The Former Lawyer Podcast

On paper, Amy Terwilliger's life as a lawyer looked great. Partner at a regional firm in Florida. Deputy general counsel. Thirteen years of business litigation. Married with two kids. And the whole time, a constant restless feeling she could not shake.What Amy eventually figured out was that she was living somebody else's perfect life. The things that mattered to her, her values, the way she thought, and who she actually was as a person were not showing up in the life she was actually living.In this episode of The Former Lawyer Podcast, Sarah Cottrell talks with Amy about what it looked like to be a Biglaw partner whose values did not match her job, why being a free thinker is not rewarded at a big firm, what finally moved her to make a change, and how she ended up working as a sex and relationship coach while still practicing law on her own terms.1:34 - Why Amy went to law school after restaurant management and the LSAT-as-decision-maker pattern2:33 - Wanting to help people through law and how recruiting funneled her into business litigation instead4:51 - The conveyor belt and why the realities of practice diverge from what brings people to law school7:48 - Why being a free thinker is not rewarded at a big firm8:48 - On paper everything looked perfect, partner, deputy general counsel, two kids, and the constant restless feeling underneath9:54 - Neurodivergence, the strong sense of justice, and why these traits do not get rewarded in big firms13:16 - Where Amy's values clashed with the actual work of business litigation18:06 - Why "just don't care" is not actually possible when someone is being rude and disrespectful20:19 - Pleasure as the body's antidote to stress and how it resets the nervous system22:43 - The early seed of wanting to be a sex coach and why Amy tucked it away for years25:38 - The reactions Amy got from colleagues, friends, and family when leaving Biglaw29:16 - You do not have to leave law entirely, you can find a way to practice that aligns with your values33:22 - What Amy recommends if you are curious about coaching as a career34:00 - What sex and relationship coaching actually is and who Amy works withMentioned In Leaving Biglaw to Become a Sex and Relationship Coach with Amy TerwilligerAmy Terwilliger's Website | LinktreeAmy Terwilliger on Instagram (@millennialdrruth)First Steps to Leaving the LawThe Former Lawyer Collaborative

If you're thinking about leaving the law, there's a good chance you've asked yourself some version of this question. Am I justified in doing this? You already know the environment isn't good for you. You already know something needs to change. But there's a sense that you need some kind of external sign-off before you can actually go, and until that shows up, you keep waiting.The waiting itself is part of what's keeping you there. The need to feel justified is almost always external, and it's often the same pattern that got you into law in the first place. Looking outside yourself for confirmation that you're on the right path, instead of trusting what you already know about your own experience.In this episode of The Former Lawyer Podcast, Sarah Cottrell talks about why so many lawyers ask whether they're justified in leaving, where that question actually comes from, and what it costs you to keep waiting for someone else to validate what you already feel. Sarah also covers why this is a skill worth building before you figure out what's next and where therapy fits into the work of untangling it.0:29 - The question that comes up most often when lawyers think about leaving the law1:02 - Why there is always someone who has it worse and why that keeps lawyers stuck1:55 - Why the struggle to feel justified in leaving is fundamentally external2:35 - "Am I justified in leaving" is really a question about who gets to say3:55 - Why so many lawyers cannot trust their own experience4:38 - What you actually need to access to find something better5:57 - Why this needs to be your choice and not something you wait for permission to do6:32 - The skill you are going to be developing as you move out of the law7:56 - What it tells Sarah when she hears lawyers asking if they are justified in leavingMentioned In Trying to Justify Leaving Law Is What’s Keeping You ThereFirst Steps to Leaving the LawThe Former Lawyer Collaborative

There are two very different situations a lawyer can be in when they start thinking about leaving. One is a job that is actively damaging their mental, physical, and emotional health. The other is a job that is just not the long-term answer. What you do to tolerate either one while you're preparing to leave is going to look pretty different.The lawyers who come to Sarah after making a move that did not work out are usually the ones who waited until they were close to leaving to start thinking about what they actually wanted to do next. By then, there is not much time left for the reflection that process requires.In this episode of The Former Lawyer Podcast, Sarah Cottrell talks about how to tell which situation you're in, why a bridge job is often the right move if your environment is genuinely toxic, and what lawyers in less extreme situations can be doing right now to make the time they're still there feel useful instead of stuck.0:56 - What a bridge job actually does when you're in a toxic environment2:23 - Why "tolerating" your job never means staying somewhere that's damaging you3:24 - Being realistic about your timeline and what the work actually looks like4:11 - How long the Collab framework typically takes when you give it a couple hours a week5:16 - Why the day you can leave is not the day to start figuring out what's next6:14 - What makes tolerating your job easier while you're preparing to leave7:40 - What to do if you see yourself leaving eventually but not soon9:15 - Why giving yourself time instead of rushing is one of the best uses of your time in a lawyer jobMentioned In Tolerating Your Lawyer Job While You're Preparing to LeaveDo You Need a Bridge Job? Key Questions for Lawyers in TransitionFirst Steps to Leaving the LawThe Former Lawyer Collaborative

