Passwords
I am registered at a LOT of sites - blogs, hosting accounts, stores, message boards, etc. A few years ago I started using the Lastpass Chrome add-in to track and remember all these passwords.
One problem though: like most people I was using the same few passwords over and over. I had fixed, mostly, the most egregious mistakes, such as using the same password for low-trust sites like bulletin boards as for critical sites like banks. But Lastpass showed me was that I still had a lot of password duplication.
The Adobe security breach finally got me off my butt. My user name and password were among those that Adobe lost (which was particularly irritating because Adobe was one of those software companies that demanded a registration even when one should not have been necessary). There was nothing at Adobe of mine they could screw up -- the registration was obviously to try to sell me more stuff but I never bought anything. But there were possibly other sites using the same password they could screw up.
So I began a mission to change my passwords to 12-digit randomly generated strings of letters and numbers. Having Fastpass helped a ton, as I would never have remembered all the sites with which I had registrations. There were hundreds.
This was a real slog, a task so boring it was equaled only by the month when I ripped all my CD's to my hard drive and surpassed only by the 3 months when I ripped all my DVD's to hard drives. The problem was that every web site was essentially a little portal-like adventure puzzle, trying to figure out where the hell the options for password change could be found. I challenge those of you who have registered at WhiteHouse.gov to sign a survey to find the place to change your password. At JetBlue, there is no such option in the user accounts -- you have to log off and click "forgot my password" at the logon screen and then click on the option to reset the password, but the reset email never shows up. At two or three sites I had to email the site web manager to send me a link to the password change page.
Anyway, it's finally done now. There are a couple of sites I use from my iPad for which I had to create unique memorable passwords because iOS does not have very good support mechanisms for such services as Lastpass, though as Chrome for iOS gets better, I expect that to make the problem easier to manage. I had forgotten how many of these passwords (Netflix, Hulu, Amazon, etc.) were plugged into things like my Roku. It was irritating with the crappy remote to enter these random strings of characters as new passwords.
Of course security of the Lastpass account becomes a problem. I guess I have to trust them. My password for them is unique and never has been used anywhere else and contains no real English words. I use 2-step verification at all times to log into it, so hopefully I am moderately well-protected.
