I'd like to think that, like opening paragraph brings up, this piece is an old snapshot that brings some embarrassment today. At the time it was posted I would have been excited about it. 15 years later, indulgently and exhaustively defining the well worn subject of heresy feels pretty dull.
Like most celebrations of heresy, this skips the fact that orthodoxy has its own value: coordination. Parents teach their kids to avoid bad words so that they can coordinate with others. This is not a bad thing.
A better thing still is for kids to understand that words aren't inherently bad but that being conscious of how others feel about them is good. The impactful heretics do the hard work of helping the orthodox world adapt to what they have discovered.
And meanwhile, the vast majority of heresies are authentically wrong. Celebrating being heretical for its own sake, rather than a combination of truth seeking and empathy, had enabled all manner of jerks and frauds over the years. Tech culture needs a more nuanced view of this topic.