Category: Software Engineering vs Law

How I left biglaw (Part III)

… Dejected, I made the long trek back to my office, where I closed my door and contemplated my future as a lawyer.  I looked at the spreadsheet that I had made, counting down the months until I my net worth was $0.  Still over two years away.  I knew I wouldn’t make it.  I abandoned my plan to stay in law, and began to draft a new resume…

This is the final part of my story, and follows the trek from abandoning my plan to go in house to the decision to leave the law entirely.  On above the law, you often come across stories of biglaw associates who burn out and leave the law to do something else entirely.  For example, there’s the lego guy and the cupcake girl.  If you’ve been reading along, you’ll know my story isn’t as glamorous as the stories of those attorneys.  It’s just an ordinary tale of one biglaw associate who in desperation, decided to leave.

Part II of this post: How I left biglaw (Part II)

Part I of this post: How I left biglaw (Part I)

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It turns out that no one outside the legal community cares that you work for a V5 law firm.  Lawyers, however, and law students in particular (myself included), are obsessed with prestige: “Where do you work?”, “How much were your bonuses?”, “Where’d you go to law school?”, “Where’d you clerk?”, “What’s your class rank?”  While in law school, I adopted this attitude, and it heavily influenced my decisions when applying to outside jobs.  After abandoning my plan to go in house, I was left with the alternative to reapply for engineering positions.  I had never stopped considering going back to engineering (from my first application submitted during Thanksgiving of the previous year), though I thought it would be more rational to try to get another job in a legal capacity first.  But after a string of failures, I reconsidered my reasons for wanting to stay in the law.  When viewed in retrospect, my reasons for wanting to stay in the law were very similar to the reasons I went to law school in the first place.  I wanted to continue telling others that I was a lawyer, I wanted to make my parents proud, and I wanted the financial security and social stature that came with being an attorney.  Compounding that was the harrowing sunk cost effect -hundreds of thousands of dollars and years of my life spent devoted to law, the mental effect of giving up, of facing my friends and family after the fact.  However, conspicuously absent from my set of reasons to stay was the desire to actually practice the law.  Law school was an isolated experience free from the restrictions of looming bills, demanding partners and a professional career.

By March, I had fully turned my attention from going in-house to going back to engineering.   When I began applying for software engineering jobs, my resume was still structured as a legal resume.  At the top, I listed my accolades: law school, legal journals, published papers, leadership experience, law firm.  Towards the bottom, I broke out my work experience into two sections, “Legal Experience” and “Software Engineering Experience.”  With each application submitted, I attached my cover letter, which I refined multiple times over the next several months of applications:

Dear [Company X],

I am a software engineer and attorney who has been working on coding projects for the [Y] since 2011 and was previously employed with [Z] in 2009 as a developer for our web portal on the __ team. I spent the last three years furthering my studies through attending law school and received my Juris Doctor degree from Stanford Law School in 2012. Since graduating and becoming an attorney, I have come to realize that my passion remains in software engineering. Though studying law is intellectually demanding and stimulating, I find software engineering to be a better outlet for my career goals. In short, I want to create products that help others and software engineering gives me that opportunity.

To that end, while I was in law school, I kept up with my software fundamentals through coding projects on the side. I am eager to more deeply engage in my software engineering career again, and I hope to be able to continue learning and doing so with [Company X]. Thank you for considering my application.

Sincerely,

Codeandcodes

I spent the next two months applying without any success.  At first, I targeted only well known companies, thinking that a bigger company would have the resources and financial security to take a chance on an ex-software engineer to do their coding.  But application after application was rejected or ignored.  By this point, I made my desire to leave biglaw public among many of my non-lawyer friends, many of whom were working in the software engineering field.  Some of them, to whom I’m still grateful, put their faith in me and referred me to positions with their companies.  I found, however, that even with their endorsement, I wasn’t able to even get past the resume screen. During this time, I kept an ace up my sleeve. I had spent several years in the software industry prior to going to law school, and one of my former companies had an office in my town. My old boss still worked there, and I had departed on good terms (for law school). I was fairly confident that if I reached out to him, he would be able to get me through the initial screen. However, I waffled back and forth on whether to reach out to him again. Part of me knew that by doing so, I had to commit to actually leaving the law or else burn bridges and perhaps my best hope of getting out. It felt final, and I kept asking myself if I was really prepared to leave everything I had spent the last four years working for. But after all my mental debate, I eventually decided to make the call. I was going to do this.

