His thoughts on life choices, education, prestige, and other subjects.
Though I liked programming, I didn’t plan to study it in college. In college I was going to study philosophy, which sounded much more powerful. It seemed, to my naive high school self, to be the study of the ultimate truths, compared to which the things studied in other fields would be mere domain knowledge. What I discovered when I got to college was that the other fields took up so much of the space of ideas that there wasn’t much left for these supposed ultimate truths. All that seemed left for philosophy were edge cases that people in other fields felt could safely be ignored.
Computer Science is an uneasy alliance between two halves, theory and systems. The theory people prove things, and the systems people build things. I wanted to build things. I had plenty of respect for theory — indeed, a sneaking suspicion that it was the more admirable of the two halves — but building things seemed so much more exciting.
The problem with systems work, though, was that it didn’t last. Any program you wrote today, no matter how good, would be obsolete in a couple decades at best. People might mention your software in footnotes, but no one would actually use it. And indeed, it would seem very feeble work. Only people with a sense of the history of the field would even realize that, in its time, it had been good.
I wanted not just to build things, but to build things that would last.
One day I went to visit the Carnegie Institute, where I’d spent a lot of time as a kid. While looking at a painting there I realized something that might seem obvious, but was a big surprise to me. There, right on the wall, was something you could make that would last. Paintings didn’t become obsolete. Some of the best ones were hundreds of years old.
[T]he most important thing I learned, and which I used in both Viaweb and Y Combinator, is that the low end eats the high end: that it’s good to be the “entry level” option, even though that will be less prestigious, because if you’re not, someone else will be, and will squash you against the ceiling. Which in turn means that prestige is a danger sign.
One day in late 1994 […] there was something on the radio about a famous fund manager. He wasn’t that much older than me, and was super rich. The thought suddenly occurred to me: why don’t I become rich? Then I’ll be able to work on whatever I want.
Meanwhile I’d been hearing more and more about this new thing called the World Wide Web. Robert Morris showed it to me when I visited him in Cambridge, where he was now in grad school at Harvard. It seemed to me that the web would be a big deal. I’d seen what graphical user interfaces had done for the popularity of microcomputers. It seemed like the web would do the same for the internet.
If I wanted to get rich, here was the next train leaving the station.
I knew that online essays would be a marginal medium at first. Socially they’d seem more like rants posted by nutjobs on their GeoCities sites than the genteel and beautifully typeset compositions published in The New Yorker. But by this point I knew enough to find that encouraging instead of discouraging.
One of the most conspicuous patterns I’ve noticed in my life is how well it has worked, for me at least, to work on things that weren’t prestigious. Still life has always been the least prestigious form of painting. Viaweb and Y Combinator both seemed lame when we started them. 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. Even Lisp, though prestigious intellectually in something like the way Latin is, also seems about as hip.
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 worked hard even at the parts I didn’t like. I was haunted by something Kevin Hale once said about companies: “No one works harder than the boss.” He meant it both descriptively and prescriptively, and it was the second part that scared me. I wanted YC to be good, so if how hard I worked set the upper bound on how hard everyone else worked, I’d better work very hard.
 There is a general lesson here that our experience with Y Combinator also teaches: Customs continue to constrain you long after the restrictions that caused them have disappeared. […]
Which in turn implies that people who are independent-minded (i.e. less influenced by custom) will have an advantage in fields affected by rapid change (where customs are more likely to be obsolete).