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't

2:04 — Why holding yourself to a higher standard than everyone else is actually about ego

3:02 — The vacuum-sealed pod problem and why "everyone makes mistakes" doesn't feel true about you

6:01 — How this mindset makes it hard to leave, from feeling like you're abandoning people to telling yourself you're just weak

7:35 — How to know if you're this person and what it actually costs you

9:17 — Why therapy is worth bringing this up in, even if Sarah's framing annoys you

10:31 — What happens when lawyers don't let themselves leave until their body forces the issue

11:48 — What to actually sit with if this episode resonated

Mentioned In The Perfectionist Trap That Makes It Hard to Leave Law

First 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 ready

0:56 — Why hobbies matter for lawyers thinking about a career change

1:11 — How work crowds out everything else and why that's so common for unhappy lawyers

1:54 — 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 you

3:25 — Why this works even if you're not close to leaving and don not have much time

3:33 — What starting small actually looks like and why going all in is not the point

6:00 — Rituals, rhythms, and reminding yourself you are a person and not a machine

7:25 — The bonus benefit of hobbies that involve other people when you are thinking about leaving law

8:27 — The real skill you are building and why it matters for your lawyer career change

Mentioned In Why Unhappy Lawyers Should Pick Up a Hobby Before They're Ready to Leave

First 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 Compass

Gallup 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