After contacting my old boss, the mental burden of leaving was lifted. I decided to widen my net.  I redoubled my efforts and by this point, 100% of my free time was devoted to applying to jobs or preparing for interviews.  I would come home weary from work each day, spend an hour or two looking at relevant job postings on any site I could find, and then spent a few hours brushing up on algorithms, data structures and catching up with the last several years of advancements made in software.  It was grueling.  Balancing individual study with a biglaw job is obviously not easy, but the allure of freedom kept up my morale.  At first, the challenge seemed insurmountable. However, with time, my efforts began paying off.  A few weeks after I started applying to startups, I actually began hearing back from recruiters.  Some were willing to talk with me, many others were simply curious about my background.  I still had many rejections.  However, even getting the opportunity to speak with a recruiter was a step in the right direction.  I even had a few phone screens in the beginning (all of which I failed miserably).  The software world had changed dramatically in the past four years that I had been out of the game.  Though I had kept up with programming on the side, I was woefully unprepared for jumping straight back in.

Then one day, which I consider the turning point of my application process, a contract recruiter contacted me regarding one of the many applications I had submitted.  She saw my background, was intrigued, and decided to submit my application to her client because she thought I was a good fit (that client eventually rejecged me without interview).  However, the most valuable thing she did for me was suggest that I remove references to my legal accolades from my resume, something I never considered.  The idea of removing my legal accolades was foreign to me. After all, they are the factors by which lawyers as distinguished.  I was skeptical about this advice, but since I wasn’t having much luck, I prepared a second resume (I still have it, and called it [codeandcodes SE.pdf).  I widened my net yet still, and began to apply to every job I could find, some with my SE.pdf resume, and others with my hybrid law/engineering resume. By the peak of my application cycle, I was applying to thirty jobs a day.  And I started getting hits back.  Previously, with only my hybrid resume, I had a response rate from recruiters of about 5% -for every 20 resumes and cover letters I wrote, I would receive about one response.  Out of all of those responses, I received only one phone screen.  With my new resume, which left off every tie to law (except my law school), my response rate from recruiters jumped to 20%.  And because my resume had no reference to the law firm at which I was currently employed, these recruiters viewed me without bias (except maybe as an unemployed software engineer with a very large gap on my resume).

Meanwhile, my late night study sessions were also paying dividends.  The concepts that I used everyday in the past as a software engineer started coming back to me, and I grew sharper and more familiar with the current technical buzzwords.  I also purchased several software engineering interview books, and attempted each problem, no matter how long it took me.  Slowly, I started getting more phone screens, and they started to go better.  I was still far from a callback, but my efforts showed promise.  This process continued for months.  By July, I had applied to hundreds of jobs and was speaking with recruiters on a regular basis.  Finally, the day came when one of my phone screens went well enough where the interviewer wanted to bring me in onsite interview.  The CEO of this startup told me that he would have his Director of Engineering contact me first to verify the interviewer’s feedback.  Long story short, after a conversation with the Director of Engineering, which fortunately was less technical in nature, the CEO and the director agreed to bring me in. The director gave me a homework assignment before my onsite interview, which I still have to this day.  He was experimenting with Scala (a functional programming language that runs on the JVM) and wanted me to research the pros and cons of Scala versus Java.  I had never heard of Scala or functional programming before, but I attacked this assignment with incredible vigor.  Before my onsite interview, I researched dozens of articles on Scala, Java and functional programming languages.  I put all my notes into a digestible chart in Microsoft OneNote, ironically my favorite application for note-taking in law school.  When the day of the onsite arrived, I was well-prepared.

The rest is mostly history.  Once I finished the onsite interview, I had a strong suspicion that an offer was coming.  But when it finally came, I didn’t celebrate or rejoice.  It wasn’t the compensation or the company.  Again, it came down to the decision to leave. Leaving the law was no longer just a fantasy.  It came down to the simple choice that I had debated all this time. All my work in the past half decade, from studying for the LSAT, to applying to law school, to my 1L year, my hours at the law firm, passing the bar, was about to become my past.  All of my fears were coming to a head.  I wasn’t sure if I was making the biggest mistake of my life by leaving the law behind and again, and the fears and doubts that I was just being immature about my job situation resurfaced.  I began reaching out to everyone I knew (including several people I didn’t know) who had left biglaw to do something else.  Over the next two weeks, before accepting, I sought the advice and counsel of many of these people.  All of them told me to take the leap of faith and leave.  In the end, their reassurances were all unnecessary, because I already knew what I wanted.  I finally realized that my life was being spent doing something I didn’t want to do.  I called up the recruiter and accepted.

Aftermath:

After accepting the position at the startup, I told my partner I was leaving.  He was respectful and supportive and wished me well.  It was done.  That moment, the moment where I gave notice that I was leaving, remains one of the happiest moments of my life.  It’s hard to describe the relief or joy, or whatever feelings that accompanied that decision.  It’s been two years since I departed, and I haven’t regretted my decision for a day.

