On Writing

For those who read, those who write, and lawyers who do both.

How Great Writing Starts With Great Sentences

I have always admired good writing. My wonderful high school English teachers introduced me to some of the writings of classic American authors like Hawthorne, Melville, Twain, Hemingway, Faulkner, and Salinger, and to European writers like Dickens, Orwell, Sartre, Camus, Hesse, and Ionesco. Outside of my course work, I discovered more contemporary and avant-garde stalwarts like Joseph Heller and Hunter S. Thompson and poets Allen Ginsberg and E. E. Cummings. Even in junior high I was constantly reading, often works of science fiction by people like Ray Bradbury and Isaac Asimov. In those days, long before PCs, the Internet, and iPhones, books accompanied me everywhere.

Thanks in part to the encouragement of my high school teachers, I chose English as my college major. I took courses in modern poetry (with a female professor who introduced the class to women poets), Romantic literature (meaning literature from the Romantic era, which is different from our common usage of the term “romantic”), Shakespeare (naturally), and a drama course featuring plays by Checkhov, Ibsen, and Strindberg. Somewhere along the way I also and importantly encountered Walt Whitman’s “Leaves of Grass.” For my junior Independent Study (the precursor to the mandatory senior year Independent Study or simply “I.S.”, for which the College of Wooster has consistently been ranked second only to Princeton University in the category of senior capstone project), I focused on several poems by T.S. Eliot. My senior I.S. was an approximately 100-page research paper covering some of the post-WWI novels of Hemingway, Fitzgerald, and Dos Passos.

Not all my college English courses were based in literature. I also studied and tried my hand at creative writing, both short stories and poetry. I wasn’t very good at either. After studying Eliot so closely, I couldn’t write a poem without subconsciously (and poorly) channeling him. And the one short story I remember writing received a so-so review from the professor, who seemed to like only the last line.

The story was about a college student (a fictionalized version of myself) who tried but failed to escape what the title referred to as “the mechanisms of death,” a metaphor for how then-ubiquitous technology overwhelmed the human spirit, a somewhat trite and possibly overworked theme to begin with. (I might have been influenced by such earlier works as “Easy Rider,” where Peter Fonda’s character throws his watch away at the beginning of the film only to reach a tragic ending in the movie’s fateful climax.)

The final scene of my story finds the young man on a bus trying to get away from college, only to realize that there is no escape -- the ”mechanisms” will follow him wherever he goes. As the bus is about to leave and he hears the engine crank up, it also starts to rain. He leans his head against the window in despair. The final sentence reads “The raindrops fell on both sides of the glass.” That sentence was my first and last success at writing fiction, and a modest one at that. (And yes, it does sound a little more like the ending of “Midnight Cowboy” than “Easy Rider,” doesn’t it?)

Contrast that feeble effort at writing a decent sentence with the first sentence of the book I’m reading now. It’s called “Crossroads,” and is written by Jonathan Franzen, a novelist I’d heard of but had never read before. I’m still not sure what I think of the characters or the story (I’m about one-third in), but the craftsmanship is superb. Here is how the book begins:

The sky broken by the bare oaks and elms of New Prospect was full of moist promise, a pair of frontal systems grayly colluding to deliver a white Christmas, when Russ Hildebrandt made his morning rounds among the homes of bedridden and senile parishioners in his Plymouth Fury wagon.

The imagery of a broken sky, the bare trees, the gray collusion of the frontal systems, the bedridden and senile parishioners, the Plymouth Fury wagon, all pack a lot of information and feeling into that very first sentence and set the tone for what is to come. Who wouldn’t want to keep reading?

As Franzen clearly knows, first sentences are supposed to be special, the opposite really of the “Peanuts” character Snoopy’s oft-repeated “It was a dark and stormy night.” But such eye-poppers permeate Franzen’s book. Here’s another example, in which he describes a Christmas night that finds one of the characters outdoors and alone:

The weather in Santa Monica was fine, the far snow-capped peaks floating bodyless above the winter haze. Everything seemed more or less in balance. A breeze from the east kept the marine layer offshore, and the sun’s downward progress was made tolerable, less alarmingly a reminder of life escaping from her, by the timeless repetition of the waves, their breathlike breaking on the wide, flat beach.

Magic.

I could show more examples from Franzen’s book, but I’ll stop there. Suffice it to say that great writing begins with great sentences, and great sentences are built on an artist’s ability to see and show the world in a way the reader has never seen it before.

I could never write like Franzen. I don’t have nearly the skill, the patience, or the imagination that such writing requires. If I ever did have potential as that kind of writer, I lost it when I became a lawyer.

How Legal Writing Ruined (And Saved) Me

Don’t get me wrong. Law school greatly improved my writing in important ways. I was fortunate to serve on the editorial board of the law review, one of the journals the school published. That position required that I spend hours every day not only working on my own article (a large special project I shared with some of my classmates), but also, and even more so, editing the writing of others – both law professors and law students. Of necessity, I immersed myself in White and Strunk’s famous little book, “The Elements of Style” (I lived by its mantra, “[o]mit needless words”), as well as other popular books about American usage. That experience transformed me from being a good but undisciplined college writer into becoming a much better and more disciplined legal writer.

