Best Software Writing I by Joel Spolsky
A good if not great book collecting essays exclusively from the Web about software and its users. The best essays—like "A Group Is Its Own Worst Enemy" by Clay Shirky; "EA: The Human Story" by ea_spouse; "Autistic Social Software" by danah boyd (already covered in this weblog)—deal with the human element (so much phenomena we think software makes new to us has already been covered by economics, sociology, psychology, etc.) or are useful in a business setting. The latter include but are not limited to "Team Compensation" [PDF] by Mary Poppendieck and "Hazards of Hiring" by Eric Sink, which both deal in the practical aspects of managing the development of software. (In fact, I submit that Eric Sink has more—and more interesting—things to say about the software startups than Paul Graham does.) While interesting for their use of cartooning, essays like "Excel as Database" by Rory Blyth and "A Quick (and Hopefully Painless) Ride Through Ruby (with Cartoon Foxes)" seem overly cute, especially the former, the cartoons not really adding much to the text.
Pointing out the obvious—this is computer software we're talking about—only 3 of the 29 essays were written by women, and all 29 essays were written in the past year or so. To Spolsky's credit, he gave the first book a number and not a year, so there's nothing preventing him or a future editor from including classic essays written about the subject as well as those from the year previous to publication. Also to Spolsky's credit, all essays are selected from texts freely available on the web (a good chunk from weblogs) so that people can forward the writing they've read in dead trees form to their those who might be interested in the articles via IM, email or weblog.