a stupid bravery

how do I write a good essay in a single sitting?

“The artist works even when he’s dreaming. Words are easy, books are not. Good writers still struggle with professionalism; balancing assertiveness and sensitivity. The artist risks failure. Don’t try to perfectly represent reality, but our experience of reality. If you can make it feel right, any note can work. We improve patterns by testing them against how we feel.”

Many-a-times when i sit at my computer, I’m visited by a vague premonition – a sense that, if I made the right moves, I could write and publish an essay in about 2-3 hours. This has happened at least a couple of dozen times in the past, so it’s not merely wishful thinking. But it happens much less frequently than I would like. And I’d like to puzzle over it and see if I can come to a useful, consequential understanding. Because, gosh, I would love to write an essay a day, and I do believe in my heart that I am capable of doing it. I do it with Twitter threads all the time, almost by accident. Sometimes I wake up with a thought and I tweet it, and the followup thoughts cascade into a 12-16 tweet thread. Sometimes I see something someone else had tweeted, and I find myself quote-tweeting and threading away. Notably, this almost always feels like something I’m an observer to, rather than the participant of. So I would guess that if I were to write essays with a similar spirit, I would feel similarly as well.

I wrote some of this current essay in my head while in the shower earlier. It went like this: “John Mayer stupid bravery… Brian Eno constraints… 12 bar blues… 12 points per essay…” I often feel like most of the work of writing for me happens away from the keyboard. I particularly love how Borges put it: that the artist is at work even when he is asleep, dreaming. I feel that very deeply. I can’t really turn it off. Everything that happens to me, everything that I notice, feel, observe, sense, hypothesize, suspect, believe – all of it finds its way into my work somehow. So everything is significant. Everything is excruciatingly meaningful.

John Mayer, in an interview with Zane Lowe, demonstrated his remarkable ability to write a song in real time, simply improvising his way through it. He said, “I don’t always do it because it requires a stupid bravery (to do it) all the time,” and I think there’s definitely a deep and important truth to that. But I’d also add that I don’t think it’s the only thing. John Mayer is obviously an accomplished musician with decades of practice and performance in his back pocket. If I were to assess myself honestly: I don’t think I’m brave all the time, but I do think I’m somewhat brave, which is how I tweet so much, and how I’ve written and published the books that I have. And yet it doesn’t feel to me like all I need to do is “be braver”. I feel like there’s more to it. In Mayer’s case, I would posit that a lot of it is his deep familiarity with his instrument, his voice, the words he likes to use, and most relevant of all to my current interest, his understanding of structure. When it comes to essays, I feel confident about my own words and voice, but it’s the structure that messes me up. But I believe I can figure it out, and I’m going to do it in real time over the course of these essays.

(source tweet)

Fran Lebowitz said “words are easy, books are not.” My view is that this is because books are not merely bundles of words, but complex, carefully ordered collections of words. Writing a good phrase, sentence or paragraph in some arbitrary context is something that can happen even by accident— and I do believe that a lot of the skillset of being a good writer is simply allowing yourself to have lots of such happy accidents, and recognizing when they’re good, and employing them accordingly. But writing a good book is a different skillset entirely. It requires concerted organization and reorganization, over and over again. It requires discarding some of the good sentences and paragraphs that you wrote because they don’t serve the book you’re writing, which can be painful to do. And I think above all else it requires tenacity, grit, a dogged persistence.¹

I’ve come to see that there are a lot of people who are talented with words who nonetheless can’t quite make a career out of writing professionally, because they struggle with the professionalism. That is, showing up regularly, meeting deadlines and so on. Creatives are quite notoriously bad at this. Which explains a fun little mystery I’ve long pondered about: how come there are people who write such legitimately brilliant analyses online about how some movie could’ve been better, in remarkable detail? Why don’t these people just… work in the movie business themselves, and make those excellent movies? Part of it is the professionalism problem. It’s easier to write for fun on a whim than it is to write for work on demand, when you have expectations to meet. (Another massive part of the professionalism problem is having to interface with other people, argue your case, build rapport, all sorts of social skills that are in practice quite unrelated to actually being able to write well.²)

I’ve often heard creatives openly fantasize that a competent manager would basically adopt them and challenge them as necessary to do the work that they know they are capable of doing. I’ve heard software engineers (who should also be considered creatives, in my view) describe a version of this too – many of them want the fun-and-interesting challenge of writing good code, but they don’t want to have to worry too much about tending to the meta-structure within which good code is written– what product to make, and why, and having to argue and negotiate with other people about it all, and so on. If only a benevolent Product Mommy would just step in and take care of all of that, wouldn’t that be wonderful?

Unfortunately, it’s very rare to find people with the precise mix of assertiveness and sensitivity that’ll be perfect for you, and the people who are highly skilled at that are typically highly in-demand, and they’re doing things like… being Taylor Swift’s tour manager, or running some other really difficult operation, and you probably can’t “afford” their time or attention³. (Which is another version of the “it takes money to make money” ‘Matthew effect’ style phenomenon, which when inverted is what I call the wretchedness problem– how the worst-of-the-worst down-bad people struggle even to ask for help, or to accept it when they receive it.)

