That's a dangerous question to ask, isn't it?
My very worst job was as a dishwasher in a restaurant - I quit when they told me to clean the inside of the oven without switching it right off!
But my worst IT job was for a government agency, working on a project that had already been through the entire design/implementation cycle twice, was years overdue, millions over budget, and had now decided to declare itself an "Agile" project in a desperate attempt to inject a sense of urgency into the whole process. The aim was to upgrade and extend an existing system to include new
J2EE internet interfaces and so on. The underlying database and core functions were not going to change, and the company's key business processes had not changed radically for about 50 years. Should have been easy, no?
Well, I joined the project about a year into the
3rd attempt, when they were hiring legions of freelance developers and testers to implement the system.
Being "Agile", they didn't have much in the way of written requirements or specifications. Unfortunately, unlike most Agile projects (although I'm no Agile expert so maybe I'm wrong here), they also had an enormously bureaucratic process of establishing the requirements, which more or less prevented developers from ever meeting users.
Also, unlike most Agile projects I've heard of, they were actually taking a kind of waterfall approach to the implementation process i.e. lots of meetings to discuss requirements (without actually including the user representatives), then tell developers to implement something (not clear what), and finally hand the results over to an army of system testers. No obvious signs of iterative development, prototyping or user feedback, things that we non-Agile-experts would ordinarily expect an Agile project to include.
As a developer, if you wanted to find out what the user expected a particular program to do, you had to submit a request to the appropriate business analyst, who would then call one of the senior business users, who would then talk to the ordinary users, which could take days. Because of this bureaucracy, they had spent over 3 years on the project, already implemented it twice, and still didn't know what they wanted their new system to do. The developers had no way to find out what functionality they were supposed to implement, and the
test team had no way to design and plan their system tests, because nobody knew what the system was supposed to do in the first place.
The organisation also had a truly toxic working atmosphere, very political, lots of people bitching and backstabbing each other. Meanwhile, a lot of freelancers got so bored waiting for something to do that they quit before ever starting any real work, despite the very generous rates of pay. As for me, I was only on the project for a few weeks, before getting fired for asking too many stupid questions, like "does anybody know what they want the system to do?" (answer: we don't know) and "where are the user representatives?" (answer: another county). Because I'd been hoping to use my ill-gotten gains from this contract to fund my Master's degree, I could not afford to go to college after being fired, and spent most of the next year out of work.
Which is why it qualifies as my worst job ever.
However, a couple of self-proclaimed "architects" and project managers got some really cool buzzwords on their CVs, because they could claim to have run an "Agile" J2EE project (right into the ground...). So I guess it wasn't a complete waste of taxpayer's money, eh?
I think it finally went live about a year after my departure, although a colleague who survived the process to the bitter end told me the system was still rubbish when they signed it off. The depressing thing is that this isn't even the most incompetent or wasteful government IT project around - this was just a low-key screw-up by UK government standards!