Words: Free Flowing vs. Painstakingly Precise

My Speech at the Annual Ideas @ Pomona Summit (San Francisco, Nov. 2019)

Happy weekend, readers! Today, I’ll be sharing a speech I gave at the 2019 Ideas @ Pomona Summit on law and creativity. Enjoy!

Have you ever felt an urge, an itch that you really, really wish to scratch?

For me, this urge has always been writing. It traces back to my childhood, really, when I would sit in the backseat of a rental car as my parents took me to explore over 20 countries. Condensed in nature, those trips, while absolutely brilliant, were exhausting — my workaholic father Frank would start driving us early in the morning; I would ask, approximately, 10,000 questions on the car about anything and everything, and sing tons of songs from Phantom of the Opera and Sound of Music until my mother Amy cajoled me into taking a break (“for the sake of your voice,” Amy claimed, although I always secretly suspected that the truth was that she got tired of my attempts at the impossibly high notes in Think of Me [sing]; well, well, well, you get the picture); we would visit different places both as planned and as improvised; and we would arrive at our lodging late at night.

Despite how alluring the thought of sweet slumber truly was after such a long, activity-packed day, each night, I wanted to reflect on what I observed and learnt through writing. Through the same kind of passionate, free-flowing prose that initially liberated my imagination and thoughts as an introverted child growing up, when I filled blank sheets of paper with my creative writing, with increasing confidence in my emerging voice as a powerful, omniscient narrator, who, by definition, knew it all.

My childhood ambition had, for some time, been publishing a book titled Around the Globe: Travel Writings of an Elementary School Student. I confess: I failed.

The 13-year-old aspiring writer should not be wholly disappointed, thankfully. Now, at 23, a second-year law student at Harvard, I keep dreaming. Ever since having the pleasure of escorting Supreme Court Justice Sonia Sotomayor around a magical place that will always be dearest to my heart — Pomona College — I dream of a fulfilling career in the law. Law — full of tensions — attracted me in an indescribable fashion. Law is broad, for it is the most all-encompassing way in which all aspects of society organize themselves; law is also intensely narrow in demanding precise thinking and minute details in each case. Law embodies grandiose principles of justice, but even landmark decisions may involve great injustice. Meanwhile, I also dream, a hopeless romantic if you will, about realising an extended version of my childhood dream: to publish my first book — a legal thriller-romance novel.

Looking back, the biggest hurdle for my younger self was a curious breed of immaturity and self-censorship. Whenever a more mature me read my earlier writings, I saw gaps that I wanted desperately to fill. And it never stopped. With sadness, I tossed my earlier creative writing projects aside. 

At Pomona, I focused primarily on academic writing in political science and Spanish, and freelance writing on the side. I also grew increasingly interested in the law, especially loving every aspect of my editing work for the Claremont Journal of Law and Public Policy throughout college. My first experience with legal research was actually for a paper I wrote in Spanish — a self-imposed challenge that, on reflection, I spent an obscene amount of time on, but sadistically enjoyed — particularly when I slipped into a judge’s robe and held a gavel, fashioning myself into a Supreme Court Justice in the landmark San Francisco bilingualism case Lau v. Nichols for my presentation. The precision of academic and legal writing demanded what I nickname “obsessive-compulsive self-editing.” Gradually, the itch I have always wanted to scratch, writing, evolved into a more specific form — an apparently endless cycle of writing and rewriting, rooted in a near-paralyzing perfectionism.

But hang on. Doesn’t “obsessive-compulsive self-editing” contradict the spirit of my passionate, free-flowing prose that is creative writing? Yes. It is precisely this growing perfectionism that effectively prevented me from [start counting with my hand] publishing my travel book and my first novel featuring witches, friendship, betrayal, and more species of plants than you would care to know that I nerdily researched in elementary school, as well as my second novel, titled Refraction, that I wrote in middle school, this time featuring an epic journey, a mysteriously charismatic yet cold-hearted mother, a bloodthirsty man from Middle Ages-Europe, and volcanoes. 

