I keep coming back to wanting to drive a truck for a living. I love to travel, I love the sounds and smells of the big diesel engines and I just plain enjoy driving trucks. I feel like a kid with a Tonka toy.
I plan to drive over the road if I ever retire from machining.
For the 4 or so years when I worked as a diesel mechanic I got to know lots of drivers. My mother used to drive and eventually started a partnership with a small trucking company and then split off on her own with a fleet of about 20 trucks. My brother and I were the mechanics for a while. I had 3 years or so of previous experience working in a fleet shop in St. Louis. She did pretty well for a while but the company went under a few years ago. The price of fuel ate away too much of their margin and with the majority of the trucks nearing one million miles and some over that mark it was only a matter of time before some big repair bills sent the company down the drain.
I know of one owner operator who hauls explosive hazmat and nets around $200,000 per year. He is ALWAYS on the road. I've known tons of company drivers who, financially, would have been better off flipping burgers. But they love being on the road and the nomadic lifestyle.
A lot of times breaking into the business is a catch 22 (unless you're willing to drive for less than the equivalent of minimum wage); you need a driving gig to get 2 or more years of experience, you need 2 or more years of experience to get a driving gig.
Some companies will pay for your schooling, if you agree to work for them for 1 or 2 years. They advertise saying you can make "up to $45,000 per year!". But, you know how that game works.
Mostly what keeps me from hopping in a truck for a living is being away from the family (already covered by several others in this thread) and the physical toll it takes on the driver. I like to lift weights at least 3 days per week and bike or box or grapple or pursue some other form of physical activity every chance I get, but you can't do that in a truck.
On top of the sedentary lifestyle you can't prepare healthy foods while tooling down the road either, so fast food garbage or truck stop fare would be the main source of sustenance. Neither one is very healthy. It is all too easy to fall into a low-paying, high demand driving job that pushes you too far physically and psychologically and will lead to chronic health issues. If you're careful you can make a good living and enjoy what you do. I've seen lots of guys who don't do either, but there are always exceptions.
When the price of oil goes back up there should be some high-paying oil patch related driving jobs. Think of all the project cars you could scope out all across the U.S.!