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?”

See show notes at formerlawyer.com/186

I'm closing enrollment for my self-paced group program, the Former Lawyer Collaborative, permanently on August 31st, 2026. If you've been thinking about joining now is the time. 

Head to formerlawyer.com/collab to join before doors close on August 31st.

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 that actually move the needle. The question becomes less about whether you can fix yourself into a better lawyer and more about whether you are playing the right game for your strengths.

In this episode of The Former Lawyer Podcast, Sarah Cottrell talks with returning guest Alex Su about what lawyers need to understand when they move out of practice and into business roles. They talk about why legal training can make that shift feel uncomfortable, how performance-based work rewards a different kind of resilience, and why the right role can make strengths visible that law may have treated like problems.

1:43 - Alex’s move from practicing law into a business career in the legal space

3:55 - Why business roles reward a different skill set than legal practice

5:49 - The comfort of hours worked and why the shift to ROI can feel difficult

7:21 - What changes when the goal is producing outcomes instead of putting in more hours

9:15 - Why experimentation requires a different relationship with failure

10:28 - How perfectionism can become counterproductive in performance-based roles

13:05 - When traits that are treated like problems in law can work well elsewhere

14:54 - Alex’s idea of game selection and choosing the right role for your strengths

21:08 - What Latitude partners do after leaving the practice of law

24:22 - Why business roles require ruthless prioritization

27:10 - The kind of resilience that business roles require

30:33 - How legal practice moralizes failure in a way other roles often do not

33:56 - Why a successful pivot requires knowing yourself and staying a student

36:34 - Head intelligence, instinct, and emotional intelligence in non-practicing roles

39:39 - Alex’s advice for lawyers considering a pivot to sales, business development, or business

Mentioned In How Lawyers Can Rethink Their Skills for Business with Alex Su

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First Steps to Leaving the Law

Former Lawyer Collaborative

I'm closing enrollment for my self-paced group program, the Former Lawyer Collaborative, permanently on August 31st, 2026. If you've been thinking about joining now is the time. 

Head to formerlawyer.com/collab to join before doors close on August 31st.

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.

Sarah is joined by Megan Nogasky to discuss taking mental health leave, what it's like, what you can expect, and some of the things to think about when you're considering it.

Show notes at https://formerlawyer.com/176

I'm closing enrollment for my self-paced group program, the Former Lawyer Collaborative, permanently on August 31st, 2026. If you've been thinking about joining now is the time. 

Head to formerlawyer.com/collab to join before doors close on August 31st.

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 cannot make any real progress. But Sarah talks about why consistency matters more than massive amounts of time, especially when everything already feels hard.

In this episode of The Former Lawyer Podcast, Sarah Cottrell talks about leaving the law when you are already burned out, why the process may require less weekly time than you think, how bridge jobs can create relief, and when mental health leave may be worth considering.

0:27 - Leaving the law when you are already burned out

1:09 - The question burned out lawyers ask when they know they need to figure out what comes next

3:14 - Why career change does not require five or ten hours a week

4:54 - How bridge jobs can help burned out lawyers get relief

6:51 - Why mental health leave exists and when lawyers should consider it

8:43 - What to remember if you are leaving the law while already burned out

Mentioned In Leaving the Law When You’re Already Burned Out

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First Steps to Leaving the Law

The Former Lawyer Collaborative

I'm closing enrollment for my self-paced group program, the Former Lawyer Collaborative, permanently on August 31st, 2026. If you've been thinking about joining now is the time. 

Head to formerlawyer.com/collab to join before doors close on August 31st.

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 by a profession that treats every mistake like malpractice, it doesn't take much to go from "I might choose wrong" to "I should never choose at all."

In this episode of The Former Lawyer Podcast, Sarah Cottrell talks with returning guest Kelcey Baker about what it actually looks like to make career moves that don't go as planned, how Kelcey navigated leaving two law firms and eventually launching a consulting business, why the idea that you only get one shot at a career change keeps lawyers stuck, and what changes when you stop trying to make the perfect decision and start making any decision at all.

1:28 - The fear of making a mistake and choosing something that's even worse than where you are now

2:59 - Kelcey's first "did I make a huge mistake" moment and why it wasn't law school

6:25 - How realizing law is a bad fit damages your ability to trust yourself to make career decisions

9:24 - Why lawyers who worked as paralegals before law school often feel an extra layer of self-blame

11:19 - The "I should have known" trap and why you couldn't have known what you didn't experience

14:35 - How the experience of a bad fit impacts the next career decision and the one after that

17:40 - Why most people who go to law school were too young to have done the inner work of knowing themselves

19:17 - Why punishing your younger self for not knowing what you know now keeps you stuck

20:57 - The pressure to find the capital-T Thing and how fear of judgment keeps lawyers in jobs that are hurting them

30:48 - The binary thinking that makes it feel like you're either a lawyer or you're nothing

33:33 - How Kelcey built a consulting business by combining what she was good at with what she actually liked

36:02 - Why perfectionist, eldest-daughter types forget they're resourceful enough to figure it out

41:03 - You will be okay, and if the next thing isn't right either, you can keep going

43:46 - Bridge jobs, lily pad jobs, and why it doesn't have to be forever to be worth doing

Mentioned In Making a Career Change When You're Afraid of Getting It Wrong with Kelcey Baker

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First Steps to Leaving the Law

The Former Lawyer Collaborative

I'm closing enrollment for my self-paced group program, the Former Lawyer Collaborative, permanently on August 31st, 2026. If you've been thinking about joining now is the time. 

