The real story behind my career pivot

How my upbringing and unique circumstances in my personal life influenced my eventual decision to leave the law

This post is going to be a bit more personal than my other articles. To be sure, this isn’t the first time I’m sharing publicly about my career pivot. What I haven’t done before, though, is to share how my upbringing and personal life influenced the path I took that led me to where I am today.

Part of why I’m writing about all this now is because of a particular type of reaction from people when they hear I left the practice of law. They think it was driven by courage or bravery. Often it’s because they’re putting themselves in my shoes, and feel an enormous amount of anxiety around possibly leaving the law themselves.

So anyone who made the leap was somehow able to overcome it. Or so the thinking goes.

But the real reason I ended up making my career pivot had nothing to do with bravery. By the time I left law, I had already suffered through several setbacks—including getting fired and failing at entrepreneurship—and was just looking for a quick win. Anywhere. That’s what led me to join a startup at a fraction of the salary.

The upside of my “bold” move though, was that it gave me the chance to start over, completely anew, without the mental burden or baggage of having my personal identity tied up with being a lawyer.

My goal today is for me to share with you what else was happening in my life that led me to make the change. Spoiler alert: There was no grand plan. Whatever happened, it was far less about bravery and far more about me scrambling to figure out my next steps.

And it all happened because of unique situational factors that took place in my personal life between 2010 and 2015.

This is my story.

The Beginning: Why I decided to be a lawyer

To get a full understanding of how I ended up in law, you have to understand where I came from. My parents are immigrants who struggled with the culture shock and language barrier in their new country. To overcome these challenges they worked insanely hard. Like, all the time. So when I was born, they had such high hopes for me.

My parents could not comprehend how someone who was born in the U.S. without the language/culture challenges they faced—could possibly struggle to do well in school.

But that was me. From elementary school and on, I was a mediocre student. There was a perception that my problems were caused by a lack of work ethic, which was understandably maddening to my parents. Even I believed it. Looking back now, I can see that a lot of it was probably due to ADHD.

In any case, struggling in school led me down a path where I became far more interested in hanging out with friends than getting good grades.

At some point my mentality changed. During my junior year of college I realized that I was tired of being an underachiever. I matured and became more aware of the many sacrifices my parents made to give me the opportunities I had. As a result I decided right then and there to reinvent myself as someone who took his future seriously. I thought that would make my parents proud.

That underlying feeling is what ultimately led me to apply to law school.

Law school gave me the chance to reinvent myself

Don’t get me wrong, wanting to make my parents proud wasn’t the *only* reason why I wanted to be a lawyer. I thought going to law school would make me articulate, polished, and potentially rich. I mean, I didn’t actually know any lawyers but my perception was that it was a fantastic career.

Plus, if I could end up at a top school and work for a fancy firm—that would overshadow all of my academic struggles growing up. As cheesy as it sounds, law gave me a path to bring honor to my family and make my parents’ struggles worth it.

Problem was, I already had terrible college grades which meant it would be very difficult to get into a top school, which would make it nearly impossible to land a fancy pants attorney job at one of the big firms. I was super determined though. And ended up spending a few years locking down, raising my GPA, working/studying for the LSAT, and doing whatever it took to get in. And in the end—it worked!

I got into Northwestern Law.

From that point on I tried to reinvent myself. Right before 1L year started I decided that I’d be a law school superstar. Problem was, you can’t just develop good study habits overnight. It was a struggle to outline and prepare for exams. But I persevered, making law school my life’s top priority, and put everything in my personal life on hold.

It wasn’t easy, but it worked. My resume/grades were strong enough to give me an outside shot at some of the country’s top law firms, and once again, I found a way to hustle/talk my way into opportunities. The summer before my second year, I secured a summer associate offer from Sullivan & Cromwell. I felt like I finally made it.

Of course, I never imagined how I’d feel once I actually started the job.

Realizing that I might have made a mistake

As a summer associate I quickly realized that I just didn’t enjoy the work. Like, I loved the idea of being a summer associate at such a great firm. And I was proud to tell people where I worked. However, spending all those hours actually *at* work was a different matter.

As a summer I sought out real assignments and substantive work (this was during the Great Financial Crisis, so we were all trying to work hard to ensure full time offers at the end of the summer). I got a taste of the work and found that I kind of hated it.

However, I couldn’t imagine leaving to do something different. Certainly not as a summer. So I kept pressing on and did what I was supposed to do: secure a full time offer at the end of the summer.

Something should’ve clued me in that I was headed down the wrong path when, as a 3L, I asked S&C to extend the deadline for my offer so I could apply for a job at the Manhattan DA. After a couple of interviews, I got cold feet, and ended up withdrawing and accepted the S&C offer.

Around that time something else happened that influenced my decision: I met a girl and I completely fell for her. Problem was, she had two more years of medical school in Chicago, which meant we’d have to do long distance after I graduated.

I came up with a long shot plan. Could I somehow figure out a way to land a one or two year judicial clerkship in Chicago? My firm told us that if we ever left the firm for a clerkship, we would always be welcomed back afterwards.

I couldn’t believe my luck when I found out that this one AUSA I admired (and met at an APALSA event) had just been nominated to the federal bench. It dawned upon me that there was a possibility that everything could work out perfectly—if I could convince him to hire me as a law clerk.

