some essays on how to write essays (p. 1)

intro / choosing a subject

Hello everyone. I’m currently about to experience the dreaded Rent Hike, and wanted to do a bit of fundraising for this newsletter. What better way of asking for your kind subscription than by offering you something useful of my own? I’ve put together a small series of essays about writing essays hoping that my own tools and perspectives can help folks who are in a slump as well as contribute to what is a lively culture of writerly discourse on substack. This first part is free, but the rest will be temporarily paywalled; hence:

A few weeks ago, I struggled with an essay to the point of abandonment for the first time in about a year. This is not to say that I rarely struggle with writing (I actually struggle more with being mentally well enough to write, if we’re being honest) but that the way I write is structured to make abandonment the path of last resort. Still, after abandoning the essay, which was about the German poet Friedrich Hölderlin and the curious dialectic of closeness and distance in his work, I became interested in how this abandonment happened, its points of failure. Breaking down this failure inevitably led to further notes on craft, which itself led to thinking about how and why I write writ large.

This is something I rarely do systematically, and something I almost never share with others, mostly because I don’t think the way one writes — or, for that matter, one’s particular success in writing — can be truly replicated. Only I can write my essays because my way of being in the world is limited to me and, furthermore, the way I learned to write was largely intuitive. I’ve never attended any retreats or seminars, nor did I major in English or journalism. There are no structures I’ve learned from others that I can impart onto you, no hot tips, no trade secrets. But as far as my practice is concerned, I’ve noticed many patterns over the years in the way I work and feel that for those first starting out or who are in a slump, these practices (and beliefs) may perhaps prove fruitful.

Writerly success, on the other hand, is more variable. Much of the writing advice on this platform is devoted not to the skill of writing (though there is plenty of that, especially with regards to fiction) but to how to make money writing. How to get published, how to maximize one’s profit from Substack, how to get views, clicks, meetings with agents, all of which, while sometimes helpful, often omits the obvious: one cannot make money from writing if a) one doesn’t write and b) the writing is bad.

The dream of writing as a kind of glamorous pastime full of fame, parties in New York, and lots of cash is more often than not sold to those who are early in their career by writers who either came up through traditional paths in publishing or who got lucky with platformization, which is to say, those whose journeys are often no longer replicable, and who should, frankly, know better than to pretend that they are. As someone who was in the right place at the right time (the 2010s), when going viral was enough to make or break a career, there is nothing I can say about making money (beyond negotiate your freelance rates if you can) that holds any water in the oversaturated and proletarianized writing landscape we are currently stuck with. In an age where almost no one is protected from the vagaries of the tech industry, private equity, and political repression, regardless of where or how we started, this is a ship we will all go down on together.

That being said, I’m exposed to a fair bit of writing from burgeoning writers via Substack Notes, and there are a few mistakes I see made repeatedly in areas where my help may be of some use. Additionally, I have developed a rigorous set of practices that I credit with my success (and I will call it that, thank you very much!) — as an architecture critic, a sportswriter, and an essayist writ large.

I need to have these practices because, well, I write a lot. In order to feed myself, I publish regularly, whether in the form of my architecture column at The Nation, when I am on site at cycling races for Escape Collective, for this Substack (a bestseller!) or my long-running blog McMansion Hell — not to mention the handful of (often large) freelance pieces I put out every year. (I am also writing a book, but we’ll have to see how it turns out before I can contribute to Book Discourse.) When thinking about craft, however, I consider long-form essays in whatever genre to be my most important work.

In this small guide I’ve decided to put together, I’ve narrowed my advice into four parts: choosing a subject matter, the pitfalls of writing about oneself, practice and discipline, and the myriad distractions and conditions (many of them mythical) people feel are essential to ‘being a writer.’ This essay will be devoted to the first of these.

The Mowing Devil (1678)

part 1: choosing a subject (write about whatever you want, but be serious about it)

I: Beware of Hot Takery

It is a mistake, especially at the beginning of one’s career, to treat writing as a kind of competition where, by publishing with immediacy about whatever the topic du jour is, you can maximize your exposure and build a career quickly on generating chatter. There may be some practical truth to this, but creatively it’s a double edged sword. Many popular subjects (political shockjockery, micro trends, TV episodes, stuff people said on this platform or others) are by their very nature ephemeral, and while gratifying in the short term, ephemerality does not lend itself well to producing writing that has lasting value either to yourself or to others. That doesn’t mean one shouldn’t write about ephemeral subjects, but that the attempt should at least be broad enough to be interesting later.

