Not really a philosopher myself, but think we need to start with definitions. Are you thinking of being a thru-hiker or a nomad living off the land? Having worked with parts of a Central Asian nomadic system, actual nomads constantly deal with settled communities over pastures (sometimes resolved over AK-47's). Why? It's tough getting enough calories to eat, even via livestock. Calories will be an issue unless you have money, without relying on others significantly.
With sustenance hunting for meat, there may be game warden problems unless you have a license. Backpacker mag had an article several years back on a lady who subsisted on poaching mostly small game (snare's, net's, etc..) with run-in's with the law, so even a diet of squirrel and assorted rodentia may bring unwanted attention. Probably depends on the state - heck, some graduate assistants at my college would cook road kill. Two sides to that, I guess, but local law needs to be looked at.
So maybe a seasonal job (mostly winter in the northern Hemisphere), or a full-time job while moonlighting a second or even third one (had 1 fulltime plus 2 part-time moonlighting jobs myself at one time). Live off your part-time gig and bank the rest (after taxes) for adventure. Kind of like thru-hiker Francis Tarpon wrote -- save money and watch expenses. Maybe learning and eventually teaching survival skills if you are interested in primitive skills? Just generating some more options.
Add: Taking a look at most thru-hikers, the vast majority work and save money by skimping in other areas, .... or find a way to make money writing about their travels, .... or computer work for traveler type backpackers, etc... There's exceptions like the CEO of Whole Foods, sponsored athletes, "trustefarians", etc..