Head to formerlawyer.com/collab to join before doors close on August 31st.

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 information changes.

In this episode of The Former Lawyer Podcast, Sarah Cottrell talks about why so many lawyers feel ashamed of wanting to change their minds, where that "don't be a quitter" conditioning comes from, why it takes maturity to look at your decisions and choose something different, and why therapy is often the best place to start untangling all of it.

0:30 - The shame lawyers feel about changing their minds and where it comes from

1:04 - How the decision to leave becomes tangled with feeling "wrong" about the original choice

2:10 - The decision to become a lawyer was made with limited information at a specific age

3:14 - Why lawyers don't apply the "new information" standard to their own experience

4:00 - The "don't be a quitter" conditioning and how good-student types absorb it

7:55 - Holding your past self to a standard no human can be held to

Mentioned In The Shame Lawyers Feel About Wanting to Leave Law

First Steps to Leaving the Law

The Former Lawyer Collaborative

I'm closing enrollment for my self-paced group program, the Former Lawyer Collaborative, permanently on August 31st, 2026. If you've been thinking about joining now is the time. 

Head to formerlawyer.com/collab to join before doors close on August 31st.

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 before he knew whether it would work. What he found was something Sarah talks about often but lawyers tend to resist. Clarity follows action.

In this episode of The Former Lawyer Podcast, Sarah talks with Zach about what made him realize Biglaw wasn't a fit and how anxiety made it difficult to tell the difference between something being scary and something being wrong, what it was actually like to go from litigation to personal training and small business ownership, and why tying your identity to achievement doesn't go away just because you change jobs.

1:27 - Why law school felt like a decent fit but practicing law did not

3:51 - Getting exactly one Biglaw offer and choosing commercial litigation without knowing what it would be like

7:29 - How anxiety made it hard to separate "this is uncomfortable" from "this is wrong for me"

8:33 - Why lawyers think they should be able to think their way through a nervous system response

12:11 - Still having nightmares about his law job and the identity crisis of feeling like he was failing

13:14 - What actually helped was the podcast, therapy, and talking to anyone who wasn't a lawyer

16:58 - Why clarity follows action and how waiting for a perfect plan keeps lawyers stuck

20:29 - Why individual interaction was the missing piece in his desire to help people

22:46 - The practical realities of becoming a personal trainer as a second career

29:19 - Why tying your identity to achievement doesn't go away just because you leave law

33:51 - Being willing to try something without knowing if it's going to work

Mentioned In From Commercial Litigator to Personal Trainer and Business Owner with Zach Reisch

Rozzie Fitness

First Steps to Leaving the Law

The Former Lawyer Collaborative

I'm closing enrollment for my self-paced group program, the Former Lawyer Collaborative, permanently on August 31st, 2026. If you've been thinking about joining now is the time. 

Head to formerlawyer.com/collab to join before doors close on August 31st.

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 because there's nothing to translate them toward yet.

In this episode of The Former Lawyer Podcast, Sarah Cottrell explains why revising your resume is actually one of the last steps in a lawyer career change, and what she has people start with instead. She talks about why trying to write 27 different resumes for 27 possible roles is a waste of time, why values are the real starting point, and why most lawyers who try to start with the resume end up more discouraged than when they began.

0:44 - Revising your resume is the worst place to start

2:29 - Knowing what you're targeting is what makes the resume easy

5:10 - What actually works when you go to revise the resume

6:32 - Values are the first part of the framework inside The Collab

8:56 - Don't start with your resume, start with values and therapy

Mentioned In Translating Legal Skills for a Non-Legal Job Doesn't Start With Your Resume

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First Steps to Leaving the Law

The Former Lawyer Collaborative

I'm closing enrollment for my self-paced group program, the Former Lawyer Collaborative, permanently on August 31st, 2026. If you've been thinking about joining now is the time. 

Head to formerlawyer.com/collab to join before doors close on August 31st.

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

I'm closing enrollment for my self-paced group program, the Former Lawyer Collaborative, permanently on August 31st, 2026. If you've been thinking about joining now is the time. 

Head to formerlawyer.com/collab to join before doors close on August 31st.

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

I'm closing enrollment for my self-paced group program, the Former Lawyer Collaborative, permanently on August 31st, 2026. If you've been thinking about joining now is the time. 

Head to formerlawyer.com/collab to join before doors close on August 31st.

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

Do You Need a Bridge Job? Key Questions for Lawyers in Transition

First Steps to Leaving the Law

The Former Lawyer Collaborative

I'm closing enrollment for my self-paced group program, the Former Lawyer Collaborative, permanently on August 31st, 2026. If you've been thinking about joining now is the time. 

Head to formerlawyer.com/collab to join before doors close on August 31st.