The spirit of the Insider has never been about reaching a massive online audience. I am not trying to aggressively grow its readership or make it go viral. Instead, I’ve found the accountability of writing to an audience nurtures a discipline to think deeply and wrestle with the ideas that arrive half-formed throughout the month. I don’t write what I’ve already learned—I write to discover what I am learning. For me, writing is wrestling. Sometimes it flows. Sometimes I find myself bent and contorted in the labor of smoothing out a jagged idea that isn’t quite ready.
I’ve begun to realize something that maybe should have been obvious long ago: I am a better writer and more courageous idea-wrestler when I know the reader has context about me. When I try to write to a faceless, monolithic audience, my writing is generic and predictable. But when I know that the reader on the other side of the screen has context, I feel braver. I hold myself to higher standards. I aspire to be honest because that shared context is a form of accountability.
The writer Jenny Odell says something so simple it’s profound: write for people who have context. Context is a thickening agent that makes our writing textured and beautifully prickly. Without it, our writing can come out wispy and bland, which is the direction I see a lot of online writing going. The architecture of platforms like X/Twitter leaves little room for context, and AI-generated writing is designed to be generic and predictable because it is the average of all the writing that’s ever been done online.
As the academic Tressie Cottom so thoughtfully frames it, we are having the thickest conversations in the thinnest spaces. In such spaces, our writing becomes disembodied from human context. We begin to write in generic platitudes and pithy maxims because that’s what feels safest to write to an audience that doesn’t have context. We begin to shape our writing—and by extension our thinking—around calculations like: what will have the greatest impact for people who don’t have much context? What will get the most shares by people I don’t know?
When you write without any ambition for scale and distribution, when you anchor your writing in the mud and muck of human context, you will write with more honesty and pluck, and your writing will become an invitation that is sometimes accepted by the people on the other side of the screen to respond and participate in that co-wrestling with you.