Quitting BigLaw: Part II — The Three-Question Roadmap

In Part I of this series, I discussed why I think BigLaw is hard to quit. Since making my escape six months ago and talking about the experience on this blog, I have gotten questions from various BigLaw associates asking me how I did it and how they could do it.

I asked myself three broad questions before I quit. While these questions are not meant to be comprehensive, some people have found them helpful in thinking through the possibility of quitting. And now I pose these questions to you, with the hope of helping you make a rational decision that is not rash in reaction to a bad day.

1. What do you like and don’t like about working in BigLaw?

The nature of your work – Are you intellectually stimulated or bored by what you do on a day-to-day basis? Do you enjoy or dread any aspect of researching legal precedents, drafting and marking up memos, briefs, agreements, issues list, negotiating with opposing counsel, etc.?

The people of your firm – Do you feel a real kinship with your colleagues or are they just cut-throat back stabbers? Do partners at your firm mentor you or just cram everything down at the last minute simply to make their lives easier?

The career path – What keeps you on the treadmill that is BigLaw? Is it the stable salary and the clarity of a relatively defined career path as part of a well-oiled hierarchical machine?

The prestige – Do you care about the prestige BigLaw confers? Do you get a high from working on headline grabbing deals or cases?

Once you make your tally, ask yourself the final question – Can you and are you willing to work long and unpredictable hours to make everything worth it? Do the rewards outweigh the sacrifices?

When I sat down to evaluate these questions, I was able to isolate the crux of what I didn’t like. I had to face the reality and admit to myself that I didn’t like drafting. I simply didn’t enjoy documenting in hundreds of pages other people’s meetings of the mind – a core function of a typical lawyer.

Both of my BigLaw firms – Davis Polk & Wardwell and Simpson Thacher & Bartlett – treated me well. I enjoyed and respected the people I worked with. I might have decided to suck it up and continue with the job if I had more control over my time. Alas, that is not meant to be in BigLaw. We are tethered to our Blackberries. Our schedules can change within the blink of a red blinking light and we could be called to the office at any time, evening or weekends, plans or no plans. To me, the all-consuming nature of the job wasn’t worth the professional perks.

Everyone will arrive at a different conclusion to this question. And quitting BigLaw is not for everyone. Depending on your answers, you may decide that lateraling to another firm or moving in-house may be a better solution than quitting law altogether.

2. What does wild success look like to you?

Yes, wild. Not achievable, not most likely, but wild.

We lawyers are trained to spot issues, think about worst case scenarios and minimize risks. We tend to succumb to the nagging voices of naysayers.

I know this can be a tricky question to answer. I struggled with this and still struggle with it sometimes. We can be confined to the tunnel vision of what we know. Especially when we are consumed by work with little opportunity to explore, it is hard to think outside the box.

But let go of that nagging voice and let your mind wander for a moment.

To get started thinking about wild success, consider the following hypothetical scenarios:

(a) If you won the lottery for, say, $2 million after tax, what would you do?

You can plug in whatever dollar amount suits you. To me, $2 million is a lot of money, but not enough to keep my current lifestyle for the rest of my life.

Would you spend more time with family and kids? Get a dog? Take a culinary class at Le Cordon Bleu? Start a farm with an organic vegetable garden and a chicken coop? Design iPhone apps?

(b) If you had seven years to live, with great health until the very last day, what would you do?

I know thinking about death is morbid, but sometimes the sense of mortality gives a unique perspective to life. I chose seven years because it is long enough to still have to live responsibly for at least a few years.

Would you be a travel writer or photographer documenting exotic experiences? Join a hedonist commune or a spiritual ashram? Watch as many movies as possible and become a film critic?

(c) If you could choose to redo you college studies based on the knowledge you now possess, what would you choose?

It may be useful to remind yourself of the ambitions of the past, thinking back to a time when things were perhaps simpler and more innocent. What were your interests then? Were there any classes you wish you had taken? If so, what were they?

Not surprisingly, none of my answers to these hypotheticals included the practice of law. I wanted to do something within my own control, something I enjoy and could uniquely excel in.

I still ask myself these hypotheticals to help crystallize my thinking. I notice that I love talking to people and learning about their inner workings. I find how people make decisions fascinating and love helping them resolve their inner conflicts. I also notice that I am passionate about animals, both in terms of caring for them as well as being an animal rights advocate. For my wild success, do I want to become like Suze Orman, but focusing on interpersonal relationships instead of personal finance, or some kind of animal-related entrepreneur surrounded by dogs and cats and other critters?

3. What is holding you back from achieving your wild success?

The answers I hear generally fall into two categories: circumstantial obstacles and emotional blockages.

Many people cite financial constraints as the most significant circumstantial obstacle to pursuing their dreams. I recognize that quitting outright is just not feasible for some people given various financial obligations. However, it may still be informative to put together a budget to figure out your burn rate and the amount of savings you need to be able to quit.

Circumstances can change and change is within your power. What changes can you make to get closer to the financial goal that would free you from the golden handcuffs of a BigLaw job?

Perhaps you are closer to the goal than you think, with only another few months or years to go on the job. Knowing your goal when you are slaving away in the office on the third consecutive Saturday may instill in you a renewed purpose and alleviate the feeling of being trapped.

Even people with the financial means can be held back from taking the leap by emotional blockages. These blockages can come in the form of doubts and fears – what would other people think of me being unemployed? How am I going to explain my decision to my parents and in-laws? Am I going to waste years worth of hard work? What if I am not good at anything outside of law? Above all, what if I fail to be happy? Work would no longer be a scapegoat. I would have no one to blame but myself. Yes, to shoulder the responsibility of being happy takes courage.

The resistance to leaving behind the familiar and the inertia against entering unfamiliar territory are hard to just sweep aside. And they shouldn’t be swept aside. I examined my emotional hang-ups and tried to understand their origins. Many of them stemmed from my insecurities, each with its own emotional logic. Recognizing the validity of these emotional blockages helped me defang their potency. Once I took responsibility for my own happiness, I learned that many emotional blockages can be unclogged by changing my priorities and reframing my thinking.

It took me many months to think through these three broad questions.

Maybe after you have gone through these questions, you conclude that you want to stay in law. That is great. Getting the clarity of why you want to stay in the practice can give you the perseverance to charge pass the tough moments ahead.

For some of you, maybe your answer tells you that you should quit at some point, but not yet. That is great too because you will at least know what you need to do to get to the point when it’s time to go.

Then for some of you, like it was for me six months ago, your answer to the question of quitting is a resounding yes.

If you are ready to take the leap, I will offer in my next installment a few practical tips on how to make the transition from giving notice to beginning a scary but exciting new chapter in your life.

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