this was a question i finally asked myself about 14 years ago. well, honestly i started asking it way before then, but the fear of living on the edge had always won out. i had gone from being a poor inner city kid to a somewhat successful software developer, with no formal education and a bit of an outsider's perspective. the idea of leaving that "career", and the life it helped me live, was quite scary. exactly up until the moment i did it.
i left the world of full-time work. i left the city i lived in (i had only ever lived in major cities my entire life). i left my wife. i sold my one asset - my suburu - to buy an old van i could live in. i signed up for unemployment, hooked up a small solar panel, and hit the road.
i learned how to live on *very* little money. i learned how to avoid the authorities when parking overnight. i started learning how to do things for myself that i typically would have looked to others for. i saw a shitload of the united states, which - who'd have thunk it - is an incredibly beautiful place (especially if you ignore most of the humans and all the damage they've done). i very quickly became disconnected from (the bulk of) the web of authoritarian bureaucracy and institutions that had always been such an annoying (and seemingly necessary) part of my life. i started feeling more free than i could ever remember as an adult.
i was shedding those responsibilities that i had not chosen to take on myself, but had been imposed on me by society. and that was the most liberating thing i have ever done.
through a friend who had lived in the area, i found some land in a remote corner of the southwest that is considered "uninhabitable", and so is essentially free to squat (and super cheap to purchase, when you know how). this area is ignored by the authorities, has no infrastructure whatsoever, has a very low population density, and often has some of the harshest conditions i have ever experienced. did i mention that it is *free*?!?!?! and i mean that as much philosophically as economically.
since then i have been, along with my best friend and landmate, creating a simple, enjoyable life on that land. the thing is, while most folks that live in this area are misfits and societal outcasts (making them much more appealing to me than most), very few (if any, apart from my landmate) share my desires for an anarchic life. there are definitely some who identify as anarchist, i just find that after talking with them for a while, it is clear they are anarchists of a different stripe. basically, progressive activist types, looking to save/change the world in all the usual ways. dime a dozen, where i come from. and just not very interesting to me. i find the old vietnam/gulf war vets with ptsd much more interesting.
the primary thing i would change about my current life, would be to have a few more folks nearby that share a bit more of my perspective, and who share my desire for the kind of simple, joyous, creative, self-engaged, self-sufficient life that i strive for. i have no desire to be part of a "community", but a few more autonomous individuals nearby that i deeply care about and trust would not break my heart. problem is, nobody i know wants to create their life here - the conditions are simply too harsh. many @ friends have visited, and they love it - but, "it's a nice place to visit...".
[edited to add a touch of context]