Privacy in a Web of meta-consciousness

I often get asked by friends and family - how can I keep my personal information online and private at the same time?  Is it safe to use Facebook or can some hacker get all my personal info? And even the old - is it safe to shop online - do you buy stuff online Chris?  My hunch is that we're not doing enough to help the average person understand how this stuff works, or maybe in fact it's just the opposite, and we're doing too much, confusing the matters through to much complexification.

We're at a major crossroads in the human-technical interface (e.g. how people interact and relate to their techie devices and the Web), and could use more philosophers shaping our understanding and future of privacy online.  For many years, we've watched and wondered how our personal information was used online, when it was abused, and when it was directly criminalized (e.g. identity theft).  We've sought methods to protect our personal email, to stop lurking advertisers from tracking our movements online, and to keep our credit card government-issued ID numbers safe.

With the rise of Webmail systems like Hotmail and Gmail, we started to ponder how all of our personal email communications might be used by the host - were they mining it for data?  About what?  Products or topics I'm talking about? Relationships I have?  What I think about?  Some of us would use encryption to keep the prying eyes out, very few of us.  Eventually most got used to the idea of using Web-based email, and just stopped wondering about how our personal messages were being analyzed or used.  Blogs came along, spreading fast, and we were able to divulge public thoughts as an author, and comment anonymously if we wanted.

Social networks arose, and privacy matters grew into something different.  Suddenly we had a Facebook or Twitter identity, and our public comments, thoughts, and private email were all tied to it.  What's more, this identity became a staple across the Web, so that each site we browsed or application we used could link us back to it whether or not we wanted it.  The proliferation of the Social-Web was documenting the thoughts of billions of people, just like millions of memories being stored in the brain.

Now the Web is growing into a meta-consciousness, ugly and crude in ways, but it seems to be happening.

Laws have scrambled to understand and establish rules and rights of privacy, often falling short.  Encrypting private data was one solution but was inaccessible to the masses who couldn't grasp the how or why of encryption.  Maybe the traditional models of privacy won't work, maybe we need to be thinking about privacy-plasticity.

Maybe the future of privacy lies in my having more individual control over who can have what information - no more of this ad network tracking business unbeknownst to the average Web citizen.  A true privacy looking glass that enables viewing who has what data about me, with the capability for me to delete it from their records with a single click.  Or maybe online privacy concerns will give way to the greater good - "the more we know each other's personal secrets the better we can all become".  After all, that's a betterment Carl Jung was sort of attempting with deep explorations into the private subconscious mind - an area that's private even to our own personality.  Or maybe governments will demand that all private information be available to them, which we've seen before in various forms of legislation.

There's a lot of "maybe's" here and I'm betting that to answer them we need less engineering, less legal compliance, and more humanism and philosophy.