Here I’m also reminded of WaitButWhy’s 2015 article about cooks vs chefs – the cooks being people who simply follow recipes that other people have written, and chefs being those who write their own recipes. I might argue that a “real” creative should be someone who writes their own recipes. But everyone starts somewhere.

When Leonardo Da Vinci was 14, he apprenticed as a ‘studio boy’ at Verrocchio’s workshop. Verrocchio was a prominent figure in Florentine art, but my understanding is that the workshop wasn’t particularly devoted to nurturing creative geniuses. Rather, it was more like a content farm, where apprentices mass-produced unsigned works, “generating Madonna paintings for merchants who wanted to display both their wealth and their piety” (h/t Walter Isaacson). Is it artistry to mass-produce commoditized artworks? I really like Steve Jobs’ definition, which is that an artist must risk failure:

“If you look at the artists, if they get really good, it always occurs to them at some point that they can do this one thing for the rest of their lives, and they can be really successful to the outside world but not really be successsful to themselves. That's the moment than an artist really decides who he or she is. If they keep on risking failure, they're still artists. Dylan and Picasso were always risking failure.” – Steve Jobs, Fortune interview (1998)

I don’t want to particularly gatekeep creativity or anything. I just want people to think more clearly about things, and I’d like to see more people make more good stuff in every domain, along every dimension, so that we can all enjoy the fruits of human flourishing and become more discerning in our tastes– and to me that includes learning how to enjoy alleged “lowbrow” art and products too.

I have digressed somewhat, but quite happily so. Let’s recap. We’ve talked about the stupid bravery necessary for creativity, the challenge of information architecture, the challenge of professionalism, and the nature of artistry itself. The core puzzle I want to solve, however, is how do I write a good essay in a single sitting? We’re returning to the challenge of information architecture. Now, I know how to write elaborate nested twitter threads, and I’m goddamn good at it if I may say so myself. (Other people have said it too.) I can sort of write essays, but it takes me a really long time to write a good one. (Several people have said that Are you serious? is one of the best essays they’ve ever read. I’d certainly point at it as the best essay I’ve written so far, though it’s not even close to the 10th best essay I have floating around in my mind’s eye.)

NYC 31, oil on canvas, by Jeremy Mann, (2016)

I keep looking for excuses to talk about one of my favorite contemporary painters, Jeremy Mann. I previously mentioned him in Dancing with constraints Pt 1 to talk about the constraints of mediums, and I’m basically going to say the same thing here. I’ve since been delighted to discover that there’s a whole documentary about him and his process, available free on YouTube: A Solitary Mann [40:30].

There’s something about what Jeremy does with his paintings that I find deeply inspiring, that I want bring out in my own work. There are so many things he says while working that have me nodding my head furiously– like how he feels that the painting shouldn’t pretend it isn’t a painting, how he focuses on getting the emotional qualities right, and how a painting that “perfectly representing reality” does not actually adequately convey our experience of reality, which is all kinds of blurry.

The central question his work makes me ask myself is, what is it that I can do with some medium that I cannot do with any other mediums? What can I do with essays that I cannot do with tweets? I explored that question in the tavern and the temple, and if I remember correctly my main answer was that an essay (the temple) can be inherently contemplative. An essay is an invitation to spend at least 5-10 minutes inhabiting someone’s thoughts. You can try to do that with a tweet, and if you’re lucky you might inspire someone to stop and stare at a tweet for a while, but you’re brushing up against a medium that’s designed against it. The most breathtaking, awe-inspiring tweet you’ve ever read will often be sandwiched in between something terminally bad and some pornbot asking you to click on a dubious link. And that’s part of the appeal of Twitter (the tavern)! It’s supposed to be rowdy, irreverent revelry!

I digress again. Why did I bring up Jeremy Mann (apart from the fact that I love his work, which is reason enough)? Right– I was thinking of the vague, nebulous quality of the essays swirling around in my mind, and my mental image of that ephemera reminded me immediately of Jeremy’s paintings. And as I keep the original question in mind– how do I write a good essay in a single sitting– I find myself reflecting on Jeremy’s style and approach. He specifically says, “You're never gonna get it if you try and get every detail. That detail is not reality, to me it's the emotion.” He also says, “When you get up close it's a sloppy mess of garbage but it feels right.”

Which in turn reminds me of musicians like Victor Wooten and Jacob Collier, who emphasize that all that really matters is the feeling. If you can make it feel right, any note can work, even the “wrong” notes. On the other hand, if you play all the ‘right’ notes with the wrong feeling, it sounds wrong.

