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.

(courtesy of www.rankuno.com)

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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15 Responses to Quitting BigLaw: Part II — The Three-Question Roadmap

  1. Pingback: Tweets that mention Quitting BigLaw: Part II — The Three-Question Roadmap | Every Six Minutes -- Topsy.com

  2. John says:

    “To me, $2 million is a lot of money, but not enough to keep my current lifestyle for the rest of my life.”

    mmm there is something wrong with this statement. It seems to me that part of your problem/dilema is that you need to find something to do which earns you a lot of money. $2 million to a lot of people, even a young couple like yourselves is more than enough (budgeted and saved wisely) to quit the rat race. But the again it depends on what your expenses are. If you are living in a manhatten penthouse then perhaps its not enough?

    Is the problem more to do with your standard of living? Have you thought about downsizing, re-evaluating your cost of living etc? I say this because money does seem to be a central issue to a lot of your posts. Outside of manhatten $2 mil goes a long way.

    • everysixminutes says:

      I appreciate your comment. I have actually already quit the rat race (even though I didn’t win any lottery). So in a way, I have already answered this question. You can get more details, including my cost cutting analysis, here.

      $2 million is a plug figure in a hypothetical question designed to make people think what they would do had there been less money pressure — but not no money pressure. I do live in Manhattan, so I think $2 million is a fair number for me. Could I downsize, move to Omaha and live frugally on this amount for the rest of my life (assuming another few decades to go)? Probably. But that’s not the type of trade off most people — people who have been making six figures — are willing to make. Indeed, money is one of the top reasons why dissatisfied and overworked lawyers feel like they are trapped and can’t make a change in their career.

      You are right that I do talk about money in many of my posts in the context of this career transition. After all who doesn’t think about finances when considering career and life choices?

  3. UWC says:

    One more question to ask yourself — this is something I picked up from Gretchen Rubin’s Happiness Project — is: “Whom do you envy?” She said she never envied lawyers but did envy writers. So if you see others doing your job and wish that was your job — that is a telling sign.

    Not to demand a Law 101 lesson, but what is “drafting” and why is it so horrible?

    • everysixminutes says:

      This is indeed a great question to consider. Thanks for reminding me of that. “Drafting” is basically memorializing parties’ agreements in convoluted legalese in a 100- or 200-page contract. Some language can be so complicated that it can take a long time to unpack. I know lawyers who love drafting and are great at it. I don’t think I have a knack and didn’t have enough interest to master the skill.

  4. It is so fantastic that you are sharing these questions – and your thought process – here. For every one of us who leaves, there are so many who stay because they feel scared, and confused, and alone. Know that you are doing so many a great service by opening up here. Bravo.

  5. John says:

    Sometimes we build our own prisons.

    Do you think that a continued focus on making six figures is going to lead to path of contentment and happiness? Isnt it possible to lead a rewarding and enriched life earning much less? Why so much pressure on yourself? Are you trying to keep up with your former self? As you know in general people earning six figures have to make a lot of sacrifices, you were not happy doing that before, what makes you think you will be again?

    Of course it is not necessary to move to Omaha, which is extreme. But it is possible to live at an expense level which enables you to spend your time in a manner which is congruent with your true desires.

    • everysixminutes says:

      I think one has to be careful not to judge how people spend their money. Every one has a different relationship to money, and each relationship has its own validity.

      I can only speak for myself, and I have made a choice to focus more on happiness than maximizing my bank account. I agree that undue emphasis on money can detract from happiness, but material success and happiness don’t necessarily have to be mutually exclusive, right?

  6. Been there , Done that says:

    I decided that private law practice (and the seemingly interminable hours that go along with it) were not my cup of tea long ago. Unfortunately, the trade off I made was to go into the public sector where tedium, boredom and numbing bureaucracy is pervasive. At least, I can look forward to getting off work at a regular time and a pension upon retirement. Whoopee! Note, at first I practiced law in the public sector, but the stress of working with substandard support staff was too much to bear and we still had deadlines to meet so working late was sometimes unavoidable. So I transitioned into public administration! At least I get time to practice my music….and play in a band. My true love!! Oh, to get a mulligan on my career. sigh.

    • everysixminutes says:

      Thank you for sharing your experience. We all try to optimize to the best we can. I wish you the best of luck!

  7. Pingback: Quitting BigLaw: Part III – Some Practical Tips | Every Six Minutes

  8. Pingback: Riding the Emotional Roller-coaster | Every Six Minutes

  9. fitch2 says:

    I find it odd that every time someone accurately notes that most of your posts center around money or materialism, you say “be careful not to judge”

    This is a pattern. Many people are reading your blog and are unable to relate to you. Is that not clear from the nature of some comments? Or do you just focus on the numerous comments praising your blog?

  10. simone says:

    Hi —

    A friend introduced me to your blog, and I just wanted to say thank you. So far, I’ve read several entries, but these three questions really speak to me. What do I like and what don’t I like about working in Biglaw? Well, I knew I didn’t like a whole lot, but the way you’ve presented it really brought home how little there is that I actually like.

    The nature of my work: I am bored out of my skull, because I cannot work on things I want to work on, and I am consumed with utter dread at the thought of each new assignment, because it will inevitably be 180 degrees away from anything I ever wanted to do in my life. One of the things that’s been so hard for me to take about Biglaw is that there is one person who gets to decide your career trajectory, and that person is not yourself — it’s the department coordinator. And I have a real problem with that (for a whole variety of reasons).

    The people of your firm: Toxic.

    The career path: For me, it comes down to the ability to acquire an in-house job that is in my area of interest. As I have not done that yet, I remain stuck here.

    The prestige: There was a time when I enjoyed this, but now, stacked up against everything else, I really couldn’t care less.

    Can you and are you willing to work long and unpredictable hours to make everything worth it? Do the rewards outweigh the sacrifices? That would be an emphatic, resounding NO. I’m tired of spending my every waking moment dealing with other people’s problems to the detriment of my own life.

    Thanks so much for your insight. It’s really helped me to understand why I’m still here, and that will hopefully help me to focus my efforts of getting that new job so I can get out.

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