Penn Law Alum Adam Pascarella On How To Craft A Nontraditional Legal Career You’ll Love

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Author Adam Pascarella (courtesy photo)

“Haters want me clapped and chromed it ain’t easy / Cops wanna knock me, D.A. wanna box me in / But somehow, I beat them charges like Rocky” — Jay-Z

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This week, I had the opportunity to catch up with Adam Pascarella, the author of “Reversed in Part: 15 Law School Grads on Pursuing Non-Traditional Careers.”

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Adam attended undergrad at University of Michigan and earned his JD from the University of Pennsylvania Carey Law School. He was a litigation associate at Baker & McKenzie LLP for over two years before leaving the firm to begin a startup in New York City.

As he mentions on his website, “the legal practice can be extremely rewarding. But what happens if you don’t want to practice law anymore? Or what if you’re in law school and discover that legal practice may not be for you?”

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In “Reversed in Part,” Adam reveals how 15 accomplished law school graduates built stellar careers outside traditional legal practice. From startups and finance to sports broadcasting and nonprofits, you will get inspiration and practical advice on how to craft a career that you love.

Fun fact: I used one of the interviewees’ companies, Sander Daniel’s Thumbtack, to hire a singer for my engagement party in Chicago back in October 2016.

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Suffice to say, I thoroughly enjoyed Adam’s book and I believe you will too. The following is a (lightly edited and condensed) write-up of our conversation:

Renwei Chung: Can you tell us a bit about your career and what you are doing today?  

Adam Pascarella: I’m a graduate of the University of Pennsylvania Carey Law School and a former litigation associate at Baker McKenzie. At the firm, I specialized in general commercial litigation, but I also worked on some white collar defense and antitrust matters.

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After several years, I decided to leave legal practice. While I wasn’t sure what it would look like, I had a deep desire to build something and take on a more entrepreneurial career. That led me to starting Second Order Capital Management, which is an investment management firm based in New York City.

RC: What motivated you to write this book and how long did it take you to complete it?

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AP: “Reversed in Part“ is the book I would have wanted when making my career switch. I was looking for a comprehensive resource that offered both inspiration and practical guidance from law school grads who succeeded outside the law.

I also wanted to examine the well-known phrase: “You can do anything with a law degree.” While I believe lawyers have plenty of soft skills that make them valuable in other sectors, going to law school in order to do something outside legal practice is an entirely separate question.

It took me around three years to finish the book. As is the case with any project, you need to put in the reps and fight what “The War of Art” author Steven Pressfield calls “Resistance.”

RC: Like the 15 individuals in the book, you left the legal field. How did you relate to those who you interviewed in the book? 

AP: I’ve developed a bias for taking action. In legal practice, our analytical minds are one of our superpowers. But when you’re building a business or trying to do something nontraditional, the rewards go to those who are decisive. Even if you experience failures or setbacks, you get real-world data that gets you closer to your goals. I’m always blending this bias for action with the analytical mind that I developed in the law.

Related to this, I always try to take calculated risks. I love searching for asymmetric bets. Like renowned investor Mohnish Pabrai says, it’s the idea of “heads I lose, tails I don’t lose much.” This mental model is powerful and helped many of the 15 individuals advance their careers outside the law.

RC: Anthony Scaramucci, former White House communications director, seems to be a polemic figure from the last administration — what do you think readers will take away from the Scaramucci chapter?

AP: Anthony is a fascinating individual. Few know that he graduated from Harvard Law School. No matter your politics, there are plenty of things that we can learn from his story.

First, the best career move may be taking a lower-paying job that better matches your skillset. For Anthony, this came from getting fired from his investment banking role at Goldman Sachs and then getting rehired in a lower-paying sales role. He naturally fit into that role, and from a long-term monetary perspective, he told me it was the greatest thing that could happen to him.

Anthony also shows the power of resiliency. Even after business failures and a notable public firing, he gets back up. It’s an admirable trait and something that we can emulate.

RC: Are there any other figures in the book you believe may be misperceived or that you simply want to shine a spotlight on today?

AP: Sander Daniels has a great story. He is a co-founder of Thumbtack, which connects users with local professionals. Sander and his co-founders developed the origins of Thumbtack while he was at Yale Law School. He spent around two years practicing before leaving to work on Thumbtack full time.

