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Boredom at the Long Tail

In this scene from Tootsie (the first minute of it) Dustin Hoffman makes a mistake - he believes that people (women in this case) really want what they ask for:

The Long Tail allows us to ask for what we think we really want - my iPod is full of stuff that (I think) really interests me - the podcasts and the music. What is missing in my iPod is a surprise. A bit of a different tune coming from nowhere, a bit of pure otherness, oddness, difference and randomness needed for inspiration. In terms of music, last.fm seems to be the half-way answer: it can surprise with a song that you haven't heard...but it cannot really, really surprise since it is still taking you on a guided tour within the confines of your taste (culture?, class?).

The current big thing in marketing seems to be targetting people with messages that they have asked for (gave permission to receive) - because of their interest, hobbies etc. Sounds good but I feel that there is some inherent paradox in this - advertising needs to surprise, needs to be unexpected and often needs to annoy in order to provoke a reaction. If you give me just what I want, I might not spill a champaign in your face but I will definitely get bored and start to ignore you.