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

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 now2:59 - Kelcey's first "did I make a huge mistake" moment and why it wasn't law school6:25 - How realizing law is a bad fit damages your ability to trust yourself to make career decisions9:24 - Why lawyers who worked as paralegals before law school often feel an extra layer of self-blame11:19 - The "I should have known" trap and why you couldn't have known what you didn't experience14:35 - How the experience of a bad fit impacts the next career decision and the one after that17:40 - Why most people who go to law school were too young to have done the inner work of knowing themselves19:17 - Why punishing your younger self for not knowing what you know now keeps you stuck20:57 - The pressure to find the capital-T Thing and how fear of judgment keeps lawyers in jobs that are hurting them30:48 - The binary thinking that makes it feel like you're either a lawyer or you're nothing33:33 - How Kelcey built a consulting business by combining what she was good at with what she actually liked36:02 - Why perfectionist, eldest-daughter types forget they're resourceful enough to figure it out41:03 - You will be okay, and if the next thing isn't right either, you can keep going43:46 - Bridge jobs, lily pad jobs, and why it doesn't have to be forever to be worth doingMentioned In Making a Career Change When You're Afraid of Getting It Wrong with Kelcey BakerKelcey Baker on LinkedInValidation: An Incredible Tool for Unhappy Lawyers with Kelcey BakerStartling Parallels Between Narcissism In Law Firms And Family UnitsHow Law Firms Avoid All Responsibility for Toxic Environments with Kelcey BakerLawyers - Hoping To Be Hit By A Bus Isn't NormalFirst Steps to Leaving the LawThe Former Lawyer Collaborative

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 from1:04 - How the decision to leave becomes tangled with feeling "wrong" about the original choice2:10 - The decision to become a lawyer was made with limited information at a specific age3:14 - Why lawyers don't apply the "new information" standard to their own experience4:00 - The "don't be a quitter" conditioning and how good-student types absorb it7:55 - Holding your past self to a standard no human can be held toMentioned In The Shame Lawyers Feel About Wanting to Leave LawFirst Steps to Leaving the LawThe Former Lawyer Collaborative

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 not3:51 - Getting exactly one Biglaw offer and choosing commercial litigation without knowing what it would be like7:29 - 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 response12:11 - Still having nightmares about his law job and the identity crisis of feeling like he was failing13:14 - What actually helped was the podcast, therapy, and talking to anyone who wasn't a lawyer16:58 - Why clarity follows action and how waiting for a perfect plan keeps lawyers stuck20:29 - Why individual interaction was the missing piece in his desire to help people22:46 - The practical realities of becoming a personal trainer as a second career29:19 - Why tying your identity to achievement doesn't go away just because you leave law33:51 - Being willing to try something without knowing if it's going to workMentioned In From Commercial Litigator to Personal Trainer and Business Owner with Zach ReischRozzie FitnessFirst Steps to Leaving the LawThe Former Lawyer Collaborative

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 start2:29 - Knowing what you're targeting is what makes the resume easy5:10 - What actually works when you go to revise the resume6:32 - Values are the first part of the framework inside The Collab8:56 - Don't start with your resume, start with values and therapyMentioned In Translating Legal Skills for a Non-Legal Job Doesn't Start With Your ResumeHow To Revise Your Resumé For A Non-Legal JobBreak Into Legal Tech and AI as a Lawyer with Ben ChiribogaFirst Steps to Leaving the LawThe Former Lawyer Collaborative

