Lessons from an Underdog: A Q&A with Author Jesse Wang ’14

J2021-01-14 Jesse Wang Professional Photos Underdog 1esse Wang ’14 transferred to Shipley from public school when he was in the tenth grade. Though he wasn’t always the best student in high school, he learned a lot about perseverance, grit, and how to be a good writer—skills that would prove useful after his less-than-stellar performance as a first-year law student. With encouragement from a mentor, Jesse drew on his law-school experience for inspiration to write Underdog: 12 Inspirational Stories for the Despondent Law Student. “The book,” he says, “tells the stories of twelve people, including law students, professors, and attorneys, who have faced incredible adversity throughout their lives, but were able to persevere using their grit and creative thinking.” The book debuted as a best-seller in its category on Amazon in December, 2020.

“Through the help of these twelve incredible, self-starting, passionate, and, above all else, persevering individuals I interviewed throughout writing this book,” explains Jesse in his Author’s Note, “I was able to discover an area of law that I am deeply passionate about: legal technology. I learned how to innovate and think creatively to find novel solutions to overcome my obstacles. I learned about appreciating the little things in life and the small wins that help with building momentum and confidence. Most importantly, I learned the importance of building a network of like-minded friends and classmates who could support me and who I could lean on in times of need. This book is about telling their stories and the invaluable wisdom they all had to offer.”

1) Why did you publish this book?
All law students, no matter which law school they attend, have a stressful first year experience. 1L year is the first of many crucibles that we all must struggle through on the path of becoming a successful lawyer. That being said, it’s still the first of many trials and, as such, its value and weight are often overemphasized by classmates, faculty, and members of the legal community at large, placing an inordinate amount of pressure on first year students to perform exceptionally well. This pressure creates a culture in which those who come out at the top believe that they are set—that they are on the path to a successful and meaningful legal career—and those at the bottom are left feeling despondent—that there is no way forward and they should give up on their dreams of becoming a lawyer. I, along with many of my classmates, came out of my first year of law school with grades that were far below my expectations, but I knew it was not the end of the road for me. I believed this because of a Chinese proverb my mother used to repeat to me as a child every time I didn’t perform well on a test: “the clumsy bird flies early.” What this proverb means is that no matter how many times you stumble or fall, every proverbial bird, law student, or young attorney is capable of finding success, so long as they put in the effort and practice.

This book serves as a reminder to law students everywhere, particularly those who came out of their first year feeling disappointed or doubting their own capabilities, that there is always another way out, another strategy to play, and another opportunity for redemption if they keep fighting to improve. This mindset of prioritizing improvement and incremental wins above all else is an overarching theme woven throughout the book and repeated by the 12 incredible individuals I interviewed during my time at USC. They each taught me that success is about appreciating small wins and using them to build momentum to achieve bigger wins in the future. Success is about resilience—persevering day in and day out and chasing down a singular goal with every ounce of your being. Most importantly, success is about building a network of like-minded individuals who you can trust and lean on in moments of adversity.

2) How did going to Shipley affect your trajectory in life and motive for writing the book?

Attending Shipley during high school was both a humbling and edifying experience. Many of my teachers and counselors shaped my outlook on life. The small, close-knit community at Shipley afforded me the care and attention that I would have lacked at a larger school. Also, without the help of my college counselor, Ms. Kobosky, I certainly wouldn’t have survived the three years I spent at Shipley, and I credit her and the rest of the college counseling team for helping me get into Emory.

Prior to transferring to Shipley, I had attended public school my entire life and didn’t have a clear idea of what I wanted to do or study. I struggled a great deal my first year, particularly in Modern European History and 10th grade Honors English, as I couldn’t understand much of the really dense readings and in-class writing assignments, or keep up with the accelerated pace of the classes. It wasn’t until my junior year, when I took Mrs. Weigel’s honors history class that I established my footing as a competent writer.

I received a C+ on my first essay in that class on the book, The Killer Angels, and Mrs. Weigel gave me an opportunity to rewrite it. Through her guidance, I eventually scored much higher the second time around. To this day, I remember that specific essay because it was the first time in my life that I felt vindicated in terms of my intelligence—it restored my confidence and gave me the strength to keep going. Since that class, I’ve earned A’s in the rest of my English and writing courses at Emory, been hired as an undergraduate writing consultant for the Emory Writing Center, written a 116-page honors thesis which earned a high honors (magna cum laude) designation, and become a published author.

While it was incredibly discouraging in the moment, the volatility of my grades at Shipley helped make me gritty. I was never the smartest student in the classroom and that remains true to this day. However, getting that second shot in Mrs. Weigel’s class demonstrated to me that success in the classroom and in life is never linear—there will always be ups and downs, and just because things don’t always pan out exactly as planned does not mean that those experiences have been a waste.

This mentality has stayed with me throughout law school and now the MBA program at USC. I’m committed to keep going, because I have always been, without a doubt, the underdog. But, it’s exactly that label and mentality that have allowed me to come this far.

3) Can you describe the process for writing the book?

Back in October of 2019, I received a message on LinkedIn from a former attorney and current professor at the Georgetown University McDonough School of Business, Eric Koester, who told me my profile intrigued him and asked if I was interested in writing a book. At first, I was hesitant, given how busy my schedule was, but I decided to give it a go, because I realized I had a lot to say about the incredible experience I had had so far at Gould. It was perfect timing, too, because I had spent my entire 1L summer reading some very powerful self-help books, such as Nassim Taleb’s Antifragile: Things That Gain From Disorder and Angela Duckworth’s Grit: The Power of Passion and Perseverence, as well as listening to podcasts like NPR’s Life Kit, This American Life, and Hidden Brain. I had been thinking about finding an outlet to express my thoughts on the topics discussed and how they could apply to my life. So, I took on the challenge of writing the book from scratch, which was an incredibly daunting task in the beginning. Although, as I progressed through the writing process, it felt less like a job and more like a hobby—almost like journaling.

