Testing a New Approach: Write Fast, Break Tihngs

Loosen up buddy

This drives my wife absolutely crazy, but I have a habit of aiming to arrive at the airport for my flights at almost the last minute.

POV: Catching an Uber to your 6:00 AM flight

This is intentional. Economist George Stigler famously said “If you never missed a plane, you’re spending too much time in airports.” and it’s a sentiment that has always resonated with me. Amazingly, the only time I have ever missed a flight was because I went to the wrong airport (a story for another time) and so the practical effect of my lackadaisical approach has been to drastically reduce the amount of my life I've wasted waiting around in airports. All benefit, no cost (so far).

The principle is broadly applicable in that it is possible to be overly cautious. As some of you may already know, writing as a vocation is something I fell into randomly. It was only possible because The Motte offered me an extremely low barrier of entry. But as Benjamin Franklin famously said “With great power comes great responsibility” or rather in my case “With great visibility comes great reluctance.” The practical effect of this ethos for me has been that, as I've developed more of a platform I've gotten increasingly reluctant about what I publish. This is a really good instinct to have in general, but not one without downsides.

The biggest problem is that it makes me hate the actual act of writing. Like when I was younger I used to love drawing with pen and pencil. There was something about the low barrier to entry combined with the precision that made me glom onto the hobby. It was effortlessly accessible, but still allowed you to craft something neat.

Sketchbook circa 2011

I thought I'd upgrade and try my hand at oil painting but after several months. eventually abandoned it because I found the translation process of lashing my mind’s eye onto canvas too frustrating. Oil, along with the endless permutations of color and medium combinations available, was just too slippery and elusive for me.

The only oil painting I managed to carry to the finish line

Maybe I had a point with this tangent but I forgot it now. Or maybe this is just a perfectly relevant illustration of how my mind typically wanders. I've always loved telling stories in person, at parties, at Tinder dates. My earliest trick as a writer was to simply pluck one of these stories that has survived this gauntlet of unwitting focus groups and just write it down. The benefit with in person is that it gives me natural constraints and allowances; I can’t keep running my mouth forever and I’m also excused the occasional missed take. But text is a wide open plain stretching over the horizon…

The anxiety manifests in a couple ways. First, I'm extremely mindful of wasting people's time. Everything is vying for the precious attention economy and it feels downright ignoble to waste any of it with anything less than perfectly poetic and vivid prose. But I've also been in the position where I've agonized over and revised a simple transitionary sentence for literally over an hour. It's probably fair to say that I'm over-calibrated on this dimension. Maybe. Sometimes.

Second, I take epistemological self-scrutiny extremely seriously, to an admittedly pathological degree. I used to be an earnestly devout Muslim before I wasn’t, and that might have contributed to some residual trauma over ever again being factually wrong or somehow irrational. I guard against this risk by contributing to a culture where admitting mistakes is cool and honorable, both major and minor. I’m never abandoning this instinct! But again, it is possible to be over-calibrated along this dimension and waste precious time in the process. Two vibrant examples come to mind: the 2020 stolen election claims, and transgender identity.

I've wasted an unfathomable amount of my time investigating completely the cavalcade of inane stolen election allegations. A significant motivator was borne out of my sky-high respect for the community on the Motte back then, which was for many years the primary exposure I had to highly intelligent right-wing perspectives. But then I watched as an increasing number of otherwise rational and erudite commentators credulously and repeatedly insisted that the next allegation du jour was for sure going to be The One, while never acknowledging the trail of dead bodies in its wake. I was much more cautious with my dismissal at first because, hey, I was before and can always again be wrong, and maybe they knew or understood something I didn't. Even when it was plainly evident that was not the case, I held out hope that folks could be snapped out of their delusions with enough patient rational discourse as a remedy. I pissed away too many hours underestimating the depths of political brain folly. Lesson learned.

Same with the transgender issue. The last effortpost on this topic I posted a year ago was the culmination of months and months of research and reading. I don't have a formal background in philosophy or “feminist” theory¹, and so I was particularly averse to grappling with concepts that were potentially above my pay grade. And so I was patient and plodding and averse of putting pixel to screen until I was damn sure of what I was saying. But the hundreds of PDFs I read basically just confirmed that my my initial instincts from several years ago were more-or-less accurate. I afforded way too much charity to the cacophony that this constellation of concepts was too enigmatic for the layperson to understand. Sometimes that bluff is just a mask for emptiness.

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I just came back from the LessOnline conference this weekend and had a phenomenal time torturing myself over the omnipresent FOMO. I met and spoke with fellow travelers who had unimpeachable integrity and who grappled with similar issues. I found out at the writer’s block session hosted by Daystar Eld that I may have been the most prolific writer there with the greatest hatred for the writing process itself, which was a good moment for introspection. I had the honor of meeting none other than my longtime intellectual hero David D. Friedman who told me that he announced his first Legal Systems Very Different from Ours course a year in advance, before he started his research, as a commitment device. Similarly, the prolific Crémieux explained to me how he commits to writing some of his posts within an aggressive one-hour window, lest it all self-destruct (he’s also commendably transparent about his errors).

So what now?

Right now I keep accumulating an inordinate amount of essay ideas and story pitches but the backlog doesn’t abate and instead just gathers dust. Whatever sphincter muscle I’m using demonstrably needs to be relaxed somewhat. How’s that for imagery?

A public declaration of “moar poasts” will be fairly toothless given the inefficacy of enforcement. What I do intend to change is to write more often and in shorter chunks. For my legal writing in particular, I very often get carried away with attaching lengthy background compendiums due to a fixation with being absolutely “comprehensive” on any topic I brush against. Those detours are often very interesting but they suck up infinite hours. I’m also going to raise my tolerance for (occasionally) being wrong, or misspelling a post title. I’ve already established an impeccable track record of being less wrong and a strident desire to course-correct in the (alhamdulillah) rare instances where I do go off-track, so I need to be less fearful of getting completely lost.

Put another way, I’m spending way too much time at the airport, and less at my destination. I need to change that. If I start missing way too many flights as a result of this approach, I’m sure y’all will let me know.

1. The quotes are not indicative of dismissal, but there to indicate that there is serious contention over what exactly counts as legitimately “feminist” within this field.