Sorry, but I don't agree. Really great software never ages. Like math: if it's correct, it never ages. Period. If it does age, it means it was not well engineered from the very beginning.

    «10 y.o. technologies are history. 10 y.o. software without major upgrades is dead. While 10 y.o. cars are quite good and decent.»

If the web does age, and it does, that should give us some pointers on what's wrong with it.

I can't decide if this post is asking people to move fast and break things, or iterate gracefully.

I think iteration is very powerful, but we don't seem to have fixed the problem of when something needs to iterate beyond its old ecosystem.

I haven't said that coherently, but I mean things like WordStar or WordPerfect moving from DOS into Windows - these two huge word processing systems failed to make the transition and are now niche products used by a tiny number of geek enthusiasts. They reached a point when iteration wasn't enough, and they needed some other thing.

Would Google fall in the "fox" category ? They created significant stuff in various domains ...