The Former Lawyer Podcast

When you're thinking about leaving law, it's easy to convince yourself that you don't have any transferable skills. You've spent years learning how to be a lawyer, and so much of what you do every day feels specific to practicing law. It's hard to imagine how any of that experience would be useful in a job that has nothing to do with the legal profession.

Something that lawyers often don't realize is that the skills they take for granted aren't necessarily things everyone else knows how to do. When you're surrounded by other lawyers, being able to...

If you want to leave law but have no idea what you want to do next, it can feel like you need to figure out at least a few possible options before you are ready to get help. For a lot of unhappy lawyers, though, the problem is not choosing between several clear career paths. Everything outside of practicing law feels like a complete black box, and they do not even know how to start figuring out what might be a good fit. 

In this episode of The Former Lawyer Podcast, Sarah Cottrell explains why not knowing w...

Being laid off from a legal job can create a lot of anxiety, financial and otherwise. If you’ve been laid off, you’re worried that a layoff might be coming, or you’ve been through one in the past, there are very real practical concerns that come with losing your job. We all have bills, we all need to be responsible adults, and sometimes getting another job practicing law is the choice that makes sense.

The question is whether you actually want another legal job or whether you’re looking for one because that feels like what you...

Staying in a toxic law firm because you want to help change it can feel like a good reason to stay. You want to get to a position where you have more influence and can use that influence to make the environment better. The question is what staying long enough to get there is costing you along the way.

The harder part is that toxic environments can change your sense of what is normal or acceptable. You can start out very clear about what feels wrong and, over time, become more comfortable with things you previously would...

When leaving law feels like letting other people down, it can become much harder to take your own unhappiness seriously. For lawyers who are women, first-gen, people of color, or part of another historically underrepresented group, there can be a very real sense that being in these spaces is not just about them. Their achievement can start to feel tied to representing other people well and showing what is possible.

The difficult part is that this sense of responsibility can mean having to get to a very bad place before being willing to prioritize yourself. Sarah sees...

Your law job may feel more unsustainable than it used to, even if you were managing it fairly well before. Maybe you already knew the environment was not great, or that the work itself was never especially sustainable, but you were making it work. Now, all of a sudden, it feels completely impossible and you are wondering what changed.

For a lot of lawyers, the instinct is to turn that question inward. Is it because you are weak? Is it because you cannot hack it anymore? Sarah talks about why being impacted by what is happening around...

“There’s a reason they call it a job.” “If it was fun, everyone would do it.” “The grass isn’t always greener.” Lawyers who hate their jobs hear some version of this all the time from people outside of the legal profession, usually when they are trying to explain just how miserable their work has become.

There is a kernel of truth in the idea that every job involves some amount of work, frustration, and things you would rather not do. The problem is that every job does not suck in the way that being a lawyer can suck...

When you start thinking about leaving the law, it is really common to realize that some of what you are trying to figure out is about your career and some of it goes much deeper than that. You may need help understanding what kind of work would actually be a good fit for you while also untangling why quitting feels so unsafe or why disappointing other people feels almost impossible.

That is part of why therapy and career coaching can work so well together. They might both help you get to the same place, but they are...

You can know that you do not want to keep practicing law and still have no idea what you want to do. You may not even know what you could do. A lot of lawyers assume they need to have some sense of the answer before they can start when the process is actually designed for people who are in exactly your position.

Part of what makes figuring out what comes next so uncomfortable is that there is no assessment that gives you one answer. You have to get a clearer picture of who you are, pay...

After years in the law, it can be easy to believe that creativity simply is not part of who you are. Maybe you stopped making time for things you used to enjoy, or maybe you decided a long time ago that being artistic was not practical, serious, or something that fit with the kind of person who becomes a lawyer.

That belief can shape more than what you do outside of work. It can also shut you off from whole groups of jobs because you think of them as jobs for creative people, and you do not...

If you have been thinking about joining the Former Lawyer Collaborative, now is the time. Enrollment is closing permanently on August 31, 2026, and while the program will remain open for another year, this is the last chance to join the community and work through the Former Lawyer Framework with Sarah’s support.

In this episode of The Former Lawyer Podcast, Sarah Cottrell talks about why she decided to close the Collaborative, what members will still have access to through August 31, 2027, and where she plans to focus her work next. She also shares what the last few years have ma...

In today’s episode, Sarah is back again with Annie Little discussing the book Bullshit Jobs by David Graeber.

The final misery covered in the book is the misery based on knowing that one is doing harm. The most obvious example of this as lawyers would be representing a person or entity, and they are asking you to do something that is itself harmful. While these situations may arise, people tend to be aware and can deal with the moral conflict. 