Legal tech comes up constantly when lawyers are thinking about leaving practice. It's legal adjacent, the field is growing, and there seem to be a lot of jobs. But when lawyers actually try to make a move, they usually don't know where to start. The roles aren't standardized, the titles don't mean the same thing across companies, and it's hard to know where a legal background even fits in.Ben Chiriboga figured this out the hard way. He spent two years after leaving practice chasing legal tech roles without any real direction, burned through his savings, and eventually found his path, going on to become a founding team member of a legal tech startup. Now he runs Reframe Lawyer, a platform built specifically to help lawyers move into legal tech and AI careers.In this episode of The Former Lawyer Podcast, Sarah Cottrell talks with Ben about the three main career tracks available to lawyers in legal tech and AI, why a JD is a bigger competitive advantage than most lawyers think, and why figuring out who you are and what you want has to happen before anything else.0:52 - Ben Chiriboga on founding Reframe Lawyer and his path from practice to legal tech2:27 - Why legal tech keeps coming up for lawyers who want to leave practice4:07 - No agreed terms, no standardized titles, and what that means for your job search4:45 - You're not alone in being confused about where to start in legal tech9:17 - The three main career paths in legal tech and AI for lawyers leaving practice11:41 - Product roles and why lawyers are better positioned for them than they think13:00 - Go-to-market roles and why a JD is a competitive advantage in sales conversations13:48 - Why operations roles are booming inside legal tech companies right now15:13 - JD required vs. JD preferred and what your legal background signals to employers17:55 - Why lawyers automatically rank in the top 1% of candidates for legal tech jobs24:52 - Why lawyers try to execute before they know their objective30:25 - Why applying for every legal tech role is a recipe for madness35:37 - How to speak to a role you've never held and start building proof of interest39:38 - Why updating your resume is the last thing you should do42:24 - Ben's closing take on legal tech as a viable career path for lawyers ready to make a moveMentioned In How to Break Into Legal Tech and AI as a Lawyer with Ben ChiribogaReframe Lawyer | Ben Chiriboga on LinkedInEscaping Lawyer Burnout for Legal Tech with Ben ChiribogaHow To Revise Your Resumé For A Non-Legal JobFrom Biglaw to Legal Tech with Alex SuThe Claude-Native Law Firm by Zack ShapiroFirst Steps to Leaving the LawThe Former Lawyer Collaborative

Responsibility is one of the things that makes lawyers good at their jobs. It also shows up, over and over, as one of the things that makes it hardest for them to leave. Not because they don't want to go, but because leaving means someone else has to pick up the work. And for a lawyer who is wired around responsibility, that can feel like something they're just not willing to do.What Sarah sees with her clients is that the sense of responsibility doesn't stay proportional. It ends up putting so much weight on what other people might have to deal with that a lawyer's own mental, physical, and emotional well-being barely registers in the calculation. Toxic environments are especially good at making this worse.In this episode of The Former Lawyer Podcast, Sarah Cottrell talks about why responsibility shows up so consistently in her clients' assessment results, what happens when it becomes overdeveloped, and why it makes it hard for lawyers to even let themselves think about leaving.1:28 - How responsibility shows up in CliftonStrengths, VIA, and the Enneagram3:01 - What Sarah sees with lawyers whose jobs aren't good for them4:26 - Why highly responsible lawyers struggle to give themselves permission to even think about leaving5:07 - What an overdeveloped sense of responsibility actually means6:03 - How toxic environments exploit lawyers who are highly responsible7:28 - The faulty logic that keeps highly responsible lawyers from cutting themselves any slack9:18 - Why it matters to know if responsibility is one of your top characteristicsMentioned In How an Overdeveloped Sense of Responsibility Keeps Lawyers StuckFirst Steps to Leaving the LawThe Former Lawyer Collaborative