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How I left biglaw (Part II)

… Of course, nothing happened at first, but even the act of sending out my resume made me feel triumphant.  Though my grand plan to work for several years and go in-house flew out the window, I felt all right.  I felt hopeful for the first time since starting work that there was an exit, and that the wheels were in motion.  It turns out however, that it would be a long and arduous eight months before I finally had my opportunity…

The following is a continuation of my story of the next eight months, and how I eventually escaped from biglaw.

Part I of this post: How I left biglaw (Part I)

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Silence.  It turns out that getting a job requires a lot more than sending out a resume.  I was also unsure of my decision.  I had just spend the last 3 years in law school, just passed the bar exam, and had secured a position at one of the nation’s top law firms.  On paper, I looked great and outsiders looking in were impressed.  On the inside however, I felt a mounting desperation that working in biglaw was unsustainable.

After my Thanksgiving plans were interrupted by the ‘short-fuse’ deal, I sent out my resume to several engineering job ads which I had been browsing in the preceding weeks.  To me, it represented a mental hurdle that I had overcome.  I was no longer the golden example, the one people envied, but I was a quitter.  That was hard to come to terms with.  Law students in particular are a stubborn breed; the vast majority make the calculated decision to go to law school, and when there, attack their courses with tenacity.  I had done the same, passed all the hurdles to landing the biglaw job, and now after three months, was ready to quit.

To describe my thought process as clear and rational at the time would be giving myself too much credit.  I didn’t know what I wanted.  Part of me thought that I was complaining about nothing, that all biglaw associates went through the same thing, and that though attrition rates were high, the vast majority still took their licks and made it out.  No one had ever heard of someone lasting only three months in biglaw.  Another part of me however, possibly the more emotional part, thought that I was uniquely unsuited to being in biglaw.  I’m fortunate.  I have a background in computer science, which happened to be in high demand.  I had a backup plan.  However, my rational side constantly warred with my desire to leave: “why would you spend three years and $200k to get a J.D., go through all the suffering of law school tests, applying, the summer associate position, and the bar exam just to quit in three months?”  This was my constant debate over the next several months, up to the point where I left.

Thanksgiving came and went, and work actually slowed down.  My partner, to be fair, recognized that I had been burning the candle at both ends and thought I needed a break.  He avoided staffing me on a deal for the remainder of the year and my holidays were actually pleasant and restful.  And I forgot about sending out my resume.  Of course, this didn’t last very long and come the new year, I found myself in the same position as before, my personal life and time living and dying by the lifecycle of the deal.  It turns out that I had done a commendable job on my past deals, and I was ready to start operating without the guiding hand of a senior associate, at least with respect to the due diligence.  My workload increased again, but without my senior associate interceding and turning down the demands of other associates and partners, I found myself buried again.  Yet this time around, I held onto my quiet defiance with knowledge of the fact that my resume was out there, circulating.

Work continued to mount and I continued my late nights, while fighting against senior associates hounding me for work product and my partner staffing me on new assignments.  I closed my door purposely, in order to deter passerby’s from dropping in and in the natural flow of any conversation, deciding I needed more work.  I kept busy, and learned to work faster and more efficiently.  By the end, diligence became old hat, and I no longer feared the large document drops as I had in the first few months of my job.  However, new challenges always presented themselves.  I got staffed on a few licensing deals, which I knew nothing about.  Often times, as a specialist, I would jump onto a deal mid-cycle, feeling lost and inundated with deal documents.  I still rarely took a Saturday or Sunday off.  On one occasion, on the eve of deal signing after spending the last several nights working, I fell asleep instead of hopping on an 11PM conference call for the corporate attorneys.  I had already submitted my portion of the diligence memo, fully negotiated the IP reps and warranties, and thought I was in the clear.  Early the next day, I remember turning to my nightstand, saw that I had missed over 100 emails and felt a sinking feeling in my stomach.  I saw that the senior associate on the deal (my friend and also a mentor) had been up all night and took my place on the call while sending out emails at 4AM.  The deal had signed overnight.  I truly felt bad that I had dropped the ball by going to sleep instead of staying up for the call.