In today’s episode, Sarah is back again with Annie Little discussing the book Bullshit Jobs by David Graeber. It’s part of a series of podcast discussions diving into the miseries of a bullshit job, and today, it’s time to dive into the third misery that comes with bullshit jobs. If you missed the first two, go back and catch up.

See show notes at formerlawyer.com/189

In today’s episode, Sarah is back again with Annie Little discussing the book Bullshit Jobs by David Graeber. It’s part of a series of podcast discussions, so check out the others before and after this one. Graeber gives four reasons why having a bullshit job feels so miserable. Last week’s discussion was all about the first reason—ambiguity and forced pretense—catch up on that one first. Then, let’s dive into the second reason.

See show notes at formerlawyer.com/188

This episode is part 2 of the series where Sarah is chatting with Annie Little about the book Bullshit Jobs by David Graeber. If you missed the first episode in this series, check that out first and learn the background of this series and more about Annie. This episode is about the misery of ambiguity and forced pretense, which is the first of four things Graeber identifies as an impact that having a bullshit job can have on you.

When it comes to ambiguity in law firms, the lack of transparency is the first thing that comes to...

Sarah revisits the Bullshit Job series on today's podcast with Annie Little, another lawyer career coach. Annie has been on the podcast a few times in the past, like the episode on ADHD. She founded her company, JD Nation, and helps lawyers find better jobs, both in and out of law. 

In this new series, the two of them discuss the book Bullshit Jobs: A Theory by David Graeber and dive into some of the book's observations. This first episode covers why you should care about this book and answer, “Is being a lawyer a bullshit job?”

...

In legal practice, it is easy to start measuring yourself by whether you can cover every detail, do everything perfectly, and keep grinding through whatever is in front of you. If that is not the way you are wired, it can feel like there is something wrong with you, instead of recognizing that the job is rewarding a narrow set of behaviors.

Alex Su describes this as game selection. In business roles, especially sales, marketing, and business development, success often depends on trying things, learning what works, moving on from what does not, and prioritizing the things...

Listen, it's the summer of 2026. Everything is a dumpster fire, and there are a lot of people who have been struggling a lot with their mental health, especially in the last two years. Sarah's seen a lot of clients take mental health leave or after taking mental health leave. 

This episode serves as a reminder that even though it's not available to everyone, because it depends a lot on your particular employer, if it is something that your employer offers, and if you are struggling, it can be an incredibly helpful tool in your mental health toolkit.

Leaving the law when you’re already burned out can feel impossible, because the job you need energy to escape is the same job draining all of your energy. You may understand that you need to figure out what comes next, but when you are scraping by energetically, even one more task can feel like too much.

That is where a lot of burned out lawyers get stuck. They assume that if they do not have hours and hours each week, whole weekends, or a huge amount of bandwidth to put toward leaving the law, then they ca...

Going to law school felt like the right call. For some lawyers it felt like the obvious call, backed up by experience, by personality, by everything they knew about themselves at the time. So when practicing law turns out to be a bad fit, the harder part is that the decision felt so right going in. If they were wrong about something they were that sure about, how can they trust themselves to choose anything else?

That fear is what keeps so many lawyers where they are, even when staying is actively hurting them. For lawyers trained...

Somewhere along the way, most lawyers picked up the idea that once you commit to something, you follow through. No exceptions. So when the thought of leaving starts to surface, it doesn't feel like a career question. It feels like there's something shameful about admitting your original decision was wrong.

But the decision to become a lawyer was made at a specific age, with a specific amount of information. The lived experience of actually practicing law is new information. And in almost any other context, no one would question whether you should update a decision when the...

Lawyers who know they want to leave often get stuck in the same place. Not because they don't want to move, but because they're waiting to feel certain about what comes next. Sarah Cottrell sees lawyers who won't make a move until they have a new 20-year plan with an absolute guarantee, and while they're waiting for that, nothing changes.

Zach Reisch didn't have a master plan when he left commercial litigation. He had a spouse building a business, a growing sense that law just wasn't compatible with who he was, and a willingness to try something...

When lawyers start thinking about doing something else, the first thing they reach for is almost always the resume. It feels like real progress. It produces something tangible. And for lawyers who are used to having clear work product, that matters a lot.

What actually happens is the opposite. You sit down to revise it, you stare at a bunch of legalese you wrote years ago, and within an hour you've convinced yourself you have no transferable skills and should probably just quit and stay in the law forever. That's not because the skills aren't there. It's...

On paper, Amy Terwilleger’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, Sa...

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...

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...

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...

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...

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...

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"...

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...

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...

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...

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...

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...

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...

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...

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...