On Will's recommendation I picked up The Future of the Internet and How to Stop It and just read the first couple chapters in the tub. It is very good so far, I'd just caution Will and other ed-tech types from reading with this orientation toward the text:
I’m not sure yet how much this parallels the lock down vs. open up choice that schools are facing right now, but I have a feeling the conversations will parallel in many ways.
My reading thus far is that it is directly focused on the issues central to education IT, its failings over the past couple decades and where we may end up if we just give up and use cell phones. Just don't read this looking to construct glib metaphors to things you already understand.