After that experience, I renewed my desire to get out.  By this time, it was around March, so I had around six months of experience under my belt.  As I said before, the rational side of me thought that by going back to software engineering, I would be throwing away years of my life and hundreds of thousands of dollars.  Yet I was still desperate to get out.  So I thought I would try my hand at applying for in-house positions.  There’s a website, called http://www.goinhouse.com, that lists in-house job postings.  I would check this site and linkedin daily for job postings for junior in house counsel positions.  Nothing took.  I prepared a detailed cover letter and resume, and submitted it to every junior in-house position I could find, but never received any response (some to this day).  I tried my network as well.  One friend, a director at his startup, told me of an opening on their legal team.  I applied there and most likely due to the strength of my friend’s recommendation, had a phone screen with the startup’s attorney.  I remember clearing my schedule that day and hopped in my car, trying to drive to a secluded parking lot where I could do the phone screen in peace.  I didn’t get far enough in time by the time the phone screen started, and ended up taking the call from my car.  The end result: while the interviewer was “impressed with my knowledge”, I was too junior.  Another time, my friend referred me to Google and I was flat out rejected for not having enough experience. After several failures, I finally found a position for a junior transactional attorney on goinhouse, with a new legal startup.  It was a contract position, which I had avoided until now.  For those readers who are not attorneys, contracting positions are generally looked upon with disfavor by law firms.  It’s a black mark on one’s resume.  Yet I was desperate enough to not care.  I reasoned to myself that even if I was leaving my law firm job after only half a year, I would still be leaving it for a legal job.  I could then evaluate whether I really wanted to leave law, so I wouldn’t be completely throwing away my education and time spent in the law.  I submitted my resume and to my surprise, heard back from the lead recruiter within a few days.  We had an initial phone screen, and she wanted to continue the conversation.

This legal startup is geared towards working mothers.  They call it “high end contracting” and claim to hire high-caliber attorneys to do biglaw type jobs at a cheaper rate.  The hours were flexible, and work could be picked up at the pace of the contract attorney.  It sounded perfect to me.  I scheduled the on-site interview for early in the morning, so I could wake up early and drive into the city and back to my law firm before the day started.  Anyone would just expect that I had gotten a late start.  On the day of the interview, I ended up underestimating traffic, and was five minutes late to the meeting.  It turns out that it didn’t matter.  I walked into the startup’s well-appointed office, took a seat and waited for my on-site interview to begin.  After a few minutes wait, the leader recruiter with whom I had spoken on the phone brought me into her office.  We started talking about my background, why I wanted to leave my law firm, and what this startup was trying to accomplish.  After half an hour of talking, the lead recruiter rejected me on the spot.  She told me that I was too junior for them to hire me, even for a contractual position.  She told me to reapply when I had more experience, and sent me on my way with some mints and lip balm.

Dejected, I made the long trek back to my office, where I closed my door and contemplated my future as a lawyer.  I looked at the spreadsheet that I had made, which counted down the months until I my net worth was $0.  Still over two years away.  I knew I wouldn’t make it.  I abandoned my plan to stay in law, and began to draft a new resume.

How I left biglaw (Part I)

Another popular question I received when I made the decision to leave biglaw was how I got out.  This is my story, and it won’t apply to everyone.  However, I hope that other associates can relate to the fears and feelings I had when I was planning my exit.  And I hope that it gives some hope to those friends and colleagues who feel stuck.  The story is long, so I’ll have to give you some background first.

———

My desire to leave biglaw really started during my summer associateship.  Bear in mind that this was back in 2011.  The legal economy was still reeling from the economic recession, law firms were facing bleak times, and though things were improving, law firms had still not recovered.  Salaries were still frozen, offer rates were way down, and law firm layoffs made the news daily.  I think Cravath’s class size had dropped from 120 to about 30.  Everyone I knew was worried about getting a job, even at the top law schools around the country.  I monitored ATL on a daily basis, had a massive spreadsheet of every law firm that had conducted layoffs (I purposefully bid them all lower during OCI) and concerned myself with finding the best law firm (read: most profitable and highest offer rate) I could get into.

The circumstances at the time colored my decision and my actions during my summer associateship. Essentially, I arrived for the summer with my other classmates fearful for my job and potential offer, so I was ready to hit the ground running.  I wanted to make sure that I stood out even among my other peers (no small task), so I would produce the best work quality I could while putting in the necessary time.  It turns out that that is a lot easier said than done.  On the third day of my summer associateship, I agreed to help one of the other junior associates with some bookkeeping tasks before a public filing goes out, a process called “circle ups.”  A circle up, for non-corporate attorneys, is essentially the process of going through a public filing (in this case, about a 100 page 10-K), identifying all the “material” numbers, then cross-referencing them with previous filings to see if they were missing any relevant information.  Then, the associate takes to the task of verifying these material numbers with accountants or other experts based on their level of significance.  It’s a ridiculously tedious task (you can imagine how many numbers there are in a public filing about 100 pages long).

