After reading all of the post I will plug in my 2 cents.....Guys think that driving a truck is all that is required to make it as an O/O or with your own authority -- this is a huge mistake. You must learn the trucking industry from a business prospective. Learn everything about it -- this means the paperwork, communication skills, etc.
Analyze your expenses, know your cpm, etc. We run dry van and I can tell you I will not put less than 1.50 freight on my truck. We avg between 1.85 & 2.00 per mile and higher for shorter runs. Good paying freight is out there but you have to understand the business of load density. I have created a spreadsheet so when I'm booking a load I plug in the miles and it tells me immediately, the rate, gallons of fuel, cost of fuel, fuel cost by cents, ROI, dh cost, profit/loss. I know immediately what it's costing me to run that load. At that point I determine whether I'm going to take it or not.
If you can't manage the paperwork then find someone to pay that will help you. Use the tools (truck, laptop, printer/fax, phone, etc) to help you succeed. Read about what's happening in the industry. Study rate trends. Know where you want your truck to be when rates are low in one area.