What was the point in your career when you realized you hated your job?

I'm in IT. My boss liked to be very vague about what he wanted so I learned early on in my career to not start any big projects unless I spelled out on paper exactly how it was to work and exactly what the finished product was and how much everything was going to cost and then have my boss (the owner of the company) sign off on it.

On this one particular project, we had probably about 80 hours of meetings to hammer out details. My other boss loved meeting but didn't know how to keep them focused or end them. I purchased hardware and expensive software from vendors and shared the job details with them. I had set up the hardware and the software and then scheduled the vendors to fly in to get everything working to specification.

On the final day, we get everything set up exactly as specified and we tested it with success. My boss walks in during the final test and says that he want's it to work as if he pulled someone off the street to do the task. He then steps up and try's to do the procedure but is mimicking the movements of a drunk person or a toddler and intentionally messing up each step in the process. Of course the task fails. He then declares that the whole process is shit and that's not what he wanted and then he walked out.

The vendors had to make their flight so I walked them outside and they just looked at me and asked what the hell happened. I was just confused and embarrassed myself. I told them not to worry about it and I would take care of it. It was then that I realized that this place wasn't for me.

/r/AskReddit Thread