You'd need a seance for a couple years now, but pretty much any truck driver you'd run into will have many opinions.

From memory... don't work for large companies, because a place that doesn't do business in NYC or LA can't even think of sending you to the streets of NYC or LA, which according to him was no picnic for a truck and I'm sure is only worse now. If you don't want the office politics drama of not picking up a load to FL, don't do business with a place that has loads to FL, its that simple. I seem to recall hearing he had a deal with a franchise farm equipment dealer where by definition he never went out of the dealership territory other than occasional horse trading between dealerships. When he got sick of living in Iowa he moved on.

Much like the computer biz, life is better if you're not in the middle of it. Not being in the middle of everything meant feast or famine, which was OK for him.

He was retired, sorta, but still needed 90s era health insurance premiums (which I'm sure was comically low compared to current costs) and he wanted to avoid 401K early withdrawal penalties, so he only worked for restaurant and bar money. That kind of personal financial position helps a lot when looking for quality of life. If you demand 10% more pay than everything else, they'll pay it, but take it right outta your hide, horrible working conditions and bad routes. Better to love life at 50% of income than to exhaustively minmax up to 110% of income and hate every millisecond of it.

Most "IT type positions" would not be amused if you decided not to work that month because you have enough cash for now. But trucking was (is?) flexible.

There is a bias in the truck driving biz that is the opposite of "IT type work" where its assumed that an old guy will naturally be more reliable, harder working, and more knowledgeable about trucks and routes and just generally a better overall trucker. In that way it can be a decent second career.

He claimed that once him and his wife saw the country, it got pretty boring. I imagine anything can become boring, eventually. So it might be super exciting for only a decade, after which "eh".

Some other advice is there are downsides of exotic travel. I live in a state with no known non-escaped pet poisonous snakes and only one species of venomous spider. You go trucking in the deep south and you'll inevitably meet some kind of swamp animal that can kill you. Also as a Midwestern boy, suddenly after decades of not caring, having to be really careful about hurricanes on coastal runs was weird. On the other hand, when he got fed up with visiting an area, in only a couple days he could be back in the western mountains. Thinking of geography in terms of time not distance was another anecdote he talked about. No matter how hot it was in Louisiana he could be back "home" so to speak in North Dakota in a couple days. His relatives (us) treated him like a sailor who could be gone for months and needs years of warning for a wedding, but crazily enough he could get around faster than people with "normal" desk jobs when he had to (sick relative, whatever).

He got tired of his truck after a decade or so just like you'd get tired of a house. Truck dealerships make some commission just on people getting tired of the layout and windows, just like houses.

I wasn't super close to him but there was some weirdness in the 90s such that his retirement fund was somehow available to him with lower (no?) penalties because he bought a truck with it. Or maybe it was accounting BS and he figured once he made 10% of the cost of the truck in profit (which didn't take long) that he "wasn't paying a penalty on his withdrawal" even though technically on paper he did. This is complicated and worthy of some research if you're serious. I wasn't close enough to him to talk taxes and accounting but I'm sure basically setting up a small business is an interesting topic. (Oh and edited to add he had some tax weirdness where he was basically homeless but it turns out renting an apartment in an income-tax-free state was cheaper than paying income tax in a income taxing state, I'd talk to a real tax accountant about that before renting anything or filing anything)