For a lot of lawyers, hearing "just do your best" as a kid didn't feel reassuring. It felt like a requirement to give every ounce of everything they had until there was literally nothing left.That's not incidental. The kind of person who interprets "do your best" that way is often exactly the kind of person who ends up becoming a lawyer. And that standard follows them.In this episode of The Former Lawyer Podcast, Sarah Cottrell talks about what that standard is actually costing lawyers who want to make a change, and why doing B-minus work might be worth considering.1:00 - What "do your best" actually means if you're wired like a lawyer1:56 - Why caring about doing good work makes this harder3:56 - The B-minus work concept and why it matters4:37 - Why this is harder for lawyers from marginalized communities5:04 - How loosening that standard makes space for other things5:24 - Why therapy is worth considering if this resonatesMentioned in What Doing Your Best Is Costing You as a LawyerFirst Steps to Leaving the LawThe Former Lawyer Collaborative

Lawyers thinking about leaving often get stuck on a question that feels practical but actually keeps them waiting longer than they need to. Do I need to quit my job before I start figuring out what I want to do instead? It sounds responsible, but for most people, it's part of what keeps them in a holding pattern.Sarah Cottrell frequently gets this question from lawyers considering The Former Lawyer Collaborative, and her answer might change how you think about the timing of your next move. She explains why the assumption that you need to be "ready" before you start often works against you, and what she's seen actually happen when people stop waiting.In this episode of The Former Lawyer Podcast, Sarah talks about why she built The Collab to fit inside the life of a working lawyer, what the time commitment really looks like, and why the lawyers who start before they feel ready often surprise themselves.0:28 - The practical question lawyers keep asking before joining The Collab0:53 - What The Former Lawyer Collaborative actually is and how it works1:38 - Do you need to quit your job before starting this process2:25 - How people find The Collab and when they typically join2:57 - Why less pressure to leave can actually mean faster progress3:29 - The time commitment question and what "a couple hours a week" really gets you5:15 - Other reasons you might quit, and why most people in The Collab don't6:23 - Why The Collab was designed to fit inside a lawyer's life7:06 - How to join and where to find more infoMentioned In You Don't Have to Quit Your Job to Start Leaving LawFive Years of Helping Lawyers Leave the Law inside The Former Lawyer CollaborativeFirst Steps to Leaving the LawThe Former Lawyer Collaborative

Lawyers who are unhappy at work often tell themselves they'll feel things later. When they retire, maybe. The sense is that feeling the full weight of what's happening would make it impossible to keep functioning, so the feelings get pushed down and the grinding continues.The problem is that feelings aren't actually optional. The physical sensations that come with emotional states are nervous system responses, not choices. Suppressing them doesn't make them go away. They get smashed down until the nervous system forces the issue, regardless.In this episode of The Former Lawyer Podcast, Sarah Cottrell talks about why lawyers operate as though their feelings are optional, where that belief comes from, and what it costs them over time. She covers how to start noticing whether this is happening to you, why irritation at other people's feelings is a flag worth paying attention to, and why therapy is often the most effective place to start unraveling something that didn't develop overnight.0:53 - Why so many lawyers believe their feelings are optional2:13 - Why feelings are nervous system responses and not actually a choice2:48 - Where the belief that feelings are optional comes from and how it gets reinforced4:16 - "I'll feel things when I retire" and why this is probably how you're functioning even if you'd never say it out loud6:19 - What happens when the nervous system finally says no and why it goes the way it does7:21 - How to notice if you're treating your feelings as optional and why irritation at other people's feelings is a flag8:44 - Why therapy is especially useful here and what to do if this resonatedMentioned In Why Lawyers Think Feelings Are Optional and What It Costs ThemWhy High-Achieving Lawyers Stay in Jobs That Are Hurting ThemFirst Steps to Leaving the LawThe Former Lawyer Collaborative

