A great deal of discussion at technology conferences involves success - what's the next big thing, how great and smart we all are, and so on. So for a while I've wanted to start to discuss the opposite and explore the lessons of failure, as I suspect that when some project succeeds, it's hard to identify exactly what made it happen, but when something goes wrong, it's pretty obvious.
Over the few years I've built a number of things, some of which succeeded spectacularly, a few of which did ok, and many that sank directly under the waves without making so much as a splash. I like to pretend that I've learned a thing or two from those failures.
So at this year's Foo Camp, I ran a session called "That Sucked" which allowed people to bring up some hairy problem they had, and how they solved it. As we went through various problems I tried to identify the true source of blame and note it on the board. Not to anyone's suprise, a great deal of angst centered around databases and encoding (especially Unicode). An especially painful story from David Heinmeier Hansson about both had everyone nodding in comisery, and Paul Graham recounted his first encounter with printf debugging.
After the session, a number of people approached me to talk about things they were too embarassed to bring up in group, many of which which were even better. I would love to see an entire meeting about this stuff, as it seems like lots of painful lessons could be applied to all. But barring that -- anyone got any particularly good stories?