he spent eight years as an international prosecutor working on cases involving genocide, war crimes, and crimes against humanity before later moving in-house at Alphabet.

In this episode, Nema joins Niraj Chhabra to discuss what those very different environments taught him about practicing law, making decisions under pressure, and viewing a problem from more than one perspective.