Go ahead and get your CDL and all the endorsements but hazmat (doubles/triples, air brakes). The reason I say don't get your hazmat is because simply it's gotta be renewed on a yearly basis (IIRC) and you gotta pay that fee every time. It's a simple written test though so you can add it at any time I think. For your CDL to be valid to drive a big truck you'll also need a current DOT medical card.
Now the issue with driving as a career is that you will have the license but not the experience that you need to be hired by the better carriers. They hire truck driving school graduates because that truck driving school counts as recent experience as the insurance is concerned. They may hire you and put you through a refresher/orientation vs. the full on CDL school or you may have to go through CDL school again. Just depends. Either way you're pretty much looking at the big starter companies (Werner, Swift, Schnieder, and so forth). There are some pretty crappy companies to work for, some tolerable ones, some a bit better, etc but regardless of what company you sign on for expect to spend a lot of time away from home as an OTR driver. If you're looking to be home on a regular basis or every night this ain't your career, particuarly starting out. You can get a local/regional gig once you've got some experience but to get there is going to generally take a year or a couple of years of OTR experience. If you're a nomadic person like me that can tolerate that, you'll do a lot better. If you've got a wife/gf that wants you home frequently and you like to be home frequently, then you're gonna be unhappy most likely. The reality of it is you're spending several days to weeks on the road, sleeping in a sleeper and taking truck stop showers and eating on the road. You've got wierd hours of service laws to contend with, too that can make for an odd schedule. And you'll spend plenty of time waiting to get loaded/unloaded, where you ain't getting paid because your wheels ain't turning. Figure an average truck driver makes from 22-26k per year starting out. If you can budget yourself on that, you'll do fine (it's what I make as a park ranger, so it can be done)
There is also stuff like expediters (you'll see them in anything from a van to a Sprinter to a straight B class truck to a class A tractor trailer). You need to contact Bogie about stuff like that.
If you can endure paying your dues as an OTR driver then you can get into some pretty good gigs that pay good. Getting that experience so you can move on to a better company with more favorable terms and higher pay is the part that really blows.
Now of course that's pure driving jobs. There are plenty of jobs out there, particuarly in the trades, where having a CDL is very advantageous because driving a bigger truck is part of the job but not the whole job (railroads, utility companies, etc).
