Lowering the bar to writing online

Be more like Simon Willison and less like Paul Graham

Two of my favorite Internet writers are Simon Willison and Paul Graham. But their approach to writing couldn’t be more different.

Simon’s position is documented here. But it essentially amounts to “write about everything you learn and build”. This approach leads to ridiculous output. Simon cranks out multiple, long posts per week.

Paul takes almost the exact opposite tactic. He thinks deeply about what constitutes a good essay, and famously spends days or weeks on the editing process, stripping every extra word and non-essential idea until the writing can be cut no further. This results in far less content, but a substantially higher density of ideas and information per-essay.

For a long time I’ve attempted the Paul Graham model—reviewing my writing over and over, cutting, simplifying, and so on. But this makes writing very slow! The average piece of writing takes me 5-10 hours to get out into the world—which means I hardly ever publish anything. The prospect of investing that kind of time is just too overwhelming, and so I don’t even try.

What I’ve come to realize is that Paul Graham’s process works well if the idea is big enough. But small ideas just don’t have the same requirements. Spending ten hours producing the perfect essay about a small idea is far more than that idea needs! That time would be better spent on ten imperfect essays about ten different small ideas. And—let’s be honest—most of my ideas are small.

So I’d like to publish more frequently, less perfectly, and more efficiently. To be more like Simon.

To help facilitate this shift, I’ve created a new category of writing on my site called “musings”. To qualify as a musing I have one rule: The content must be written and published in a single session. This means no substantial editing, no reviews from others, no time spent fiddling with images. Just thought → writing → review → publish. The average musing should take less than an hour to put into the world.

I’ll also streamline the process of “promoting” musings—which is to say that I won’t really promote them. I’ll just post in a few places on social media and move on. This will hopefully eliminate another source of mental overhead around the publishing process, and make it easier to produce more of them.

I like the idea of having musings as a separate category because it still gives me the option to try and write something more polished. Mentally, I can decide if I’m in “Simon” mode or “Paul” mode and that informs how much effort I need to plan for. Will I ever opt into the intimidating baggage of “Paul” mode again? Only time will tell…

Anyway, this was my first musing! It felt a bit weird to focus on the process so much, but when I think about what gets in my way from producing a musing-sized piece of writing it has often been simply not having a good place to put it. Hopefully that barrier has now been removed.