@Jeremymday--Love this thread idea, I've actually thought about this many times in my head before...the perpetual "What if" roller coaster. :)
I'd have to echo the sentiments of many others that posted above--hindsight is 20/20, the fun is in the journey, etc, yada-yada. At the "ripe old age" of 26, I'm able to look back and reflect a bit now. I have a 19 year old brother I'm trying to advise on the same principles mentioned here, actually. Would I have gone to college? My parents paid for it (lucky me, I know), so I probably still would have done college. My degree was in Economics, and I truly enjoyed it--I took a few C.S. courses and hated every minute of it, so engineering and C.S. would not be an option. I would possibly do accounting, but that field would be terribly boring as a career for even a few years.
Now that I've said all of that, what would I do? I would do one of the following plans:
a.)Learn a trade such as: Electical, plumbing, or carpentry (in that order), save 80-90% of my income, then start/buy a business pertaining to that trade once I'm 27-28. By the time you're 30, you have everybody working for you and you could "work" 5-10 hours per week checking on things and being more or less retired making six-figures every year for as long as you wanted. You could then sell the business for a nice profit at the time of your liking.
b.)Go to college, go in the military afterwards and start as an officer, save your $$, come back, start a business of your choice, possibly pertaining to said trade(s) stated above in section a. There's a plethora of things you could be trained for in the military, on their dollar.
c.)If you can stomach it, work in restaurants, preferably in a state where all minimum wage workers are paid the same (i.e. not California, Arizona, etc.). Some states allow workers that are compensated with tips to be paid a lower hourly wage, sometimes in the $2-3/hr range. I'd start as a server/busser making $35-40k a year at a decent restaurant, and work my way into bartending. As a bartender you should be able to make a minimum of $50-60k per year, or more working 4 days a week or less. Additionally, a good chunk of your money is cash, and is difficult to be taxed by Uncle Sam. Live a frugal lifestyle, save your income, no student loans to speak of, and you're done by 30+/-. At a bar I used to work at, most of the bartenders were making $6-7k per month AFTER taxes.
I've always been a fan of the trades, such an applicable skill and you get paid while you learn...does it get better than that???