Quitting Your “Dream” Job as a Lawyer: How To Stop Planning and Start Living (Some Tips!)

Taly Matiteyahu
10 min readMar 28, 2020

Since sharing my story about leaving legal practice and becoming a “recovering lawyer”, I’ve had former classmates, friends of friends, and total strangers reach out to me. I’ve been emailed, messaged on LinkedIn, called, and even DM’d on Instagram by people asking me for advice on leaving law.

There isn’t a set method for quitting law, but I’m happy to share my experience and insight in case it may help others.

1) Accept your feelings

Looking back, I realize that I was depressed during my time at the law firm. I’m going to briefly take this to a dark place for a moment (but I think it‘s worth it if it helps others realize they’re not alone)… I remember actively wanting to get sick, regularly hoping to get mildly injured during my daily bike commute, and constantly wishing for reasons to work from home or have reason to not be working at all.

I had never felt that way before and it was disturbing. So I buried it for a while, told myself it might get better, and tried to will the problem away. At a certain point, though, I had to accept that I was miserable (and probably depressed) and that it wouldn’t change unless I made a change.

Be honest with yourself. If you’re unhappy, that’s ok. Not everyone is meant to be a lawyer. You might be the type of person who comes to tolerate or even like something you previously hated… but you might also be the type of person that will never enjoy practicing law. And that’s ok.

Photo by Emma Matthews Digital Content Production on Unsplash

2) Realize your feelings about work aren’t a reflection of your work ethic

I’m a type A personality. I worked hard throughout school and at all the jobs I’d worked at before. I throw myself into things and like getting shit done. I’m self-motivated, ambitious, and very driven. But… not when it came to my job at the law firm. I didn’t care about the work, didn’t want to learn about the deals, tried to avoid meetings and calls, and generally didn’t want to work on anything I was assigned. Writing all of that out now, I can’t help but think “gosh, what a lazy person” about past, firm-life me.

Working at a firm made me question my work ethic, my capabilities, and my self worth. It was really hard to reconcile who I knew (or at that time, thought) I was with my performance at work. But ultimately, I realized my lack of desire to do that specific job didn’t mean I was a slacker — it just meant that I needed to apply my skills and passion elsewhere.

So if you’re feeling guilty for doing a half-assed job at something you hate, don’t — of course you won’t want to give it your all. It is not a reflection of who you are.

3) Let go of the anxiety about what other people will think

I spent a fair amount of time feeling anxious about what other people would think about my decision to stop practicing. Looking back, my concern about potential judgment might have been more a reflection of own fears than genuine concern about what others thought.

You may frequently hear about lawyers being unhappy, but not many people really talk about leaving law. When I posted my article about leaving practice, the outpouring of support was incredible. It was quite the reminder that I wasn’t alone, despite how lonely going through the process of leaving practice felt.

Regardless of what other people may think about your decision to leave practice, remember that you’ll never lose the achievements you’ve earned. You will always have your law degree. Besides, it’s way braver to embrace an ambiguous future than to stick to a known (albeit miserable) path… so ignore the judgment and know that you’re doing what’s best for you.

4) Forgive yourself for “giving up”

I spent a lot of time and money becoming a lawyer, only to leave practice after a year and a half. That decision came with a lot of guilt and a lot of self-doubt. Was I making a bad decision leaving the career that I worked so hard for? Did I waste 3+ years of my life and a lot of money for nothing? Was I letting down my parents, who were so proud of my achievements (I’m pretty sure my mom might still tell people I’m a lawyer when they ask about what I do, even though I don’t practice anymore)?

Maybe I was making a decision others might think was bad, maybe I sank a lot of time and money into becoming a lawyer, and maybe I did let some people down. BUT I was miserable and the idea of going to a job I hated so desperately for the rest of my life was thoroughly depressing.

So… forgive yourself. You’re not giving up — you’re just letting something go in order to make room for something else… something that will ideally be much better.

5) Let go of the fear of moving to a new career that you’ll dislike

I’m going to generalize for a moment for the sake of this point — folks who go to law school tend to be a certain type of person. They’re risk averse and seek stable, secure careers and financial futures.

I remember thinking “what if I hate my next job too… then I’ll have given up the cushy salary for nothing and be worse off for it.” It’s scary trying to figure out what you want to do. It feels like the stakes are high and there are a lot of risks.

The way I ultimately figured, moving to something else and trying it, even if only to find that it’s not quite what you want, is better than staying somewhere you know you don’t want to be. You shouldn’t feel like your next step has to be the step or the right thing, it can just be something you want to explore. And sure, maybe you’ll lose the cushy salary, but even if you earn less, you’ll probably earn enough and you’ll be working towards something you actually want.

Photo by Bluehouse Skis on Unsplash

If whatever you do next isn’t right for you, you can transition to something else…. until you do find the right thing. If you’re smart and capable, don’t fret about the next thing being the right thing — as long as you’re not doing something you already know you hate, it’s probably a step forward.

6) Talk to as many people as you can in fields you’re curious about & leverage them

Let me start by explaining how I got connected to the person who referred me for my first post-firm job.

