Organizing Passwords, PII and Email

As I prepare to start a new job on Monday, the first new job I’ll have started for more than seven years (God, please don’t let me get beaten up behind the bike sheds on my first day!), I’ve been making an effort to organize the detritus of my online life.

Loyal readers of this blog—if indeed such emotionally troubled individuals are currently blessed with reading privileges in the various jailhouses and detention centers they occupy—will recall my inaugural post about a password manager application I’ve been using called 1Password, made by a Canadian software company called AgileBits. As the name “1Password” suggests, the (IMO truly magnificent) app allows you to create one strong, memorable password that gives you access to a database into which you can enter all your other Web site log-in credentials, the passwords for which can be as strong and unmemorable as you wish. As if this functionality were not useful enough, the app also gives you the ability to log in to your favorite Web sites automatically, which in effect frees you from the very 21st-century hassle of entering slight variants of the same credentials into Web-based log-in forms time after tedious time.

In more recent days I’ve also been exploring some of 1Password’s additional capabilities, such as the way it allows you to store personal information (e.g., bank account, credit card and driver’s license information), in what the app calls “Wallet items.” Given my increasing reliance on the Web for performing financial and commercial transactions, having this information stored centrally in such a fashion has been proving pretty useful. Now, for instance, I don’t have to search my coat pockets for my actual wallet whenever I need my credit card for Turnov’s Small and Short men’s shop, a card whose number, expiry date and security code have escaped—or indeed have never been stored in—my memory. This liberating upshot is all the more satisfying given the numerous types of coat I’ve had to wear this winter here in the environs of Alexandria, Va., where the weather has been changing as much as a chameleon with multiple personality disorder in a dressing room.

To turn to, or at least look askance at, the subject of email organization, I’ve also been striving to exert a measure of control over my hitherto untamed Gmail inbox. This effort has necessitated creating a large number of labels and a not small number of filters. I now have as many as 17 top-level labels for my received mail, each of which has sub-labels that allow for more specific content characterization. Without wishing to give you too much insight into my personal life, here are the top-level labels I’ve settled on to-date:

  • Banking
  • Car (“Pollution-Spewing Heap of Rust” would be more accurate)
  • Credit Cards
  • Entertainment
  • Health & Fitness (just the one email under this label so far)
  • Home
  • Insurance
  • Investments
  • Local Government
  • Meetups (nice to get out of Chez Smith from time to time)
  • Personal
  • Personal Finance
  • Shopping
  • Taxes (would “Death and Taxes” last longer?)
  • Travel & Transit
  • Web Services
  • Work

Readers who take their mobility for granted might argue that going to such organizational lengths as these evinces a certain anal-retentiveness in me. And while I wouldn’t render them entirely unable to walk for arguing this way, I would suggest that if the feeling one gets from having an organized inbox is preferable to the feeling one gets from having a disorganized inbox, then the better feeling alone justifies the effort one has made in organizing it. So there, with highly polished brass knobs on!

In conclusion, I think “personal information architecture” projects like these will increase in importance as our weird, wired world becomes more data-centric and IT-reliant. Instead of finishing with a supposition, however, I’ll finish with a question: Do you—my loyal, incarcerated readers—attempt to organize your inboxes? Or do you allow them to grow untamed, like the tangled hair of an aging hippie?

1Password: The Summit of Password Managers?

If I were to suggest to you that global warming, population growth and password management were among the 21st century’s greatest problems, you would of course be perfectly justified in observing that only two of these topics deserve such weighty description: As we all know, the dangers to mankind of global warming are vastly overstated and in fact may be apocryphal.

Before any partisan bickering that my previous assertion might have provoked descends into outright violence, allow me to raise my voice above the din for a moment to plead, “I was only joking!” Compared to the mountainous environmental and demographic issues already identified, the personal tech problem of managing one’s Web site login credentials seems molehill-like indeed. Modest though its heights may be, however, they still must be scaled. It pleases me to report that with the aid of a trusty Sherpa I have in recent days been able to scale them!

Playing Tenzing Norgay to my Edmund Hillary is 1Password, a desktop password-management application from the privately held Canadian company AgileBits. According to the manufacturer’s Web site, versions for Mac, Windows, iPhone, iPad and Android are available. This discussion concerns 1Password 3 for Mac, which requires OS X Snow Leopard and higher. (Tiger and Leopard users, the manufacturer mollifies, can use 1Password 2 and sync their data with Snow Leopard or Lion.) A single-user license cost me $49.99 from the manufacturer’s Web site.

The central idea of 1Password is straightforward:

  1. You create a single, master password to the app.
  2. You enter your login credentials for any given Web site into the app’s database.
  3. The app, upon entry of the correct master password, gives you access to all the credentials you’ve entered.

The upshot is that you only have to remember one password (hence the name, duh!) in order to have access to your login credentials for any given site. This comes in especially handy if, like me, you have accumulated several variations of usernames and passwords since Web time (Berners-Lee time?) began. I, for instance, have amassed as many as 20 unique usernames!

Having only one password to remember also enables you to practice good Web security and create a strong, unique password for each of your stored sites. 1Password conveniently includes a random-password generator for the purpose. The generator features several password-customization options, including the number of characters the password should contain, the number of digits or special characters it should contain, whether it can contain the same character more than once, and even whether it should be pronounceable!

1Password also includes a delightfully time-saving auto-login feature, which alone justifies the app’s license fee IMHO. Double-click the name of any given Web site from within the app to be instantly directed to and logged into that site. For even quicker, one-click access, install the app’s Web browser extension, in which you can also perform other common tasks, such as data entry.

What happens if a Web site requires you to enter your username on one screen and your password on another? Simply create two records in the database: one for the username screen and one for the password screen, taking care to name each record meaningfully. Then simply choose the relevant record from the app or browser extension.

Do you use a Mac at home and a PC at work? Combine 1Password with the built-in 1PasswordAnywhere and the file-hosting service Dropbox for access to your login credentials from wherever you happen to be doing your Web browsing. In addition to login credentials, 1Password also promises the ability to store other types of sensitive information, such as software licenses, free-form text, and personal and financial information. I’m looking forward to trying these features out in the coming days.

In the meantime you can color me impressed. Although there may be freely available alternatives that perform just as well, I feel as though my money has been well-spent on 1Password. A piece of software that saves me time and makes me feel a bit more organized seems to me invaluable in this time-crunched era of ours. If these do not strike you as reasons enough to reach for the summit of your own password management mountain (or molehill), then why not turn to the sentiments of another celebrated Everest assaulter: Do it because it’s there!