How I Quit Biglaw

We had these sudden revelations that employment, the daily nine-to-five, was driving us far from our better selves. Should we quit? Would that solve it? Or were those qualities innate, dooming us to nastiness and paucity of spirit? We hoped not.— Joshua Ferris, And Then We Came To An End

Last week, I quit my biglaw job. “Biglaw,” for the uninitiated, refers to that breed of corporate law known (mostly) for bigness in size. A career in biglaw involves climbing a very long ladder at the top of which, if you’re very lucky and very patient, sits a great big prize: partnership. Except (surprise!) the prize ends up being a longer, steeper ladder. To borrow a cliché from too many others, it’s like a pie-eating contest where the prize for winning is more pie.

All of which is to say, it’s hardly uncommon for associates to quit the ladder-climbing when they realize how little they like pie. It’s a bit more uncommon for people to do what I did and leave the legal industry entirely. Though, at least based on an unscientific — but sizable — sample of associates who have asked me about my decision to leave, it’s not for lack of desire. I say this because the question people keep asking me about my departure is not why are you leaving (this much is apparently self-evident), but how. How did you get out?

Peter Thiel writes about this phenomenon in Zero to One:

When I left — after seven months and three days — one of the lawyers down the hall from me said, “You know, I had no idea it was possible to escape from Alcatraz.” Of course that was not literally true, since all you had to do was go out the front door and not come back.

He has a point. On some level, the answer has to be quite easy: how did I do it? Well, I walked out the door — and you can too! And yet, even the unhappiest, most desperate-to-get-out lawyers are generally still exceptionally skilled at erecting mental roadblocks just shy of that door. It’s a phenomenon that baffles outsiders, for whom the solution to the problem of dissatisfaction and ennui that plagues so many biglaw lawyers appears so simple: if you hate it so much, why don’t you just fucking quit already?

Because, because, because. Because you don’t know how to leave. Because in order to know how to leave, you have to do the hard mental work of slogging through the who/what/where/when/why. Hence what follows: a dissection of how to get to the how. (Note before I go any further: this should go without saying, but what follows is for the sad biglaw lawyers, not the happy ones. For people in the latter category, I sure wish I could have been one of you.)

Who are you leaving?

I believe it was the jilted boyfriend from The Devil Wears Prada who observed of the protagonist and her relationship with her cell phone aka her boss (aka Meryl Streep!):

You know, in case you were wondering… the person whose calls you always take, that’s the relationship you’re in. I hope you two are very happy together.

<Spoiler alert> Oh jilted boyfriend — it was your wisdom that drew her back to you! But seriously: this is just a fact of life. A biglaw job isn’t a career so much as a boy/girlfriend. Except this boyfriend demands your full attention at all hours of the day and often upsets you — though to be fair, he does buy you lots of alcohol, upon which you will come to depend to get you through the days. So go on taking his calls and frantically responding to his emails while you’re at dinner with your real-life boyfriend/wife/friend/parent. Hopefully your relationship with biglaw is more fulfilling than the ones you’re leaving behind.

What are you leaving?

See above description of pie-eating ladder-climbing contest.

From where are you leaving?

Purgatory. I call it purgatory because most biglaw attorneys who are unhappy seem to be so because they are stuck. Ever since they stopped wanting to be the lawyer five years their senior, they no longer feel like they’re advancing towards a goal — but alas, they also have no time to figure out what else they’d rather be doing with their lives. They have long since left behind passions that motivated them when they started, and have even begun to question whether those passions ever existed to begin with. They’re unhappy not because they’re working hard, but because the hard work isn’t yielding returns. The phenomenon commonly described as “burnout,” by the way, is, I think, generally not due to people working too hard, but people accepting the futility of it all or resenting their jobs for taking them away from the things they’d rather be doing. But what are those things? Don’t know? Purgatory.

When are you leaving?

There are always a million reasons why tomorrow/next week/next year is a better time, but if you’ve been unhappy for more days than you care to admit to yourself in your most private moments, the best time was probably yesterday. For the first two years I was an attorney, my plan was to wait until my six-figure student debt was paid off. I hoped that by then, I’d magically grow to love my work. I didn’t wait. Instead, I internalized something wiser individuals had been trying to tell me for years: that time is the most valuable thing any of us have, next to health and relationships. That I wouldn’t put a price on health and relationships, so I shouldn’t sell my time off on the cheap either. (And by that, I don’t mean that the pay at a biglaw shop isn’t great — it is, and you’ll be hard-pressed to find a job that matches the salary if you leave — but imo it’s not worth the 2000+ hours a year you’ll never get back.)

Now, add the who, what, where, and when together to get the why. Why?

