Spend your money as soon as you get it, on anything you want. Buy stuff! Now! Don’t save any money. Put off everything but spending money. Shop. Shop a lot. Go to the thrift store. Get on ebay – don’t bid, overbid! Scour Craig’s List. Make cash deals with strangers. Buy a lot of things that cost a little. All the time. Also, drink beer – it’s cheap and plentiful enough to crush a chunk of your budget without you even realizing it. Drink a lot of beer. Buy your friends beer. Then go shopping.
And (if someone gives you one) have a car (you will never save enough money to buy a car). This will ensure a constant squeeze on your finances. For added debt, never pay attention to where you park and watch the tickets pile up. Then just borrow money from your friends and/or family to pay for consequent boots and tows. Owing people money is another good way to keep humble, as it supports the requisite feeling of vague shame and the fundamental paralyzing sense of overwhelming dread.
Poverty is imperative for wasting your youth (for fun and profit!). It keeps you hungry (both literally and figuratively), crazed, and vapid – three keys to ultimate creative and financial success.