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, 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 pattern

2:33 - Wanting to help people through law and how recruiting funneled her into business litigation instead

4:51 - The conveyor belt and why the realities of practice diverge from what brings people to law school

7:48 - Why being a free thinker is not rewarded at a big firm

8:48 - On paper everything looked perfect, partner, deputy general counsel, two kids, and the constant restless feeling underneath

9:54 - Neurodivergence, the strong sense of justice, and why these traits do not get rewarded in big firms

13:16 - Where Amy's values clashed with the actual work of business litigation

18:06 - Why "just don't care" is not actually possible when someone is being rude and disrespectful

20:19 - Pleasure as the body's antidote to stress and how it resets the nervous system

22:43 - The early seed of wanting to be a sex coach and why Amy tucked it away for years

25:38 - The reactions Amy got from colleagues, friends, and family when leaving Biglaw

29:16 - You do not have to leave law entirely, you can find a way to practice that aligns with your values

33:22 - What Amy recommends if you are curious about coaching as a career

34:00 - What sex and relationship coaching actually is and who Amy works with

Mentioned In Leaving Biglaw to Become a Sex and Relationship Coach with Amy Terwilleger

Amy Terwilleger's Website | Linktree

Amy Terwilleger on Instagram (@millennialdrruth)

First Steps to Leaving the Law

The 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 law

1:02 - Why there is always someone who has it worse and why that keeps lawyers stuck

1:55 - Why the struggle to feel justified in leaving is fundamentally external

2:35 - "Am I justified in leaving" is really a question about who gets to say

3:55 - Why so many lawyers cannot trust their own experience

4:38 - What you actually need to access to find something better

5:57 - Why this needs to be your choice and not something you wait for permission to do

6:32 - The skill you are going to be developing as you move out of the law

7:56 - What it tells Sarah when she hears lawyers asking if they are justified in leaving

Mentioned In Trying to Justify Leaving Law Is What’s Keeping You There

First Steps to Leaving the Law

The 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 environment

2:23 - Why "tolerating" your job never means staying somewhere that's damaging you

3:24 - Being realistic about your timeline and what the work actually looks like

4:11 - How long the Collab framework typically takes when you give it a couple hours a week

5:16 - Why the day you can leave is not the day to start figuring out what's next

6:14 - What makes tolerating your job easier while you're preparing to leave

7:40 - What to do if you see yourself leaving eventually but not soon

9:15 - Why giving yourself time instead of rushing is one of the best uses of your time in a lawyer job

Mentioned In Tolerating Your Lawyer Job While You're Preparing to Leave

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First Steps to Leaving the Law

The 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 tech

2:27 - Why legal tech keeps coming up for lawyers who want to leave practice

4:07 - No agreed terms, no standardized titles, and what that means for your job search

4:45 - You're not alone in being confused about where to start in legal tech

9:17 - The three main career paths in legal tech and AI for lawyers leaving practice

11:41 - Product roles and why lawyers are better positioned for them than they think

13:00 - Go-to-market roles and why a JD is a competitive advantage in sales conversations

13:48 - Why operations roles are booming inside legal tech companies right now

15:13 - JD required vs. JD preferred and what your legal background signals to employers

17:55 - Why lawyers automatically rank in the top 1% of candidates for legal tech jobs

24:52 - Why lawyers try to execute before they know their objective

30:25 - Why applying for every legal tech role is a recipe for madness

35:37 - How to speak to a role you've never held and start building proof of interest

39:38 - Why updating your resume is the last thing you should do

42:24 - Ben's closing take on legal tech as a viable career path for lawyers ready to make a move

Mentioned In How to Break Into Legal Tech and AI as a Lawyer with Ben Chiriboga

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First Steps to Leaving the Law

The 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 Enneagram

3:01 - What Sarah sees with lawyers whose jobs aren't good for them

4:26 - Why highly responsible lawyers struggle to give themselves permission to even think about leaving

5:07 - What an overdeveloped sense of responsibility actually means

6:03 - How toxic environments exploit lawyers who are highly responsible

7:28 - The faulty logic that keeps highly responsible lawyers from cutting themselves any slack

9:18 - Why it matters to know if responsibility is one of your top characteristics

Mentioned In How an Overdeveloped Sense of Responsibility Keeps Lawyers Stuck

First Steps to Leaving the Law

The 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 lawyer

1:56 - Why caring about doing good work makes this harder

3:56 - The B-minus work concept and why it matters

4:37 - Why this is harder for lawyers from marginalized communities

5:04 - How loosening that standard makes space for other things

5:24 - Why therapy is worth considering if this resonates

Mentioned in What Doing Your Best Is Costing You as a Lawyer

First Steps to Leaving the Law

The 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 Collab

0:53 - What The Former Lawyer Collaborative actually is and how it works

1:38 - Do you need to quit your job before starting this process

2:25 - How people find The Collab and when they typically join

2:57 - Why less pressure to leave can actually mean faster progress

3:29 - The time commitment question and what "a couple hours a week" really gets you

5:15 - Other reasons you might quit, and why most people in The Collab don't

6:23 - Why The Collab was designed to fit inside a lawyer's life

7:06 - How to join and where to find more info

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

Five Years of Helping Lawyers Leave the Law inside The Former Lawyer Collaborative

First Steps to Leaving the Law

The 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 optional

2:13 - Why feelings are nervous system responses and not actually a choice

2:48 - Where the belief that feelings are optional comes from and how it gets reinforced

4:16 - "I'll feel things when I retire" and why this is probably how you're functioning even if you'd never say it out loud

6:19 - What happens when the nervous system finally says no and why it goes the way it does

7:21 - How to notice if you're treating your feelings as optional and why irritation at other people's feelings is a flag

8:44 - Why therapy is especially useful here and what to do if this resonated

Mentioned In Why Lawyers Think Feelings Are Optional and What It Costs Them

Why High-Achieving Lawyers Stay in Jobs That Are Hurting Them

First Steps to Leaving the Law

The 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 them

1:28 - The "I can do this so I should do this" trap and why external markers are not the whole picture

3:24 - How ADHD brains create urgency to initiate tasks and what that costs your nervous system

4:28 - Why doing well as a lawyer can feel like proof you are meant to stay

5:16 - How PTSD and CPTSD factor in and why so many lawyers are highly adapted to deal with difficult conditions

6:43 - How perfectionism develops as a survival strategy and why it follows lawyers into their careers

7:41 - The belief that you are only valuable when you are achieving and why it makes it so hard to leave

8:36 - Why therapy matters so much for lawyers who are high achievers thinking about leaving

10:01 - What Sarah wants you to know if the job is crushing you but you feel like you have to stay

Mentioned In Why High-Achieving Lawyers Stay in Jobs That Are Hurting Them

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First Steps to Leaving the Law

The 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'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