That day I ended up staying in the office until around 1:30AM to finish circling and sticking post it notes next to all the numbers in the 10-K.  Tired from the long task, I turned in my work to the junior corporate associate thinking that I would finally go home.  However, much to my surprise/dismay, she said that we would be hopping on a call shortly to go over the results with a senior associate (also my associate mentor for the summer).  I was completely shocked.  It was already 1:30 in the morning, I had just spend the last 15 hours in the office circling hundreds of numbers and now it was time to verify them?  This was my first taste of the “real work” that corporate attorneys do.  I wondered what I had gotten myself into.  Things progressed much the same for the rest of the summer, but still at the end, and despite the long hours, I stilled needed a job offer (which I ultimately received).  I already knew I wouldn’t like the job, but I needed one because my student loans were mounting.  I remember on the last day of my summer associateship when my offer arrived, I felt a wave of relief but also the first feeling of desperation that this would be my life.  While waiting to go home on that day, I started browsing our school’s career website for other firms to interview at 3L year in case I wanted to go somewhere less intense.  I never tried.

Fast forward a year to my orientation week at this same law firm.  The law firm flew the incoming first-year associate class out first-class (my first time), put us up in luxurious accommodations and eased us into the law firm experience with relaxed sessions where other more senior lawyers told us battle stories and how to succeed at the firm.  In short, orientation week was good.  We celebrated the end of the week with a night out where we heard whispers of new associates already being contacted by partners looking for people to work the weekend (the partner eventually changed his mind when he learned that the new associate hadn’t been issued a laptop yet).  Though I laughed it off nervously, it turns out that this practice was not out of the ordinary at all, and the same fate was about to befall me.

Orientation week was the last time while at the firm that I called it a night at 5:00PM.  Pretty much from the next Monday on, I started getting slammed with work.  The trial run was over; this was real life.  I had chosen this career, my fate, my means of survival, and it would be a long stretch before getting out.  For the first three months, I never took a day off. I was on back to back deals, learning the ropes, drinking from the firehose, and working all the time.  I hated it.  My original plan of just biding my time for 4 years until I had saved enough to pay off my loans and gotten enough experience to jump in house eventually decreased in duration to three years, then to two, then finally to one.  Each day was tortuous, and while I liked my coworkers and the pay, I lived in constant fear that my schedule and life would get interrupted by a “hot” deal.  By November, I felt like I was burning out, and I looked forward to some respite over Thanksgiving.  I made plans with my family to go away for the long weekend, to relax somewhere and not think about work.  The plans were made, we were set to go.  Then it hit.  The Tuesday before Thanksgiving at 5:30PM, I received an email from our of counsel: “We just found out about a ‘short-fuse’ deal and need someone to staff it.  Looks like it will run over Thanksgiving.  Sorry.’  My heart sank.  I felt empty, broken, powerless.

I had thought about leaving before then.  It only takes so many late Friday night emails to break one’s spirit.  Maybe my peers or others have more guts or a stronger will than me, but every time I got a message like that, my desperation grew.  Somewhere during the two month marathon of work, I had actually prepared a resume, highlighting my software engineering background, which I planned to send out if things ever got really bad.  It was a symbol of defeat, my ace up my sleeve, but something to keep in the back pocket just in case.  I sent it out the same day the email came.

Of course, nothing happened at first, but even the act of sending out my resume made me feel triumphant.  Though my grand plan to work for several years and go in-house flew out the window, I felt all right.  I felt hopeful for the first time since starting work that there was an exit, and that the wheels were in motion.  It turns out however, that it would be a long and arduous eight months before I finally had my opportunity.

Joining the flock

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I’ve decided to the join the flock. That probably doesn’t mean anything to a whole lot of people except perhaps those in the engineering community, but “joining the flock” is Twitter parlance for joining their company. A little bit of background about me for new readers: Back in 2013, I took a leap of faith and left my life as a lawyer and a highly profitable law firm to go back into software engineering at a small silicon valley startup *(See here). At the time I left, my life at the law firm had ironically increased my tolerance for risk because of how unenjoyable the work was. I honestly felt that any non-law opportunity, even if it had a dubious potential upside, would be better than grueling it out for several more years only to enter into an in-house counsel gig. In retrospect, I didn’t even want the position of in-house counsel; I think I was just looking for meaningful work and better work-life balance without having to be electronically tethered to my phone.

In the following months after leaving big law, I drank from the proverbial firehose. It’s hard to overstate the degree to which the software engineering community and tools had changed within the past few years. I had missed much. While it felt good to be programming again, I constantly battled feeling overwhelmed with relearning old coding techniques, digesting new paradigms and finding my place in the software community again. I remember picking up javascript for the first time in years and thinking to myself how foreign everything looked. Playing around in jquery, seeing all the dollar signs, variable names without associated types, and nested callbacks and closures made my head spin. However, after overcoming that initial shock, things started quickly becoming familiar again. Coding eight to ten hours a day definitely fast-tracked my improvement as a software engineer in ways that coding on my own after normal working hours while I was with the law firm couldn’t.

