Enterprise IT organizations attract and foster mediocrity. This is a fundamental reason why large enterprises don't outperform leaner organizations even though they have more resources. This talk describes a fictional organization (albeit slightly inspired from reality) with huge cultural problems to illustrate how bad enterprise IT can be and how it came to be this way. In the first half of this session, we describe the mess we're in and how we got there; in the second half, we consider how we could have avoided this situation and how we can get out of it. Our premise is that a solid culture of learning and continuous improvement as well as a focus on good software architecture and practices could have prevented the mess, and that it is not too late to turn it around. I promise an entertaining talk with a lot of humor, and possibly some insights that you can take back to your organization so that you don't end up in the same mess (if you aren't already there).