My writing continued to improve in my first law firm, thanks to the influence of more senior attorneys who also prided themselves on that skill set. My greatest influence was the head of the firm’s litigation practice, a consummate writer and Shakespeare aficionado. I had the good fortune of working closely with him on a major and somewhat famous lawsuit that wound its way through the courts for more than six years. Our writing went both ways – sometimes I wrote drafts that he edited (often with harsh but instructive criticism), while he wrote drafts that I reviewed and for which I gave him input. Over time, I learned from him the importance of rewriting and rewriting until you have a polished and persuasive final product, and he gained some degree of confidence in the quality of the feedback I provided on his drafts.

But legal writing is very different from writing fiction because it has a different purpose. A brief submitted to a court is designed to persuade the judge to rule the writer’s way on the issue at hand. It typically begins with an introduction that summarizes the ensuing argument, a statement of the facts relevant to the issue, a description of the procedural history that brought the issue to the court, an argument that presents the legal analysis and support for deciding the issue the writer’s way, and finally a short conclusion that usually does no more than repeat the request for the court to rule in the writer’s favor. (Much later in my career, I learned a technique of good legal brief writing attributed to “the Chicago School” from a colleague who had attended the University of Chicago Law School, and I adopted it in all my subsequent briefs.)

After years of writing like a lawyer, I’m convinced that any hope I might have had of writing good fiction is a pipe dream, even if I had the inclination (I don’t). Still, effective legal writing, and effective writing for any other business or professional pursuit, does not have to be boring. It can and, when appropriate, should incorporate techniques of good creative writing to make an argument come alive.

I endeavored to do so a couple of years ago in an article I had written for an American Bar Association conference, which was later published in the Loyola Consumer Law Review. The piece, “The Arc of Class Actions: A View from the Trenches,” describes how, over the past 25 years, the Supreme Court has significantly constricted the class action device without entirely eliminating its ability to strike terror into the hearts of corporate defendants. (Yes, I know, corporations don’t have hearts, but many of the people who run them do, and “terror” may be hyperbole, but not by much.)

I showed a draft to a friend who also practices class action law and is on the law review’s editorial board. He thought the draft was a little dry, and I’m sure he was right. The draft began:

There has been much scholarly debate about the direction of class action practice.

The next few sentences did a respectable job of summarizing the theme of the article, but were as dull as that first sentence.

I then rewrote the introductory paragraphs, and came up with a very different first sentence. It read:

Think of the class action as a wounded beast – limited in its range of motion, yet dangerous to those within its reach.

That single metaphor captured the overriding theme of the article in a way that, I hoped, would more effectively grab the reader’s attention and illustrate my thesis. The rest of the revised paragraph described the legal debate using similarly concrete imagery meant to conjure interested parties’ active and spirited engagement in defining the contours of the judicially whittled-down rule:

Plaintiffs’ and defendants’ class action lawyers frequently debate the continued vitality of class action practice, the former decrying their setbacks, the latter reveling in their victories, and both sides determined to fight on. Academics sift through the rubble of class action jurisprudence, attempting to discern patterns and to predict what lies ahead. Judges struggle to apply conflicting precedents and fill in gaps, at times reluctantly surrendering to rigid pronouncements from on high.

Note the active verbs: debate, decry, revel, fight, sift, discern, predict, struggle, surrender. My goal was to present not a boringly-passive academic analysis, but an energetic response by actual human beings to a series of Supreme Court decisions that shattered the reality they had inhabited.

Other than it being accepted for publication, I don’t know how readers reacted to my article. I also would have written it differently had it been a brief to a court. But I thought the effort to enliven it with metaphor and action was worth it. After all, if someone, whether by choice or necessity, is going to read your writing, you might as well try to make the experience rewarding for them.

How to Become a Good Writer

So how does one become a good writer? There are several ways:

• Read books and articles about writing.

• Read books and articles by good writers.

• Show your writing to writers you respect and ask them for constructive criticism.

• Enroll in online or in-person classes about writing.

• Write material that you would be interested in reading.

• Write what you’re passionate about.

• Most of all, rewrite, rewrite, rewrite.

But don’t, please don’t, use this newsletter as a benchmark. I do my best and I hope you enjoy my posts, but with a weekly publication schedule and many other activities on my plate, I am unable to do the careful editing and rewriting that I expect of myself when I undertake a more ambitious project.

I suppose that’s the final, though related, lesson. What counts as good writing depends on the genre and the context. So write for your target audience, write as well as your time and the situation allow, and write for the purpose of bringing joy, enlightenment, or both to your readers.

One final tip about quality writing being genre-specific. A few years ago (pre-pandemic) I tried my hand at writing poetry. After decades of writing legal briefs and editing the drafts of younger colleagues, I couldn’t shake the habit of trying to shorten every piece. Each poem would go through many iterations, in which my main revisions were to cut and tighten the language, much as I would do with a draft brief. But this was poetry, not brief writing. “Omit needless words” did not apply.

For now, I’ll stick to prose.