Advice: Don't patronize readers
Dave Winer has a habit of linking uncommon words to their definition at dictionary.com. For example, in this post, he links 'doldrums' as so. He also does it on this post for the word 'iconoclast'. And I'm sure I could find other examples.
I find this habit slightly annoying. For one, it assumes that the reader doesn't know as much English vocabulary as the author. This is patronizing, and therefore alienating for the reader. It is probably not Winer's intention to connote his intellectual superiority via his sesquipedality. Perhaps his intention is to provide a useful link for people wishing to build their vocabulary.
On the other hand, a writer should assume that the reader knows the definitions his or her words. And in the case that the reader doesn't, a writer should assume that the reader has the means to learn the definitions of those words. Winer, in the cases above, assumes neither. And while he may have had his reader's best intentions in mind, his style comes across as pretentious. Kind of like me using the word 'sesquipedality', which I had to look up.