Now when I started driving I was 21 years old, hadn't traveled too much, had never been married, and had no children. The idea of traveling all of the time and living in the truck sounded AWESOME, and it was! The better part of my first 9 years of driving was over the road. I would stay on the road for weeks and sometimes months at a time. I just totally loved it! It really suited my personality and lifestyle. I was able to give up my apartment and vehicle and just let the money pile up in the bank. I usually found myself driving a lot during the week and having a lot of free time on the weekends to entertain myself. I'd go to bars, sporting events, concerts, and do the “tourist thing” like in Las Vegas or New Orleans. It was spectacular!
So your first consideration should be home time. But please be honest with yourself. Don't convince yourself to do something that deep down inside you probably have some serious doubts about. If you have a family please try to find a job with as much home time as possible. If you absolutely NEED to make as much money as possible at least for a little while then at least try to formulate a solid plan that will get you out of your money crunch and into a position to take a job that will get you home as often as possible. I'm telling you, too much time away from home can ruin a family. Try to avoid it.
The next big consideration will be the size of the company you choose to work for. I have worked for companies with over 5,000 trucks and for companies with as few as four. It's a huge cultural difference.
The larger companies have a huge amount of resources available. They have tons and tons of different types of freight and driving opportunities. They often have local jobs, dedicated jobs - where you remain with one customer or run one route all the time, regional jobs, and over the road. They have much more flexibility when it comes to home time and will allow you to freely move between different divisions within the company when you feel an opportunity presents itself.
Larger companies also have accounts set up with customers, lumpers, repair shops, towing companies, motels, bus companies, and truck stops. These accounts generally allow you to walk in the door, tell them who you work for, and get what you need taken care of without doing a thing. Repairs, towing, showering, getting bus tickets when needed, and picking up or delivering freight becomes much faster and easier under this system. To me this was always a really big deal.
Larger companies also have a large pool of equipment to use. A variety of tractors to choose from and a huge number of additional trailers available make life much nicer for the driver. With the extra trailers you get to do a lot of “drop and hooks” where you pull into the customer, drop your trailer, grab a different trailer, and leave. You don't have to wait around to be loaded or unloaded. This is really huge because most jobs pay by the mile so the time you spend sitting around waiting to load or unload is unpaid, wasted time. You want to keep rolling as much as possible and drop and hooks can help you make a lot more money in a lot less time. Drop and hooks also give you more flexibility as far as when you make your pickups and deliveries.
Often times they will give you a deadline to pickup or deliver but you can generally get in there as early as you like, 24 hours a day. So if you have to pick up a load that's sitting in a trailer in downtown Chicago you don't have to try to push through rush hour traffic to arrive at a certain time. You can go in late at night when traffic is light. Or maybe you're gonna get there really early but you really would love to take a nap for an hour or two or sit down for a nice meal first. Go for it. As long as you arrive ahead of the deadline everyone is happy. Believe me you're gonna LOVE having this kind of flexibility.
To continue with this theme larger companies tend to have a long list of perks. I've worked for companies that had things like free family counseling, large plush driver facilities with arcades, big screen TVs, and restaurants, free 24 hour medical phone lines where you can call and talk to nurses confidentially about any medical questions you might have, discounts on travel accommodations, top of the line health insurance, 401k and direct deposit, free high speed wireless networks, shower facilities, and on and on and on. I must say at times we'd wish they would just pay us more instead, but you know how that goes. The perks really are unbelievable though.