How flexible work arrangements are enabling lawyers’ creativity

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For many lawyers, the idea of creative expression seems like a pipe dream — a luxury reserved for people who don’t measure time against a billable hour. In a life of competing priorities, artistic expression seems to always get pushed to the bottom.

However, for a growing group of lawyers who have embraced remote work technologies — especially in today’s crisis environment — the choice between practicing law and pursuing one’s passion is no longer an either/or proposition. The adoption of cloud computing, SaaS contract management tools, and collaborative document production has enabled a cohort of freelance lawyers to deliver the same client service without sacrificing innovation or creativity.

Whereas lawyers were once bound by rigid office cultures, geographic limitations, and demanding hours, technology now allows lawyers to design a practice around their personal passions and pursuits. From starting a business, to moving to the other side of the world, to going back to school, here are the stories of three lawyers who explored their full range of creative interests and found a new beginning.

The lawyer as supportive culture champion

Jeremy Fischbach was working at a law firm in New Orleans when inspiration struck. He graduated from NYU School of Law just after the 2008 financial crisis and spent several years marching down the predetermined corporate lawyer path. His post-law school years were a particularly difficult time for Fischbach, both personally and professionally, but he found solace in the support of his friends and family with whom he had lost touch while pursuing his legal career.

“I learned that the most important questions for me are whether I feel supported and whether I’m spending enough time supporting the people around me,” says Fischbach.

Inspired by his own network of caregivers, Fischbach set out to build a community where anyone can connect to the most caring people in the country. In 2018, he launched Happy, a tech-enabled platform of exceptionally compassionate peers (termed “Support Givers”) who are available 24/7 to listen, accept, encourage, and offer genuine human connection.

With COVID-19 social distancing measures in place around the world, Fischbach is grateful for technology that helps him connect people who are feeling isolated. He continues to develop Happy’s technology, expand its roster of partners, as well as maintain a legal practice. “My family thinks I work too much,” he says. “But I love my work.”

The lawyer as permaculture farmer

When a friend told Rebecca Stellato about an alternative legal service provider (ALSP) that would allow her to work on an exclusively remote, freelance basis, she began to wonder if her fantasy of building an artist and maker colony on a sustainable farm could finally become reality.

After six years in the capital markets practice of a global law firm, Stellato, a Georgetown Law graduate, along with her neuroscientist husband James, packed up and moved to Portugal, ultimately purchasing 50 acres of abandoned farmland. Together, they are building The Surrender Homestead, a permaculture farm that’s home to a future artists-in-residence program and a meditation retreat.

Stellato says she spends the majority of her day clearing paths through her land, tending to her budding vegetable garden, and restoring the property’s farmhouse. In between her myriad chores, she pops online via satellite and checks in on her legal clients and the status of their various contract negotiations. “I finally feel engaged in my own life,” says Stellato. “It’s rewarding to work for oneself — building my house, feeding myself, setting my own hours — there’s such peace and freedom knowing I’m less dependent on the outside world.”

Stellato explains that she would have started the homestead sooner had she known there were platforms that would allow her to work remotely as a lawyer. “I always wanted to do something artistic and creative,” she adds. “I’ve daydreamed about building something like this since my law school days, I just didn’t realize these remote legal services platforms even existed.”

The lawyer as computer scientist

As a high school student, Steven Church was fascinated with technology. His extracurricular hours were spent building computers, dissecting digital consoles, and creating custom games with Raspberry Pi. But for Church, technology was a hobby, not a career. He studied industrial and labor relations as an undergrad at Cornell, and ultimately decided to go to law school at the encouragement of his labor law professor.

After graduating from Columbia Law, Church practiced at a large New York law firm and worked in-house at a multinational investment bank. As a bank lawyer, Church faced unique data privacy and cybersecurity challenges. He wondered if his approach to the application of banking regulations would be better served by a deeper understanding of the underlying technology surrounding customer data.

Armed with a business case for his interest in technology, Church enrolled in a master’s program in computer science at the University of Pennsylvania. He also started a freelance solo practice to allow him the flexibility to focus on his studies. “My goal is to bring a technical component to the work product I provide my clients,” says Church. “Lawyers need to think like programmers to produce quality advice — be concise, make the answer interactive, and think about the end-user.”

Church says he is happy to no longer keep his interests siloed. He enjoys being a lawyer but wants to be creative in how he applies the law and gives legal advice. “There is a lot of crossover in law and computer science in terms of problem solving,” he adds. “They are both logical disciplines where you break down complex problems into discrete steps.”

Between his freelance legal practice and online computer science courses, Church hasn’t noticed much change in his day-to-day life now that mandatory social distancing measures are in place in his home state of New York. And he’s not alone.

As the COVID-19 global health crisis transforms the world’s acceptance of remote work businesses like these, lawyers like Church, Stellato, and Fischbach may become less rare but no less remarkable.