Spend All Your Money, Right Away

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.

Watch Way Too Much TV

Watch a lot of TV. A lot. Don’t just watch one episode, watch all the episodes. Watch from the very first to the very last. Watch the whole series. At once. Twice. But don’t just watch the series. Become the series. Don’t just come to know the characters, come to know yourself through the characters. And then do it over and over again with another series and then another. Once you start understanding your life as a narrative, it will make a lot more sense.

Never Finish Anything

Take the incomplete. Abort. Let the half-finished, half-assed projects pile up around you. Make things difficult for yourself. Self-sabatoge. Fail. Fail often.
Like this blog: Did I really think I would want to maintain this tongue in cheek, self help voice indefinitley? Did I really think THIS was the blog I wanted as my name .com?
No. The point is, I didn’t think. Learning not to think and to be spontaneous is difficult, but important. It teaches you how to adapt. You must throw yourself passionately into things and then leave them just as passionately. Abandon with reckless abandon.
Rip it up and start over.

Move to The City

The nearest and cheapest, if you’re not already there. Baltimore, Pitttsburg, Boston, Chicago. New York is too crowded and your chances of falling into serious debt, addiction, depression or prostitution are far too likely.
Use your retail/restaurant experience to get a job and your drop-out street cred to get some friends/roommates. In the city, you’ll cultivate your angst and get plenty of fodder for your art.

Drop Out of College

It should only take a year or two to realize you’re in way over your head. Drop out. College makes a lot more sense for people over 25 (at least), anyway. The best part about youth is that it’s yours to waste and you’re just dumb enough to do it. Finishing college right away in four years is the quickest way to force you into a dull, grown-up life of 9-5 and business casual khaki.

Don’t take all the college at once. It’s nice to save some college for later, as you’re going to want it to go back to (maybe more than once). Getting kicked out for something simple like drinking or smoking pot is alright, but anything more serious may alert the law and/or mental health officials. Remember, it’s important to stay under the radar. Also, you can always TELL people you got kicked out in order to gain more credibility once you’ve moved to the nearest city and met your fellow derelicts.