Why staying at your law firm is riskier than quitting (Part 1)

This is Part 1 of a series on how to be a happier lawyer. If you’re interested in getting support to find more fulfillment or balance in your current job or just need an understanding ear, please email me at sunshine.w.yin at gmail dot com.

I wrote this because often people ask me how I left my firm, and I suspect many others are also trying to leave but want some encouragement. I want to stress that I speak from a very specific experience — that of being disillusioned with working as a litigation associate at a big law firm — so my perspective will be limited. Many of my friends have found fulfilling ways to practice law both inside and outside of the firm setting; I admire them for that and only wish there were more of them.

Like many of you reading this, I fell into law. By that I mean I made a series of safe, unobjectionable decisions to achieve a goal I thought I wanted but didn’t actually bother to examine beforehand. Also, I was decent at most things in school but not “passionate” about any particular one. Except reading — I loved to read. And arguing with my parents — that was my second favorite hobby. Based on these two data points, my parents decided the only reasonable career choice for me was that of a lawyer.

Fine, I shrugged. I didn’t have any better ideas at the time, and this — getting into law school — gave me a goal to work toward, a next rung on the ladder. So I applied and got in.

Fast-forward three years. I graduate, pass the bar, woo! (That third year of law school was fun, wasn’t it? Like summer camp! Totallly worth the seven years I’ll spend paying it off.) I get my own office, and I have a secretary! I can’t believe they’re paying me this much — when are they going to find out I have no idea what I’m doing, and I can’t possibly be worth this much?

One year later. They’re not paying me nearly enough for this. How much longer do I have until my loans are paid off?

My second year as a law firm associate was one of the hardest years of my life. It wasn’t because my firm treated me poorly, or because my hours were overwhelming. In fact, I actually liked my firm and grew close to many of the people I worked with. Plus, I had a kick-ass assistant, one of the best at the firm.

No, I became depressed because of the sinking realization that I’d worked my whole life to end up here: to be constantly under someone else’s thumb, inefficiently fighting other people’s foolish battles in an exorbitantly expensive yet broken system that incentivizes posturing and manipulation, marking my time in 6-minute increments. Wasn’t this all I wanted? The unobjectionable future I’d marched so steadily toward? Just nine more years, and I might be up for partnership, right?

I didn’t understand why I couldn’t suck it up and keep at it with my head down like everyone else. I became joyless, listless, and withdrawn. I listened to a lot of Pink Floyd, which probably didn’t help. I blamed myself for being mentally weak. I berated myself for not appreciating my own privilege — some people would kill for my job! I read self-help books. I talked to a therapist. I took cold showers. I took personality quizzes to figure out how to get my motivation back. I tried meditation, yoga. And yet, every night, I dreaded going to sleep because it meant tomorrow would only be a blink away, and that it would bring the same as yesterday. I encountered this quote by Thoreau:

“The mass of men lead lives of quiet desperation, and go to the grave with the song still in them.”

This was the most depressing and truest thing I’d read all year, and I thought it definitely applied to me.

For those lucky enough to have found meaning and satisfaction in working at a law firm (and I do know a handful of you), you are heroes! The legal world needs more people like you. For others who feel similarly as I did, and especially for those who are too busy logging hours to be able to process how you feel when you are not working, I have three general pieces of advice:

(1) Don’t fall prey to status quo bias

I’m sure you’ve come across it, but status quo bias is the tendency for people to let things remain the way they are, even when they should rationally do something about it. Usually it’s because they’d rather put off having to make a decision, or they feel that keeping the status quo is safer than making a change. This inclination is strong even when people know the “cost” of making a change is tiny and the magnitude of the decision is huge. (For example, accepting the default 401K plan that your employer has set up for you instead of doing even minimal research to decide how to invest your retirement funds. Yup, you know who you are.)

Status quo bias is rampant in the law firm world because we are an inherently conservative bunch, and on top of that we are groomed by our environment to be even more risk-adverse. (Hell, the whole concept of case law is premised on preserving the status quo! We are trained to keep things the way they are.) Couple that with herd mentality — that of looking to the behavior of our peers for validation of our own choices — and this is a winning formula for staying at jobs that clearly make us miserable.

