One reason I can still happily read blogs by principals, while just about any other blogs about education make me grind my teeth, is that principals, by their nature, have to have a concrete vision of what a school, or learning in general, should look like. They cannot simply criticize the status quo, belittle or ignore existing reforms and wonder about some still undefined perfect solution just over the horizon.
Similarly, one reason I think Will is "stuck," is because he has never been willing to place his bets on any existing model of school or education reform. Just like metal bands have pretty much maxed out the possibilities of "louder" and "faster," the territory on the "free" and "unschooling" side of education is well mapped out. Homeschooling is well-established in the US and growing. Same for virtual charter schools and elearning in general. Deschooling Society was written over 25 years ago; Summerhill was started in 1921; a "network of learning" is part of Christopher Alexander's original Pattern Language; etc., etc., ad nauseum. You've got The Big Picture Company, High Tech High, the good old Coalition of Essential Schools, KIPP, and charter schools and alternative programs of all sorts, some radical, some re-imaginings of more "traditional" approaches, scattered all over the country. Reading and writing workshop is old as I am, the Writing Project has branches everywhere.
My point here is not to point out yet again that there is nothing new under the sun. None of the aforementioned is the perfect school for 2050 or 2100, but certainly we should be able to at least have a conversation in terms of current reform models. We don't have to conjour images out of thin air, we can say things like, "we need schools like the Big Picture model, but including internships distributed out all over the world, not just locally" (I'd guess they've started doing this already, but I don't know).
And beyond that, at a certain point you just have to take your chips and push them onto a number. You have to be willing to say, "it may not be perfect yet, but I support the Big Picture model" or KIPP, or homeschooling, or whatever. Otherwise, this is just stemwinding.
OTOH, I simplify my consideration of the present and future of learning by disregarding the needs of the privileged. School reform for the wealthy is both vastly easier and harder than for the poor. It is easy because it is very difficult to genuinely screw up, i.e., end up with illiterate kids. It is difficult because the privileged are complacent, but you've got the resources to do just about anything (homeschooling is an option, for example). Here in the 'hood, in contrast, we've got all kinds of obstacles to overcome to get kids learning, but a greater willingness to take risks to do it, at least in the community, but at the same time, lots of more radical speculative options are clearly off the table, e.g., whatever happens in the school, there has to be a school building. The kids have to have somewhere to go. They can't be expected to stay home alone in their possibly unheated, lunch-less tenement, sitting in front of a computer monitor, or to be homeschooled by their parent who is illiterate in their native language and doesn't speak English very well.
I think if I was trying to figure out school reform for the wealthy, I'd feel like Will (which is not, btw, meant as an insult to Will).