4 Steps To Growing A Legal Career In Sweatpants

Many years ago, after a cold email to Etsy’s Founder/CEO, I flew myself from Rochester, New York, to New York City and used research, writing, and speaking accomplishments to convince him to hire me for a position that only existed in my head, Etsy’s first lawyer (I’ll save the entire story for another column). After over a decade of working in-house at Baby Unicorns, I entered the next phase of my career the only way I knew how: by creating my own opportunity. This time, after reaching out to an acquaintance, I took a subway to a ramen restaurant and used my handmade career to convince the executive co-director of the NYU Law School Engelberg Center to hire me as a legal fellow. One project would be mentoring students who are interested in the intersection between in-house law, technology, and startups.

A Google Doc was sent around to several law school student groups with various dates and times for small-group lunches. The document was oversubscribed within an hour. I proudly cracked the code to getting law students’ attention: free food.

The first mentorship meal consisted of a mix of 1Ls, 2Ls, and even a 3L with unique business law aspirations. One student hoped to land a position at a startup after gaining big law patent experience. Another student was looking to enter the world of art law. After graduation, a third student hoped to launch a sustainable furniture company. The first mentorship meeting was a success, but it was also my last “normal” meal out. The next day, COVID-19 officially changed the way New York City operated.

My in-person plans magically evaporated. They were replaced by the desire to flatten the curve; a newfound appreciation for toilet paper; and financial, societal, and health concerns. So, I did what any business-savvy self-isolated professional in the 2020 pandemic would do. I put on sweatpants and pivoted some plans, including the mentorship project, to Zoom.

I predicted a drop off in attendance for an online mentoring lunch given that virtual free food typically has less appeal than actual free food. I was wrong.  As we chatted about career aspirations and brainstormed next steps, I realized that in today’s climate, both law students and experienced lawyers are facing an unknown future and similar feelings of unease. Our profession has seemingly changed overnight.

As we cope with feelings of a loss of control, perhaps we can focus on adding value to communities. As a side effect of these efforts, the practice of law may improve, and careers may scale. If you’re fortunate enough to be healthy and safe, here are four opportunity-creating tips (all of which comply with social-distancing measures).

Tip Explanation My Example
1) Connect with your legal motivation(s). What subjects, cases, or news stories spark your legal curiosity? What drew you to law school or to your specific practice areas?


You may have several legal motivations, and they may be related or unrelated to your past expertise.

I was initially motivated by the copyrights, trademarks, and small, creative businesses.


2) Research and connect with legal and nonlegal communities.



What communities are impacted by your legal motivation? Where does each community (virtually) share information, meet, and connect? Who are the players and the decision makers?


Join these communities.  Nonlegal groups may support and benefit from your projects. Legal communities may collaborate on projects or offer insights.

I completed some art classes, met with artists and gallery owners, and subscribed to several craft-focused newsletters and magazines. I absorbed content and participated in Etsy’s community.


I met generous thought leaders, attended seminars, and participated in legal committees. I asked targeted questions when I cold-contacted experts, authors, professors, and attorneys who specialized in various aspects of art law, startups, and small businesses.


3) Listen, learn, and prioritize (or pitch) to add immediate value.



What are the community’s legal or business concerns?  Who is currently addressing these issues and adding value? What are some projects you can complete to add value?


Prioritize the projects and set reasonable deadlines for yourself.

Small businesses and artists seemed confused about aspects of intellectual property law and fair use.


I aimed to pitch one piece of writing or speaking gig per week. I outlined plain-English copyright articles to the editors of a handful of niche magazines. I asked the owner of a local gallery if I could teach an IP seminar to small businesses. I self-published a legal e-book.


4) Get out of your own way.



Be kind to yourself and others. Your legal brain may warn you that you’re not qualified. It may demand perfection. It could paralyze you with fear that you’ll get sued.


Congrats! I’m officially calling you qualified and giving you permission complete a project imperfectly. Keep iterating as you learn. And, be smart, add a disclaimer, get insurance, you know the drill.


When faced with rejection, keep positive. When you earn good news, make note of the accomplishments.

I aimed for quality work and for progress. Many contacts and pitches were rejected. Worse, and more often than not, I never received a reply.  But sometimes I was introduced to a mentor, had an empowering conversation, joined a group, had a piece published, or spoke at an event.


I imperfectly and quickly created a personal website, posted on social media, and updated my resume.  My personal brand keeps evolving over time.



By focusing on others’ needs, I created career opportunities for myself, which led me to Baby Unicorns and to Zoom calls with NYU law students. We have the power to emerge on the other side of this worldwide trauma with value added to our careers and to the communities that need bright legal minds. Each of us can drive positive impact. We are responsible for our own journey, whether it consists of physically slurping ramen or socially distancing ourselves while wearing sweatpants.

Sarah was the General Counsel / first Lawyer at Etsy and Vroom.  She’s a co-founder of The Fourth Floor, a creator and producer of Legal Madness, an NYU Law School Engelberg Center fellow, a board member, an investor, and a speaker. You can also find Sarah hammering silver, eating candy, and chasing her child. sarahfeingold.com.

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