Why I Swiped Left on Big Law

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A few years ago it was quite en vogue to criticize everything about Big Law — from the grueling hours to the fierce competition or the less-than-legal work that filled an associate’s plate — but that is not what this article is about. Rather, it is about the journey of letting go of my own Big Law fantasy in favor of a future where I could help to reshape the practice of law and bridge the gaps that made my experience less than enjoyable. 

The winding road from playground to Big Law

My story, like that of many professionals who end up in the hallowed halls of Big Law, started long before law school. Sitting on a swing, at the tender age of 10, I decided that since I was good at arithmetic and writing, my only two career options were obviously doctor or lawyer. I further mused that in the event I ever made a mistake as a doctor I would be out of luck to fix it, while as a lawyer I could always appeal. So, lawyer it was! 

While my path from that swing to the top of the Am Law 200 was a long and winding one, my ambition never wavered. From law school, through nearly a decade and a half in increasingly senior roles at legal technology companies and stints at two of the Big Four, I continued to craft myself to the type of professional that was right for Big Law. When I found myself sitting comfortably 55 stories up overlooking Manhattan in the Big Law office I had always envisioned, I realized that I had never once stopped to wonder in my 15-year journey if Big Law was right for me.

Less Alcatraz, more “Groundhog Day” 

For Type A personalities, conditioned to reach for the gold star and win at any cost, it is incredibly easy to lose yourself in the sweet intoxication of succeeding and achieving goals you set for yourself. What is harder to do is objectively analyze whether the goal you have been striving towards is right for you, and if the better course of action is to pivot to a new better-suited goal. 

When I left — after seven months and three days — one of the lawyers down the hall from me said, “You know, I had no idea it was possible to escape from Alcatraz.” - Peter Thiel

Billionaire investor Peter Thiel once likened his departure from Big Law (after exactly seven months and three days) to escaping Alcatraz. But for me the truth was more complex than that. While I was most certainly boxed in by my own identity being so reliant on competition and achievement that Big Law represented, my mind remained conflicted. More than simply winning, I wanted to be impactful. 

For me, the allure of law through college and law school and the decade and a half that followed was not the status it afforded. It was about being able to make a change, improve the practice of law, and help people have access to justice. The very big-ness of Big Law, the rigidness of its reputation and risk aversion that engendered, made innovation and change extremely challenging. I was riding an aircraft carrier and desperately wanted a way to pivot the slow-moving ship. 

Why didn’t Big Law get my rose? 

Many refugees from Big Law claim that their experience felt like a bait and switch, that their expectations were completely unfounded and the reality was nightmarishly different. For me, that simply was not the case. My vision of Big Law was surprisingly accurate. I worked on the biggest cases, with brilliant people in a way that felt impactful. I worked harder than any point in my life and enjoyed the challenge, I was respected and heard and valued. But this ultimately was not enough. 

If Big Law was everything I dreamed of, why did I jump ship? The difference between the dream and reality was me: what I wanted from a career and how I wanted to impact the practice of law. Rather than simply besting an opponent in the courtroom or drafting a beautiful ESI protocol, I wanted to materially impact access to justice and the actual practice of law. I was tired of settling for the technology (rife with limitations) on hand and wanted to be a part of improving the legal experience, outcomes, and access to legal services regardless of budget. And this wish list required taking a leap outside of the hallowed walls of Big Law. 

Beyond the humble goal of reshaping the practice of law through technology, I also missed having a voice. In a large organization with high visibility (and risk aversion) it is hard to have a platform to share your insights and authentically help educate. This is especially true as a non-lawyer in a law firm. In my time at Big Law, my longtime blog went dormant and my LinkedIn feed may as well have grown spider webs from how infrequently I signed in and posted. I desperately missed connecting with and engaging with the strange, wonderful ediscoveryverse. 

It’s okay to have a Goldilocks moment

People sometimes feel a pang of guilt when looking for the perfect job, often being chastised to appreciate the achievement and success at hand instead of pining for different or more. I am here to say otherwise. Sometimes this insatiable desire for a more perfect fit can yield results that not only benefit the seeker but the industry at large. 

In the halls of Big Law I was limited by annual budgets, partner steering committees, and the constant need to demonstrate growth even at the expense of investing in innovation. I had arguably my dream job but was bored and wanted to do more. Companies like DISCO were embracing the cloud, creatively engaging with AI to accelerate time to evidence, and, frankly, breaking the rules — and I wanted to be a part of it! 

I realized that to move the needle on how the practice of law evolved and embraced the future, I had to be in an organization that had the freedom to take risks and rapidly adapt to the changing dataverse. Ultimately it is the disruptors, like DISCO, that move even the most established industries and help the biggest players adapt as well.

Escape velocity achieved, now what? 

To make the type of systemic impact I so craved, I had to say goodbye to Big Law — but beyond that was unclear. I happened to spend the several months prior to my eventual departure from Big Law manning a brutal 55-vendor RFP covering everything from information governance to AI-powered review and everything in between. This comprehensive process helped me narrow down my options to the organizations that seemed most able to evolve with the changing and expanding demands the digital ecosystem placed on legal practitioners. 

The pain of 2 a.m. software patching and annual and ever-increasing infrastructure for on-premise solutions quickly ruled them out as a viable option for my next chapter. The future was and is clearly in the cloud, because it is cost-prohibitive to manage the infrastructure and security needs to continue to meet the expanding threat landscape and scale facing practitioners today with the on-premise model. 

When I started looking under the hood at all of the cloud next-generation ediscovery providers, it quickly became apparent that some were more fog than cloud, and had the same issues around speed, scale, and ability to adapt to future needs. Only a truly cloud-native solution, architected from the ground up to capitalize on the unique elasticity and scale of cloud infrastructure, could support the dramatic and ongoing increase in volume, variety, and velocity of data and at the same time have the computational heft to support advanced AI and machine learning necessary to parse it. 

The final factor, once I had narrowed down to cloud-native and AI-powered, was the culture of the organization. I did not want to leave one large immovable object for another. Rather, I sought a place that wanted to revolutionize the practice of law and was not afraid to take risks, innovate, and take a fundamentally different approach. 

Most of the next-gen providers simply sought to replace legacy tools but in the cloud. Thankfully I found an organization that has at its core a mission of the inventor’s spirit: create impactful solutions for important problems, have courage to pursue new and better ways, and understand that even ambitious goals may have humble methods. 

One year and four months later

Since swiping left on Big Law, it has felt a bit like a butterfly finally escaping its cocoon. After a nearly three-year hiatus from writing, I now am able to blog and publish articles at a breakneck pace, and my formerly hibernating LinkedIn profile is a fertile ground for learning and collaborating across the industry. I have spoken in dozens of cities, in multiple countries, and with dozens of the leaders of the industry — and more importantly reconnected with the things that are most important to me personally and professionally. 

I also have the pleasure of working with some of the most brilliant minds in ediscovery (if you don’t believe me, try reading Alan Lockett’s intimidatingly sharp book) to solve the problems that drove me nuts throughout my legal career. From streamlining ingest from a hundred clicks to three to applying advanced neural networking powered by Google’s BERT to accelerate time to evidence and making usable data visualization that dramatically improves data insights, it is intoxicating to be part of moving the needle. 


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