The Former Lawyer Podcast

You're a lawyer who's good at your job but something feels off. You're performing well, making good money, checking all the boxes that are supposed to matter. But there's a growing disconnect between who you are and what you're doing every day. Sound familiar? Ben Chiriboga lived this exact experience. Today he's an executive at Nexl, a legal tech company, but his leg...

You've taken CliftonStrengths . You've done the MBTI. Maybe you've worked through a few other career assessments too. You have pages of results about your strengths, your work style, your preferences. And you're still sitting there thinking, "Okay, but what am I supposed to do with my life?" Sound familiar? Sarah gets emails about this all the time. Lawyers who'v...

You've probably seen the headlines about major law firms pulling out of diversity programs and capitulating to executive orders. Sarah has been calling out these decisions and explaining why DEI isn't actually the problem in Biglaw . But what does someone who works specifically with diverse attorneys see when firms make these choices? Sarah recently talked with Bryson Malcolm , a legal r...

Experiencing lawyer burnout but telling yourself you shouldn't be struggling because you don't have kids or a partner? You're not alone. Many single and childless lawyers dismiss their burnout because they think others have it harder.  In this episode, Sarah addresses why lawyer burnout is valid regardless of your relationship status or family situation. She explains how lawyers par...

You're a senior associate who keeps telling yourself, "it'll get better when I make partner." But what if it doesn't? What if making partner actually makes things worse? In this episode, Sarah addresses the common misconception that partnership will solve the problems you hate about being a lawyer. She breaks down why so many lawyers who finally make partner realize they&a...

Dan Lemon thought Biglaw was the peak—until the job started crushing his mental health. What looked like success on paper was making his life unlivable.  In this conversation, Dan shares how he went from corporate litigation to a more meaningful career in family law. We talk about the lies lawyers are told about prestige, the realities of mental health in the profession, and what it actually takes...

Biglaw has a cowardice problem, and it’s more visible than ever. In this episode, Sarah Cottrell breaks down how toxic law firm culture grooms and rewards leaders who prioritize self-preservation over real change.  From the recent DEI rollbacks to everyday office dynamics, Sarah explains why cowardice thrives in Biglaw and how it impacts more than just the lawyers trapped inside these firms. If yo...

Sarah shares why she donates to The Legal Accountability Project , a nonprofit working to bring transparency to the judicial clerkship system.  She talks about the power judges hold, how law schools often ignore bad behavior, and why more information—not more prestige—is what law students really need.  If you've ever wondered why the legal profession protects its own at the expense of young l...

Reddit and Fishbowl can feel like the only places lawyers can be honest about how bad it really is. But even in these “safe” spaces, the lawyer bubble shows up.  In this episode, Sarah shares what she sees in these anonymous forums, why the advice often misses the mark, and how to recognize when toxic thinking is disguised as tough love. See show notes at formerlawyer.com/269 . I'm closing en...

Sarah is celebrating five years of The Former Lawyer Collab—and reflecting on what it’s taught her about helping lawyers leave the law. In this episode, she shares the behind-the-scenes of building the program, the patterns she’s seen in the hundreds of lawyers she’s worked with, and why the first step is always about knowing yourself better—not just updating your resume.  She also talks about the...

Lawyer and certified ADHD coach Annie Little returns to talk with Sarah about executive function, ADHD in the legal profession, and why so many lawyers struggle with time, organization, and burnout.  They break down how ADHD brains actually work, what interest-based motivation means, and how understanding your brain can help you build a career that works for you—not against you.  Whether you'...

Is DEI really the problem in Biglaw? Sarah doesn’t think so, and she’s not alone. In this episode, she breaks down why blaming diversity, equity, and inclusion for the profession’s longstanding issues is not only inaccurate, but dangerously out of touch.  If you’re tired of the gaslighting and performative change in legal spaces, this conversation will help you feel seen, and remind you that you’r...

