Art Kavanagh

Criticism, fiction and other writing

Paul Graham and the online essay

I read Paul Graham’s recent essay, What I worked on, because someone tweeted a longish quote from it including this paragraph:

It’s not that unprestigious types of work are good per se. But when you find yourself drawn to some kind of work despite its current lack of prestige, it’s a sign both that there’s something real to be discovered there, and that you have the right kind of motives. Impure motives are a big danger for the ambitious. If anything is going to lead you astray, it will be the desire to impress people. So while working on things that aren’t prestigious doesn’t guarantee you’re on the right track, it at least guarantees you’re not on the most common type of wrong one.

I found that the essay contains a lot more than that nugget of wisdom. The whole piece is a personal memoir of — the title’s a bit of a giveaway — the things he’s worked on in the course of his career. Those things include the origins of “Software as a service” (SaaS), Lisp (which he describes as “a language defined by writing an interpreter in itself”) and an approach to funding startups that doesn’t mean gigantic investments of venture capital right from the start. He studied painting in Florence and RISD, and spent substantial periods working on still life paintings.

His essay reads in part like a history of tech startup culture, something that isn’t necessarily going to appeal to everyone. Graham makes it interesting because he has an idiosyncratic way of looking at things. (That passage about working on unregarded projects is a good example.) He’s highly intelligent and perceptive and has a knack for seeing a problem or situation from an unexpected angle. His work as cofounder of Y Combinator came about, not because he particularly wanted to mentor and fund startups, but because he believed “that the best sources of seed funding were successful startup founders, because then they'd be sources of advice too”.

It’s worth noting in passing that, while Graham is an impressive writer and thinker, it doesn’t follow that these qualities will necessarily lead to benign results. Y Combinator’s two greatest successes have been AirBnB and Dropbox, neither of which I consider a net benefit to the world.

In cities like Dublin, the effect of AirBnB has been to restrict the supply of residential property available for longer term letting, and therefore driving rents up to unaffordable levels.

I know many people who use Dropbox all the time and who can’t imagine being without it. I’ve been suspicious of it since reading a few stories like this one from Daring Fireball. Perhaps I’m being unnecessarily suspicious but I’m going to continue to avoid it.

The main thing I’ll take away from the essay might well be the word “essay” itself. Around 2001, Graham posted something on his website,, “which I’d created years before … but never used for anything”. It was a talk he’d given about Lisp at a conference. Somebody linked to it on Slashdot and he got 30,000 page views in a day.

Wow, I thought, there’s an audience. If I write something and put it on the web, anyone can read it. That may seem obvious now, but it was surprising then. …
This had been possible in principle since 1993, but not many people had realized it yet. I had been intimately involved with building the infrastructure of the web for most of that time, and a writer as well, and it had taken me 8 years to realize it. Even then it took me several years to understand the implications. It meant there would be a whole new generation of essays.

He concluded:

I’ve worked on several different things, but to the extent there was a turning point where I figured out what to work on, it was when I started publishing essays online. From then on I knew that whatever else I did, I’d always write essays too.

It was that recognition that led to his observation about the value of working on things that aren’t prestigious: “I still get the glassy eye from strangers when they ask what I’m writing, and I explain that it’s an essay I’m going to publish on my web site.”

Since I started to post more writing online about 4 years ago, I’ve been self-conscious about not being quite sure what to call it. “Posts” seems to come naturally but it’s easy to overuse, and then what’s the appropriate verb? “I posted a post” won’t really do. “I wrote a post” is OK, and I suppose the noun implies that I didn’t just write it but put it online also. Another term I’m perhaps too fond of it “piece”: I wonder if it sounds affected, as if I’m pretending to be a journalist? I very occasionally use “article” but I think it applies better to a piece that appears in a journal or magazine. So, I’m grateful to Paul Graham for reminding me about “essays”.

It’s not a term that I had previously associated with the web or the internet. Essays, surely, belonged in dusty, leather-bound volumes by Hazlitt or Carlyle. But it seems they can also be found on Paul Graham’s website.

I’ve been finding it easy to write something quick and disposable on a topic I’ve got a bee in my bonnet about: something like the future of search or of the web, the relative merits of Markdown and LaTeX, or of HTML and RSS, or ePub and PDF. This feels satisfying, and it’s obviously “writing” — but then I notice that months have gone by and I haven’t written anything about Andrew Marvell, who is supposed to be my principal subject.

I had been a bit puzzled by my decision to send out a newsletter on Substack, when I’ve said in the past that I consider email an out-of-date technology and a poor alternative to RSS or the web. It was only after I read Graham’s encomium to the essay that I realized that I chose to write a newsletter not because I like the medium of distribution but because it gives me the opportunity to write longer, more discursive and (I hope) more considered pieces that are in some sense walled off from less weighty and more ephemeral posts. So, Talk about books is my commitment to write a regular essay on a bookish or literary topic. It’s a relief as well as a surprise to have figured out, three and a half months in, what I’m doing with it.

Posted by Art on 06-Mar-2021, updated 07-Mar-2021.