Willian McKeen has written a compelling defense of the value of serendipity, prompting an annoyed Steven Johnson to ask for the meme to be killed, only to revive it.
In my humble opinion, the debate needs to draw some distinctions. We can't accuse the web as a whole of being bad or good for serendipity; and we need to distinguish between different types of serendipity.
On the first point: while it is true that the better search engines are the quicker we get to what we want (without having time to glance at the unexpected), search engines are not the extent of the web. Portals, blogs, and even RSS (all forms of aggregates) feeds provide much of the serendipity found outside the web.
On the second point: it is one thing to stumble upon the unexpected, and another thing to stumble upon something someone put where we are, next to what we are looking for (if indeed we are looking for something, which is not always the case). Machines can provide the first type of serendipity, which I agree is of a poor kind. But editorially-curated aggregates are also pervasive on the web, and these have much of the richness found in real life.
For a more elaborate discussion of these issues see my recent post on the subject.
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