Because life is not a dress rehearsal, and you only get one chance to do something you’re proud of. Because your time matters, and shouldn’t be invested in people who don’t value your physical and emotional well-being. Because if you’re an unhappy lawyer and it’s not because you have horrible bosses, it’s probably because you’re bored by the work, not doing what you’re best at doing, not as interested or interesting as you could be, or all of the above.

Let me pause for a second on a little emotion called fear.

Lawyers like to pride themselves on being rational, logical (and above all!) thinking people. And while most are, a little thing called fear (euphemistically known as “risk aversion”) gets in the way of the thinking.

For example, if you were rational, you would have no choice but to figure out the how part as soon as you’d figured out the why. You’ve already built the case; the rest is just execution. But fear gets in the way.

Speaking personally, I think that from the moment I entered biglaw, I became a more fearful person. Clients were paying literally hundreds of dollars an hour for perfect work, so I was afraid of, in descending order: typos, not responding to emails within 10 minutes of receipt, sending stupid emails, getting yelled at, getting noticed at meetings, not getting noticed at meetings, saying something stupid out loud, thinking stupid things, being stupid, getting fired. This environment of institutionalized fear clouded my judgment, and literally paralyzed me from exiting.

At some point, it occurred to me that I had become a way less interesting person than I had been when I started out. (I know this because I keep a journal, and my journal entries during my last year in biglaw were getting reeeaaal crusty.) So I went to a gathering of female law school alumni hosted by a career counselor. We ate dinner in a dark cave of a restaurant. As is typical of functions involving lawyers, lots of wine was poured. Around me sat all these brilliant women who had attained some of the most coveted jobs in the industry: general counsel of one of the Big Three TV networks; assistant US attorney; partner at a biglaw firm, the list goes on. The one thing all these women had in common? After decades of practice, they desperately wanted to get out. So much so that when I said that I was planning to leave the law, I actually got applause. Um…say what? Scary, right?

The point of the story is this: taking the plunge is scary. But not taking the plunge is far scarier.

Once you get over your fear, you’ll have no choice but to think about the how.

In many ways, the “how” part of leaving is a lot less interesting than the why; the how is just logistics. Everyone’s “how” will be different, but here’s how I became one of many biglaw refugees who did it:

1. I spent months consciously exiting the mindframe of a biglaw associate. This involved exploring all the things I’d rather be doing and identifying the commonalities uniting those things. (Note: if this sounds like an exercise your high school or college counselor forced upon you, it’s because it probably is. Big oops for not taking that assignment seriously a million years ago.) I realized that for me, I liked creative processes much more than repetitive practices, which explained why I didn’t like being a lawyer (because law is, by necessity and design, built on repetition and precedent).
2. So I tried to start a startup. Trying to do this was super fun, even though it took some amount of commitment. I’d wake up at 5 and devote the best two hours of my day to educating myself about the industry, then a couple times a week would meet up with my partner to brainstorm and plan. And who knows if our startup baby is ever going to grow up; this exercise was valuable because it taught me that I could actually have fun doing something (and at 5 am, no less)! Oh the possibilities!
3. Realizing that I’d probably never be able to feed myself if I quit and went full hog on a startup, I applied to non-legal jobs at tech companies for which I had zero qualifications. I sowed my seeds far and wide. Though I didn’t count on actually getting any of these jobs, I nevertheless continued onto Step 4:
4. I wrote a “personal manifesto,” which included a drop-dead quit date of June 1. I then publicized this drop-dead date. This was important because it forced me to take quitting seriously. And I knew I needed to take quitting seriously because I was not willing to waste any more time developing skills that were generally irrelevant to the things I wanted to do. This realization dawned on me after I learned that most of my legal skills were too narrow to apply to most other business-related professions. (As an aside: you know how they tell you before and during law school that your legal skills are “broadly transferable?” This may be true in theory, but fun fact: in practice, it’s almost always a lie.) Anyway, my drop-dead quit date was June 1 — though in the interests of full disclosure, I didn’t actually give notice until about 10 days later because I wasn’t good enough at Step 5:
5. Making a solid financial plan. This is an obvious step whose importance is extremely difficult to value appropriately. By that I mean, it’s difficult to not over/undervalue the importance of having a financial cushion. For me, I initially undervalued the importance of having enough money (Who needs rent? I can crash on friends’ couches, right?), and as my drop-dead date approached I overvalued it due to anxiety (I am literally going to be homeless and will never be able to pay off my student loans. Ever). I’m not very money-smart and so don’t really have good advice on this, other than to save money (shameless plug to use my Digit code!) and see if you can live without living like a lawyer.
6. Be there when luck meets opportunity. This happened for me when one of the places I applied to in Step 2 actually said they wanted me. I gave notice the next day.