In the not too distant future, I'll be lucky enough to have the opportunity to retire at 50 years old from my current profession. I'm financially secure with good pension and retirement savings. However, I don't want to sit idle. If I could wave a magic wand, my goal would be to buy a decent used truck outright, chuck the wife in the passenger seat and hit the road, wherever I want to go, taking time off whenever we wanted. Now, I know that no such magic wand exists and there are many considerations to be made. I understand that jumping right into owner/operator isn't viable due to experience requirements by carriers and insurance, etc. I fully grasp the concept of "paying your dues" and the last thing I want to do is give the impression that I'm minimizing the hard work and years put in by those in the industry. From the research I've done it looks like the best thing to do will be to become a company driver to get some experience under my belt. With that said, because I'm not forced to drive to pay the bills, and I do have the financial backing to purchase a truck and drive with low overhead, AND I already have health/life insurance...after getting some company OTR experience under my belt, is this a viable goal? For example, drive for 6 months and take a couple months off, then pick up again when I'm ready to get back on the road. I appreciate any insight.