Not too soon after I joined the startup did I begin searching out different opportunities. There was no real impetus towards my search; rather it was exploratory in nature. There was nothing that I particularly disliked about the startup, however I knew it wasn’t a place where I could really thrive. It was a small shop laden with past encumbrances that it couldn’t shake and simply wasn’t in a position for growth. Subsequently, I landed at a large hardware/software company in the networking market segment where I set to work on more interesting and difficult engineering problems. Essentially, the type of work I was doing at this company is what I’ve been blogging about for the past several months. The software issues I dealt with were engaging. I built an analytics stack from the ground up, and spent a good bit of time figuring out how to scaling the analytics processing and increasing node.js and mongoDB performance, and had fun developing the logical software frameworks and architecture to improve my software’s maintainability and scalability. In short, it was a great experience, and I was thriving at the company.

So then why did I leave? There are a few reasons: First, Sallie Mae. As all you lawyers can relate, law school is insanely expensive. Second, my company only deals in the enterprise space, which isn’t very exciting. I used to joke with my coworker that on the day we had one user using the software suite, we would have cause for celebration. Third, this past year and a half has been … awkward for me. I’ve gone from being deeply invested in the law to deeply invested in software engineering. I’ve grown much faster in this past year in my software engineering ability and competence than I have at any other part in my career (and maybe life), in part because of my dedication to software engineering and becoming a better engineer, but also vastly due to me simply remembering old techniques, design patterns, abstract data types, and software methodology that I had forgotten. Spending the majority of my free time coding has also certainly propelled me much further than just my day job alone. The crux is that it’s been a struggle to find where I belong back in the community of software engineers. My resume still remains a source of question and curiosity to both recruiters and interviewers alike. It probably will continue for the long run. Thus, at least in this hot economy for software engineers, it’s been difficult to estimate my market value when dealing with so many variables. I don’t blame prospective employers for having questions when reviewing a candidate like me. As I’ve come back up to speed though, my market value has risen and I’ve been hungry for new challenges.

I know that I’ll get left behind again if I don’t continue pushing myself in my free time. While it’s my belief that there will always be a great market for great software engineers, I recognize that dropping from great to good to mediocre can happen quickly through complacency. And apparently, the reverse is true through hard work and natural ability. In essence, software engineering is the path I’ve chosen and I’m pot-committed. I threw away a promising career in law that I didn’t love to do what I do love now, and I intend to see it through to my maximum ability. And that means I want to be at a company where I can push and be pushed in engineering quality and knowledge, where my weekend work and exploration helps me develop my edge and promotes my future, and where excellence is recognized by the company. I think I’ve found it with Twitter. Twitter’s engineering team is outstanding; their employees are young, hungry and eager to learn and do great things. Twitter as a platform has also not peaked (in my opinion), so there are great opportunities for growth within the company. Although Twitter is much bigger than some of the other startups that I’ve considered, there is still the opportunity to dive in and do impactful things at the company. I’m definitely looking forward to the first hack week.

Lastly, now that I’m fully integrated back into the software community, there’s perhaps a greater penchant for financial conservatism. I’m getting older, but my debt acts as an albatross around my neck, so it’ll be nice to have some financial security for a change. I should also say that many startups in the valley also have excellent engineering teams and hiring standards and are solving interesting issues. Yet many of those startups do not enjoy public recognition of that fact, so recruiters can’t easily get a good gauge of the caliber of engineer. At a large company like Twitter, Google or Facebook, the software engineers enjoy the reputation of having survived the interview gauntlet. In other words, such engineers are generally of high quality and will be known as such. While I still have the desire to do things on my own such as exploring the intersections of law and software engineering, I see no reason that such a goal is mutually exclusive with working at a large software company. I’ll continue doing what I’ve always done, spending my time improving my skills, building tools that may or may not have merit, but always and ceaselessly bettering myself.

A candid look at biglaw and big law firms from a biglaw dropout

Leaving biglaw behind

To any readers out there, whether you’re a biglaw attorney, law student, engineer, working professional considering law school or spambot, here’s an update on my life just over a year after my exodus from biglaw. It’s been just over a year since I left:

Giving notice

I still remember the day I gave my notice to my boss, a young and rising partner in my law firm, that I was leaving for a startup. My former partner, a highly intelligent and skilled attorney, of course sensed my reasons for leaving. But instead of speaking candidly about my experience, we spoke through with the layers of etiquette built up over time by biglaw attorneys.

I told him how much I enjoyed working with my fellow associates and for him, how much I respected him and appreciated his mentorship, and how the opportunity was too good to pass up. He told me how he appreciated my contributions to the law firm, how I was practicing at a level beyond my seniority and about my bright future at the firm and that he would regret seeing me go. And though we spoke truthfully to one another, we managed to miss the truth entirely.

