Ian Clark's long academic paper in the Journal of Radical Librarianship takes a while to get to the point, but when it arrives, it's a very, very good one: in the post-Snowden era, we can no longer address the "digital divide" just by providing access — we also have to teach people how their online usage is spied on, how that will harm them, and what to do about it.
Scout Sinclair Brody (previously) is executive director of Simply Secure, a nonprofit I volunteer for that works on impriving the usability of privacy tools so that normal people can understand and benefit from them.
Another amazing Shmoocon talk is "Users Are People Too: How to Make Your Tools Not Suck for Humans," presented by two key people from Simply Secure, a nonprofit devoted to improving security tool usability (I am a volunteer advisor to Simply Secure).
Simply Secure, a nonprofit I volunteer for, is launching a new series of usability programs for organizations, companies and individuals who are making cryptographic/privacy/security tools.