Great distinction between creative and "destructive" surprises or serendipity, based on (too-)complete social contracts, that unwittingly remove all healthy space for experimentation. If you think about it, Clay Shirky's ideas here support N.N. Taleb's concept from _The Black Swan_ that real, creative innovations arise in environments that promote serendipity (i.e. "good" Black Swans) rather than Innovation Departments(tm) that are run according to old-school command-and-control type management structures. "Ok, here's where we at StuffyCorp innovate. Ready? 1, 2, 3, ... innovate! " These, according to Taleb - and here, Shirky - nearly invariably produce nothing of any particularly significant value, unlike environments that promote creative "surprises."
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