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 pattern2:33 - Wanting to help people through law and how recruiting funneled her into business litigation instead4:51 - The conveyor belt and why the realities of practice diverge from what brings people to law school7:48 - Why being a free thinker is not rewarded at a big firm8:48 - On paper everything looked perfect, partner, deputy general counsel, two kids, and the constant restless feeling underneath9:54 - Neurodivergence, the strong sense of justice, and why these traits do not get rewarded in big firms13:16 - Where Amy's values clashed with the actual work of business litigation18:06 - Why "just don't care" is not actually possible when someone is being rude and disrespectful20:19 - Pleasure as the body's antidote to stress and how it resets the nervous system22:43 - The early seed of wanting to be a sex coach and why Amy tucked it away for years25:38 - The reactions Amy got from colleagues, friends, and family when leaving Biglaw29:16 - You do not have to leave law entirely, you can find a way to practice that aligns with your values33:22 - What Amy recommends if you are curious about coaching as a career34:00 - What sex and relationship coaching actually is and who Amy works withMentioned In Leaving Biglaw to Become a Sex and Relationship Coach with Amy TerwillegerAmy Terwilleger's Website | LinktreeAmy Terwilleger on Instagram (@millennialdrruth)First Steps to Leaving the LawThe 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 law1:02 - Why there is always someone who has it worse and why that keeps lawyers stuck1:55 - Why the struggle to feel justified in leaving is fundamentally external2:35 - "Am I justified in leaving" is really a question about who gets to say3:55 - Why so many lawyers cannot trust their own experience4:38 - What you actually need to access to find something better5:57 - Why this needs to be your choice and not something you wait for permission to do6:32 - The skill you are going to be developing as you move out of the law7:56 - What it tells Sarah when she hears lawyers asking if they are justified in leavingMentioned In Trying to Justify Leaving Law Is What’s Keeping You ThereFirst Steps to Leaving the LawThe 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 environment2:23 - Why "tolerating" your job never means staying somewhere that's damaging you3:24 - Being realistic about your timeline and what the work actually looks like4:11 - How long the Collab framework typically takes when you give it a couple hours a week5:16 - Why the day you can leave is not the day to start figuring out what's next6:14 - What makes tolerating your job easier while you're preparing to leave7:40 - What to do if you see yourself leaving eventually but not soon9:15 - Why giving yourself time instead of rushing is one of the best uses of your time in a lawyer jobMentioned In Tolerating Your Lawyer Job While You're Preparing to LeaveDo You Need a Bridge Job? Key Questions for Lawyers in TransitionFirst Steps to Leaving the LawThe 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 tech2:27 - Why legal tech keeps coming up for lawyers who want to leave practice4:07 - No agreed terms, no standardized titles, and what that means for your job search4:45 - You're not alone in being confused about where to start in legal tech9:17 - The three main career paths in legal tech and AI for lawyers leaving practice11:41 - Product roles and why lawyers are better positioned for them than they think13:00 - Go-to-market roles and why a JD is a competitive advantage in sales conversations13:48 - Why operations roles are booming inside legal tech companies right now15:13 - JD required vs. JD preferred and what your legal background signals to employers17:55 - Why lawyers automatically rank in the top 1% of candidates for legal tech jobs24:52 - Why lawyers try to execute before they know their objective30:25 - Why applying for every legal tech role is a recipe for madness35:37 - How to speak to a role you've never held and start building proof of interest39:38 - Why updating your resume is the last thing you should do42:24 - Ben's closing take on legal tech as a viable career path for lawyers ready to make a moveMentioned In How to Break Into Legal Tech and AI as a Lawyer with Ben ChiribogaReframe Lawyer | Ben Chiriboga on LinkedInEscaping Lawyer Burnout for Legal Tech with Ben ChiribogaHow To Revise Your Resumé For A Non-Legal JobFrom Biglaw to Legal Tech with Alex SuThe Claude-Native Law Firm by Zack ShapiroFirst Steps to Leaving the LawThe 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 Enneagram3:01 - What Sarah sees with lawyers whose jobs aren't good for them4:26 - Why highly responsible lawyers struggle to give themselves permission to even think about leaving5:07 - What an overdeveloped sense of responsibility actually means6:03 - How toxic environments exploit lawyers who are highly responsible7:28 - The faulty logic that keeps highly responsible lawyers from cutting themselves any slack9:18 - Why it matters to know if responsibility is one of your top characteristicsMentioned In How an Overdeveloped Sense of Responsibility Keeps Lawyers StuckFirst Steps to Leaving the LawThe 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 lawyer1:56 - Why caring about doing good work makes this harder3:56 - The B-minus work concept and why it matters4:37 - Why this is harder for lawyers from marginalized communities5:04 - How loosening that standard makes space for other things5:24 - Why therapy is worth considering if this resonatesMentioned in What Doing Your Best Is Costing You as a LawyerFirst Steps to Leaving the LawThe Former Lawyer Collaborative