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PODCAST

The Former Lawyer Podcast

Do you hate working as a lawyer? Are you an unhappy lawyer who wants to leave the law, but isn"t sure what to do next? Do your family and friends think you"re crazy for wanting to leave the law, or are you too afraid to tell them you don"t want to be a lawyer? The Former Lawyer Podcast is for you! Each week, host Sarah Cottrell interviews a different former lawyer who has left the law behind. Hear inspiring stories about how these former lawyers are thriving and found their way to careers and lives

business careers

All Episodes

10:00

Translating Legal Skills for a Non-Legal Job Doesn't...

The Former Lawyer Podcast ·

2026/05/18

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

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38:07

Leaving Biglaw to Become a Sex and Relationship Coach...

The Former Lawyer Podcast ·

2026/05/11

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

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8:53

Trying to Justify Leaving Law Is What’s Keeping You...

The Former Lawyer Podcast ·

2026/05/04

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

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10:45

Tolerating Your Lawyer Job While You're Preparing to...

The Former Lawyer Podcast ·

2026/04/27

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

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45:53

How to Break Into Legal Tech and AI as a Lawyer with...

The Former Lawyer Podcast ·

2026/04/20

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

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11:10

How an Overdeveloped Sense of Responsibility Keeps...

The Former Lawyer Podcast ·

2026/04/13

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

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6:32

What Doing Your Best Is Costing You as a Lawyer

The Former Lawyer Podcast ·

2026/04/06

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

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8:13

You Don't Have to Quit Your Job to Start Leaving Law

The Former Lawyer Podcast ·

2026/03/30

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

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9:45

Why Lawyers Think Feelings Are Optional and What It...

The Former Lawyer Podcast ·

2026/03/23

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

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11:22

Why High-Achieving Lawyers Stay in Jobs That Are...

The Former Lawyer Podcast ·

2026/03/16

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

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12:48

The Perfectionist Trap That Makes It Hard to Leave Law

The Former Lawyer Podcast ·

2026/03/09

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

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9:42

Why Unhappy Lawyers Should Pick Up a Hobby Before...

The Former Lawyer Podcast ·

2026/03/02

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 ac...

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17:33

What Lawyers Wish They'd Asked Before Going to Law...

The Former Lawyer Podcast ·

2026/02/23

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

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7:02

Hard Things Feel Hard Because They Are Hard

The Former Lawyer Podcast ·

2026/02/16

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

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41:27

Escaping the Legal Grind to Build a Balanced Life...

The Former Lawyer Podcast ·

2026/02/09

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

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10:03

How to Explore Your Career Options After Law with...

The Former Lawyer Podcast ·

2026/02/02

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

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42:40

From Law School to Literary Agent with Lilly Ghahremani

The Former Lawyer Podcast ·

2026/01/26

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

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41:43

How a Misalignment of Values and Career Helped a...

The Former Lawyer Podcast ·

2026/01/19

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,

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12:58

How Multiple Assessments Help Lawyers Changing Careers

The Former Lawyer Podcast ·

2026/01/12

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

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9:08

Don't Wait for the World to Stabilize Before You...

The Former Lawyer Podcast ·

2026/01/05

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

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