I didn’t tell him how much I disliked working at the law firm; nor did I tell him that I probably would have accepted any position that gave me the opportunity to leave. I didn’t tell him about the aggregate toll that responding to emails 18 hours a day had taken on my sense of normalcy and happiness. I didn’t tell him how I, in desperation after having worked the first 8 weekends in a row, applied to engineering jobs after just two months in biglaw. I didn’t tell him about the numerous spreadsheets I had created and obsessively updated detailing how much money I would have each month, the day my net worth would be zero, and the day when my ROI on law school would overcome the opportunity cost of giving up my past engineering career. I didn’t tell him how many late nights I had spent in the past 6 months fighting to keep my eyes open while I watched old CS lectures and studied abstract data types and binary tree implementations. I didn’t tell him how scared I was to accept the position because I seriously doubted the viability of the startup and knew that it was completely leaving behind my legal background to perhaps never be used again. I didn’t tell him that despite all my fears and doubts, how easy it was me for to make the decision.

The decision to leave

What had caused my desperation to get out after just two months? It wasn’t just the long hours. I thought that might be the case, that perhaps I was just lazy, but in the aftermath of leaving my law firm, I still continued to work 50 hour weeks with about 20 hours of work a week on my personal projects. In fact, I was still putting in more time than I had at the firm. That actually led me to discover about myself that I didn’t shy away from work.

It wasn’t just the unpredictability of work, although that was a huge contributing factor. It’s really hard to describe what it’s like being tethered to your work phone and being on hook for any quantity of incoming work at any waking hour on any day of the week. I lived in fear of my phone, having been burned many times in the past by “short fuse” deals that needed me to drop everything and work the weekend. Like a traumatized animal, I learned to fear the words “what are you working on at the moment,” knowing that my answer would inevitably lead to more work. It turns out that it only took a few months of Friday night emails asking me to drop everything and work the weekend to break me.

It wasn’t just the nature of the work either, although each deal on which I was staffed meant the drudgery of hundreds of agreements, leases, and licenses being dropped into the dataroom at any time of day, waiting to be reviewed and summarized by me. It wasn’t solely the environment either, although it was astonishing to see the facades of contentment when so many associates were unhappy. You see, biglaw attorneys are exceedingly polite to one another. So polite, in fact, that the real feelings of biglaw attorneys rarely manifest themselves, except to those closest to the associate. This can’t be unknown by biglaw partners, but because associates don’t openly vocalize their discontent, biglaw partners have no incentive to improve conditions. Instead, we pretended to have fun, making casual jokes or observations about current affairs. We had RC car races, eating contents, a goodbye party for every associate or staffer who left. These events made for great PR to those outside the firm, but it was never mentioned how the attorneys would just sit there either awkwardly making small talk or checking their mobile devices waiting for an excuse to get back to work. It was of course all of these things, and more, that brought me to my breaking point.

In the month leading up to my departure, after I had my offer in hand from the startup, I constantly wondered to myself if I was insane for wanting to leave my biglaw career behind. I was at one of the most prestigious law firms in the country, had spent the last 4 years of my life devoted to learning the law and had a clear ticket to society’s elite and comfortable wealth if I could just put in the time. I sought counsel from others who had made the leap. Perhaps not coincidentally, almost all of them are startup founders. They, for the same reasons as me (and probably all associates), hated the biglaw machine and wanted out. Unlike me however, they had already mustered the courage and taken the leap. I was still waffling back and forth with whether it would be worth trying to make it to another year or at least six months until I received my year-end bonus. Ultimately, it wasn’t anything any one of those other biglaw deserters told me. In fact, I heard nothing new from them. If you’re a biglaw reader, you’re also likely not reading anything new. No, I knew all the facts, had considered the cost numerous times, and was just trying to convince myself to do something about it. It turn out that I already had made my decision.

Once I decided I was leaving, I knew that nothing my partner or anything other associates could say would convince me to stay. I knew that it was the right decision to leave, not in a year, not in six months, but at the very moment I was planning. It wasn’t about the startup or all the work I had put in to get back to the level of engineering competence to get hired. It turns out that it was just about the opportunity to leave. It turns out that any opportunity to leave was good enough. I’ll never forget the feeling when I gave my notice to that young partner. I didn’t begrudge him at all, not for the weekends he made me work, the workload, or anything else at the firm. I knew it was just part of his job. Instead, my sense of unadulterated joy came instead from the hope of a better future and of a happier life that leaving instilled. As I told that partner that I was leaving, I felt an enormous weight lifted off my shoulders like nothing in the world was or could go wrong. I felt emboldened, powerful and most importantly, free. I joke to my friends that I’ll never have as good a feeling in my life ever again, not unless I become a slave and receive my freedom.

