Almost done with Outlook

Posted 2 November 2006

I’ve been using Outlook for a long time, for email, calendar, contacts, and notes. (I realize this may immediately lower your estimation of me, but at each step of the way it seemed a sensible thing to do for one reason or another—most recently because of Adobe’s edict that ‘thou shalt use Outlook’.) Now that I’m on my own, and trying to embrace the idea of hosted applications and transparent use of multiple computers to access a single source of data in the cloud, I’m working on weaning myself. So far, it’s been modestly successful.

For email, I wasn’t satisfied with any of the webmail clients offered by my hosting company; they just seemed too clunky. Gmail was attractive, but I didn’t want to give up using my personal domain. Then along came Google Apps for Your Domain, and now I have the best of both worlds. I still have my own domain name, but Google hosts my mail and provides a Gmail interface. I’ve been using this for a few weeks now and it has been working quite well.

I expected to feel a big loss in the quality of the interaction, but I haven’t. The AJAX interface is pretty responsive, although I have seen it fail from time to time. I’ve also been accustomed to filing my mail in an array of hierarchical folders, and Gmail’s “archive and then search” approach at first seemed limited. But then I realized that since I’ve had desktop search on my PC, I’ve found it easier to use that than to sort through the folders anyway. So now I have essentially the same behavior, my PC doesn’t have to spend cycles indexing my mail, and I don’t have to file any of it.

There are some things I miss, though:

• The Delete button (along with the Archive button and other controls) scrolls away when you scroll down a message. There’s another set at the bottom of the message, but for long messages, I find it a pain to have to scroll to get to the buttons. It would be nice if the buttons stayed put instead of scrolling away.

• I enabled the shortcut keys and learned a few of them, which reduces the need to scroll to find the buttons. But there seems to be no shortcut key for Delete—an action I use often. Google seems to want you to archive instead (for which there is a shortcut key), but I get a lot of mail that I just don’t see a reason to archive. Why should I archive daily news updates or mailing list postings when there’s a much better archive readily available online?

• The action I most frequently want to take when going through my mail is “delete and read the next message”. Since there’s no shortcut key for delete, this requires scrolling until the Delete button is visible, clicking the button (which returns you to the message list), and then clicking on the next message. I’d sure like to have a shortcut key that would do this.

• There’s no support for embedding images in HTML email. I really miss this.

• You can’t drag and drop a file from the file system into a message. You have to click Attach and then browse the file system, which I find to be slower.

• Typing names doesn’t automatically look them up in the contact list. If it is an address I’ve sent to recently, it appears in the type-ahead pop-up list, which works fine. But if it isn’t in this list, I have to go to contacts, find the person, and then start the email again.

I’m sure that many, if not most, of these limitations will be fixed in time, and so far I can live with them. Perhaps the most fundamental limitation is the inability to do anything off-line. With Outlook, I could read mail, write messages to be queued for later sending, and search existing mail, even if I was on an airplane or otherwise without a network connection. If I end up traveling a lot, I may start using Gmail’s POP3 option and going back to a desktop client at these times.

For my calendar, I’ve switched to Google Calendar. So far, this is working well, and I haven’t found anything I miss about the Outlook calendar (other than the frequent opportunity to swear at my computer). I like the quick entry mode of Google calendar—you can type “Lunch November 15 at 12:00” and it will put it on your calendar. And I love being able to easily share my calendar with my wife.

The Outlook calendar as used at Adobe is a complete mess. It’s model of managing meeting invitations by sending messages back and forth, and then storing state information independently in each client, is a horrible idea and has caused no end of grief for hundreds of people there. Not only do you get a constant stream of calendar notices to which you have to respond, but the system is full of bugs (for example, sometimes marking the recipient’s time as busy even when a calendar event invitation says to mark it as free) and limitations (e.g., meetings you’ve declined are gone forever and there’s no easy way to change your mind). This is an application that should be centralized, not distributed in this way. Being out of a big organization now, my needs are much simpler, so I’m certainly not stressing the Google Calendar to the degree I stressed Outlook. But so far, so good.

The two other things I use Outlook for, contacts and notes, surprisingly haven’t been quite as obvious how to switch over to hosted solutions. Gmail will import the Outlook contacts, but it is clearly designed just for an email address list and isn’t adequate as a general-purpose contact manager. Plaxo seems like one possibility, but I’m still looking.

As for notes, I’m converting tem to a series of documents in my Basecamp account, but this doesn’t feel quite right yet.