Being good at your job and being in the right job are not the same thing. For lawyers who are high achievers, that distinction can be almost impossible to see when every external signal, strong reviews, steady advancement, a reputation for getting things done, is telling you that you must be in the right place.That disconnect often has roots in neurodiversity or trauma history. Both can produce someone who is exceptionally good at pushing through, sublimating their own needs, and performing under conditions that are genuinely harmful to their mental, physical, and emotional health. And because the external picture looks fine, it can be very hard to see.In this episode of The Former Lawyer Podcast, Sarah Cottrell walks through why this happens, how ADHD, PTSD, and CPTSD can all factor in, why the belief that achievement equals worth makes it so hard to let go even when something is hurting you, and why therapy is such an important part of unraveling it.0:30 - Why lawyers who are high achievers can be good at something that is not sustainable for them1:28 - The "I can do this so I should do this" trap and why external markers are not the whole picture3:24 - How ADHD brains create urgency to initiate tasks and what that costs your nervous system4:28 - Why doing well as a lawyer can feel like proof you are meant to stay5:16 - How PTSD and CPTSD factor in and why so many lawyers are highly adapted to deal with difficult conditions6:43 - How perfectionism develops as a survival strategy and why it follows lawyers into their careers7:41 - The belief that you are only valuable when you are achieving and why it makes it so hard to leave8:36 - Why therapy matters so much for lawyers who are high achievers thinking about leaving10:01 - What Sarah wants you to know if the job is crushing you but you feel like you have to stayMentioned In Why High-Achieving Lawyers Stay in Jobs That Are Hurting ThemSigns of Malignant Narcissism in the Legal Profession [TFLP 127]Does Being a Lawyer Lead to ADHD? Unpacking the Relationship with Annie Little [TFLP206]First Steps to Leaving the LawThe Former Lawyer Collaborative

Lawyers are, as a group, highly responsible, hard on themselves, and convinced they should be able to handle more than anyone else around them. That combination does not just make for a stressful career. It makes it genuinely difficult to acknowledge that something is wrong, let alone do anything about it.That is where perfectionism becomes a trap. When you hold yourself to a standard you would never apply to anyone else, leaving starts to feel like weakness, or like you are abandoning the people around you. The result is that lawyers who are deeply miserable keep going, often until their body forces the issue for them.In this episode of The Former Lawyer Podcast, Sarah Cottrell breaks down why this kind of perfectionism is more common than most lawyers want to admit, where it comes from, and why recognizing it is one of the most important things you can do if you are thinking about leaving law.1:03 — Why being highly responsible and hard on yourself feels like humility but isn't2:04 — Why holding yourself to a higher standard than everyone else is actually about ego3:02 — The vacuum-sealed pod problem and why "everyone makes mistakes" doesn't feel true about you6:01 — How this mindset makes it hard to leave, from feeling like you're abandoning people to telling yourself you're just weak7:35 — How to know if you're this person and what it actually costs you9:17 — Why therapy is worth bringing this up in, even if Sarah's framing annoys you10:31 — What happens when lawyers don't let themselves leave until their body forces the issue11:48 — What to actually sit with if this episode resonatedMentioned In The Perfectionist Trap That Makes It Hard to Leave LawFirst Steps to Leaving the Law The Former Lawyer Collaborative

For lawyers who know they are unhappy but are not ready to make any real moves yet, the waiting period can feel like dead time. There are things you can be doing right now, though, that will set you up for success when you are ready to go through the process of figuring out what comes next.One of those things is reconnecting with a hobby. Not in a hardcore, train-for-a-marathon way, but in a small, low-stakes way that starts to rebuild the muscle of knowing what you actually like and what actually feels good to you. That skill, knowing what you want and acting on it, is one of the most important things you can develop when it comes time to figure out what your next career looks like.In this episode of The Former Lawyer Podcast, Sarah Cottrell walks through why hobbies matter more than most unhappy lawyers would expect, how to think about starting small, and why reconnecting with the things that bring you joy makes it easier to leave when you are ready.0:02 — What you can do right now to set yourself up for leaving law, even before you're ready0:56 — Why hobbies matter for lawyers thinking about a career change1:11 — How work crowds out everything else and why that's so common for unhappy lawyers1:54 — The grocery and dry cleaning hobby era (you are not alone)2:23 — How reconnecting with what you like helps you figure out what career actually fits you3:25 — Why this works even if you're not close to leaving and don not have much time3:33 — What starting small actually looks like and why going all in is not the point6:00 — Rituals, rhythms, and reminding yourself you are a person and not a machine7:25 — The bonus benefit of hobbies that involve other people when you are thinking about leaving law8:27 — The real skill you are building and why it matters for your lawyer career changeMentioned In Why Unhappy Lawyers Should Pick Up a Hobby Before They're Ready to LeaveFirst Steps to Leaving the Law The Former Lawyer Collaborative

