Lawyering without a life preserver

The practice of law can be a high-stakes profession, with lives, livelihoods and billions of dollars on the line. Unfortunately, law schools typically teach their students precious little about how to actually practice law. Most young lawyers begin their careers suffering through a period of intense trial by fire, worried that every day they are committing multiple counts of malpractice.[*]

As they progress from junior associates to mid-levels, mid-levels to seniors, and seniors to partners, at each transition they face an onslaught of new challenges coupled with ever-increasing levels of responsibility. Each time they finally swim back to the shallow end of the pool – where they can just begin to feel the bottom with the tips of their toes – that’s­ usually when they are thrown right back in the deep end (and dunked, for good measure). As a result, the everyday reality for many lawyers is one that feels like perpetually trying to fake it until they make it. Imposter syndrome runs rampant even among the most seasoned lawyers, particularly when they face unfamiliar issues or take on matters that are outside of their comfort zones.

I have experienced the feeling of lawyering without a life preserver firsthand in my own career, though not as keenly as other lawyers who work at smaller firms or in solo practices surely have. At the big New York law firm that I joined straight out of law school, most of my work was heavily supervised by several tiers of more senior lawyers before ever seeing the light of day or making its way to a client’s inbox. I had access to a wide array of internal and external training materials, treatises and law librarians, as well as experienced attorneys in every specialty area of law that might be relevant to the capital markets transactions I was working on.

Nevertheless, even with all the resources of a large international firm at my disposal, I almost constantly had the lurking suspicion that everything I was doing was wrong and that, somehow, I would be discovered as a fraud and unceremoniously given the boot. The treatises and training materials were typically not up to the challenge of explaining in sufficient detail what I was supposed to be doing on my deals or helping me to resolve the issues that arose. The more senior attorneys at the firm were very busy and didn’t always have time to answer a seemingly endless parade of questions from a lawyer just starting out. I kept treading water, worrying every day that this would be the day my legs would give out.

When I made a lateral move as a mid-level associate to a boutique firm with a practice focusing on tech startups and venture capital, I found myself instantly back in the deep end of the pool. I had to learn a whole new practice area from scratch, while simultaneously meeting the expectations that, as a mid-level associate with training and experience from a top law firm, I could handle greater responsibility and work more independently (and more directly with clients) than a junior lawyer.

In addition, my new role required me to field questions in far-flung areas of law, many of which were completely foreign to me. As outside general counsel to dozens of startups, I was regularly asked to advise my startup clients on a range of issues well beyond the relatively narrow realm of capital markets transactions on which I had cut my teeth at my previous firm. This type of practice was more akin to practicing at a smaller law firm or in-house than at a Big Law firm; it required me to become a generalist who could handle whatever came in the door with fewer resources than I had available at my first firm.

Learning this new practice and the various unfamiliar areas of law that were often cropping up was a painstaking process filled with trial and error. I tried watching CLEs, but they either assumed too much knowledge or were pitched at such a high level that they were useless in my day-to-day tasks. There was also no shortage of information on the internet (in the form of blog posts and articles from founders, venture capitalists, accelerators, trade associations and the like), but I quickly learned that many of the “hot takes” on issues facing startups from these sources were unreliable and based on miniscule sample sizes and shallow experience.

Eventually, through brute force of repetition over the course of hundreds of deals and thousands of random questions from clients, I made my way back to the shallow end of the pool. But the time it took me to get my feet under me felt excessive, and I knew there would always be more unfamiliar transactions and issues on the horizon.

When I was recruited by Practical Law to become their resident expert on startup law, I was excited by the prospect of creating the tools and resources that I needed in practice – to be the life preserver I never felt like I had. The first thing I did when I started the job was to take an inventory of everything Practical Law already had that might be relevant when representing a startup company. I was gob smacked by what I found. Every resource that I read made me think of specific instances from my time in practice when – if I’d only had that information at my fingertips – it would have saved me a great deal of time and agita and saved my cash-strapped clients a great deal of money.

I now understood why every lateral attorney who joined my last firm from other firms that had Practical Law subscriptions expressed shock and dismay that they would be expected to practice without it. They considered it an essential tool, and I could see why. It was like having 24/7 access to the more experienced trusted colleague I always wished had the time to answer all my questions, whatever the topic.

Discovering the breadth and depth of coverage at Practical Law also helped me realize its immense value for lawyers who find themselves having (or wanting) to take on matters outside of their comfort zones, regardless of the lawyers’ seniority and experience. Practical Law makes it possible for lawyers of all stripes to save time and avoid frustration digging for answers and getting up to speed on the unfamiliar. Better yet, it allows any lawyer to practice with the confidence of an expert in the field.

I find it deeply gratifying to help provide a service that not only makes lawyers – from white shoe New York firms to solo practitioners – more efficient and effective but that also helps alleviate the stress and anxiety that comes from feeling like an imposter. Keeping your head above water while practicing law is hard enough – no one should have to do it without a life preserver.

[*] For the record (in case anyone from the bar association is reading this), I have not, to the best of my knowledge, committed any actual malpractice. It was just a feeling. You know you’ve felt the same way.