My partner had a friend from college who he played baseball with (who I’d met a few times). That friend was friends with a younger student who also played baseball (who I spoke to on the phone for like, 5 minutes). That younger student had an older brother who went to Stanford Law and started a legal tech startup (who I spoke to on the phone about his work for about 30 minutes one time and then stayed in sporadic touch with on LinkedIn & email). That startup founder was connected to someone on LinkedIn who worked at a company that had a position I was interested in (which I saw when I was applying for the position, months after first talking to the startup founder). When I asked for an introduction to the employee, the startup founder said “[I] wouldn’t say I know him well”, but that he would be happy to try to help.

The startup founder connected me to that employee via an email, I chatted with the employee for maybe 20–30 minutes on the phone on a Tuesday, the employee put in a referral for me that day, I was emailed by the recruiter for the position on Wednesday, spoke with the recruiter on Thursday, went in for an interview the following Monday, and was offered the job on Tuesday. I gave notice at my firm that Friday and started the new job two weeks later.

Was that confusing? Convoluted? Is your head slightly tilted or is your face making one of these expressions — 🤨😖🤔😵😴. Yeah. It was pretty random and incredible and I feel very lucky. But what I’m trying to say is that you never know what connections may bear fruit one day. If I hadn’t spoken with my partner’s baseball friend’s younger friend’s older startup founder brother, I wouldn’t have had a connection to this company. If I hadn’t reached out to the startup founder to ask if he’d be willing to connect me to someone at this company, I wouldn’t have gotten a referral. Sure, maybe I would’ve gotten an interview anyway (for what it’s worth, I actually did apply via the website *before* getting the referral and didn’t hear from the company), but I believe that the employee’s referral got my application to the top of the pile and was a key reason the recruiter contacted me.

Photo by Adam Solomon on Unsplash

7) Don’t be afraid to apply for jobs where you don’t have a connection

After #6, you might be like “well wtf, why is this #7?”

Because although it’s statistically harder to get a job without an “in”, it’s totally possible. And you shouldn’t avoid applying for positions you’re interested in just because you don’t know anyone at the company. Trying and failing is better than not trying at all.

8) Don’t beat yourself up if it takes you time to find a new job¹

Unless you’re one of those miraculous unicorns that’s recruited by places like Facebook, Apple, Netflix, or Google, bouncing around top-tier companies year after year (which, as a young attorney, you probably aren’t), you’ll probably find it challenging to find a new job outside of the legal industry.

When I was looking for a new job, someone told me that it takes an average of six months to find a new job. I have no idea where that statistic came from (were they talking about lawyers specifically? people looking for salaried roles? people within a certain age range?) and I have no idea if it’s true, but I found it comforting to hold onto as I struggled to get any job offers.

Photo by Who’s Denilo ? on Unsplash

Although there are plenty of articles out there that encourage lawyers to change careers and say lawyers make great project managers, journalists, CFOs, and more, I think that being a fairly new lawyer trying to leave practice makes job hunting more complicated than not. You’re underqualified for most roles that require even a year or two of experience (those will go to folks who have had comparable roles in junior positions) and overqualified for roles that require no experience (those roles will go to more typical candidates, the new college grads — why would an educated lawyer want to be a marketing assistant, anyway?) If you’re lucky enough to get an interview for a non-legal position someplace, I’ll wager there’s a 75% chance they’ll ask or tell you that the role you’re interviewing for isn’t intended to be a stepping stone to an in-house counsel position.

Don’t get down on yourself if you have trouble getting interviews and/or offers. All it takes to change everything is one offer — it might just take a bit of time to get it.

9) Embrace the ambiguity

There’s so much uncertainty throughout this process — what will others think, will I be able to make enough money, what if I hate my new job, is starting over in a new career a good idea, what if I’m underqualified, what if I’m overqualified, what if I’m just bad at adulting, will I ever feel fulfilled, will people be willing to talk to me about what they do, will I ever find a new job — the questions and the anxieties and the fears can be overwhelming.

Don’t let fear of the unknown paralyze you into maintaining the status quo. As silly as it may sound, embrace the possibilities that the unknown holds.

10) Design Your Life!

Check out Designing Your Life. Someone recommended it to me when I was trying to figure things out and it was a great read. Through prompts, exercises, and anecdotes, it helped me hone in on how to identify professional interests, reframe how I thought about finding work I enjoyed, and embrace ambiguity in the interest of designing a life I wanted.

¹ This post was written before the COVID-19 pandemic and I haven’t changed my original post. Looking for a job is challenging even in normal times, but it will likely be even more challenging for the next few months (if not longer). You may need to be more conservative and mindful for a time than you would have needed to be otherwise. With that said, if you’re currently working from home and/or have more free time than usual, try to set aside time for career change planning — whether it’s reading up on different industries, updating your resume, or having informational phone calls. Being homebound doesn’t mean you have to stop moving towards your goal of leaving law!

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Taly Matiteyahu

Crazy dog lady and recovering lawyer who suffers from a serious case of wanderlust and a shortage of hours in the day.