A lot of people end up going to law school without ever really asking themselves whether it's what they want to do.The questions in this episode are the real questions you should be asking yourself if you're considering law school. And if you're already a lawyer, these same questions will be helpful for you too.See show notes at formerlawyer.com/297

2026 is kicking a lot of people's asses, including Sarah's. She gets into what the last few weeks have actually looked like, and shares the reminder she keeps coming back to. Hard things feel hard because they are hard. Not because you're doing anything wrong. She also talks about what Former Lawyer stands for, where your money goes if you work with her, and why she will probably never stop telling you to go to therapy.See show notes at formerlawyer.com/296

When lawyers look back at why they entered the profession, they often find the answer is less about a lifelong passion and more about a lack of other plans. Dan Branagan, a former bankruptcy associate turned data analyst, describes his journey into law as a classic example of the "conveyor belt" metaphor. As a liberal arts major with an interest in history and political science, law school seemed like the next logical step that promised both prestige and a high salary. It wasn't until he was working through the self-examination process in the Collab that he realized how passive he had been in his own career path.The disillusionment began during law school, where he first encountered the all-consuming culture of Biglaw. While his peers seemed 100% focused on their identity as attorneys, Dan realized early on that having a life outside of work was essential to his well-being. He found that the "gifted kid" track often conditions people to ignore their own needs in favor of high expectations, but he was never able to shake the feeling that something was internally off.See show notes at formerlawyer.com/248

When Sarah looks back at her time in practice, she can see a pattern that shows up for almost every lawyer who thinks about leaving the law. She would have a kernel of interest in a career path outside of the law, but her brain would immediately start telling her why it was a bad fit. It became an instant cycle of negativity.If you find yourself doing this, you are "lawyering yourself". You are taking an idea and prematurely deciding it is impossible before you have actually spent any time looking into it. You start worrying about finances, your perceived lack of skills, or what other people might think. Essentially, you are shutting down the process before it even begins.See show notes at formerlawyer.com/235

Maybe you've thought about it. You love books, you love reading, and somewhere in the back of your mind, you've wondered if there's a way to turn that passion into a career that uses your legal skills without actually practicing law.Lilly Ghahremani knew on day one of law school that it wasn't the right fit. She called her mom from a pay phone and said she'd made a mistake. Her mom convinced her to finish the semester, then the year, then the whole degree. Lilly graduated from UCLA Law in 2002 and stumbled into a job with a small practitioner who worked in publishing. That random job listing became the foundation for a 20-plus year career as a literary agent.See show notes at formerlawyer.com/250

Former litigator David Sazant spent years bouncing between practice areas, convinced that if he just worked hard enough and found the right fit, everything would click into place. He moved from insurance defense to construction and commercial litigation, dealing with persistent imposter syndrome the entire time. But the problem wasn't the type of law he practiced—it was that litigation fundamentally contradicted his core values of authenticity and meaningful connection. In this conversation, David shares the moment he realized he needed to leave law entirely, how a single question from a career coach clarified his path forward, and what it was really like to go back to grad school to become a therapist. He also explains why understanding your values is critical for career satisfaction and how acting against those values can lead to anxiety, depression, and declining self-esteem.See show notes at formerlawyer.com/246

Lawyers love a good assessment. Sarah has learned this running The Collab. There's something appealing about taking a test that promises clear answers about who you are and what you should do next.That appeal is also the problem. When you rely on just one assessment, it's easy to treat the results as the definitive answer. You think, "This is who I am. Now I need to find the career that matches." That kind of tunnel vision is exactly why Sarah uses multiple assessments with clients.Every assessment is a tool. It can be valuable and provide insight. But being useful and being something you should govern your career decisions on are two different things. Using multiple assessments means you can see patterns and themes that are more reliable than any single result.Assessments Sarah Uses:Values in Action (VIA) Chestnut Paes Sullivan (CPS) Enneagram CompassGallup CliftonStrengths Assessment (formerly StrengthsFinder)See show notes at formerlawyer.com/295

When the world feels unstable, the idea of introducing more instability into your life by leaving your job can feel impossible. But waiting for things to stabilize before you address your career unhappiness might mean waiting forever.2025 was a difficult year. If you're already in an overwhelming job, everything else happening in the world makes it even harder to think clearly about your career.But even in difficult years, lawyers leave the legal profession and find work they actually want to do. Even when things are rough, it's still possible.See show notes at formerlawyer.com/294

