Well, I'm probably not the best person to attempt an explanation b.c I haven't read Deschooling Society (Ivan Illich), but I think that's the origin of the term. What the hell. Deschooling is, i think, is reclaiming education as something internally inspired, liberating, joyous, social. To be schooled seems to be trained in submission to "authority". An authority that decides what gets learned when and by whom. The same vague authority that demands everyone be on the same page at the same time. Schooling seems to be all the other stuff one is taught while the interesting, important content is dissected, reconfigured, pre-digested and spoonfed back in SAT-sized bites. I think there's probably a fair bit of anarchy there, but anarchy in the best sense of the word. Deschooling seems to be much more about working within a real community, rather than the contrived community one finds in schools.