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After the Bar

Personal & Financial

Lawyers as Side Hustlers: How Problem-Solving and Purpose Can Lead to Entrepreneurship

Shontavia Jackson Johnson

Lawyers as Side Hustlers: How Problem-Solving and Purpose Can Lead to Entrepreneurship
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Driving into my office’s parking garage, I could feel the hot tears welling up in my eyes. After 18 months, it was painfully clear that my Big Law firm and I were not a good match. For months prior, I dreaded walking into the office, and the tears I felt that day were not uncommon. I did not realize it then, but it would be only a few weeks until I handed in my letter of resignation. Shortly thereafter, I traveled to South Africa for a few months before beginning a two-year teaching fellowship in New Orleans. This career pivot came with a nearly $100,000 pay cut, required me to move more than 600 miles, and doubled my living expenses. While my mental health and general happiness improved, my financial situation was shaky. Creating a side hustle was the logical next step.

As a strategist for the past decade, I have learned two valuable lessons: lawyers are uniquely qualified to have side hustles; and you must find your “why” outside of money. These two keys have been essential to my growth.

Before leaving Big Law, my experience was primarily in intellectual property law. My diverse experiences and interests, however, allowed me to advise and consult on a wide range of legal and law-adjacent issues. When my client base grew, I created a formal business. Nine years later, I serve as an associate vice president at a large, public university, and I still maintain a side hustle. My focus has shifted from money to meaning. I help people start the businesses they have been dreaming about while working full-time. Much like me more than a decade ago, they want to find their purpose, create additional income streams, and positively impact the lives of others. Lawyers are overrepresented in my group of clients.

Although lawyers tend to be risk-averse and do not consider themselves entrepreneurs, our legal training prepares us to identify issues and solve complex problems quickly. According to Nicaila Matthews Okome, founder of the Side Hustle Pro podcast, all successful businesses solve a problem. Many businesses fail because their founders do not recognize or articulate the problem that needs to be solved. The skills we acquire from law school and law practice can put us ahead of the curve, particularly when it comes to identifying a viable business idea that solves others’ problems.

Finding your “why” outside of money is imperative. The legal profession is not viewed as one where people need side hustles. In 2019, lawyers in the United States made an average salary of $144,000—more than three times that of the average American. Unfortunately, these high salaries are often offset by rapidly increasing costs of living and hefty student loans. For example, the median debt for law school graduates was about $110,000 in 2019. Despite high earnings, the legal profession is consistently ranked as the unhappiest profession in America.

For those lawyers unready to give up their full-time job in the legal profession, a side hustle can help them lead a more fulfilling life. Consider this: nearly half of all Americans have at least one side hustle, and 70 percent of those people engage in their side hustles because they love the work, not to make ends meet. Take, for example, Kevin Ha, a full-time lawyer with 13 non-law-related side hustles. Ha originally started side hustling to pay off $87,000 in law school loans, which he accomplished after two-and-a-half years. Four years later, he continues to side hustle because he’s found multiple “whys,” including getting more exercise and getting enjoyment out of it. In my side hustle, I have found it rewarding to help other working professionals realize their entrepreneurial dreams. This “why” has kept me motivated through difficult times in and outside of my full-time work. Being of service to others feels like a manifestation of why I went to law school in the first place.

Ultimately, lawyers with diverse interests should consider if a side hustle is right for them. We have acquired, and continue to acquire, the kinds of skills that make businesses successful. In a generally unhappy profession, lawyers can find joy in meaningful side-hustle work.

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