The Agony of Writing

My dislike of drafting was a significant factor contributing to me quitting law. But drafting legal documents was considerably easier than personal writing. There are no penalties for lacking word variety or having half-page long sentences with multiple subordinate clauses. In personal writing, so much hinges on aesthetics and clarity. I disliked drafting, but I hate writing. How ironic that I am now writing a blog.

My husband loves writing, but I have never fully understood that desire. To me, writing is like descending deep into the dark damp recess of the brain searching for light, a maddeningly frustrating and inefficient process of expression.

I don’t know about other people, but I don’t think in sentences. I think in vivid images, seemingly incongruent analogies, disconnected words (often multisyllabic), and senses recalling the past. I wished there were a breast-pump-like device that could be plugged into my skull to extract all the thoughts and convert them into carefully and elegantly arranged words full of meaning.

But alas, there is no such device. If I want to communicate and be understood — which is indeed a strong desire — I need to package my multi-layer, multi-dimensional thoughts into a straight line of words. The packaging, flattening, and linearization of thoughts does not come naturally for me. I am decent in structuring the overarching theme when writing, but not so great when it comes to arranging words at the sentence level.

Writing beautiful sentences seems so easy for others. I’ve often felt discouraged when watching movie scenes portraying someone writing productively. They usually start with the writer sitting in front of an old-fashioned typewriter or a sleek MacBook, typing feverishly while sucking on a nearly finished cigarette. Then comes the gentle voiceover of the florid yet elegant sentences representing the finished work product. Perhaps tedious editing is only for inexperienced or untalented writers, I think to myself.

To make the matter worse, I’ve always been insecure about my mastery of English grammar. English was not my first language. I learned English at the age of 13 by spending a summer watching Days of Our Lives and All My Children and memorizing 50 vocabulary words a day (which may explain why I think in multisyllabic words). Even though my English is proficient and I think and dream in English, I never systematically learned English grammar. Trying to parse the verb tenses like future perfect continuous still makes my head ache. I still get confused when to use definite versus indefinite articles, singular versus plural nouns. Many of these concepts don’t exist in my native Chinese, and I suppose I never developed the natural language faculties for them. People often tell me to read a sentence out loud and hear what sounds right, but I don’t seem to possess the right kind of ears either.

My friends used to lovingly tease me by compiling a list of “Jenisms”, such as “let’s play by my ears” (instead of “let’s play it by ear”), “don’t jump on the gun” (instead of “don’t jump the gun”), or “bull in the china store” (instead of “bull in a china shop”). I have learned to laugh at these Jenisms and even purposefully use them for emphasis, but for a long time I was self-conscious.

I carried both types of self-consciousness — believing I didn’t have the knack for elegant writing while lacking mastery of English grammar — when writing. More formal the piece, more debilitating the dread. And that became my dirty secret.

I did have to write quite a bit when I added literature as my second major the second semester of my junior year at MIT, after my mother passed away from lung cancer. (I was very lonely then and reading the words of bygone authors was one of the few things that alleviated my pain and made me feel understood.) Writing came with the territory of literature. I crammed in many literature classes in my last three semesters and had to write many papers as a result. I never looked forward to any writing assignment, but I didn’t dread. Why? MIT had a writing center staffed with several patient high-caliber instructors. I quickly became a fixture there. Unlike many people, I never suffered a dearth of ideas; my problem was more stylistic. Because I didn’t have many substantive issues with my writing, the instructors always happily corrected my grammatical mistakes and Jenisms and helped to refine my sentences.

It was not until recently that it dawned on me that although I learned a great deal from the instructors, I never learned to edit my writing myself. I relied on them, almost exclusively, to ease my self-consciousness. They became my crutchers (yes, that is a Jenism). Without my crutchers after graduation, self-consciousness and the dread returned with a vengeance. Once again, I would fret over sentences and worry about grammatical mistakes that might be apparent to others. Outwardly, I did fine. No one criticized or questioned my writing ability, probably attributing any grammatical mistakes to carelessness. But that gave me no solace; I still dreaded.

I have carried this secret insecurity with me, allowing it to plague me through law school and six years of legal practice. I have had enough. And this is the top reason why I am spending hours doing something I hate: writing.

Before I embarked on this writing-improvement project, I knew I needed an intended audience for my writing. If I were writing a diary, I would never conquer my self-consciousness. Thus, a blog became the perfect forum. I enlisted my supportive husband to be my editor, giving him the moniker “hubbitor”. He helps in all the ways a good editor does, from clarifying ideas to correcting grammatical mistakes and awkward sentences. Soon, I realized that I was falling back into the same bad habit when it came to the basics of writing: my hubbitor became the crutcher.

A good writer must also be a good editor. I needed to learn to edit my own rough drafts and the first thing was to learn English grammar properly.

I bought “Barron’s Grammar in Plain English”, which touts itself as “a valuable study aid for adults preparing to take the GED.” Ouch! Since putting my pride aside I have been dutifully going through the exercises in the book (which has been far less engaging than watching Stefano DiMera’s seduction in Days of Our Lives), keeping my promise that I will master English grammar once and for all. I also bought Jack Hart’s “A Writer’s Coach, The Complete Guide to Writing Strategies That Work.” The book helped to demystify the apparent ease of beautiful writing by breaking down the process into manageable steps.

I applied what I had learned so far when I wrote my last post about money. I took me over five hours of actual writing time to draft it. Then I spent another couple of hours polishing the draft, much longer than I did for previous posts. I edited and re-edited each sentence in an effort to make them both refined and grammatically correct. I re-crafted several sentences at least 20 times, making sure they accurately described the sentiment of a personally charged issue. After painstakingly scrubbing the entire draft on my own, I felt less embarrassed and self-conscious about what I had written, even if further editing was needed. I was also encouraged because I realized that this process actually helped to clarify and solidify my thoughts.

When I quit my job, I thought I was going to find my passion and only do things I enjoy. I am still on that journey, but the journey may lead me on a detour, a necessarily agonizing but ultimately worthwhile detour.

NOTE: If you are interested to see a draft version of this post prior to my hubbitor’s edit, please email me at and I will send you a copy.


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