One of the most common questions lawyers ask when they're thinking about leaving is whether they need a bridge job. It's a fair question, but before Sarah can answer it, she needs to know which type of bridge job you're talking about.Because there are actually two very different kinds.See show notes at formerlawyer.com/239

Sometimes people ask Sarah, "Do all the lawyers you work with end up leaving law?" She gets the sense they think she's trying to convince people to abandon their legal careers, like she's running some kind of exit campaign.Let her be clear. She's not here to convince anyone to leave the law.See show notes at formerlawyer.com/251

Maybe you're thinking about leaving the law, but you aren't quite sure you're ready to start working through the process. You're thinking, "I really think this isn't for me, I definitely want to get out eventually, but maybe not at this exact moment." If that sounds like you, there's something you can do.This is going to be the most unsurprising recommendation, but one of the things that's really important for lawyers who are going through the process of figuring out what they want to do that isn't practicing law is therapy.See show notes at formerlawyer.com/293

When lawyers start thinking about leaving, they focus on the practical steps. What career should I pursue? How do I update my resume? What skills do I need? Those things matter, but Sarah consistently hears from lawyers that they underestimated something else. They didn't realize how much they needed to know they weren't alone.The legal profession can be deeply isolating, especially for people who are unhappy. In a field focused on prestige, lawyers often feel like they have to maintain a professional persona just to be taken seriously. It becomes hard to admit that the work doesn't fit, even to yourself. Lawyers who want out often believe they're the only ones who feel that way. They look around at colleagues who seem fine and wonder what's wrong with them for struggling.In this episode Sarah shares why finding even just one or two other people also going through this process can make leaving the law so much easier. See show notes at formerlawyer.com/292

Most people who are thinking about leaving the law spend a long time in a familiar place. They know their job feels awful, they say it to themselves and to other people, and they imagine how much better things could be somewhere else. But imagining you'd like to leave is not the same thing as deciding that you want to. That shift sounds simple, but it's tied up in identity, prestige, sunk costs, and everything you've been taught about what it means to be successful. It's the first real hurdle for a lot of lawyers, and one that's easy to avoid.See show notes at formerlawyer.com/291

There comes a point where the math you’ve been doing in your head stops adding up. You spent years in school. You passed the bar. You took on the loans. You built the career you were told would make it all worth it. Now you’re tired, anxious, or checked out, but the idea of leaving makes your stomach drop. It feels like walking away means none of it mattered.That’s how the sunk cost trap works. It convinces smart people that the only respectable choice is to stick with a decision that’s hurting them. It tells you that if you bail now, everything you put into becoming a lawyer disappears.If you’re stuck in the “I can’t throw this away” spiral and need help figuring out your next step you need to listen to this. See show notes at formerlawyer.com/249

Zi Lin did everything “right.” Philosophy major, law school, great grades, OCI, Biglaw offer, six-figure salary. From the outside, the path looked impressive. From the inside, it felt like being processed through a conveyor belt. No one asked whether the career actually fit. It was just the obvious next step. Parents approved. Professors approved. Colleagues approved. When everyone around you nods along, it’s easy to assume there’s nothing to think about.The problem came later, once Zi was actually practicing. The culture inside the firm didn’t match what was promised. “Bring your whole self to work” sounds supportive until you realize it only applies if your whole self fits the mold. Zi found herself performing a version of “acceptable lawyer,” constantly adjusting how she acted, talked, socialized, even reacted. When your value comes from churning out work and avoiding the wrong reactions, there’s no space to be a person. There’s only survival.In this episode Zi Lin joins Sarah to talk about her experience leaving Biglaw and what she's doing now.Website & PortfolioZori Nori Instagram (@zori_nori)Personal Art Instagram (@garbage_collector_s)Linktree (for all other links, shops, etc.)

A lot of lawyers assume that making more money will make leaving easier. In reality, the opposite often happens. Once you are in a high-paying legal job, it can feel like there is no other path that will work. People outside the profession are usually surprised by this. They assume lawyers have endless options, but many lawyers feel they have to hang on to what they have because there may not be anything else that fits.See show notes at formerlawyer.com/289

A lot of lawyers believe they shouldn’t feel burned out because they haven’t been practicing very long. But burnout isn’t measured by years in the profession. For many lawyers, it started long before their first legal job. Sarah hears from people who have only been in practice a few years and are already exhausted, overwhelmed, or checked out. They feel embarrassed or confused because they can point to colleagues who have been doing it longer. But measuring burnout by the calendar misses the reality of how it develops—especially for high-achieving perfectionists who have been pushing themselves for years before they ever set foot in a law firm.See show notes at formerlawyer.com/288