Sander and his co-founders hit a home run with Thumbtack. At the same time, his experience shows how lawyers can leverage their intangible skills to help startups grow. Sander relied on his judgment, hard work, and operational expertise to help the Thumbtack become a so-called unicorn. I think that’s really inspiring to lawyers who may want to start a startup or work for a startup in a nonlegal role. You have plenty of skills that you can leverage.

RC: Can you highlight a few of the “Twenty-Five Key Takeaways” you outlined in Chapter 17 of the book?

AP: I think one of the more important takeaways is to avoid premature optimization. A term that originated in software development, premature optimization means that you are improving (even perfecting) something too early. For our careers, it can mean taking a job or internship without testing the assumptions of why we want to pursue that opportunity in the first place. Especially if you are leaving legal practice to do something substantially different, it’s helpful to stress test your assumptions before making a move.

Another is that there may be hidden risk in not making a career move. It’s much easier to identify the risks associated with major change. That said, the greater career risks may come from maintaining the status quo.

RC: What other overarching themes did you notice amongst the 15 featured law school grads who pursued nontraditional careers?

AP: They weren’t hesitant to use their legal training and experiences in different domains. While they weren’t writing briefs or arguing in court, they were using soft skills that they developed as lawyers. Those include problem-solving skills, time management skills, research skills, oral advocacy skills, and attention to detail. They even used their knowledge of the legal industry and applied it in creative ways. For instance, Melinda Snodgrass, a well-known science fiction author and screenwriter, used the legal industry as the background for her “White Fang Law“ fantasy series.

Then, there is sheer hustle. Instead of waiting for opportunity to knock, they built doors. If you’re going to have a nontraditional career like these 15 individuals, you need to be aggressive and take calculated risks.

RC: You mentioned that you believe “there is power in hearing these individuals’ stories… . They can provide light in a tunnel full of anxiety, fear, or doubt” — can you expound on this concept?

AP: Leaving legal practice can be intimidating. Unlike other professions, there is a significant lead time before we actually begin our professional work. Once we do start practicing, there are plenty of obstacles that can make it difficult to leave. Clearly, you’ll want to be on sound financial footing before making a substantial career move. That said, the psychological roadblocks — like the sunk cost fallacy, golden handcuffs syndrome, and general loss aversion — can be even more challenging.

These individuals’ stories show that there are massive opportunities outside the law. Granted, if you leave legal practice, there’s no guarantee that you’ll reach your goals. At the same time, I wanted these stories to show that we can overcome many of the psychological objections in our minds.

RC:  What advice do you have for other attorneys who believe they have a book inside them they want to share with the world?

AP: Creating anything requires some initial action and discipline. You just have to get started, whether that means writing before work or late at night. From there, as Tim Ferriss says, it’s about being consistent and writing two crappy pages per day. While it may not feel like it in the moment, you are building momentum and are increasing the chances that you’ll actually finish the book.

Also, don’t ignore marketing. Many authors focus on the manuscript itself and don’t consider how their book will get discovered. It’s much easier if you already have an audience, which can come from things like a large social media presence, an ongoing email list, or a blog. Often, it’s better to build the audience before writing the book itself.

RC: If you could post a message on billboards outside of every law school, what would it be?

AP: Build strong relationships with your classmates and professors.

In law school, it’s easy to exclusively focus on academics. Obviously, strong grades — especially 1L grades — are key in getting your first practicing job out of law school. But zooming out and looking at one’s overall career arc, it is personal relationships that unlock some of the more exciting opportunities. There are plenty of examples of this in the book.

Law school is an excellent place to build strong relationships. You are surrounded by extremely bright and driven classmates. You’re also going through an intense experience together, which helps you build closer bonds. Ultimately, building great relationships with your colleagues and professors — and maintaining those relationships after graduation — lets you leverage serendipity throughout your career.

On behalf of everyone here at Above the Law, I would like to thank Adam Pascarella for sharing his story with our audience. We wish him continued success in his career. Adam can be reached via Twitter (https://twitter.com/apascar), LinkedIn (https://www.linkedin.com/in/adampascarella/), and his work website (www.secondordercapital.com).

Renwei Chung is the DEI Columnist at Above the Law. You can contact him by email at [email protected], follow him on Twitter (@fnfour), or connect with him on LinkedIn.

Topics

Adam Pascarella, Books, Career Alternatives, Reversed In Part