While insatiable perfectionism can inspire introspection and progress, it is essentially a kind of insecurity that defined my immaturity as a young creative writer. As I learnt from my professors at Pomona, you just have to let go of your academic writing at some point. Oftentimes, all that requires is an external due date imposed somewhat arbitrarily by a journal or a course syllabus, or you can literally self-edit indefinitely. I think the same lesson should apply, if not even more, to creative writing.

Thanks to my Pomona-grown liberal arts spirit, I did keep up with the creative side of me through theatre and English classes. As my late mentor Professor Art Horowitz, whom I miss so very much every day, frequently encouraged me in office hours, the creative writing process requires no filtering of ideas. In Phantom of the Opera terms, let your thoughts take you where you long to be, and let that part of our soul take flight!

If the biggest hurdle for my 13-year-old self was a mix of immaturity and self-censorship, what, then, is my new excuse as a — hmm, hopefully mature? — 23-year-old, for working on my novel at a very slow pace? 

The answer may be summed up in three alphabets: L A W. Or so I thought is the legitimate excuse. Around this time last week, I met renowned legal thriller writer John Grisham in person. The next evening, I met celebrated non-fiction writer Bill Bryson. As many fans here know, Grisham is a lawyer by training, while Bryson is most noted for his travel writings. Both writers kindly answered my burning question: how can I reconcile, on the one hand, my free-flowing, passionate prose, and on the other, the painstakingly precise legal writing that I grew to embrace as well? Bryson quickly replied, “you can’t.” Voilà, perhaps I have an excuse to write slowly, after all. Grisham, while somewhat dodging the question itself, said that I need to write at least a page a day. No excuses. Law school is no excuse, Mr. Grisham warned me, rather sternly and emphatically. Oops, ok-ie. That sounds…challenging.

As Harvard Law Professor Noah Feldman shared with my section over lunch, law school is a process of deconstruction, of seeing everything through an X-ray. Instead of reading cases as normal humans do, we focus on abstract elements of the law; as Professor Feldman analogized, nothing looks that pretty under an X-ray. I will add, seeing things through an X-ray also sounds radically different from the colourful creative writing I have so cherished. 

In law school, I often feel my heart pounding. Sometimes, it is a criminal law case that triggered consecutive nightmares, haunting me with ethical questions. Sometimes, it is an appellate brief whose fact pattern is very unfavorable to my assigned position and issue, given the relevant caselaw in the jurisdiction. Like solving a jigsaw puzzle, working on the brief invited me to confront the messiness within the case that the control-freak in me found initially disconcerting. Distilling elements from specific facts and precedents and framing them in a way that would strengthen my arguments as much as possible for each section, subsection, and sub-subsection one-by-one felt incredibly rewarding. Head over heels, I felt genuinely in love with the law during these times. Other times, I would fall out of love with the law, frustrated by a real fear that the law would once again stifle my creative tendencies, perhaps once and for all. This cycle continues.

Along the way, I continue to seek an appropriate answer to the question I posed to Grisham and Bryson. Admittedly, my weekend escape from my casebooks in Cambridge, MA to my beloved Golden State is partly self-interested: while I cannot claim to have found a way to resolve my struggles in balancing the 2 types of writing I adore so much — the itch I constantly wish to scratch — I am eager to hear my fellow Sagehens’ thoughts. 

I will share my initial findings, nonetheless: if my days strolling across sunlit Marston Quad and greeting each well-fed squirrel with a smile taught me anything, it is that liberal artsy individuals can have multiple dimensions.

For now, I do try to work on both my dreams of becoming a lawyer and writer, and let them positively reinforce each other instead of furthering the vicious cycle of a perfectionist complex. On the one hand, the intensely logical, rational side of my legal brain helps with my plotting and scheming in my novel-writing endeavors. On the other hand, the fiercely imaginative side of me motivates me to think outside the box in my legal adventures. This time round, I promise not to let my 13-year-old self down. You will be pleased to hear that the liberal arts spirit in me lives on — for one, I took on a new challenge of starting French from scratch this semester.

Alors, merci beaucoup for joining me, and I wish you bon voyage with your own intellectual journeys — ideas at Pomona and beyond its gates.

P.S. Special thanks to Harvard’s Radcliffe Institute for sharing a condensed version of this article! https://www.radcliffe.harvard.edu/news-and-ideas/reflections-on-law-and-creativity