For years, the idea of leaving the law can sit quietly in the back of your mind. You tell yourself you’ll figure it out eventually, that one day you’ll know it’s time. But months turn into years, and the only thing that changes is how tired you feel saying, “I don’t want to do this forever.” The biggest mistake most lawyers make when they want to leave is assuming it will just happen on its own.See show notes at formerlawyer.com/287

Lawyers often describe feeling like they can never fully turn their brains off. Even during downtime, there’s a sense of waiting for the next email, the next call, or the next fire to put out. It’s not simply overthinking. It’s the body staying on alert, a nervous system trained to expect that something could go wrong at any time.Sarah explains why this constant state of vigilance makes sense, why it’s not a personal failing, and what it means for lawyers trying to find relief from the pressure.Anchored: How to Befriend Your Nervous System Using Polyvagal Theory by Deb DanaSee show notes at formerlawyer.com/286

The first year after leaving law is a strange mix of freedom and fatigue. There is relief in stepping away from billable hours, but the exhaustion runs deeper than expected. Sarah Cottrell hears it constantly from clients. They imagined a clean break. Instead, it feels like living in a body still bracing for impact.At first there’s quiet. The noise of practice fades, and breathing feels easier. Then comes the question no one expects. What now? For years the answer was always clear. Get through the case. Close the deal. Survive the week. Outside that system, there’s no obvious next step, only space that feels both exciting and uncertain.Sarah describes the first year as less about reinvention and more about recovery. It’s about realizing how much the profession shaped your sense of worth and how long it takes to stop living like every moment has to be optimized.See show notes at formerlawyer.com/285

Ever feel trapped in the cycle where one week you swear you have to get out of law, and the next you convince yourself it isn’t so bad? That back-and-forth isn’t clarity, it’s burnout and fear of judgment keeping you stuck. In this episode, Sarah Cottrell breaks down how to recognize the outrage complacency cycle and what it takes to finally step out of it. Join Sarah for a free live masterclass on October 10, Five Simple Steps to Identify a Career You Actually Like.Sign up at formerlawyer.com/masterclass.See show notes at formerlawyer.com/284

Many lawyers, when they stop and reflect, realize that one of the reasons they went to law school was to impress other people. Prestige mattered. But the moment they name it, the shame sets in — “That was a bad reason. I shouldn’t care what others think.” Sarah Cottrell pushes back on that belief, reminding lawyers that caring about opinions is normal and human. In this episode, she shares how caring becomes a problem only when it outweighs your own needs, especially if you’re considering leaving the law. You’ll hear how to notice when you’ve given outside voices too much power, how to decide whose opinions really matter, and why therapy can help you find the right balance. If guilt or fear of judgment has been keeping you stuck, this conversation will help you put those concerns in perspective.See show notes at formerlawyer.com/283

The Former Lawyer framework has recently received a glow-up, and this podcast episode covers all the fun updates. Sarah has a few things that stuck out to her and would be the most helpful to anyone considering becoming a former lawyer. She covers those items in this episode to highlight them for all the podcast listeners considering joining.Reserve your seat to learn The Simple 5-Step Framework To Identify An Alternative Career (That You Actually Like!) on October 10th.See show notes at formerlawyer.com/241

You’ve been in therapy. You’ve talked through your career. You understand, logically, that your boss’s mood isn’t your responsibility, that your worth isn’t measured by productivity, and that burnout doesn’t mean you’re broken. And yet… you’re still panicking every time Outlook pings. You’re still second-guessing every boundary. You’re still bracing for impact.For many lawyers, this is the point where talk therapy hits a wall. You’ve intellectually processed the stress, but your body hasn’t caught up. That disconnect between what you know and how you feel isn’t a failure. It’s a signal.See show notes at formerlawyer.com/282

Today’s podcast episode is an important reminder every lawyer needs to hear. Sarah reminds listeners that nothing about your job is as important as you and your emotional, mental, and physical health. For lawyers, it’s easy to feel their value as human beings is basically in job performance. See show notes at formerlawyer.com/229

2025 is more than halfway through, and if you told yourself this was the year you’d leave practice, this is your check-in. September is basically here, which means four months left in the year. That’s still plenty of time to make progress. And honestly, the start of fall always feels like a reset — school year vibes, even for those of us who haven’t been in school for decades. So if you haven’t taken steps yet, you haven’t missed your chance.See show notes at formerlawyer.com/281

