I’m a big believer in the old adage, “Those who do not learn from history are doomed to repeat it.” You need to examine your mistakes, figure out why and how you made them, and then use those lessons so you can do better the next time. In addition, I would prefer to learn from other people’s mistakes rather than committing them myself — it’s gain without the pain. So I asked myself the question, “What are the biggest IT fails in history?” And then the more important follow-up, “What can I learn from them?”

I wanted to find the failures that were significant and spectacular. They had to be impactful and memorable. There are plenty of stories about failed IT projects that “just” wasted a lot of money like this one from the Air Force (there’s a lot to be learned from them, too). But I wanted the projects that culminated in a momentous, go-out-in-a-blaze-of-glory, end-up-on-the-evening-news kind of failure.

Here’s my short list along with the lessons I took away from each.
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