Kottke on the Art and Power of Hypertextual Writing

Jason Kottke, going meta on that one-paragraph hypertext editorial from the NYT that I linked to yesterday:

What makes this piece so effective is its plain language and its information density. This density is a real strength of hypertext that is often overlooked and taken for granted. Only 110 words in that paragraph but it contains 27 links to other NYT opinion pieces published over the last several months that expand on each linked statement or argument. If you were inclined to follow these links, you could spend hours reading about how unfit Trump is for office.

A simple list of headlines would have done the same basic job, but by presenting it this way, the Times editorial board is simultaneously able to deliver a strong opinion; each of those links is like a fist pounding on the desk for emphasis. Lies, threat, corruption, cruel, autocrats — bam! bam! bam! bam! bam! Here! Are! The! Fucking! Receipts!

How the links are deployed is an integral part of how the piece is read; it’s a style of writing that is native to the web, pioneered by sites like Suck in the mid-90s. It looks so simple, but IMO, this is top-notch, subtle information design.

Kottke often posts something and says exactly what I’d like to have said about it. But this one feels pulled from my own mind, almost word-for-word. I decided against going meta on the hypertextual nature of the editorial, to let it speak for itself, and keep my series of posts yesterday focused on the election itself. But now I can’t resist.

Writing for the web came pretty naturally for me. But that’s because reading on the web also came naturally to me. But nothing builds muscles like exercising them regularly. And now, 20+ years into writing Daring Fireball, I don’t really think of writing in hypertext as a special form of writing. It’s just writing. It’s non-hypertext writing that now feels slightly weird to me. Limiting.

It’s not that different a thing, being able to link words within one’s prose to other pages on the web. But it is different. Being able to apply italics or boldfacing to words is somewhat more expressive than being limited to un-styled plain text. Talented writers don’t need italics, but they can make good use of it if it’s available.1 Being able to add hypertext links to certain words is like that, but so much more powerful. Italic and bold emphasis are information-density additives. But as Kottke observes, used deftly, hypertext links are an information-density multiplier.

The way I’ve long thought about it is that traditional writing — like for print — feels two-dimensional. Writing for the web adds a third dimension. It’s not an equal dimension, though. It doesn’t turn writing from a flat plane into a full three-dimensional cube. It’s still primarily about the same two dimensions as old-fashioned writing. What hypertext links provide is an extra layer of depth. Just the fact that the links are there — even if you, the reader, don’t follow them — makes a sentence read slightly differently. It adds meaning in a way that is unique to the web as a medium for prose.

What made the Times’s editorial stand out to me, like a clarion jolt, was not just that it was so simultaneously incredibly thorough yet remarkably brief, but that the Times just doesn’t write like that very often. When they produce things that are web-exclusive or clearly intended first and foremost for consumption on the web, it tends to be interactive multimedia, like their famous presentation of John Branch’s “Snow Fall” in 2012. If anything, in their prose, the Times — like most longstanding publications rooted in print — is generally stingy with links. Reading this 110-word/27-link firecracker of an exhortation to end the Trump era wasn’t just pleasing to my reading ear, it was like hearing a beautiful song sung by a voice — that of the Times editorial board — that I can only recall heretofore having spoken. I didn’t know they could sing, let alone sing like that.

It also brought to mind how social media has largely kneecapped true hypertextual writing by not enabling it. You can, of course, add links to web pages in social media posts on any of the various basically-the-same-concept-as-Twitter platforms like X, Threads, Bluesky, or Mastodon2, but you do so by pasting raw URLs into posts. (Instagram, by far the world’s most popular such social network, doesn’t even let you paste hyperlinked URLs into the text of posts.) The only links that work like web links, where readers can just tap them and “go there” are @username mentions. On social media you write in plain un-styled text and just paste URLs after you describe them. It’s more like texting in public than writing for the real web. A few years ago these social networks (and private messaging platforms like iMessage and WhatsApp) started turning URLs into “preview cards”, which is much nicer than looking at an ugly raw URLs. But it’s not the web. It’s not writing — or reading — with the power of hyperlinks as an information-density multiplier. If anything, turning links into preview cards significantly decreases information density. That feels like a regression, not progress.


  1. That’s the whole premise behind Markdown’s syntax. It strives to allow plain un-styled text to feel — or, if you prefer, *feel* — like styled hypertext. ↩︎︎

  2. Mastodon technically allows web-style hyperlinks on words, but few instances support it, and thus almost no client apps support it in their editors for writing posts. Micro.blog is an exception↩︎︎