My current advice/hints/practice (note: this is from a non-US perspective, but apart from the content of emails/phonecalls, most of the points below would still be applicable even if I thought I technically had 4th amendment protections):
Make sure you've got GPG/PGP installed and configured, that you've got a working keypair (with "enough" bits and a securely stored private key and passphrase), make sure your public key is "findable" either on a public keyserver in an identifiable/searchable form or on your own site/blog/.finger/where-ever - and occasionally use it for completely innocuous communication. (I've committed to sending at least one GPG encrypted email a week, and regularly communication with friends who'll deal with it without getting asnnoyed)
Make sure you've got some "disk encryption" installed and configured. Put an encrypted partition on DropBox/GoogleDrive/SkyDrive/BTSync. Keep some innocuous (but regularly changing) data in there - as well as using it to store the occasional file that your really do want encrypted. (I'm using encfs, and the commercial version BoxCryptor on MacOS)
Download and install the TorBrowser bundle - possibly in your encrypted cloud-stored partition. Use it every now and then - I make a habit of using it when browsing government sites for mundane inquiries - including occasionally intentionally "leaking" personally identifying information over an SSL/Tor connection, just so if anyone goes looking they'll see a regular law-abiding(enough) citizen doing mundane law-abiding government interaction over strongly private connections.
Raise the privacy/spying issue when appropriate to people who've probably not considered it. Mention that while Google Docs and Gmail are convenient and inexpensive - that someone might be required to answer due diligence questions about choosing them over on-premises alternatives one day. Point out that Skype/Yammer/AIM/gTalk might not be the appropriate channel for discussing corporate-in-confidence matters. Ask the question about whether the data jurisdiction of MessageLabs or Outlook.com email meets regulatory obligations for business or customer (or patient or child) privacy. Don't be a pain in the ass about it - but become known as "the guy who always makes sure those points get raised and minuted at the appropriate meetings".
I'd love additional input/ideas for that list…
(signed with bigiain@mightymedia.com.au - 432263ED - available from pgp.mit.edu)
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