The Creator Institute, which is the book writing program that Professor Koester had founded, was an incredible vehicle in making this project come to life, because it held me accountable. I had to meet with my editor every week to discuss my progress, keep up with a strict revision schedule, meet with cover designers to figure out how the book would look aesthetically, raise $5000 from pre-orders to fund the publication process by reaching out to my network, and so on and so forth. In the end, while it was an exhausting time, it was one of the most rewarding experiences in my life and I could not have done it without the support of my fellow Trojans—the USC alumni, professors, and classmates that made up the majority of the 165 donors who helped fund the book’s publication and gave this book the legs to move forward.

4) What do you hope to accomplish with this book?

The most important accomplishment of this book for me was celebrating the diversity, strength, and legal brilliance of the USC student body and faculty. This project would not have been possible without their profound insight and support. Thanks to everyone who believed in me and supported my campaign, Underdog debuted as the #1 Best Seller and #1 New Release in its category on Amazon eBooks. This accomplishment is a victory for everyone at Gould, and it demonstrates how much those in the legal community want to have an open and honest conversation about addressing the stresses of law school.

In addition to this accomplishment, there are three main goals I hope the book will achieve: (1) Provide support to the USC Barbara F. Bice Public Interest Law Foundation and the Small Business Clinic by donating all profits from book sales to both organizations, (2) encourage law students to be more creative and to look within themselves to figure out their “ultimate concern” (i.e. their purpose for becoming a lawyer), and (3) motivate law schools, law students, and practicing attorneys to speak honestly about the importance of mental health and establishing healthy work-life boundaries in the legal field.

Prior to the book release, I spoke with the former and current presidents of the Public Interest Law Foundation, Mirelle Raza and Johnathan “Chief” Coleman, as well as the director of the Small Business Clinic, Professor Michael Chasalow, to coordinate how I could donate the profits to their respective organizations. At the time, the pandemic had reached its peak and I wanted to do all that I could to provide my full support in helping vulnerable communities and the small businesses in the Los Angeles area that are struggling the most from the fallout. PILF is an organization that provides funding for law students fighting to promote social justice, equal access to the law, and empowering marginalized and underrepresented communities by providing pro bono clinic opportunities at local organizations such as the Legal Aid Foundation of Los Angeles (LAFLA), Neighborhood Legal Services of Los Angeles (NLSLA), and Community Legal Aid SoCal. I’m incredibly humbled by the work that they have done, and I know that the funds from book sales will be well spent toward an important cause.

Secondly, I hope this book encourages law students to think more creatively in figuring out their true purpose for becoming lawyers. In the book, I speak about my experience taking two life-changing courses at Gould: Professor Dorna Moini’s Legal Innovations Lab and Professor Beverly Rich’s Legal Technology course. Professor Moini is a Sidley Austin LLP associate turned founder and CEO of the legal technology startup, Documate, and Professor Rich is a former litigator turned Ph.D. candidate in Strategy at USC Marshall School of Business. Both professors taught me a great deal about how versatile the J.D. degree can be and inspired me to think innovatively about how I could find success outside of the traditional path that I had become so attached to.

Of course, I intend to complete my JD-MBA program, take the bar, and practice law for a period of time, but their courses and guest speakers demonstrated to me how quickly the legal field is changing and how many practicing lawyers leverage their legal skills to find success in a multitude of industries, including entrepreneurship, compliance work, and consulting. As a result, I was inspired to participate in the 2020 Global Legal Hackathon, a competition in which participants ideate, develop and pitch original ideas using technology to solve a particular legal need. I developed a mental health application for law firms, “MentalBrief,” alongside a senior data scientist from Capgemini, Kevin Coyle, and third-year law student at Gould, Michael B., which ultimately earned third place. I hope that my experience participating in the competition inspires law students to think hard about what it is they seek to accomplish once they graduate and how thinking outside the box can be enormously valuable in the legal field.

Finally, I know this book will motivate law students and those in the legal community in general to speak honestly about the importance of mental health. There are so many unfortunate stories and statistics that were highlighted during law school orientation about how lawyers are the most depressed professionals. According to the American Bar Association and a Hazelden Betty Ford Foundation study, lawyers are 3.6 times as likely to be depressed as people in other jobs and 28 percent of licensed, employed lawyers suffer with depression. Much of this comes down to the fact that those who pursue careers in law are more likely to have type-A personality traits, be driven perfectionists, and experience major anxiety from being responsible for handling their clients’ fate.

While many believe that these struggles will disappear once we graduate, the stories of those I interviewed demonstrate that they may very well get worse without establishing proper coping mechanisms and a strong emotional support system. While the book’s position as a #1 best-seller and #1 new release is cause for celebration in the short-term, this is only the first step in influencing law schools on a broader scale to take preemptive measures in bettering students’ mental health prior to facing the exacting standards required by the profession in the real world.

Purchase Underdog: 12 Inspirational Stories for the Despondent Law Student from Amazon.

Learn more about Jesse Wang ’14 and his book, Underdog: 12 Inspirational Stories for the Despondent Law Student.

Listen to Jesse Wang '14' on Take a Seat: Shipley's podcast about flourishing.

About the Author


The Shipley School is an independent, coeducational day school in Bryn Mawr for pre-kindergarten through 12th grade students. Through our commitment to educational excellence, we develop within each student a love of learning and a desire for compassionate participation in the world. Through a strong college-preparatory curriculum in the humanities and sciences, our school encourages curiosity, creativity, and respect for intellectual effort. Shipley upholds and promotes moral integrity, a sense of personal achievement and worth, and concern for others at school and in the larger community.