The Former Lawyer Podcast

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 s...

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 rol...

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...

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 hour...

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 choos...

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 am...

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 p...

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&a...

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...

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 wait...

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 t...

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 backgro...

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 Sa...

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 the...

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...

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...

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 s...

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 n...

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 smal...

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 I'm closing enrollment for...

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 n...

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 scho...

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"....

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 mistak...

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 funda...