Oregon State Bar Bulletin — JANUARY 2011
The Legal Writer
Painful Prose:
The Difficulty of Writing
By Suzanne E. Rowe

Easy reading is damn hard writing.
—Nathaniel Hawthorne

The process of writing can be painfully hard, as all professional writers know. Too often, we lawyers forget that we are professional writers: we write contracts, wills, leases, court pleadings, jury instructions, appellate briefs, memoranda, letters, settlement agreements, articles and endless other documents.

If we forget that we are at heart professional writers, we might gloss over the difficulty of writing. We might assume that documents should fly off our printers with ease. They don’t. Or if they do, maybe they shouldn’t.

I offer this article as encouragement for each writer who has experienced the pain of producing good writing. Remember the support offered here the next time you’re hunched over a yellow legal pad filled with scribbles, staring at a jumble of words on a computer screen, scratching out words on your eighth draft, or pondering a markup so detailed that no white space is left on the page. Whenever you wonder why this particular document is so difficult to put together, remember that writing is hard. If you’re in pain, you’re in good company.

Painful Writing

Writing is hard, even for authors who do it all the time.
—Roger Angell

In the foreword to The Elements of Style, Roger Angell describes the familiar pattern of his stepfather, E. B. White, who would spend a whole day to produce a few hundred words of commentary for The New Yorker. Invariably, when the famous E. B. White sent off his copy, he was not satisfied. “It isn’t good enough.... I wish it were better.”

Of course, Mr. White’s writing was good enough. And ours often is, too. If you’re suffering over a document, it likely means that you care deeply about your client’s cause and your professional reputation. Embrace the pain as a rite of passage, from unformed thought to clear expression.

Keep the pain in perspective, though. We perfectionists sometimes put too much pressure on our writing, assuming that only our absolute best will suffice in every situation. Against the desire for perfection, we need to balance the client’s purse, the deadlines inherent in each project and the personal life we’d all like to enjoy.

Painful Rewriting

Write your first draft with your heart. Re-write with your head.
From the movie “Finding Forrester

One of the most painful aspects of writing is rewriting. For this step to be productive, we need to see the words from the new reader’s perspective. That requires a different kind of mental work; we have to forget what we know and look at the words with the uninformed eyes of a reader. When the words aren’t clear or when the links between ideas are missing, we need to rethink and rewrite.

Painful Un-writing

I try to leave out the parts that people skip.
—Elmore Leonard

Sometimes we need to delete parts of our writing, and that can be hard when we’ve invested so much time and energy into a particular argument, paragraph or sentence. If you have grown too attached to your dear creations to delete them in cold blood, try moving them to a separate document. When the final document is complete, dumping the leftovers won’t be so hard.

Painful Proofing

I was working on the proof of one of my poems all the morning, and took out a comma. In the afternoon I put it back in again.
—Oscar Wilde

When I was clerking for a trial judge, a clerk for an appellate judge down the hall announced at lunch that he’d spent the morning poring over a paragraph. He thought he had just about gotten it right.

Few lawyers have that kind of time to devote to writing; we certainly didn’t at the trial court. But this careful, painstaking proofing is critical to excellent writing.

Sleep on your writing; take a walk over it; scrutinize it of a morning; review it of an afternoon; digest it after a meal…
—A. Bronson Alcott

Be sure to leave time to proof a document several times, preferably at several different times. A fresh look in the morning is likely to identify more mistakes than an extra hour at the end of a long day.

Start proofing once in the middle of the document to ensure that it gets your full attention. Use colored sheets of paper to keep your tired eyes focused on a single line of text. Dig deep for that last bit of energy that proofing requires. Proofing probably won’t be pain-free, but it will produce a stronger document. (For more suggestions, see “Perfect Proofing,” December 2006.)

Painful Criticism

Asking a writer what he thinks about criticism is like asking a lamppost what it feels about dogs.
—John Osborne

It’s painful to receive feedback on our work, especially when the most useful feedback is often criticism. We all want our work to be praised, our effort affirmed. That’s like a diet of chocolate; it feels great in the moment, but it’s not going to carry you very far.

I learned this truth when I sent a manuscript to trusted colleagues and asked for feedback. The easiest comments to hear simply said, “It’s great!” The most helpful comments came from people who were willing to invest serious time to identify my mistakes and explain them to me.

Anne Lamott, the author of many wonderful nonlegal books, writes about the difficulty of getting criticism on her drafts from friends:

“My first response if they have a lot of suggestions is never profound relief that I have someone in my life who will be honest with me and help me do the very best work of which I am capable. No, my first thought is, ‘Well, I’m sorry, but I can’t be friends with you anymore, because you have too many problems. And you have a bad personality. And a bad character.’

“Sometimes I can’t get the words to come out of my mouth because I am so disappointed.... Criticism is very hard to take. But then whichever friend is savaging my work will suggest that we go through it together page by page, line by line, …and if I’ll hang in there, they’ll have found a number of places where things could be so much stronger, or funnier, or more real, or more interesting or less tedious. They may even have ideas on how to fix those places, and so, by the end, I am breathing a great sigh of relief and even gratitude.”

Criticism is especially hard to take when it comes from your supervisor, the very person you need to please to succeed in your job. But a supervisor who is willing to invest the time in you — pointing out mistakes and demonstrating improvements — is worth the pain of the experience. (See Rebekah Hanley’s article “Constructive Criticism” from December 2009.)


What is written without effort is in general read without pleasure.
—Samuel Johnson

If the process of writing isn’t painful to the writer, the document that results might be painful to the reader. If that reader is your client, a supervisor or the judge ruling on your case, consider whom you’d rather suffer. But as you suffer, remember that you’re in good company.

Suzanne E. Rowe is an Associate Professor and Dean’s Distinguished Faculty Fellow at the University of Oregon School of Law, where she directs the Legal Research and Writing Program. She is grateful for the assistance of Jason Poss in locating most of the quotes used in this article.


Anne Lamott, Bird by Bird: Some Instructions on Writing and Life 166-67 (1995).

William Strunk, Jr. & E. B. White, The Elements of Style ix (4th ed. 2000).

For some of the quotes in this article, and for additional inspiration about writing, please visit the following web sites:

The Quotations Page, www.quotationspage. com/subjects/writing/31.html

Suzanne E. Rowe is an Associate Professor and Dean’s Distinguished Faculty Fellow at the University of Oregon School of Law, where she directs the Legal Research and Writing Program. She is grateful for the assistance of Jason Poss in locating most of the quotes used in this article.

An archive of  The Legal Writer articles is available here.

© 2011 Suzanne E. Rowe

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