Some good posts here. I'm an "old guy," and I'm hitting the OTR trail for reasons of my own. Mostly, I took a beating in the Bush Depression, my retirement account, my real property value, and my job all headed in the Down Direction. The "failure is not an option" is a good thread. There's no magic carpet: I'm sure the first year, or two, I'll be paying my dues, figuring it out, working to achieve my goals. You gotta start at the beginning, and I'll be starting with Conway Truckload. With a smile!
Old guy here also. Like any job- there are some milestones you have to get over. I've been out almost three months and 30K and this last trip was the first time I wasn't grinning. It seemed like work and there was a bunch of things at home that I wanted to get done. Then I got my reload info and it was a pretty exciting spot and load(flat bedder) and suddenly it was steering, gearing and grinning again. I would expect that 3 months, your first ticket, and 1 year are the normal milestones when you reassess your career choice. I actually feel pretty lucky to be truckin' right now. I spend very little time in the truck stops but the drivers I have met have been pretty descent guys and ladies and everybody has an interesting story and its always nice to meet and talk to a career trucker.
any ways- good luck and I hope you enjoy being a driver.