The Wikipedia entry on Paul Goodman states:
As a child, Goodman freely roamed the streets and public libraries of his native New York City, experiences which later inspired his radical concept of "the educative city").
This concept is best expressed in his novel The Empire City. But if we are to try to pull this take on "de-schooling" up to the present day, we need to take some broader cultural changes into effect.
Specifically, the collapse of young people's freedom to roam. This article from The Daily Mail nicely charts the changes experience by one family over four generations, which seems typical. Great-grandfather George, born in 1911, same as Paul Goodman, at age 8 walked six miles unaccompanied through Sheffield to fish. Today, his great-grandson Ed, also at age 8, has a permitted range of about 300 yards (the map representation of this is recommended).
If we are going to de-emphasize school, we have to explain where students are going to go and how they are going to get there, and how this will be sold politically. In the US, that is a non-trivial problem, in terms of parents' expectations, lack of public transportation, lack of public space, separation of work and residence, class segregation, etc.
Above all, encourage the formation of seminars and workshops in people's homes - Home Workshop (157); make sure that each city has a "path" where young children can safely wander on their own - Children In The City (57); build extra public "homes" for children, one to every neighborhood at least - Children's Home (86); create a large number of work-oriented small schools in those parts of town dominated by work and commercial activity - Shopfront Schools (85); encourage teenagers to work out a self-organized learning society of their own - Teenage Soclety (84); treat the university as scattered adult learning for all the adults in the region - University As A Marketplace (43); and use the real work of professionals and tradesmen as the basic nodes in the network - Master And Apprentices (83) ....
Now, I'm in favor of all this stuff, but we have to be mindful of how hard it cuts against the zeitgeist and how ill-suited our communities are to support this kind of learning. Certainly technology can support and enhance learning networks -- and I'm only thinking about primary and secondary age learners here -- but I contend that the physical network of learning is still most important, and I'll take good community-based schools over any "de-schooling" that circumscribes kids to their own houses and corporate franchises.