I think for the "working from home" folks, many either plan it far ahead of time or stumble into it. A lot depends on your current age, family size and demands, and long term available income.
There are some younger folks with families that hit the road and live the nomadic life style. Usually, those are by careful design. Home schooling the kids, and dad has steady employment, either "at home" or an occupation that requires him to travel so he takes his home with him (literally).
Some others have stumbled into work from home opportunities because of their long-standing companies they've been associated with all their lives. (My company is an example of changing attitudes toward working from home. I work in information technology). More and more we are doing work form home, which affords opportunity to travel more and work while on the road. But these opportunities are usually long waiting and long deserved and not given to everyone who isn't disciplined enough to even make it into the office on time in the morning or makes every excuse in the book to miss a day at work.
Next is your age. If you are a bit older, kids gone, and have some kind of supplimental steady income, a lot of folks can get away with "work camping" or work as a "camp host" and move from campground to campground. Camp Hosts usually don't get a salary, but in exchange for their services, get a free campsite. "Work camping" would be landing a position in a campground where you get paid something (but usually a penance salary) to help supplement you. Done right, folks can be very successful.
Some folks work full time jobs in a stick and brick location, and just 'camp' at various places around the job site so they have a bed room to return to at night.
If you have school age kids, you really need to plan for their education. This is not an easy task and it takes a strong willed, strong disciplined husband and wife to enforce and make it work.
There are lots and lots of people out there, doing it, and are quite successful. But I don't think too many of them simply said, "Today we jump into the RV and never look back." It's a slower progression, and deliberate life style choices that eventually lead in that direction.
