I need some confidence

Just like the robots that were supposed to paint cars in the factory in the 1980's were painting each other! LOL

 

Matt
The point in going to college is learn some business and accounting knowledge. If your goal is to be a O/O someday, you are running your own business, not just driving, so you need that knowledge to have a chance of being successful.
At least look into going to a Community College for 2 years. The cost would be reasonable. Do you do sports, maybe a sport scolarship???

I see you live in Elk River. Go over to LeFebvre & Sons and talk to Chuck or Buck. They may even let you do a ridalong with one of their drivers. They haul mostly concrete pipe so you may want to wait till spring and it warms up a bit. I drive for them down here in K.C. area.

 

I would first learn how to budget your expenses, what ever that may be at your age. Learn Quick books, or any other related software. Start to save your money now, if you are working I would save atleast 10% or your wage earned and put it a blue chip stock that pays dividends. Hopefully Obama wont raise capital gains tax by the time you decide to become a trucker and withdraw on that. Or if you want to be ultra safe with your money, you can open a ING savings account, probably only get .5% on what you will save.
If you do decide to go to school, go for something relevant for your future trucking job, like a BA, when you are out of school at 22 you will have you bachelors in BA. At 22 you can drive anywhere.
For myself I budget like a nut, its the only way you know how much goes to my priorities and the rest can go for fun. Remember don't get into debt, don't have to many credit cards, don't buy something that you can not afford or do not have any intent on affording it years to come. Remember if you buy a car at 16, not only you will have payment but you will have insurance, always think before you jump. All Im saying is for you now to start to practice basic finance, you will need these skills in order to own your own rig and not get into trouble. Good luck, seeya on the road!