Can we ever truly get away from categories?

On "Serendip's Evolving Web Principles":

I'm interested in Grobstein's thoughts on categories/databases as restricting structures, rather than gateways to unlimited knowledge.  In the above-mentioned segment it is written that "The disorder of the Web is one of its greatest virtues."  It seems that Grobstein, who was thoroughly involved in the making of the site (I'm not sure if he wrote this segment, though) would have a problem with "categorizing," that is placing people/things/ideas/perspectives into rigid categories.  However, in "On Beyond a Critical Stance" Grobstein writes "Skepticism is valuable in the service of moving beyond existing understandings, by whatever route they have been achieved, to understandings more satisfying than any of those that currently exist."  Who is it that judges which things are "more satisfying" than others?  And while doing this are you not putting ideas/perspectives into the categories of 'satisfying' and 'more satisfying' and thus devaluing the ideas placed into the former category?