Post your job progression:

[kyleb]

Under-the-table pizza maker/dishwasher
Library Page
Best Buy Sales
Best Buy Computer Tech
Library Supervisor
Game store employee
Formalwear sales
Dot-com technical assistant
Formalwear asst. manager
Formalwear store manager
Server/Waiter
Game store manager
Fine dining server/waiter
PokerStars CSR
Self-Employed

That was cool to type up. Good OP.

EDIT: The last five positions I had I was also supplementing my income with poker, and at times I was unemployed and living off of poker.