My life on the road singing and playing folksong gigs, while trying to keep my calendar full, has always been, pretty much, a lot like this free falling you mention here. Mainly, it was the only way to do it from where I sit. It meant being my own boss---and it was the only way to go.
It's what this freedom thing is all about. Like Kris Kristofferson said, It's just another word for nothing left to lose. Quite exhilerating!