This is the 12th essay in my 30-30 series. Clearly, I have not completed 30 essays within the year that I turned 30. Today, I’m 31 and about 2 months. Not that I’m justifying why I did not manage to achieve that goal – quite a few things happened in 2020. Chief of which is that I changed my day job, from being a public school teacher for the past 5 years to taking on a design role at a university. The most important thing to me is that I am still writing, arriving at a certain quantity by a specified date is secondary.

I decided to write an essay on essays because I thought it is a good juncture for me to reflect on my writing practice and consolidate it as a working guide (I almost wrote manifesto 🤔) for the direction I would like to take my writing next.

I used to think that the more I wrote, the easier the process of writing will become. That’s true to some extent, perhaps in the sense of sentence structure. In most other ways, however, it has either stayed similarly difficult or become seemingly more challenging. Researching topics is a really tedious task that can sometimes draw me into deep rabbit holes. It can be hard to determine how much I should know before I should write about it. That leads me to the other difficulty of scoping essays. The previous essay on the limitations to understanding ended up feeling like an “almost everything” essay that attempted to capture and condense entire bodies of human knowledge. It was one of those instances where, at the start, I naively thought that such a topic can allow me to write freely and meander around various associated topics. Instead, what ended up happening was being intimidated by the enormity of the task and getting caught in thought loops and knots. Another difficulty that I’ve encountered is organizing ideas into a linear format and ensuring that there is a good flow from one idea to the next – sometimes having to enter subdiscussions and then exit back into the main thread. I also encountered the limits of planning – sometimes the intuition in the act of writing dictates that it go in a different direction than what was initially laid out. (This essay was supposed to begin with an etymological analysis of the word “essay”, lol… it’ll come later.) Sometimes, it becomes a matter of wanting to finish and letting that urge lead toward finality.

Writing these essays has definitely exposed me to the craft of writing. I often feel that I have blunted tastes in many things that I do, resulting in work that can perhaps seem “low-fidelity” and unfinished. What I’ve learned (or been reminded of) is that craft only develops through sustained practice – if something seems too easy or if I’m too easily satisfied by the outcome, I just have not spent a sufficient amount of time doing that particular activity, or understanding what it is the people are trying to do with the activity. One truly cannot swim without getting wet – and swimming is an interplay of sinking and floating. I would not say that writing comes naturally to me, at least not as much as making physical objects, but it is something that I desire to get better at. I have completed essays that I felt disappointed with, which can be discouraging. However, looking at it from a different perspective, I guess it shows that I am developing a more discerning eye toward what I am producing. What needs to be done is to hold on to the aspiration, struggle with the disappointment, and, echoing Gladwell, put in the hours.

I’m a big fan of the Green Brothers’ eponymously named podcast, “Dear Hank and John”. In a recent episode, John mentions a quote, “I hate to write, but I love having written”, a sentiment expressed by many authors, with variations in wording. I am glad to be in good company. I’ve come to realize that it is not just about the process – having small accomplishments along the way helps a great deal in the longer journey of continual practice. I keep getting reminded that the world is never “either-or” and often some balanced combination of supposed opposites.

I find a lot of beauty in the word “essay” and its origins – it is derived from the Old French word, “essai” which translates as a “trial [or] attempt”. It resonates with what I’ve written here thus far, about giving myself the chance to try. To push beyond paralysis and risk failure to translate intangible hope into form. Some may argue against it, but I feel that the act of creation is fundamentally an optimistic one because it is an attempt.

I recently revisited Montaigne’s essays (he is arguably the OG of this form). In his foreword to the reader, he mentions that, “I myself am the subject of my book: it is not reasonable that you should employ your leisure on a topic so frivolous and so vain.” Montaigne is self-aware of his subjectivity from the start and is cognizant of the personal nature of his motivations. At the same time, he knows that his essays were going to be published (only a fraction of his work was posthumously published). There is, therefore, a balance between a self-centered and other-centered act.

Personally, I’ve found my essays to have drifted too far away from myself. It often feels too sterile and rid of character. This essay signals a shifting of weight back toward my subjectivity and being more obvious about it. I will stop consciously avoiding the “I” pronoun, which previously perhaps was an attempt to sound more academic and legitimate. This may make the writing feel more self-indulgent and (annoyingly) self-aware at times – I am going to give it a shot and calibrate it over time. I got reminded of how I fell in love with words and writing through my high school teachers Ms. Foo and Ms. Sim, whose passion infected me.

Similar to this one, some future essays may have a faster and scrappier feel: more spontaneous and stream of consciousness. This probably means less well-researched facts and more opinions. It also translates into shifting the scale from planning to intuition. This essay, for instance, lurked in my head for months, was planned as a 9-square grid of ideas on Miro, and was written in one sitting of ~four hours. It feels more repeatable than some of my other essays, where research itself can take a few weeks, causing the outcome to feel increasingly distant.

Writing essays also made me aware of the limitations of their expression. I never felt I can write fiction, but I’m increasingly compelled to do so as I want my words to make others feel in ways that perhaps only fiction can achieve. So… there may be a short story coming up.

Finally, for anyone out there who’s searching and not quite sure what it is they are looking for – hang in there and keep going at it. Try, (maybe) get it, definitely lose it, and try to find it again – it’s like trying to grasp sand. C’est la vie! Thanks for indulging me with your attention in a world where it is a scarce resource.

“One must imagine Sisyphus happy.”