When Laura Markham suddenly lost her husband, everything changed—including how she viewed her legal career. In this episode, Laura shares her path from real estate litigation to finding a more flexible, values-aligned role after loss. She talks about parenting through grief, rethinking the billable hour, and how the Collab helped her reconnect with what she actually wanted from work and life.  If...

Feeling overwhelmed, unmotivated, or like you're barely keeping up? You’re not alone. In this episode, Sarah shares a simple but powerful reframe for lawyers who are just trying to make it through right now. If you’ve caught yourself saying you’re doing “the bare minimum,” this conversation will help you shift that narrative and offer yourself more grace.  Whether you're thinking about l...

Are you questioning whether practicing law is really the right path for you? You're not alone—and you're not wrong for feeling that way. In this episode, Sarah talks about why so many lawyers feel stuck in careers that no longer fit, and why changing your mind isn't a failure—it's a sign of growth. If you've ever felt guilty for wanting something different, or worried that...

If you feel like all you do is complain about your job, you’re not alone. Many lawyers reach a point where they’re exhausted, not just by their work, but by how much they talk about how miserable it makes them. In this episode of The Former Lawyer Podcast , Sarah Cottrell addresses what happens when you reach that breaking point. She explains why you don’t have to wait until you can leave your job...

On today’s podcast, Sarah is chatting with a familiar guest who has been on the podcast several times. It’s her husband, Ed Cottrell . They met in law school and graduated at the same time.  Ed’s path took a different route than Sarah’s, and he now works in the tech field after leaving law. Today's conversation explores the common interest of many lawyers Sarah speaks with to explore jobs in...

Many lawyers contemplating leaving the profession assume the process is complicated. The reality? It’s actually very simple. But that doesn’t mean it’s easy.  In this episode of The Former Lawyer Podcast , Sarah Cottrell breaks down the difference between something being simple but difficult versus complicated but easy, and how this applies to leaving the law.  The truth is, figuring out what’s ne...

If you’re thinking about leaving the law but feel stuck, ask yourself this question. Who are you waiting for permission from? Many lawyers aren’t just worried about logistics. They feel like they need approval. They worry about how their family, friends, or partner will react. They feel the need to justify their decision and have others validate that leaving is the right move. But the only permiss...

Sarah Cottrell talks with Amisha DeYoung-Dominguez, a former lawyer who transitioned into public service, on this episode of The Former Lawyer Podcast . Amisha, now a congressional staffer, shares her winding journey through law school, legal aid, and government work—ultimately realizing that practicing law wasn’t the right fit.  Her story highlights the struggle many lawyers face, the pressure to...

Many former lawyers who stepped away from their careers to be stay-at-home parents eventually find themselves wondering how to re-enter the workforce—without going back to practicing law.  On this episode of The Former Lawyer Podcast , host Sarah Cottrell addresses this exact challenge, breaking down the key steps for making the transition while avoiding the pressure to return to legal practice. S...

In this re-released episode, Former Lawyer Collab members share the biggest surprises they’ve encountered while figuring out what’s next. From discovering unexpected support from other former lawyers to realizing just how much law school and legal practice shaped their identity, these insights reveal what happens when you step outside the legal bubble. If you're considering leaving the law, t...

In this re-released episode, Former Lawyer Collab members share the biggest myths they believed about leaving the law—myths that held them back from making a change. From the fear of being seen as a failure to the belief that legal work has to be miserable, these insights highlight how shifting your mindset can open up new possibilities. Sarah also shares an update on Former Lawyer’s commitment to...

This week, I'm re-releasing an episode featuring Former Lawyer Collab members sharing the simple yet transformative realizations that helped them move forward in their journey out of the law. From understanding their values to accepting that it’s okay to want something different, these stories highlight the small mindset shifts that can make a huge impact. Sarah also shares an update about Fo...

In this episode of The Former Lawyer Podcast , Sarah Cottrell gets real about why so many Millennials feel stuck in the pursuit of success. As an elder Millennial herself, she unpacks the pressures lawyers face to maintain a certain lifestyle or salary—pressures that often come from family expectations, societal norms, and internalized beliefs about what success “should” look like. Sarah shares pe...