The question comes up constantly - in podcast interviews, on Collab group calls, and in emails from listeners. "What if the grass isn't greener on the other side?"It's tied to this idea that maybe being miserable at work is just what it means to be an adult with a job. Maybe every workplace is toxic. Maybe no one really likes what they do. You'll even hear people outside the law say things like "Well, no one likes their job."There's something almost protective about believing this. If you don't believe it will be better elsewhere, it's easier to keep doing the thing you're doing, even if the thing that you're doing is painful and not great for your mental and physical and emotional well-being.But after six years of interviewing former lawyers, I can tell you the grass really is greener.See show notes at formerlawyer.com/280

There's a partner at your firm. Everyone knows about them. Multiple people have quit working for them. Multiple people have gone out on mental health leave. When people talk about this partner, they use phrases like "difficult" or "has sharp elbows."If you listen to Sarah's episode about the no-asshole rule, you know that “has sharp elbows” generally means they're abusive. But somehow, despite the clear pattern of destruction in their wake, you're supposed to act like this is normal. Like maybe you'll be different.This is not normal. This is nuts.See show notes at formerlawyer.com/279

In today’s podcast, Sarah discusses how to know when it’s the right time to leave law. Many people listening are grappling with this question, and often, when they ask it, they are looking for an external answer. There is no external answer. You are the only person that can decide when the time is right.The reality is that you need to ask yourself two questions to know if now is the right time for YOU to leave the law.See show notes at formerlawyer.com/231

You're exhausted from work and catch yourself thinking, "I wish I could get hit by a bus just a little bit so I could finally get a break." If that sounds familiar, you're not alone - and it's definitely not normal.This disturbing thought is surprisingly common among lawyers in toxic work environments. Sarah and returning guest Kelcey Baker dive into why so many lawyers fantasize about minor injuries as their only escape from work pressure, and why even vacation doesn't provide real relief.If you've ever had thoughts like this, this episode will help you understand it's not your fault - it's your environment. Content warning: Discussion includes narcissistic abuse, self-harm, and suicidal ideation.See show notes at formerlawyer.com/236

You're successful on paper but can't shake the feeling you haven't really "made it" without a prestigious law firm on your resume. Tiffany Obeng lived with that impostor syndrome for over a decade before finally getting her shot at Biglaw in 2023. Nine months later, she was back out. In this episode, Tiffany shares what she learned during those nine months that changed everything about how she views success, plus how she's built a children's book publishing company focused on diverse representation while working full-time in employment consulting. If you've ever wondered whether the grass is really greener at a prestigious firm, this episode is for you.See show notes at formerlawyer.com/278

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 legal tech transition wasn't linear. Sarah recently talked with Ben about his journey from maritime litigation to legal tech leadership, and his story touches on so many themes that resonate with lawyers considering their own legal tech transition.See show notes at formerlawyer.com/277

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've done all the career assessments, who have detailed information about themselves, but still feel completely stuck about their next career move.If this is you, there are two possible reasons why you're still feeling unclear after taking career assessments.See show notes at formerlawyer.com/276

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 recruiter who has unique insight into how these changes are playing out. He owns Mosaic Search Partners, a recruitment firm that focuses on historically underrepresented attorneys in Biglaw. When firms started abandoning their diversity commitments, Bryson had a front-row seat to the consequences.See show notes at formerlawyer.com/275

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 participate in "misery Olympics," comparing struggles instead of acknowledging that toxic work environments affect everyone's mental health. If you're a single or childless lawyer struggling with burnout, this episode will help you stop gaslighting yourself and start taking your mental health seriously.See show notes at formerlawyer.com/274

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've made a terrible mistake, and explains the real reasons partnership decisions aren't actually merit-based.If you're a senior associate considering the partnership track, this episode will help you ask the right questions before you commit to a process that might not give you what you think it will.See show notes at formerlawyer.com/273

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 to build something better. Whether you’re thinking about leaving law or just changing how you practice it, Dan’s story is proof that you’re not trapped.See show notes at formerlawyer.com/272

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 you’re feeling stuck in a toxic workplace or questioning whether it’s time to leave, this conversation will give you clarity—and your first steps toward getting out.See show notes at formerlawyer.com/271

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 lawyers, this episode offers a candid look at what needs to change.See show notes at formerlawyer.com/270