I've often thought of what it would be like to go back in time and talk to a younger version of yourself. Wow, it would be cool to run into a 22 year old Joey, just starting out in the trucking industry and share some wisdom.
As I said in the introduction, I've heard that question posed to successful entrepreneurs many times during interviews and the answers are always similar and revealing of a pattern of self doubt. Usually the advice goes something like this,"the things you were worried about didn't 
happen, so that challenge you're considering.....Go for it!
I wanted to be an owner-operator many years before I took the leap. However, I was too risk adverse and possessed a lot of self-doubt as to whether or not I could pull it off. My advice to a younger me would be to buy a truck and lease on to a carrier after a few years of professional driving under my belt. A lot of the tough decisions that an owner-operator has to make actually become easy decisions. Many times there aren't many good options so doing the best thing presents itself very clearly.
In the military, they teach us to Ready, Aim and Fire...in that order. However, regarding entrepreneurial endeavors, sometimes it's most prudent to Ready, Fire and Aim! You can adjust your trajectory once you're in motion. Like I've said before, it's hard to steer a parked truck.