Essay is highly recommended; I've started Red Plenty after reading it, and am a little disappointed it's fiction rather than a nonfiction treatment of linear optimization. :)
The author of the book Shalizi is discussing comments in the giant (154+) comment thread for Shalizi's essay, incidentally: http://crookedtimber.org/2012/05/30/in-soviet-union-optimization-problem-solves-you/comment-page-1/
Three Toed Sloth has a nice exposition on the difficulties of optimizing an economy, including the best explanation of convex optimization ever: