First of all, I do not know about the legality of this, but here is what I have in mind.
I have taught in public schools for over 34 years. During summers I did stuff like work as a car mechanic, janitor, unloaded heavy equipment from tractor trailer vans, even flew a small plane (have a single engine land commercial pilot's license), and drove very little (1000 miles) CDL-A van between LA and PHX. I am air-brake, and fork-lift certified. I grew up on a farm, drove a lot of combinations with farm tractor, haywagon, etc, so I had kind of a natural talent for driving, though I always can learn.
Now, I am retired from teaching and I wonder if I can help someone not only drive, but load, unload, etc. Maybe I could find a few truckers to help so that I can work a schedule (for myself) so I could be a day in NM and a day in FL (to visit wife and children - hey I am still a family oriented person - so why not ask?).
I am a Christian and I can also tutor in algebra, algebra 2, pre-calculus, some calculus, chemistry, physics. I could teach the basics of flying using a computer flight simulator. Also, I just finished taking a business course with University of Central Florida, and so maybe I can help someone interested in starting a business in Florida.
Ok, so any advice, answers, anyone need my help?

My first thought is you'd need to dumb yourself down quite abit.
On a serious note most companies will not allow you to ride along due to liability, you may find an exception here or there but for the most part I think not. You would also stand a good chance of being stranded somewhere. Ever think about lumping at one warehouse? Or maybe a part time gig driving a forklift, I know guys doing that full time making $20-25 hr plus bennies I wish I knew them well enough to get me on!