Yet it’s understandable: changing the status quo requires an affirmative act, while maintaining the status quo requires just a failure to act, which admittedly seems easier. However, the failure to act — an omission — is itself a decision, and it impacts your future just as much as making a change does.

If you do nothing — i.e., by spending all your waking hours simply responding to demands that others place upon you — nothing will change. Doing nothing comes in many forms, including:

  • Doing nothing and hoping the partner you work for is miraculously going to give you less work next year
  • Doing nothing and hoping that your next project will just be “better”
  • Doing nothing except idly browsing LinkedIn, secretly hoping that an opportunity will land in your lap
  • Doing nothing and feeling guilty about the lack of time you are spending with the people you love
  • Doing nothing while texting with your lawyer friends about how much you’re working, how much you dislike it, and how little you’re sleeping

If you do the above, your situation will get worse. And with every day that passes, it will become harder and harder to make a change. You get used to certain standards of living and spending. Or you buy a house. You have babies. You’ll feel more trapped. You’ll wonder how you could possibly take a salary cut while other people are relying on you, and you’ll have less time and energy to figure it out.

If you are unhappy now, then doing nothing will guarantee that you will continue to be unhappy. Yes, you will continue to get assigned the same work. Yes, your billable requirements will be the same, and you’ll keep working yourself to the ground chomping at the bit that is “bonus.” And yes, most likely, you will continue to work with the same people — the ones you complain about to your friends. On the other hand, if you make a change — if you take a chance on yourself — you at least increase the likelihood that you will be happier.

But here’s the kicker: even if you “fail” in your next venture, whatever it may be, you are still better off. As a risk-averse bunch, lawyers have a hard time internalizing this. Failure feels bad. It threatens your ego. But failure is progress. It means you either learned some very valuable information about yourself and about the world, or you are able to eliminate an option that is wrong for you, often both. (To learn more about this, read about growth mindset.) Either way, that is infinitely better than staying in a situation that you already know is wrong for you.

But still, you have doubts. You want reassurance that if you leave your law firm, you won’t regret it. Regret — this is ultimately your biggest fear. Listen to me: I have never in my life met anyone who regretted their decision to quit their job as a law firm associate. Never.

I do know many, many people who left, and who are now exponentially happier at their new occupations while still living in nice neighborhoods, supporting families, and even spending time with those families (!).

The transition I personally made was drastic — I switched fields entirely and became a software engineer — and I am immeasurably happier as a result. This is certainly not the only way to go about it, so I’ve tried to generalize my experience and some of the lessons I learned. Some of them will seem obvious, but you may want someone to say it to you anyway.

(2) Learn to say “no”

We are ambitious people who are deeply afraid of disappointing others. We hold ourselves to absurdly high standards and are very unforgiving when we fail to meet them. We got to where we are by being exceptional rule-followers. We are smart and capable people who desire a purpose but usually don’t have a good idea of what we really want to do. Unfortunately, these traits combined make us easily exploitable.

If you don’t set boundaries, you will always be an accessory for implementing someone else’s agenda, instead of the originator of your own. Try this: make a list of things you care about, and things you actually spend your time doing. How much do they overlap?

I know, work is consuming. Most days, when you get home from work (if you get home from work), you’re physically and emotionally exhausted. You have no energy to do anything but watch Netflix. You probably meant to go to the gym, but once again, did not.

But work is as consuming as you let it be. There are a lot of times when you could have said “no” or even “not now,” yet out of a vague sense of fear, you said yes. A partner asked you out to lunch even when you are already swamped, and you don’t want to offend him or her. Say no, politely. Your work coordinator asked for “just a couple hours help” on a research assignment. Refuse, politely. The summer associates are here, and you’re expected to make an appearance at afterwork social events. Decline, politely.

