If I had to do it all over again, starting in 1993 as a 20 year old, I would. Driving and the trucking industry has given me a very good life. However, I started when I was single and had no family. I always knew that this is a volatile industry, and saved my pennies because of that. If I had to start fresh in 2009, I would not going into trucking as a driver. If I had a wife and kids, I would not go OTR, for sure. I would probably spend the money that I would have spent on trucking school on learning a portable trade like being an electrician. I have a friend who fixes electric engines and he has travelled all over the world as a contractor with those job skills. In any event, I would find a trade that has a higher bar for entry than driving.
Everybody's situation is different. And a lot of us were different people when we started out. So it's hard to go back and say what I would've done now, because I'm different person than I was then. However, I think you're approaching this from a "knowing what I know now" angle. I didn't exactly quit college to go into trucking. I was partying too much and not making enough money in college to keep up with my partying. I went to truck driving school and then got into fights with two trainers at two different companies I started at. Then I ended up driving a taxi for about 7 years before coming back to trucking and finally getting through it with a trainer. When I went into it at that time, I would do it again because it was better money than driving a taxi, in the city I was in, and health insurance was the main thing as I had developed some physical problems. If I could go back to when I was in college, I definitely would have finished college and never gone near trucking. I would say it took about 3 years for me to become really comfortable living on the road and getting with a small company where you aren't bothered all the time with little things. Also, in 2006 I went to Iraq working as a contract driver. With the money I made there I traveled to Amsterdam, Israel, Bucharest, and lived in Buenos Aires for four months. If I never had gone into trucking, I may have never got to see and experience all that.