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.