So I guess what I’m converging on is… what really matters for me is how my essays feel.⁴ And that might mean some people criticize them on the basis of “it’s a sloppy mess of garbage”. And I realize… I might be troubled by that criticism if my essays feel wrong or ‘off’ to me– but if the essay feels right to me, then no criticism of it could possibly bother me. I’ve felt that way about both of my books, which I am more than happy to cheerfully criticize at length. They have many flaws and imperfections! But they feel right to me, and that’s actually what really matters, that what makes them feel alive. The quality I look for, I tend to describe as “animating spirit”, and it’s what I strive to invoke in all of my works across all mediums.

And… I believe we have just reinvented some Christopher Alexander here, where he talks about The Quality With No Name… lemme glance at my notes… “we may gradually improve patterns by testing them against experience – see whether our surroundings live, or not, by recognizing how we feel”. Hah!!

“We find out that we already know how to make buildings live, but that the power has been frozen in us: that we have it, but are afraid to use it: that we are crippled by our fears; and crippled by the methods and images which we use to overcome these fears.
And what happens finally, is that we learn to overcome our fears, and reach that portion of our selves which knows exactly how to make a building live, instinctively. But we learn too, that this capacity in us is not accessible, unless we first go through the discipline which teaches us to let go of our fears." – Christopher Alexander, The Timeless Way of Building (1979)

I remember being so amused when I first read that, because I had picked up The Timeless Way Of Building for some light reading to take a break from the emotionally harrowing project of writing Introspect, which is all about facing your feelings, and it turns out that building, too, is all about facing your feelings. Which brings us back to Stupid Bravery!! Wow! This is not where I expected to go– and you can check this yourself by scrolling back up to see me say surely there’s more to the process than just the bravery. But I see so clearly right now that… past the bravery to begin creating, is architecture, which requires still more bravery. So it turns out “be brave” WAS the core thing after all, in more ways than I was appreciating. It’s fractal and recursive, it’s necessary at every stage of the process.

I just accomplished something here which I was not expecting to do when I started writing this, which is the synthesis of several ideas that are really important to me. I have “thinking is easy, information architecture is hard”, and “you can’t think your way out of a courage deficit”, and “make elaborate plans and then disregard them completely to make whatever you think is most compelling”, and now, via a confluence of Christopher Alexander and Jeremy Mann and Victor Wooten, I have “architecture is about feeling” and/or “architecture requires courage”. They’re all related. Information architecture is hard not just because it’s a technical challenge, it’s hard because it requires the courage to face and acknowledge your feelings. I “knew” this in a more shallow and fragmented sense — I had the component parts scattered around my mind, but this is the first time I’ve really brought it together in this way, intertwined with so many of the things I care about. Oh yeahhh, it’s all coming together.

So.

It’s now 1:21 AM. My draft history tells me that I started writing this at 10:25PM. That puts us at just under 3 hours, which fits quite nicely for an example of a single sitting. It also gratuitously fulfills my intuitive criteria for “good essay” in that it led me to what feels like a significant and important connection, that quite possibly may turn out to be a significant breakthrough— that information architecture is about feelings.⁵

Remember, the opening question was “how do I write a good essay in a single sitting?” I believe that I’ve just done this, right here, right now. How did I do it? I didn’t even actually take the path that I thought I was going to go on! I mentioned wanting to talk about Brian Eno and twelve-bar blues, but I got gloriously distracted from that. I’m tempted to say “I’ll save that for another day”– I do believe that I will inevitably write about those things, since I keep circling back to my long-recurring interests, but the more important truth I’m discerning is: for me to write a good essay in a single setting, I have to almost completely discard everything that I thought I was going to write, and simply write whatever feels deeply resonant in the moment.

(source tweet)

Let’s get groovy, baby.

1. Haruki Murakami addresses this well in What I Talk About When I Talk About Running. I mention this because recently rediscovered that my cursory read of that book turned out to have been a direct influence on me starting my @1000wordvomits writing project — I was persuaded by Murakami’s perspective that if I wanted to write for a living, as a vocation, I was going to have to write a lot more, over an extended period of time.

2. David Ogilvy had some great bit about this that I love, eg: “The business community wants remarkable advertising, but turns a cold shoulder to the kind of people who can produce it. That is why most advertisements are so infernally dull. Albert Lasker made $50m partly because he could stomach the atrocious manners of his great copywriters.”

3. This also explains why people are so often dissatisfied with their BDSM doms.

4. As I reread this essay to check for typos etc, it’s striking to me that I’ve put so much time and energy into thinking extensively about what my essays should look like, what their structure should be, what the topics should be, etc, but I’ve spent comparatively little time really just exploring how my essays should FEEL. I mean, I have thought about that too– ‘all the channels at once’, ‘afterimages’, etc– but the disparity is making me question right now, what if I did it the other way around? What if, having thought so much about the details, I now focused on whatever feels most compelling?

5. There are many opportunities for elaborating here: what is a good essay to me? and what does the “architecture is about feelings” insight look like in practice? I might explore those branching paths at a later date, but really, this essay is a demonstration of both of those things.)