Kicking the Outlook Habit

As a professional with over 8K contacts and over 2K appointments, I am a hopeless Microsoft Outlook addict. However, as any power user of Outlook will tell you, it becomes massively bloated, slow as molasses, and utterly frustrating with even the slightest extended usage. Worse, there is no way to make it go back to even resembling a responsive application once the damage has been done. Why, then, you ask, do I continue to use it?

- It is still the best email application, with it's MS Word integration with the only true inline spell correct on the market.
- It is the defacto standard for corporate mail and appointment requests.
- It is the best all in one application.

However, like any Outlook power user, I have found that I need to add things on to it to make it usable. This is where it gets fun: each of those add-ons makes Outlook massively harder to use. For instance:

- Spam control. Outlook's spam filters are laughable. I could use our server's draconian spam controls, but would easily miss emails from my clients.
Instead, I happily subscribe to Cloudmark Desktop: for $5 a month, I get incredibly intelligent spam protection, with built in crowdsourcing from over half a million users. The first user who gets a spam email marks it as such in Outlook, using the Outlook-integrated Cloudmark Desktop. The next person does the same. If a few more do, every other person who gets that email will automatically have it thrown in the spam folder. Using Cloudmark, I went from over 100 emails a day I had to delete as spam to less then 2. It works, period.

- Syncing. I sync my contacts and tasks with Salesforce, so I can keep up with my organization's workload. I sync everything with Plaxo, so I can have my information synchronized across Google, Yahoo, etc. Until last week, I synced with Palm for my Treo. Each of these require a little add-on to Outlook.

- Lookout. Though no longer made, and no longer available (Microsoft acquired the company, and replaced it with the far more bloated Windows Search), it can still be found, if you know where to look for it. It adds a powerful search, Google-style, to Outlook that makes it easy to find any email or contact, ever, in your Outlook. Outlook's own built-in search is so woefully painful, Lookout is simply a must-have.

However, time has marched on, and ever so slowly, there have started to appear a crop of combinations that tempt me to finally break my Outlook addiction. First, let me say it: I would LOVE to switch to Gmail exclusively. The calendar functions are perfect (actually, superior to Outlook by far), and play nicely with Outlook meeting requests. Their email interface is incredibly powerful, with integrated Google search that is truly the gold standard, and their spam detection is incredibly good, with almost no errors. With Plaxo integration, it even satisfies most of my syncing habits. However, the biggest Outlook withdrawal I would feel is the lack of realtime inline spell correction. I've written about this before, but it amazes me still this hasn't been solved. I've recently given As-U-Type a more thorough try, and, with some tweaking of the settings, it actually seems to do what I want without annoying the hell out of me. So, it seems possible this might be my Methadone.

Syncing? Well, Plaxo does 50% of the work. However, it lacks 2 major sync points: Salesforce and my new iPhone. For Salesforce, the picture looks pretty bleak: while there are definitely tools coming to sync Salesforce's Calendar to Google Calendar, I have found nothing for the contacts. Ouch. Given the announced partnership between the two companies, I expected something, but so far it's only seemed to yield AdWords and Google Maps integration.

For the iPhone, the future looks much brighter. First, there is Yahoo Contacts syncing built into iTunes. However, it means either dealing with Yahoo's abominable mail interface (uh...can I actually see my mail, or are there only ads in there?), or ponying up $20 for a Yahoo Plus account. Alas, the Plaxo/Yahoo sync is offline for now, and importing my contacts from a CSV seemed to top out at 1K or so, leaving me with no contacts past the letter "C." Not a real confidence builder, but the built-in iTunes sync is pretty tempting...

Even better, GooSync offers over-the-air based synchronization of Google Calendars, for free, and it even works with the iPhone. A paid version gets you more bells and whistles, but, alas, still no contact syncing. The problem seems to lie with Google, not providing an API for Gmail Contacts like they do for Calendar. There are some promising developments coming, not the least of which is Apple's February release of the iPhone SDK, but there is also the tantalizing temptation of Funambol, which claims they will have an over-the-air mobile contact sync soon:

"Compatible with Gmail, Yahoo! Mail, AOL, Microsoft Outlook as well as other email systems, the software interfaces with the free myFUNAMBOL portal which stores the most up-to-date collection of your PIM data. By the end of this year, Funambol expect to have a basic, contacts-sync’ing version available."

For now, it appears I am still stuck sucking on the Outlook glass pipe while Google and Apple chortle at a new addiction they are cooking up. Hey, I'm open to ideas here: anyone??