Hi Mark - welcome to Permies.
You sound like my kind of guy. I'm a total cheapskate and I run my own company. Health insurance? Ha! Vacations? HA!
Unlike many, I worked hard at low-paying gigs, invested and saved up
enough money over about ten years to buy a house flat-out (with some help from my wife's leftover college fund). Over the years I've gone dumpster-diving, gone without air conditioning, eaten lots of rice and beans, not eaten out, paid midwives for home births rather than hospital births, lived with a single vehicle, etc. My wife is a homemaker (praise God) and homeschools the kids, which allows us a lot of flexibility. We also grow a lot of our own food. Obviously, this isn't living "without money," but it's the best way I could figure things out.
All that said... many people are totally buried in debt. If I had made a few more materialist choices (buying the "nice" house instead of the tiny affordable one, going to college on loans, not working extra gigs, etc.), we'd be totally tied to the debt-slave wheel.
If you were to talk with someone in that situation (and I do all the time), what would you say? They're slaves to the banks... slaves to their cars... slaves to their spouses' desires for stuff... ack. It almost seems crazy to say "give up on the money thing," when they're drowning already. They think I'm "lucky" for being out of debt... but they're addicts to stuff and won't make the serious cuts we made to get here. It's frustrating - and I want to help (heck, I've thought about doing financial counseling... and I seem to do it as a layman now) but I feel like it's almost hopeless. I just want to scream "WAKE UP, DANG IT! SHRUG IT OFF! FIGHT!" It hurts to care... but I do care.
Where would you start?