Tension between my professional goals and my personal life

I ended up getting the clerkship. There’s an entire story behind it that I’ll write about someday.¹ But basically I was the luckiest guy on earth. Not only did I land a clerkship I felt barely qualified for—it fit in *perfectly* with my desire to be nearby my new girlfriend.

I spent 20 incredible months clerking for my judge. It was the best law job I’ve ever had, hands down. As the clerkship came to an end, I was faced with yet another decision. Where should I work afterwards? Should I return to S&C or try to find another job that I might like better?

My immediate reaction was to go somewhere else. I ended up re-interviewing with the Manhattan DA, and also interviewed with a top-end plaintiffs’ class action firm in NYC. But then something unexpected happened.

My girlfriend, who I thought would do her medical residency in NYC unexpectedly matched at a hospital in California. Once again I was faced with a decision point. What should I do next?

To be quite honest, I wasn’t ready to follow her to the west coast—after all I’d just spent two years clerking in a city I didn’t plan to stay in. I was also already licensed in New York. So the plan was to work in New York and see how the next few years played out.

Once I decided to go back to NYC, I had to figure out what job to take. From a career perspective, I had a hunch I’d enjoy being a trial lawyer or plaintiffs’ lawyer far more than working in Biglaw. But taking that path was risky. If those jobs were a bad fit, I’d have very few exit options. And if I did decide to eventually move to California, I’d have even fewer options.

Based on all of these considerations, I decided to return to S&C. I knew it wasn’t a great fit for my personality. But I knew it would preserve a ton of exit options, which given the uncertainty around my future plans, was going to b super important.

That’s how I ended up deliberately choosing to work at a job I knew I’d hate.

What it was like to take a job purely for the exit options

For the next two years my girlfriend and I did the whole long distance thing. Which wasn’t as bad as you might think, given that we were both super busy with our work lives. However these two years were tough on me, mentally and professionally. Because I naturally struggled with focus and attention to detail, I ended up putting in extra hours to make sure my work product didn’t have mistakes.

At the end of my two years, I decided enough was enough. By then I was 30 years old and just exhausted. So I decided to make two huge decisions that would change the course of my life.

First, I decided to move to California. It was not an easy decision, since my family, friends, and network were all in New York. But by then I knew I wanted to marry this girl, and also knew that she loved being in California. In my mind, there wasn’t a question of what the right (geographical) move was.

Second, I decided that my next job would *have* to be something I’d enjoy. No more working for the money or exit options. I was 4 years out of law school, and by then I’d paid off my student loans and saved up enough money for a ring and a modest wedding. Given my struggles at S&C, I decided to not apply to any Biglaw firms.

Setbacks and failures

My decision to relocate to California and step off the Biglaw path had pretty huge ramifications for my future. In the end, it took far longer than I ever expected to get my California bar license. As a result, I ended up getting fired from my next job (which happened to be at a plaintiffs’ firm).

Getting fired unexpectedly led me to rush off to my next venture, which was to open a solo practice. That practice ended up getting shut down a year later, after I struggled to break even financially.

All of my worst career nightmares suddenly became reality. I was 33 years old, six years out of law school. With nothing really to show for it.

And yet now—with the benefit of hindsight—I have come to realize that losing everything that I had that gave me the chance to find something better. My whole life I had struggled with school and work. I chose my career path for many reasons (good reasons) but never based on what I actually thought I might enjoy.

But now I could.²

Conclusion

I’m sharing all of these details because the details played such an important part of my journey that I rarely ever touch upon publicly. As I mentioned in the intro, usually my posts about career pivots are fairly sterile. Narrative: I figured out what I was good at, ran into some setbacks, and then took some risks and ended up in a good place.

Life is a lot messier than that. My feelings and circumstances pushed all of my career decisions in a certain direction that otherwise might not have happened.

I chose a career path that was not aligned with my personality. And when I realized what was happening, instead of leaving—I chose to remain on the wrong path. I felt like I needed exit options, because it would help me down the road if I needed to move to California to be with my girlfriend. All of those decisions led to a spectacular blow up of my legal career.

Let me be clear: I have zero regrets about everything that happened. Because this story did have a fairy tale ending.

I ended up marrying that girl, and we now live in California together with our two beautiful children. On the work front, I now have a unicorn job I truly enjoy. The coolest part is that I’ve been able to tie everything in my past together. I get to work with people, doing sales and marketing—and am still deeply connected to the legal community.

My life isn’t perfect. And I’m not certain where my career will end up. But I can’t deny the fact that the way my work and personal life has played out—I’ve had some pretty good luck. I certainly wouldn’t have everything I have today, had I not gone through all of the ups and downs of the past ten years.

That’s why I’m writing this article. Because I genuinely wish the same thing to all of you. The ups *and* the downs. It’s really hard to say, when something happens, whether that’s actually good or bad for you in the long run.

But if you remain authentic to yourself and trust your instincts on the things you value and want out of life—I truly believe it will all work out.

1. I shared part of the story on Twitter a couple of years ago.

2. If you’re curious about how those setbacks led me to legal tech startups, I shared more details in my article How I Found My First Legal Tech Job