If you were trying to make your bones, how would you prove yourself? How would you earn that dough to impress the hierarchy?

Australian,

I guess I would do something white collar, semi-legit to minimize the risk of a long prison sentence, maybe stock manipulation, mortgage fraud or a ponzi scheme with several shell companies that lead no where and front men. I don't have what it takes, I go back into the store and make it right when the cashier gives me too much change.

Warning label:
Please do not try this at home. Making your bones carries significant side effects such as guilt, imprisonment, retribution, runny nose, nausea, and erections lasting longer than four hours. It should only be attempted by professional cold blooded criminals. Any such acts seen on television are fictional and performed by trained actors.

You have to be able to rob kill steal have knowledge of MS Office + Photoshop and also be also to fill out a Speedo.

The lowest risk of jail.

I'd run high end escort girls and local massage parlors and have them held in shell company after shell company. Plus, you can always find some washed out girl to run the thing (madam) and take the fall.

Maybe get into the Pawn Shop game, since they're crooks anyway, lol...Used car lots, canteen trucks, etc