The w3 Principles of Design is an interesting read. In particular, the Principle of Least Power is interesting. This principle doesn’t seem to get much attention these days in software design with DSLs being often embedded. That is “internal” rather than “external” (in Fowlers terminology). This makes the languages harder to analyse and therefore tools are harder to build.
I’ve read the original Worse Is Better article by Richard Gabriel a couple of times now. I discovered it via my interest in programming languages (Lisp in this case).
Jim Waldo reminds us that Better really is *better* in Artima article Worse is worse.