Rob Chesnut, former general counsel, writes on in-house, corporate, and ethics issues. He has advice for lawyers seeking to make a big change—he successfully jumped from being a long-time prosecutor to in-house at a tech start-up.
A lot of lawyers feel trapped in their career. You get out of law school, join a firm, and start to specialize. Maybe you move in house, it’s so easy to get labeled. Corporate lawyer. A litigator. Contracts. Employment.
So often your employer wants you to specialize, become an expert. But after five years, maybe ten years, it starts to feel a little tired. You look at the senior lawyer down the hall (or on the Zoom call), and you ask yourself: Do I want to be doing this when I’m 50? 60? (gulp) 70? You know the answer deep down, but there’s no clear way to hit the reset button. You’re in a career escape room—how are you going to get out?
My natural tendency has always been to change things up. Before law school it was everything from dishwashing to lawn care to sales and scooping ice cream. After law school and a clerkship, I did civil constitutional litigation for three years. Moved over to federal criminal prosecution, where I did everything from traffic cases to narcotics gangs, prison murders, bankruptcy fraud and espionage cases.
Then I spent five years as one of eBay’s first lawyers handling just everything that came in the door, and another five years there in a non-legal role starting the internet’s first e-commerce trust and safety department. Back into the legal world for stints as the general counsel at Chegg and Airbnb. I finished my time in the corporate world as Airbnb’s chief ethics officer, which led to authoring a best-selling business integrity book and keynote speaking.
Obviously, I’m a fan of changing things up—you stay fresh, you become a lifelong learner, and the varied knowledge you pick up along the way is actually wind at your career back. You can bring so many experiences to the table when you apply for your next job. Sound like an appealing career journey? Here are four tips to help you navigate a big change.
Be Curious
I’ve spent a lot of time around successful people, and one quality they all share is a natural desire to learn about new things. Curiosity played a big role in my toughest career move, from prosecutor to in-house internet lawyer.
It all started when a friend suggested I needed a hobby that would bring out my “creative side.” I was a little skeptical, but I bought my first camera and took a photography class. When I got serious about it, another friend suggested that this tiny little internet website called eBay was a great place to find deals on photographic equipment.
It was 1997, and my journey as a buyer and seller on eBay in that next year helped me learn all about internet ecommerce and led me to take the leap and apply for a job with the company.
Coincidentally, my best friend was going through a similar career journey at the same time. He was an associate at a small Virginia law firm doing personal injury work, and he wanted a change. He spent his spare time going to hear other lawyers speak about their careers, and by chance one night he attended a presentation by an attorney who had recently started a business immigration practice. “I can do that,” he thought, and he spent a year training himself on the law in his spare time before taking on his first client.
Within 20 years, he built one of the largest business immigration law firms in the country, with over 200 lawyers and paralegals generating tens of millions of dollars a year serving many of the top tech companies in the world. He was curious, he pushed himself to learn new things and he blossomed.
Be a Customer
When you’re trying to change career gears, your resume might not be exactly what your target employer is used to seeing. One way to make your resume stand out is to be a customer of a business first, before you apply for a job. Your specific skill set might not wow them, but you can demonstrate a deep understanding of their business issues and your passion for their mission by talking about your experience as a customer.
For example, when I applied for a job with eBay back in 1998, there was no job opening on their website, just an email address—jobs@ebay.com. I prepared a cover letter that talked about how eBay had transformed my photography hobby, connecting me with other enthusiasts around the country and enabling me to make some money on the side.
As it turned out, I had done more eBay transactions than most of the executive team at that time, and my passion for the business—and understanding of their challenges from the perspective of a customer—helped my resume stand out.
Similarly, when I applied for the general counsel role at Airbnb, I was able to talk about a powerful personal experience I had in Cuba while staying in a neighborhood Airbnb. I didn’t just read about Airbnb’s business—I experienced it and loved it before I submitted a resume.
Be Creative
At first blush, it might have appeared that a federal prosecutor didn’t have the skill set to be an in-house lawyer at a fast growing tech company. But I didn’t sell myself short—when I thought about it, a lot of my criminal work made me a strong, unique candidate for the eBay role.
As a prosecutor, I had more in-court litigation experience than most civil lawyers. The skills I acquired when negotiating hundreds of plea agreements would come in handy when drafting contracts and negotiating deals. I prosecuted cases involving counterfeit goods, illegal firearms and stolen property, all of which were challenges that eBay dealt with. My work with numerous federal agencies gave me unique insights and credibility when dealing with regulatory issues that eBay faced in its early days. When framed in that light, my weaknesses became unique strengths.
In today’s job market where your resume might be screened by software, you’ll have to work extra hard to describe your skill set in a way that can get through the screens and help your new potential employer understand why your atypical background is just what they need.
Be Persistent
Prepare yourself. You’re about to get rejected. A lot. When I was trying to make the jump from federal prosecutor to in-house lawyer, I applied to well over 100 companies in 18 months. Most never responded, and when they did, it was something like “you’re a great prosecutor, but we don’t prosecute people here.” Getting rejected can either grind you down into discouragement and inaction, or it can challenge you to meet more people and think creatively.
The choice is yours—don’t expect it to be easy but know that the rewards of making the leap will go to those who take a risk and find a way to make it happen.
(Corrects 14th paragraph to clarify general counsel role was at Airbnb)
Rob Chesnut consults on legal and ethical issues and was formerly general counsel and chief ethics officer at Airbnb. He spent more than a decade as a Justice Department prosecutor.
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