I’ve learned this lesson the hard way myself — after all, my career took off in 2016, at the beginning of the hot take era. I wrote a lot of essays that are either dated, irrelevant, or come off as amateurish because they were all impassioned opinion and no deeper substantiation. Some of these pieces were popular and successful at the time, but in the long run they haven’t amounted to much. Though this is less true about politics than it is culture, when I see something I feel is urgently relevant, I often ask myself: will people forget about this next week? Do I really want to waste prime Baudrillard on Bombadilo Crocodilo? (Though the thought is tempting.)

Hot take writing quickly becomes exhausting. Heat requires combustion and sometimes we just run out of tinder. The pressure to publish a piece every time something happens on TV, social media, in celebrity or internet culture (the latter of which now moves too quickly and is too disposable to write about effectively even in the short term) is an immediate ticket to burn-out land. Furthermore, the combative tone of hot-takery inherently invites conflict, and conflict, while sometimes lucrative, is mostly upsetting and taxing, even if you think you can transcend it. More of us can’t than can. I’ve learned that it’s sometimes better to avoid writing (and even better to avoid posting) during moments of extreme anger or indignation, and instead wait for my brain to cool down so that it can make new, more substantial connections linking my subject and my feelings towards it to other mediums, events, and ideas. If you do have one bullet you really need to unload, try to aim as accurately as possible.

It’s seen as a given that we must live and die by the oscillation of the hype cycle. But after each cycle is completed, then what? In the long run, I feel it’s better to write a good essay a week or a month or even a year from whatever happens than a mediocre one in the moment. (And after a certain point, one does know when what one’s writing is mediocre.) When it comes to thinking about contemporary culture, instead of caving to the pressure of producing work now, ask yourself: wouldn’t you rather write the essay on this? Five or ten years from now, when people are revisiting this subject as a cohesive or completed work or event, don’t you want to be the one to have addressed it most cohesively within its social, cultural or historical milieu? In other words, what would the final word on this look like?¹

More often than not, we can’t truly understand a subject until time separates it from us. Only looking backward does it begin, and continute to make more sense. It’s quite possible that, despite all the likes and all the virality I see out in the world, the best essay on Severance or The White Lotus has yet to be written. In general, it’s hard to gain perspective on our time while we are living in it. Even when writing in the past tense, we are more often than not still writing in a kind of present tense. To look back on the contemporary is to make use of untrodden rather than exhausted territory. There are few pastimes more fruitful than walking among the graveyard of takes. Fredric Jameson’s imperative still rings true and serves as advice in its own right: “Always historicize.”

II: write about what you want to, actually

This is an obvious corollary to the first point, but there is never a wrong time to write about something. There are more subjects in the world than there are writers to write about them. Curiosity is, as always, the oxygen that gives life to fire. Some of my best essays are on random (for me), obscure or antiquated subjects — Formula One, pictures of KMarts on Flickr, the Ring cycle. My favorite piece of writing from the last two years is an essay I wrote for Protean (which will soon be online) about the Yugoslav painter France Mihelič, whom most of you have probably never heard of. I’d wanted to write about Mihelič for awhile, because his work about death and life, decay and regeneration, is imperative in a time where life itself is increasingly devalued and instrumentalized. I pitched the editors there off the cuff about this guy practically unknown outside of the post-Yugoslav world, and you know what? There wasn’t even a back and forth — they took it as soon as I pitched it.

This brings me to another point: It’s a waste of time agonizing over whether your subject matter will come off as weird to editors or whether it fits into what magazines think are profitable stories.² The point is to convince them that what you want to write about is worthwhile.³ Furthermore, you never know in what ways an essay will be successful. We default to virality, to likes and shares as currencies of whether an essay is good or not. But there are discrepencies even between these.

The Substack algorithm, for example, works in mysterious ways and does not reward expediency the same as other forms of social media. We forget that not everyone wants to bother signing in to click the little heart at the end of the email. (I almost never interact with essays I read via my own inbox for this reason.) The essays I write on Substack often do better on other platforms because most of my readers are not Substack readers. Twitter, meanwhile, is dead, but for writers and editors (whether we like it or not), Bluesky is less dead. Meatspace, one must remember, is forever, which is why it’s still a privilege to write for print.

