Hmmm.

Probably 2001, the year that I sat on my backside sponging off the state and my parents and being absolutely hopeless at applying for jobs. Getting put on New Deal (a school-like government scheme for bums, idiots and criminals claiming jobseekers allowance to try and coerce them into getting a job) was also highly humiliating - getting treated like a naughty schoolkid when you're 19 is not good.

Plus of course the world changing for the worse on 9/11, if you were to factor world events into it.