It requires a great leap of faith.

I had a bit of a panic attack, at first, because I had very specific skills that did me no good in the outside world.

My first post-corporate job was as a groundsman in an apartment complex for $6/hr. Within a couple of years, I became manager of that same apartment complex, and then things became too corporate again, so I quit to explore alternative lifestyles, such as the aforementioned "intentional communities".

If you are flipping houses, then you have a lot more skills than I had when I first left the rat race.