Every once in a while, an essay of mine goes viral on whatever platform or platforms (my most recent one was for Lux about sex and surveillance.) Whenever that happens, I get to go on radio or podcasts, I get new ins, I make more money, and all is grand. This is always a surprise for me which is why I don’t bother trying to replicate it. Instead, I trust my gut and know that for me the point is to publish a piece because it needs to be in the world. The rest is a gamble. For example, my essays on the Ring rarely broached the 100 like mark on here and yet they were widely circulated among those who care about that kind of thing. They earned me a seat at the table writing about classical music for other publications. Some were even taught in university classrooms. Those essays didn’t make me lots of money (maybe a thousand dollars collectively), but there isn’t a world in which I’d deem them unsuccessful.

Pillow Study by Albrecht Dürer

Anyway, when you’ve found a subject, devote yourself to it for a while. This can mean a few weeks, a few months, or even a few years. Each new essay, if you really think about it, is already the culmination of your entire writing life, and a writing life is never wasted. This might make it seem like it requires infinite leisure hours to get to the point, but almost every single writer I know has a day or night job. I work on-topic during the day and spend my nights and weekends on my obsessions. I’ll get to this in a later essay, but I do a lot of writing “for free” because I have personal projects I care about and find personally enriching — each of these also helps shape my development as a writer. If I want to do something, I make time to do it. I once wrote a magazine profile of the Dutch cyclist Mathieu van der Poel on a 9 hour return flight from France.

If you’re in need of a new obsession (this also doubles as writer’s block advice), read an old book or choose a poet whose work you’ve always wondered about. Spend an hour with a painting that moves you; spend two weeks reading about the artist. Do the John Berger thing where you come up with a tight, sparkling 1500 words on any given picture. Even if writing about place isn’t your cup of tea, take in, and write about, landscapes. This is generative in its own right and also a useful skill to give depth to whatever else you’re writing about. Whenever I’m stuck, I ride the L or the Metra back and forth in order to feel the effortless passage of my body through space, to devote myself to looking without obligation.

Travel is generative even locally, at the scale of the neighborhood. The architecture critic Michael Sorkin once wrote a delightful book just about the walk from his flat to his New York office. Even the most quotidian objects and fixtures in the world can be remarkably expansive. I think often of Shannon Mattern’s deep dive on cardboard boxes in Places, and Lisa Hix’s Collector’s Weekly essay about the history of the “grandma couch.” The architectural historian Siegfried Giedion, in his book Mechanization Takes Command, which is about the mass production of everyday items, once remarked: “[No] more in history than in painting is it the impressiveness of the subject that matters. The sun is mirrored even in a coffee spoon.”

III: the juxtaposition and feeling traps

The trouble with writing is that it can take a long time to figure out what you want to say about whatever passion you’ve gotten yourself into. Like I said about myself in the introduction to this guide, the good news is only you can write your essay about whatever it is you’ve chosen. Only you can relate your subject to yourself, to how you view the world, to all the other things you’ve read and done in life.

Still, there are two common traps I see people fall into time and time again. The first is the juxtaposition trap. Juxtaposition works best when it is tight and specific. One text, one artwork. One poem, one current event. One philosophical theme and one quotidian fixture of our lives. The more elements you add, the less effective juxtaposition as a structure becomes. ( In fact, your structure is no longer juxtaposition, which is fine, it’s just that the essay now needs further development and will probably be longer.)

What’s worse, however, is that writers too often use systemic problems or frameworks in ways that merely amount to juxtaposition. This is more understandable if you’re writing something that’s opinionated and quite short or if you need to do a bit of rhetorical agitprop, but the longer the piece, the more you’ll need to define and clarify the systems you’re putting to use. If you want to say that capitalism causes something, I am begging you to give me a mechanism by which it does so. Through what industry? What processes? Who, exactly, is profiting and by what means? (Also, in culture writing, too many equate capitalism with ‘the pressure of the market’ which is not the same thing.)

The same goes for feminism which has, in the wake of choice feminism, become a catch-all vibe of ‘being a woman’ completely separated from its rich body of theoretical work. There are so many feminisms, each rife with its own ideas, and just one idea is often enough to structure one if not multiple essays. You don’t even need to pull an “as so and so says” — you can just structure around the idea as you interpret it. (For example, the seminal first chapter of John Berger’s Ways of Seeing is a reinterpretation of Walter Benjamin’s essay “Art in the Age of Mechanical Reproduction,” which is credited only in a blurb at the end.)

