LOL - I think the fun part has me stumped.
I have been a software support specialist, IT Manager and web designer (all of them with "added" duties).
Currently, I work for myself as a IT consultant supporting end-users and companies along with web design/hosting.
Working for myself is not really fun but it is a lot less stressful than working for someone else.
A career I heard of recently that looks like it could be interesting is a computer forsenic - someone who looks for evidence on computers and systems. A geeky detective!