Here are some guidelines for saying “no”:

  • You do not need to include a reason. You could, but then you are perpetuating the belief that the firm is your warden, that it is entitled to know of your whereabouts at all times. This is not true. Your firm does not own you. Simply saying, “I won’t be available from 6–8 pm,” is sufficient. And then, do not be available from 6–8 pm!
  • You have to be okay with people being mildly upset with you.This is hard, but they will get over it, and so will you. If no one is ever upset with you, that should alarm you because it suggests you are consistently sweeping your own interests under the rug. Winston Churchill said, “You have enemies? Good. That means you’ve stood up for something, sometime in your life.”
  • Envision the very worst thing that will happen if you say “no” or “not now.” No, you won’t get fired. (Do you realize how much it costs to find, hire, and train someone to replace you? There is a reason they are willing to pay you tens of thousands for a referral.) But maybe a partner will yell at you. That sucks. Maybe you won’t make bonus this year. That might suck, too. But will your friends and family still love you? Will you still have a place to sleep tonight? Yes.

Saying “no” to work is very hard. Yet saying it to friends, family, and yourself is very easy. Make it the opposite. You have to train yourself to do it and to realize that things are going to be okay even when you do. Saying no allows you to carve out space, time, and energy for yourself to figure out what your next steps are, what you actually enjoy, and what your own vision for your life is. (And actually, it goes without saying that getting more sleep and spending time away from work will actually make you better at your job.)

(3) Don’t fall into these traps

Don’t buy the conventional wisdom that you need to put in 4–5 years before you’ll be taken seriously

First, ask yourself if you are saying this to excuse yourself for being lazy and doing nothing.

It is true that many companies — even ones considered progressive — look for years of experience instead of relevance of that experience. Often they may hire someone with more years of irrelevant experience than fewer years of relevant experience. This is illogical, of course. (If you are an employer or recruiter reading this, you are missing out on a huge workforce of smart, motivated people.)

But there are plenty of companies that are more sensible about this. These tend to be smaller and scrappier companies who are keen to find someone who can do the work or figure it out if need be, and they are less worried about having to justify hiring decisions to higher-ups. Seek out these companies.

Don’t fool yourself into thinking that you can change the type of work you do at the firm

Is there a way to continue working at your firm in a capacity that you enjoy? Unlikely, but perhaps. Before you call it quits, it may be worth asking whether you can do something different or do something differently at your current firm that would enable you to keep working there but be happier. It would be a low cost way to explore something new, and the firm usually wants to try to accommodate you because it would rather retain you in any capacity than to suffer the expense of losing you altogether. You have nothing to lose, right?

But beware of promises. I don’t think work supervisors intend to deceive, but at the very least they may be overly optimistic about your chances of switching to a different project within a reasonable timeline. Litigation is a long, protracted process. Deadlines are constantly postponed. And once you’re on a case, you’re on it for the long haul, because it would be too expensive to replace you in the middle of a case. So there will always be compelling reasons to keep you on it.

But also beware that even if you are assigned to a different team or a different industry, your day-to-day work will largely remain the same. Most litigation associates I know are not bored by the what, but infuriated by the how. So switching to a different team or industry is not going to fix that. Let’s say you were doing copyright law and you think you might like environmental law instead. Maybe initially you’d be more motivated by the change in subject matter, but when that sense of novelty wears off, you are still left with the same routine: drafting complaints, propounding discovery requests, reviewing documents, researching Westlaw, and dealing with uncooperative opposing counsel.

I’m not saying not to give it a shot. But set a deadline. Reevaluate in, say, 3 months. If by then you still feel like you’re in a rut, then it’s time to make a change, regardless of what promises are made to you.

Don’t be afraid of hurting other people’s feelings

One of the hardest things about quitting was the fear that I was disappointing and hurting the people who had supported and invested in me. These included my parents, who were upset and bewildered; college professors who wrote me recommendation letters when I applied to law school; lawyer friends who I felt I was abandoning; and mentors at the firm who had stuck their necks out for me.

But, to my surprise, I learned that the people who really care about you will cheer you on in your pursuit of happiness instead of resenting you for it. You will realize this, too.