This is not an invocation to be more academic, but rather to be more focused. The only cure for a lack of focus is reading more. Honestly, sometimes I get the feeling, especially from young writers, that if they cite another’s idea it makes them somehow unoriginal or derivative, when the opposite is true — new relations between subjects and ideas can only ever be generative. This fear of being unoriginal or insecurity towards how much one has read (or rather hasn’t read) in part explains why so many writers start out by rooting their writing in — and becoming over-reliant on — the self, a topic I’ll address in the second part of this series.

Scene from Henry IV, Samuel Middiman after Robert Smirke

Lets look at another trap: emotion. It’s easy to get stuck on feeling and hard to transform emotion into more productive results. This was the problem at the root of my aborted Hölderlin essay. For reasons both aesthetic and personal, I felt so close to Hölderlin, his work, and the time he lived in, but could not channel that closeness into something new or interesting to say about the work itself. This wheel-spinning never amounted to anything analytical or even directional, instead it became an exercise in pure, messy sensation.

I know that the only answer to this problem is not to abandon Hölderlin per se but to read more about him until a path forward emerges. I had this same problem when I was writing about Siegmund from Wagner’s Ring. He left such a profound impression on me, it took literal months to untangle my attachment to him from why I found him compelling as a character within a larger work. The key to unlocking him as a subject came from, of all things, Simone de Beauvoir’s The Second Sex, which, at the time, I was rereading on a whim.

More straightforward criticism is not exempt from the feeling trap. There are many times (especially when thinking about novels) where I find it hard to move past the “I like this” or “I disagree” stage; to dig deeper into the marrow of the thing. Many people love and write about books, but the best book reviewers are the ones who not only integrate the book with the outside world, history, culture, or other works but also metabolize it via their own analytical practice.

An essay can wax lyrical all it wants but interpretation and criticism are best thought of as closed systems. It’s a common misconception that the point of an essay is always overt persuasion. If an essay is disciplined within its own structure — if it says what it needs to effectively — it can exist and be secure in its own right, no matter how weird or off the cuff it is. Be forewarned, however, that it is blatantly obvious when vibes are prioritized over cohesion, when people write without having anything to say. There’s nothing more boring than an essay that goes nowhere and merely rides out the tepid momentum of its own prose.

I suppose I’ll end this piece with my best advice when it comes to choosing a subject: nothing is irrelevant. History is a continuum in which everything is irrevocably enmeshed, and the system of relations is by its very nature infinite. Maybe the brouhaha over autofiction is not only an opportunity to write about the business of publishing or the pervasiveness of internet thinking in our lives, but about psychoanalysis or the autobiographical novels of the 18th century. Maybe the incest brothers in The White Lotus have more in common with the Southern Gothic than they do the ills of contemporary pornography and television spectacle. If you’re a good writer, you can make anything interesting and the only way to become a good writer in this vein is to write about everything, even if you think you won’t be good at it, because the only way to become good at something is to do it. So goes, unfortunately, the tautology of practice.

1. Whenever I’m stuck on this question, I like to return to the work of the architecture critic Michael Sorkin who had a special, politically energetic way of reconciling the building with the world it’s built in or the film critic AS Hamrah, who manages to write timelessly about movies that we might not even remember two years from now.

2. In general people think way too much like temporarily embarrassed magazine executives and less like writers. Have some dignity, girl!!! You are an artist!!! And even more than an artist you are a worker!!!!! People spend years reading the tips and gaming the system in order to get a proposal read or a pitch in at a major publication only to get fucked over because they didn’t negotiate their rate. You want to make more money? Talk to other writers!!! Demand more!!!! ORGANIZE!!!!

3. On the matter of pitching, there are some publications I haven’t pitched not because I don’t believe I’m good enough to be accepted but simply because I haven’t come up with a piece that would a) have a better shot in terms of tone, format, length, etc, and b) fits the scope of the publication. Do you know how hard it is to produce 10,000 words of reported criticism for example? I see countless people be like “I need to be on the front page of Harper’s before 30 or I’m washed” WRONG!!! GROW UP!!!! GET BACK TO WORK!!! You’ll hit 30 ANYWAY and no one will CARE!!!!