Breaking Up is Hard to Do: Part III – The Risk Factors of Quitting Law

Part I and Part II of this series covered how I came to the conclusion that I didn’t want to stay in law. So, what’s next?

I knew I wasn’t going to be able to explore what I wanted to do while continuing to work as a BigLaw associate. If you are drunk and want to get sober, the first step is to stop downing the shots, then to detox (an uncomfortable but necessary step which I’m in right now), and finally to gain the clarity to look objectively at the future. Practicing law is a completely consuming profession and the only way for me to figure out my next step was to quit cold turkey.

Sure, I could have done a half-assed job until I got fired, but I was too proud and obsessive to hand in sub-par work product. There was a stretch of time when I constantly experienced tension headaches due to lack of sleep and my dad implored me to call in sick and not check my email. It sounded so rational, but I simply couldn’t refrain from checking my Blackberry and answering the emails. I was of the mindset that the work couldn’t wait and only I could do it. I took ownership of my deals.

Alternatively, I could ask for a leave of absence. In fact, when I gave notice, I was offered one on the spot. It was a tempting offer, but I decided against taking it, also on the spot. If I had those training wheels, I would never learn how to bike. Sometimes necessity is the mother of all inventions.

Of course, the subject of quitting was something I discussed with my husband ad nauseum. I wouldn’t have been able to quit if my husband hadn’t been encouraging AND had the means to support our lifestyle. I am well aware of the fact that I am very privileged in this regard, and don’t want to make light of it. This is also why I do feel the pressure to make the most of this opportunity.

I thought through the implications of me quitting and mentally put together a list of risk factors (something I was good at thanks to all the securities offerings I did while in Hong Kong, including the IPO for Baidu, the Chinese search engine).

• I may never find my passion. — This risk is an obvious one and is still being assessed. I think I need to first define “passion” for myself. Perhaps it is more than something that I enjoy doing, though I do think this is a key pre-requisite. It also needs to be something that I can uniquely excel at, fully engaged and consumed, without getting bored over time. Starting tomorrow, I am going to take a three-day aptitude test at The Johnson O’Connor Research Foundation, a non-profit research and testing organization highly recommended by a Simpson partner when she found out I was leaving. I will let you know what I find out.

• Even if I find my passion, there is no assurance that it will become a career, or a career that will generate any income or income that is commensurate to the compensation received from working at BigLaw. — Again, this is still being assessed. I have been grappling with the issue of money and perhaps it wouldn’t necessarily be so awful if my new career is not lucrative.

• My husband could lose his job and if neither he nor I found another job and we depleted our savings, then we’d be “screwed”. — Rationally, I know a lot of “ifs” have to happen before we’d become derelict, but this is a real fear at some subconscious level. I do remind myself that even if I didn’t quit, this risk could still materialize. It is not as if my job at Simpson was iron-clad.

• My husband could become disabled (although he does carry disability insurance), could die (leaving me with an insufficient life insurance payout) or could simply leave me (though highly unlikely), and in each case I’d be “screwed”. — If any of these scenarios happens, I’d have a much bigger problem than having quit my job as a lawyer. I would be a lot worse than “screwed”; I’d be devastated.

• I could be bored at home and not know what to do with myself. — It is probably too early to tell, but so far, I feel like there isn’t enough time to do all the projects that I want to do.

• I could focus too much on finding a career that I forget to actually enjoy the process. — It is too early to tell, but the recent road trip was helpful. I treated it as a vacation within my sabbatical/”retirement” to decompress/detox first, and as described in my previous trip report posts, I have also gained some new perspectives.

• I will no longer be able to cite “busy at work” as a legitimate excuse if my family ask me to visit. — So far this hasn’t been a problem, and I do secretly look forward to visiting my dad in Houston.

• I might not be able to deliver my notice well and thus burn bridges with Simpson. — It was and still is important to me to maintain a good relationship with Simpson, not because I want to have the safety net to return to the firm, but because I respect the people I worked with. I was concerned that my decision to leave law could be interpreted by my colleagues as a rejection of their career choices or a belittlement of their efforts to make partner. Good thing that my worry turned out to be unnecessary. I was frank with people about my decision process and the reasons that were specific to me, and people reacted positively, mostly with genuine support and good wishes. I think my departure ended on a great note and, more importantly, I felt at peace with my decision (in part, thanks to my dumpster-dive). The reality is that firms see people leave all the time. It is part of the cycle. Nothing personal.

• I could lose the camaraderie and friendships developed through work. It is possible that the dynamics of these friendships would change because my ex-colleagues would feel that I was no longer in the same trench as them. — So far, I have been able to keep in touch with many of my friends from Simpson and Davis Polk, not least through this blog.

Finally, I am saving the best for last.

• I have no one to blame but myself if I fail to be happy. — It was so easy to blame work, whether rightfully or wrongfully, for everything awry in my life. If I was grumpy it was because I worked too long and didn’t get enough sleep (although it could have been from irresponsibly watching too much TV the night before). If I became uninformed of world affairs it was because I read too many contracts and my eyes were tired; it was easier to read Perezhilton.com rather than the New Yorker (although it was entirely possible that I had become a bore). If I was fat it was because I worked too much and didn’t have time to go to the gym (although it could have easily been due to gluttony and laziness). If I was impatient waiting in line for something it was because my time was precious — how dare they make me wait for 10 minutes when I was billed out at $500+ per hour (actually I don’t remember my exact billing rate, but it was definitely much higher than $500). Anyway, you get the drift. Now, I need to be responsible for my own actions and it is an uneasy feeling. Maybe I am just a grumpy person by nature. Will I have the ability to change?

Well, I wouldn’t know the answer unless I tried it. I couldn’t know the future as the future is inherently uncertain. Hell, if people only focused on the risk factors, no lucrative investments would be made. (Baidu, which IPO’ed at $27 a share, is now worth $86 a share after splitting 10:1, an almost 600% increase.) I wouldn’t let the parade of horribles prevent me from going forward.

Making the list of risk factors was helpful for me to think through the worst case scenario. That led me to my final step in quitting law, also the most difficult in a way: confronting several major niggles before pulling the trigger. Every now and then, some of these niggles still surface. These niggles will be the subject of my next post.