The aftermath

So then, what’s the postscript after leaving -has my attitude changed in the last year?
No. The short answer is that I have not regretted once leaving biglaw for engineering. I regret some of the things biglaw afforded, like the salary or prestige of being able to call myself a lawyer. But when evaluating things as a whole, I would change nothing about my departure.

In the past year, I’ve set to work on several projects, one of which I’ve described on this blog called Dockumo. I have other projects in the queue, like building a solution to bluebooking, an insane kind of drudgery that law students subject themselves to involving following imprecise rules on how to cite certain legal works. As I stated before, I still work long hours, but the biggest difference is the fact that I’m now working for myself. The work that I do feels like it has purpose, that it is bettering me and my skills as an engineer, and can build upon itself to enable me to create bigger and more expansive projects -projects that can help others. Software, to me, is still the most efficient solution to many of the world’s biggest problems. Being able to program software is a powerful concept and skill, and it leads to ability to create anything I can dream of if I just put in the time and effort. That feeling of hope and potential to me is the greatest motivator of all; it is what gives my work purpose and it was exactly what I was missing when I was a biglaw attorney.

One month+ in … no regrets so far!

So it’s been about 5 weeks since I left my job at the firm and started as a senior software engineer at my tiny four-person startup. So far, I have to say that things are going well. There are lots of pros and cons to my having changed careers, so I’ll just list them in bullet format.

Pro:

  • I like coding

    • So first, coding is actually enjoyable for me. There are times when I feel kinda like I’m hacking aimlessly, but there are times when things come together. In either case, it’s still better than circle ups, form-checks or due diligence. One difference between coding and law is that software engineering always consists of coding. Yes, there are variations in the complexity of the code that one writes, but by and large, I’m of the opinion that any coding will help you become a better coder. The same may be true about due diligence, but I’m not sure sure about circle-ups or form-checks. Another difference is that coding is in some ways more permanent. I can point to a project and say “hey, I did that!” whereas many aspects of law is aimed toward the prevention of risk, which of course, is much harder to prove.

  • Software engineering makes me optimistic

    • Another important element of my job and software engineering in general is that I’m honing my skills in preparation to build something on my own someday. There are so many tools, applications, games and projects in general out there that can all be built with software. Law, on the other hand, is aimed towards a particular client for solving a particular need. No one learns beach volleyball law because no such thing exists. In software, if something doesn’t exist the potential exists to create it. Although it may never be used by anyone, that prospect of creating something at all is empowering. I suppose you could say the same thing about law. For instance, I could write the code for beach volleyball, and perhaps no one would use it, but it would always be my creation. It’s probably hard to argue with that, but (excuse the pun) not all “coding” is coding.

  • Software engineering is more marketable

    • At least in today’s market, there’s much bigger demand for software engineers, even junior ones, than the demand for junior lawyers in the legal market. Being more employable (at least in the short term) makes me feel more mobile, which makes me feel less trapped, which ultimately makes me feel happier that I’m doing what I’m doing because I want to do it at this point in time. Several of my friends have already offered to submit my resume to their employers. I haven’t taken them up on the offer yet, but it doesn’t seem like the pace of hiring for great engineers will slow.

  • Software is probably smarter

    • I feel that the pace of innovation in software is really commendable and daunting at the same time. It seems like every month there is some new and all-powerful tool that is the flavor of the month to help you solve [x] problem. The corollary to that is that one could spend his entire day learning what the new tools do and never actually spend the time learning how to use them! I’ve felt daunted by the fact that there are 50 frameworks for every aspect of the traditional MVC architecture software stack. It feels like an impossible task to learn everything, which forces me to take bets on what technologies will have lasting power. The law, on the other hand, seems steeped in tradition. You hear of stories about using parentheses around numbers to help prevent fraud in written contracts, which allegedly was relevant before print. There are stories about partners formatting their documents in one way, thus creating and perpetuating a manner of doing things whose meaning becomes lost over time. There are certainly similar aspects about software, but by virtue of the fact that software is not an oligarchy (of partners, for instance), it becomes much harder to entrench one’s idiosyncrasies.

Of course, software isn’t all sunshine and rainbows. I’ve considered carefully what my career my entail when I am over the hump at 35 or 40. I’m realistic that I won’t always be able to spend my weekends reading about node.js and angular.js or whatever hot new technology there is. There are also other aspects of software engineering aside from employability or job satisfaction that vary wildly from being a lawyer. What are they? I’ve considered many, but you’ll have to stay tuned until next time to find out …